Design, synthesis and biological evaluation of novel 5H-chromenopyridines as potential anti-cancer agents

Molecules

Volumn 20, Issue 9, 2015, Pages 17152-17165

  Banerjee, Souvik ^a   Wang, Jin ^a   Pfeffer, Susan ^a   Ma, Dejian ^a   Pfeffer, Lawrence M ^a   Patil, Shivaputra A ^a   Li, Wei ^a   Miller, Duane D ^a  

^a UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

Author keywords

Anti proliferative activity; Chromene; Chromenopyridine; Glioma; Melanoma

Indexed keywords

ANTINEOPLASTIC AGENT; BENZOPYRAN DERIVATIVE; MOLECULAR LIBRARY; PYRIDINE DERIVATIVE;

CELL PROLIFERATION; CHEMISTRY; DRUG DEVELOPMENT; DRUG EFFECTS; GLIOMA; HUMAN; MELANOMA; MOLECULAR LIBRARY; PHARMACOLOGY; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; BENZOPYRANS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DISCOVERY; GLIOMA; HUMANS; MELANOMA; PYRIDINES; SMALL MOLECULE LIBRARIES;

EID: 84947967805     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules200917152     Document Type: Article

References (22)

1. Jemal, A., Bray, F., Center, M.M., Ferlay, J., Ward, E., Forman, D. Global cancer statistics. CA Cancer J. Clin. 2011, 61, 69-90.
2. Siegel, R., Ma, J., Zou, Z., Jemal, A. Cancer statistics, 2014. CA Cancer J. Clin. 2014, 64, 9-29.
3. Lu, Y., Chen, J., Xiao, M., Li, W., Miller, D.D. An Overview of Tubulin Inhibitors That Interact with the Colchicine Binding Site. Pharm. Res. 2012, 29, 2943-2971.
4. Patil, S.A., Patil, R., Pfeffer, L.M., Miller, D.D. Chromenes: Potential new chemotherapeutic agents for cancer. Future Med. Chem. 2013, 5, 1647-1660.
5. Patil, S.A., Wang, J., Li, X.S., Chen, J., Jones, T.S., Hosni-Ahmed, A., Patil, R., Seibel, W.L., Li, W., Miller, D.D. New substituted 4H-chromenes as anticancer agents. Bioorg. Med. Chem. Lett. 2012, 22, 4458-4461.
6. Patil, S.A., Pfeffer, L.M., Miller, D.D. Gliomas: Classification, Symptoms, Treatment and Prognosis; Nova Science Pub Inc: Hauppauge, NY, USA, 2014.
7. Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Wang, Y., Zhao, J., Jia, S., Herich, J., Labreque, D., Storer, R., et al. Discovery of 4-Aryl-4H-chromenes as a new series of apoptosis inducers using a cell-And caspase-based high-Dhroughput screening assay. 1. Structure-Activity relationships of the 4-Aryl group. J. Med. Chem. 2004, 47, 6299-6310.
8. Kemnitzer, W., Kasibhatla, S., Jiang, S., Zhang, H., Zhao, J., Jia, S., Xu, L., Crogan-Grundy, C., Denis, R., Barriault, N., et al. Discovery of 4-Aryl-4H-chromenes as a new series of apoptosis inducers using a cell-And caspase-based high-Dhroughput screening assay. 2. Structure-Activity relationships of the 7-And 5-, 6-, 8-positions. Bioorg. Med. Chem. Lett. 2005, 15, 4745-4751.
9. Shestopalov, A.M., Litvinov, Y.M., Rodinovskaya, L.A., Malyshev, O.R., Semenova, M.N., Semenov, V.V. Polyalkoxy Substituted 4H-Chromenes: Synthesis by Domino Reaction and Anticancer Activity. ACS Comb. Sci. 2012, 14, 484-490.
10. Gourdeau, H., Leblond, L., Hamelin, B., Desputeau, C., Dong, K., Kianicka, I., Custeau, D., Boudreau, C., Geerts, L., Cai, S.X., et al. Antivascular and antitumor evaluation of 2-Amino-4-(3-bromo-4, 5-dimethoxy-phenyl)-3-cyano-4H-chromenes, a novel series of anticancer agents. Mol. Cancer Ther. 2004, 3, 1375-1384.
11. Azizmohammadi, M., Khoobi, M., Ramazani, A., Emami, S., Zarrin, A., Firuzi, O., Miri, R., Shafiee, A. 2H-chromene derivatives bearing thiazolidine-2, 4-dione, rhodanine or hydantoin moieties as potential anticancer agents. Eur. J. Med. Chem. 2013, 59, 15-22.
12. Mansouri, K., Khodarahmi, R., Foroumadi, A., Mostafaie, A., Mohammadi Motlagh, H. Anti-Angiogenic/proliferative behavior of a ?4-Aryl-4H-chromene? on blood vessel?s endothelial cells: A possible evidence on dual ?anti-Dumor? activity. Med. Chem. Res. 2011, 20, 920-929.
13. Hussain, M.K., Ansari, M.I., Yadav, N., Gupta, P.K., Gupta, A.K., Saxena, R., Fatima, I., Manohar, M., Kushwaha, P., Khedgikar, V., et al. Design and synthesis of ERα/ERβ selective coumarin and chromene derivatives as potential anti-breast cancer and anti-osteoporotic agents. RSC Adv. 2014, 4, 8828-8845.
14. Thapa, U., Thapa, P., Karki, R., Yun, M., Choi, J.H., Jahng, Y., Lee, E., Jeon, K.H., Na, Y., Ha, E.M., et al. Synthesis of 2, 4-diaryl chromenopyridines and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-Activity relationship. Eur. J. Med. Chem. 2011, 46, 3201-3209.
15. Al-Said, M., Ghorab, M., Nissan, Y. Dapson in heterocyclic chemistry, part VIII: Synthesis, molecular docking and anticancer activity of some novel sulfonylbiscompounds carrying biologically active 1, 3-dihydropyridine, chromene and chromenopyridine moieties. Chem. Cent. J. 2012, 6, doi:10.1186/1752-153X-6-64.
16. Anderson, D.R., Hegde, S., Reinhard, E., Gomez, L., Vernier, W.F., Lee, L., Liu, S., Sambandam, S., Snider, P.A., Masih, L. Aminocyanopyridine inhibitors of mitogen activated protein kinase-Activated protein kinase 2 (MK-2). Bioorg. Med. Chem. Lett. 2005, 15, 1587-1590.
17. Melekhin, E.A., Bardasov, I.N., Ershov, O.V., Eremkin, A.V., Kayukov, Y.S., Nasakin, O.E. Synthesis of 5-Aryl-2, 4-diamino-8-hydroxy-5H-chromeno[2, 3-b]pyridine-3-carbonitriles. Russ. J. Org. Chem. 2006, 42, 622-623.
18. Evdokimov, N.M., Kireev, A.S., Yakovenko, A.A., Antipin, M.Y., Magedov, I.V., Kornienko, A. One-Step Synthesis of Heterocyclic Privileged Medicinal Scaffolds by a Multicomponent Reