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1 | Compound | SMILES | IC50 ABCB1 [uM] | ± | Deviation [µM] | ABCB1 Assay | IC50 ABCB1 [uM] | ± | Deviation [µM] | ABCB1 Assay | IC50 ABCB1 [uM] | ± | Deviation [µM] | ABCB1 Assay | IC50 ABCB1 [uM] | ± | Deviation [µM] | ABCB1 Assay | IC50 ABCC1 [uM] | ± | Deviation [µM] | ABCC1 Assay | IC50 ABCC1 [uM] | ± | Deviation [µM] | ABCC1 Assay | IC50 ABCC1 [uM] | ± | Deviation [µM] | ABCC1 Assay | IC50 ABCG2 [uM] | ± | Deviation [µM] | ABCG2 Assay | IC50 ABCG2 [uM] | ± | Deviation [µM] | ABCG2 Assay | IC50 ABCG2 [uM] | ± | Deviation [µM] | ABCG2 Assay | IC50 ABCG2 [uM] | ± | Deviation [µM] | ABCG2 Assay | IC50 ABCG2 [uM] | ± | Deviation [µM] | ABCG2 Assay | Journal | Year | Volume | Issue | Starting Page | Pubmed ID | DOI | Journal | Year | Volume | Issue | Starting Page | Pubmed ID | DOI | Journal | Year | Volume | Issue | Starting Page | Pubmed ID | DOI | Journal | Year | Volume | Issue | Starting Page | Pubmed ID | DOI |
2 | Ureidocarboxylic acid derivative 4 | O=C(N(C)C1CCCCC1)NC2=CC=CC=C2C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 12.3 | ± | 2.8 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
3 | Ureidocarboxylic acid derivative 16 | O=C(N(CC)CC)NC1=CC(C=CC=C2)=C2C=C1C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 5.38 | ± | 0.68 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
4 | Thioureidocarboxylic acid derivative 18 | S=C(N(C)C1CCCCC1)NC2=CC=CC=C2C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 16.2 | ± | 4.2 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
5 | Ureidothiophene derivative 25 | O=C(N(CC)CC)NC(SC1=C2CCC1)=C2C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 11.6 | ± | 3.1 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
6 | Ureidothiophene derivative 27 | O=C(N(CC)CC)NC(SC1=C2CCCC1)=C2C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 8.29 | ± | 4.22 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
7 | Thioureidothiophene derivative 29 | S=C(N(CC)CC)NC(C=CS1)=C1C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 4.18 | ± | 0.70 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
8 | Thioureidothiophene derivative 30 | S=C(N(CC)CC)NC(SC=C1)=C1C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 4.46 | ± | 0.58 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
9 | Thioureidothiophene derivative 31 | S=C(NC1=C(C(O)=O)C=CS1)N(C)C2CCCCC2 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 4.51 | ± | 0.49 | Calcein AM (2008/ABCC1) | ± | ± | 10.2 | ± | 3.6 | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | |||||||||||||||||||||||||||||||||||||||||||||||||
10 | Thioureidothiophene derivative 37 | S=C(N(C)C1CCCCC1)NC(SC(C)=C2C)=C2C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 4.19 | ± | 1.51 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
11 | Thioureidothiophene derivative 40 | S=C(N(CC)CC)NC(SC1=C2CCC1)=C2C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 2.56 | ± | 1.11 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
12 | Thioureidothiophene derivative 42 | S=C(N(CC)CC)NC(SC1=C2CCCC1)=C2C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 2.71 | ± | 0.35 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
13 | Thioureidothiophene derivative 46 | S=C(NC1=C(C(O)=O)C2=C(CCCC2C)S1)N(CC)CC | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 4.06 | ± | 1.05 | Calcein AM (2008/ABCC1) | ± | ± | 9.10 | ± | 1.71 | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | |||||||||||||||||||||||||||||||||||||||||||||||||
14 | Thioureidothiophene derivative 47 | S=C(N(CC)CC)NC(SC1=C2CCCCC1)=C2C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 5.97 | ± | 3.83 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
15 | Thioureidothiophene derivative 48 | S=C(NC1=C(C(O)=O)C2=C(C=CC=C2)S1)N(CC)CC | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 0.932 | ± | 0.041 | Calcein AM (2008/ABCC1) | ± | ± | 6.16 | ± | 1.36 | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | |||||||||||||||||||||||||||||||||||||||||||||||||
16 | Thioureidothiophene derivative 49 | S=C(N(C)C1CCCCC1)NC(SC2=C3C=CC=C2)=C3C(O)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 1.23 | ± | 0.29 | Calcein AM (2008/ABCC1) | ± | ± | inactive | ± | Hoechst 33342 (MCF-7/MX) | ± | ± | ± | ± | J. Med. Chem | 2009 | 52 | 15 | 4586 | 19580319 | 10.1021/jm900688v | ||||||||||||||||||||||||||||||||||||||||||||||||||
17 | Thienopyridine derivative 6a | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)S2)C(C4=CC(OC)=C(OC)C(OC)=C4)=C1C(C)=O | 3.8 | ± | 0.1 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | 6.6 | ± | 1.0 | Calcein AM (H69AR) | ± | ± | 2.6 | ± | 0.6 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | ||||||||||||||||||||||||||||||||||||||||||||||||
18 | Thienopyridine derivative 6b | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)S2)C(C4=CC=C(OC)C=C4)=C1C(OC)=O | 4.5 | ± | 0.2 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.7 | ± | 0.1 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||
19 | Thienopyridine derivative 6c | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)S2)C(C4=CC=C(OC)C(OC)=C4)=C1C(OC)=O | 5.6 | ± | 0.2 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | 11.9 | ± | 1.3 | Calcein AM (H69AR) | ± | ± | 3.6 | ± | 0.6 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | ||||||||||||||||||||||||||||||||||||||||||||||||
20 | Thienopyridine derivative 6d | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3OC)=O)S2)C(C4=CC=C(OC)C(OC)=C4)=C1C(OC)=O | 10.3 | ± | 1.5 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | 41.4 | ± | Calcein AM (H69AR) | ± | ± | 4.1 | ± | 0.9 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||
21 | Thienopyridine derivative 6e | CC1=NC2=C(C(C3=CC(OC)=C(C(OC)=C3)OC)=C1C(OC)=O)C(N)=C(S2)C(C4=CC=C(C(OC)=C4)OC)=O | inactive | ± | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | inactive | ± | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||||
22 | Thienopyridine derivative 6f | CC1=NC2=C(C(C3=CC=CC=C3)=C1C(OCC)=O)C(N)=C(S2)C(C4=CC=C(C=C4)OC)=O | inactive | ± | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | inactive | ± | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||||
23 | Thienopyridine derivative 6g | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)S2)C(C4=CC=C(OC)C=C4)=C1C(OCC)=O | 6.5 | ± | 0.9 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.4 | ± | 0.1 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||
24 | Thienopyridine derivative 6j | CC1=NC2=C(C(N)=C(C(C3=CC=CC=C3)=O)S2)C(C4=CC(OC)=C(OC)C(OC)=C4)=C1C(OCC)=O | 9.0 | ± | 0.5 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | 5.2 | ± | 0.8 | Calcein AM (H69AR) | ± | ± | 1.5 | ± | 0.0 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | ||||||||||||||||||||||||||||||||||||||||||||||||
25 | Thienopyridine derivative 6k | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)S2)C(C4=CC(OC)=C(OC)C(OC)=C4)=C1C(OCC)=O | 0.3 | ± | 0.1 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | 5.2 | ± | 0.6 | Calcein AM (H69AR) | ± | ± | 0.7 | ± | 0.3 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | ||||||||||||||||||||||||||||||||||||||||||||||||
26 | Thienopyridine derivative 6l | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3OC)=O)S2)C(C4=CC(OC)=C(OC)C(OC)=C4)=C1C(OCC)=O | 6.4 | ± | 0.6 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | 12.4 | ± | 0.4 | Calcein AM (H69AR) | ± | ± | 2.6 | ± | 0.3 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | ||||||||||||||||||||||||||||||||||||||||||||||||
27 | Thienopyridine derivative 6m | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)S2)C(C4=CC=C(OCC)C=C4)=C1C(OCC)=O | 4.2 | ± | 0.7 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.3 | ± | 0.2 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||
28 | Thienopyridine derivative 6n | CC1=NC2=C(C(C3=CC=C(OCCCC)C=C3)=C1C(OCC)=O)C(N)=C(S2)C(C4=CC=C(C=C4)OC)=O | inactive | ± | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | inactive | ± | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||||
29 | Thienopyridine derivative 6o | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)S2)C(C4=CC(OC)=C(OC)C(OC)=C4)=C1C(OCCCC)=O | 1.5 | ± | 0.1 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.4 | ± | 0.08 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||
30 | Thienopyridine derivative 6p | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)S2)C(C4=CC=C(OC)C=C4)=C1C(OCCOC)=O | 1.0 | ± | 0.1 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.8 | ± | 0.1 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||
31 | Thienopyridine derivative 6q | CC1=NC2=C(C(N)=C(C(C3=CC=CC=C3)=O)S2)C(C4=CC(OC)=C(OC)C(OC)=C4)=C1C(OCCOC)=O | 1.4 | ± | 0.1 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | 3.9 | ± | 0.6 | Calcein AM (H69AR) | ± | ± | 1.3 | ± | 0.2 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | ||||||||||||||||||||||||||||||||||||||||||||||||
32 | Thienopyridine derivative 6r | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)S2)C(C4=CC(OC)=C(OC)C(OC)=C4)=C1C(OCCOC)=O | 0.3 | ± | 0.2 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | 1.1 | ± | 0.1 | Calcein AM (H69AR) | ± | ± | 0.2 | ± | 0.05 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | ||||||||||||||||||||||||||||||||||||||||||||||||
33 | Thienopyridine derivative 6s | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3OC)=O)S2)C(C4=CC(OC)=C(OC)C(OC)=C4)=C1C(OCCOC)=O | 2.0 | ± | 0.0 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | 7.0 | ± | 1.0 | Calcein AM (H69AR) | ± | ± | 2.5 | ± | 0.5 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | ||||||||||||||||||||||||||||||||||||||||||||||||
34 | Thienopyridine derivative 6t | CC1=NC2=C(C(C3=CC(OC)=C(C(OC)=C3)OC)=C1C(OCCOC)=O)C(N)=C(S2)C(C4=CC(OC)=C(C(OC)=C4)OC)=O | inactive | ± | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | inactive | ± | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||||
35 | Thienopyridine derivative 6u | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)S2)C(C4=CC(OC)=C(OC)C(OC)=C4)=C1C(OCCOCCC)=O | 0.6 | ± | 0.1 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.6 | ± | 0.1 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||
36 | Thienopyridine derivative 6v | O=C(C1=CC=C(OC)C=C1)C(S2)=C(N)C3=C2N=C(C4=CC(OC)=C(OC)C(OC)=C4)C(C(OCC)=O)=C3C5=CC(OC)=C(OC)C(OC)=C5 | 22.0 | ± | 0.5 | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 3.0 | ± | 0.3 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||
37 | Thienopyridine derivative 6w | O=C(C(SC1=C2C(C3=CC(OC)=C(C(OC)=C3)OC)=C(C#N)C(N)=N1)=C2N)C4=CC=C(C=C4)OC | inactive | ± | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | inactive | ± | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||||
38 | Thienopyridine derivative 6x | O=C(C(SC1=C2C(C)=CC(C)=N1)=C2N)C3=C(OC)C=C(C=C3)OC | inactive | ± | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | inactive | ± | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||||
39 | Thienopyridine derivative 6y | O=C(C(SC1=C2C(C3=CC(OC)=C(OC)C(OC)=C3)=CC(C)=N1)=C2N)C4=CC=C(C=C4)OC | inactive | ± | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | inactive | ± | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||||
40 | Thienopyridine derivative 7 | O=C(C(SC1=C2C(C3=CC(OC)=C(OC)C(OC)=C3)=C(C(OCCOC)=O)C(C)=N1)=C2NC(C)=O)C4=CC=C(C=C4)OC | inactive | ± | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | inactive | ± | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||||
41 | Thienopyridine derivative 14a | CC1=NC2=C(C(N)=C(C(C3=CC=C(OC)C=C3)=O)O2)C(C4=CC(OC)=C(OC)C(OC)=C4)=C1C(OCC)=O | inactive | ± | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 3.4 | ± | 0.7 | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | ||||||||||||||||||||||||||||||||||||||||||||||||||
42 | Thienopyridine derivative 14b | CC1=NC2=C(C(C3=CC=C(C=C3)OC)=C1C(OCC)=O)C(N)=C(O2)C(C4=CC(OC)=C(C(OC)=C4)OC)=O | inactive | ± | Rhodamine 123 (MES-SA/Dx5) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | inactive | ± | Hoechst 33342 (MES-SA/MX2) | ± | ± | ± | ± | Bioorg. Med. Chem. | 2014 | 22 | 21 | 5860 | 25311564 | 10.1016/j.bmc.2014.09.023 | |||||||||||||||||||||||||||||||||||||||||||||||||||
43 | 4-Anilinoquinazoline derivative 1 | N#CC(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.0699 | ± | 0.010 | Hoechst 33342 (MDCK II ABCG2) | 0.0845 | ± | 0.017 | Pheophorbide A (MDCK II ABCG2) | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||
44 | 4-Anilinoquinazoline derivative 2 | OC(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.204 | ± | 0.037 | Hoechst 33342 (MDCK II ABCG2) | 0.304 | ± | 0.082 | Pheophorbide A (MDCK II ABCG2) | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||
45 | 4-Anilinoquinazoline derivative 3 | O=S(C(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42)(F)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.556 | ± | 0.068 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
46 | 4-Anilinoquinazoline derivative 4 | OC(C=C1)=C([N+]([O-])=O)C=C1NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.0800 | ± | 0.0091 | Hoechst 33342 (MDCK II ABCG2) | 0.113 | ± | 0.017 | Pheophorbide A (MDCK II ABCG2) | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||
47 | 4-Anilinoquinazoline derivative 5 | O=[N+](C1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4)=C1)[O-] | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.130 | ± | 0.030 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
48 | 4-Anilinoquinazoline derivative 6 | N#CC1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.140 | ± | 0.040 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
49 | 4-Anilinoquinazoline derivative 7 | CC(NC1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4)=C1)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.278 | ± | 0.033 | Hoechst 33342 (MDCK II ABCG2) | 0.224 | ± | 0.043 | Pheophorbide A (MDCK II ABCG2) | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||
50 | 4-Anilinoquinazoline derivative 8 | CSC1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 3.73 | ± | 0.51 | Calcein AM (H69AR) | ± | ± | 1.190 | ± | 0.031 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||||
51 | 4-Anilinoquinazoline derivative 9 | COC1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.320 | ± | 0.100 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
52 | 4-Anilinoquinazoline derivative 10 | COC(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.930 | ± | 0.110 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
53 | 4-Anilinoquinazoline derivative 11 | COC(C=C1)=C(OC)C=C1NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4 | 1.86 | ± | 0.30 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.152 | ± | 0.019 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||||
54 | 4-Anilinoquinazoline derivative 12 | COC(C=C1)=C(F)C=C1NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.872 | ± | 0.201 | Hoechst 33342 (MDCK II ABCG2) | 0.689 | ± | 0.149 | Pheophorbide A (MDCK II ABCG2) | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||
55 | 4-Anilinoquinazoline derivative 13 | BrC(C=C1)=C(OC)C=C1NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.289 | ± | 0.034 | Hoechst 33342 (MDCK II ABCG2) | 0.202 | ± | 0.044 | Pheophorbide A (MDCK II ABCG2) | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||
56 | 4-Anilinoquinazoline derivative 14 | IC(C=C1)=C(C)C=C1NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.460 | ± | 0.070 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
57 | 4-Anilinoquinazoline derivative 15 | FC1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.355 | ± | 0.053 | Hoechst 33342 (MDCK II ABCG2) | 0.405 | ± | 0.066 | Pheophorbide A (MDCK II ABCG2) | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||
58 | 4-Anilinoquinazoline derivative 16 | FC(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.060 | ± | 0.170 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
59 | 4-Anilinoquinazoline derivative 17 | ClC(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.830 | ± | 0.118 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
60 | 4-Anilinoquinazoline derivative 18 | IC1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.791 | ± | 0.199 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
61 | 4-Anilinoquinazoline derivative 19 | IC(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=C2C=CC=C4 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.612 | ± | 0.062 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
62 | 4-Anilinoquinazoline derivative 20 | O=C(OC)C(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 8.13 | ± | 1.4 | Calcein AM (H69AR) | ± | ± | 0.944 | ± | 0.164 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||||
63 | 4-Anilinoquinazoline derivative 21 | CC(C)(C)OC(C(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 5.650 | ± | 0.920 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
64 | 4-Anilinoquinazoline derivative 22 | O=C(C(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42)O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 8.77 | ± | 0.77 | Calcein AM (H69AR) | ± | ± | 6.380 | ± | 1.390 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||||
65 | 4-Anilinoquinazoline derivative 23 | C#CC1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.672 | ± | 0.096 | Hoechst 33342 (MDCK II ABCG2) | 0.513 | ± | 0.136 | Pheophorbide A (MDCK II ABCG2) | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||
66 | 4-Anilinoquinazoline derivative 24 | CC1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42)=C1 | 3.00 | ± | 0.26 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.150 | ± | 0.160 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||||
67 | 4-Anilinoquinazoline derivative 25 | CC(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.480 | ± | 0.230 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
68 | 4-Anilinoquinazoline derivative 26 | CC(C)(C)C1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.070 | ± | 0.110 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
69 | 4-Anilinoquinazoline derivative 27 | CC(C)(C)C(C=C1)=CC=C1NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.060 | ± | 0.200 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
70 | 4-Anilinoquinoline derivative 28 | COC1=CC=CC(NC2=CC(C3=CC=CC=C3)=NC4=C2C=CC=C4)=C1 | 2.87 | ± | 0.20 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.951 | ± | 0.296 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||||
71 | 4-Anilinoquinoline derivative 29 | CSC1=CC=CC(NC2=CC(C3=CC=CC=C3)=NC4=C2C=CC=C4)=C1 | 1.42 | ± | 0.14 | Calcein AM (A2780/ADR) | ± | ± | ± | 2.98 | ± | 0.38 | Calcein AM (H69AR) | ± | ± | 1.900 | ± | 0.130 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||
72 | 4-Anilinoquinoline derivative 30 | CC(NC1=CC=CC(NC2=CC(C3=CC=CC=C3)=NC4=C2C=CC=C4)=C1)=O | 0.66 | ± | 0.17 | Calcein AM (A2780/ADR) | ± | ± | ± | 5.80 | ± | 0.94 | Calcein AM (H69AR) | ± | ± | 1.630 | ± | 0.330 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||
73 | 4-Anilinoquinoline derivative 31 | N#CC(C=C1)=CC=C1NC2=CC(C3=CC=CC=C3)=NC4=CC=CC=C42 | 4.74 | ± | 0.32 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.846 | ± | 0.169 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | |||||||||||||||||||||||||||||||||||||||||||||||||
74 | 4-Anilinoquinoline derivative 32 | FC1=CC=CC(NC2=NC(C3=CC=CC=C3)=NC4=CC=CC=C42)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 2.130 | ± | 0.460 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2016 | 59 | 11 | 5449 | 27148793 | 10.1021/acs.jmedchem.6b00330 | ||||||||||||||||||||||||||||||||||||||||||||||||||
75 | 4-Anilino-2-pyridylquinazoline derivative 11 | O=[N+](C1=CC(NC2=NC(C3=CC=CC=N3)=NC4=C2C=CC=C4)=CC=C1)[O-] | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.376 | ± | 0.091 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
76 | 4-Anilino-2-pyridylquinazoline derivative 12 | O=[N+](C1=CC(NC2=NC(C3=CC=CN=C3)=NC4=C2C=CC=C4)=CC=C1)[O-] | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.105 | ± | 0.035 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
77 | 4-Anilino-2-pyridylquinazoline derivative 13 | O=[N+](C1=CC(NC2=NC(C3=CC=NC=C3)=NC4=C2C=CC=C4)=CC=C1)[O-] | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.117 | ± | 0.029 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
78 | 4-Anilino-2-pyridylquinazoline derivative 14 | O=[N+](C(C=C1)=CC=C1NC2=NC(C3=CC=CN=C3)=NC4=C2C=CC=C4)[O-] | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.0641 | ± | 0.0085 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
79 | 4-Anilino-2-pyridylquinazoline derivative 15 | N#CC1=CC(NC2=NC(C3=NC=CC=C3)=NC4=C2C=CC=C4)=CC=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.507 | ± | 0.061 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
80 | 4-Anilino-2-pyridylquinazoline derivative 16 | N#CC1=CC(NC2=NC(C3=CN=CC=C3)=NC4=C2C=CC=C4)=CC=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.108 | ± | 0.021 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
81 | 4-Anilino-2-pyridylquinazoline derivative 17 | N#CC1=CC(NC2=NC(C3=CC=NC=C3)=NC4=C2C=CC=C4)=CC=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.134 | ± | 0.010 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
82 | 4-Anilino-2-pyridylquinazoline derivative 18 | N#CC1=CC=C(C=C1)NC2=NC(C3=CN=CC=C3)=NC4=C2C=CC=C4 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.166 | ± | 0.029 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
83 | 4-Anilino-2-pyridylquinazoline derivative 19 | COC1=CC(NC2=NC(C3=NC=CC=C3)=NC4=C2C=CC=C4)=CC=C1 | 12.7 | ± | 1.8 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.630 | ± | 0.320 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | |||||||||||||||||||||||||||||||||||||||||||||||||
84 | 4-Anilino-2-pyridylquinazoline derivative 20 | COC1=CC(NC2=NC(C3=CN=CC=C3)=NC4=C2C=CC=C4)=CC=C1 | 4.78 | ± | 0.57 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.020 | ± | 0.180 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | |||||||||||||||||||||||||||||||||||||||||||||||||
85 | 4-Anilino-2-pyridylquinazoline derivative 21 | COC1=CC(NC2=NC(C3=CC=NC=C3)=NC4=C2C=CC=C4)=CC=C1 | 5.43 | ± | 0.83 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.558 | ± | 0.111 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | |||||||||||||||||||||||||||||||||||||||||||||||||
86 | 4-Anilino-2-pyridylquinazoline derivative 22 | COC1=CC=C(C=C1)NC2=NC(C3=CC=NC=C3)=NC4=C2C=CC=C4 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | 17.9 | ± | 2.1 | Calcein AM (H69AR) | ± | ± | 0.742 | ± | 0.021 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | |||||||||||||||||||||||||||||||||||||||||||||||||
87 | 4-Anilino-2-pyridylquinazoline derivative 23 | COC1=CC=C(C=C1OC)NC2=NC(C3=NC=CC=C3)=NC4=C2C=CC=C4 | 6.30 | ± | 0.36 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.060 | ± | 0.080 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | |||||||||||||||||||||||||||||||||||||||||||||||||
88 | 4-Anilino-2-pyridylquinazoline derivative 24 | COC1=CC=C(C=C1OC)NC2=NC(C3=CN=CC=C3)=NC4=C2C=CC=C4 | 3.11 | ± | 0.21 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.753 | ± | 0.151 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | |||||||||||||||||||||||||||||||||||||||||||||||||
89 | 4-Anilino-2-pyridylquinazoline derivative 25 | COC1=CC=C(C=C1OC)NC2=NC(C3=CC=NC=C3)=NC4=C2C=CC=C4 | 2.08 | ± | 0.36 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.545 | ± | 0.113 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | |||||||||||||||||||||||||||||||||||||||||||||||||
90 | 4-Anilino-2-pyridylquinazoline derivative 26 | FC(C1=CC(NC2=NC(C3=CC=NC=C3)=NC4=C2C=CC=C4)=CC=C1)(F)F | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.216 | ± | 0.040 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
91 | 4-Anilino-2-pyridylquinazoline derivative 27 | FC(C1=CC=C(C=C1)NC2=NC(C3=CC=NC=C3)=NC4=C2C=CC=C4)(F)F | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.488 | ± | 0.038 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
92 | 4-Anilino-2-pyridylquinazoline derivative 28 | COC1=CC=C(C=C1C(F)(F)F)NC2=NC(C3=CC=NC=C3)=NC4=C2C=CC=C4 | 2.78 | ± | 0.50 | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.146 | ± | 0.023 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | |||||||||||||||||||||||||||||||||||||||||||||||||
93 | 4-Anilino-2-pyridylquinazoline derivative 29 | FC1=CC(NC2=NC(C3=CN=CC=C3)=NC4=C2C=CC=C4)=CC=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.156 | ± | 0.037 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
94 | 4-Anilino-2-pyridylquinazoline derivative 30 | O=S(C1=CC(NC2=NC(C3=CC=NC=C3)=NC4=C2C=CC=C4)=CC=C1)(F)=O | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.380 | ± | 0.184 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
95 | 4-Anilino-2-pyridylquinazoline derivative 31 | CN(C1=CC=CC(NC2=NC(C3=CC=CN=C3)=NC4=CC=CC=C42)=C1)C | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.200 | ± | 0.210 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
96 | 4-Anilino-2-pyridylquinazoline derivative 32 | OC1=CC=CC(NC2=NC(C3=CC=NC=C3)=NC4=CC=CC=C42)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 1.070 | ± | 0.190 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
97 | 4-Anilino-2-pyridylquinazoline derivative 33 | OC(C=C1)=CC=C1NC2=NC(C3=CC=NC=C3)=NC4=CC=CC=C42 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 4.260 | ± | 1.220 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
98 | 4-Anilino-2-pyridylquinazoline derivative 34 | OCC1=CC=CC(NC2=NC(C3=CC=CN=C3)=NC4=CC=CC=C42)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.810 | ± | 0.239 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
99 | 4-Anilino-2-pyridylquinazoline derivative 35 | OCC1=CC=CC(NC2=NC(C3=CC=NC=C3)=NC4=CC=CC=C42)=C1 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.921 | ± | 0.216 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 | ||||||||||||||||||||||||||||||||||||||||||||||||||
100 | 4-Anilino-2-pyridylquinazoline derivative 36 | OC(C=C1)=C([N+]([O-])=O)C=C1NC2=NC(C3=CC=CN=C3)=NC4=CC=CC=C42 | inactive | ± | Calcein AM (A2780/ADR) | ± | ± | ± | inactive | ± | Calcein AM (H69AR) | ± | ± | 0.245 | ± | 0.021 | Hoechst 33342 (MDCK II ABCG2) | ± | ± | ± | ± | J. Med. Chem. | 2017 | 60 | 10 | 4474 | 28471656 | 10.1021/acs.jmedchem.7b00441 |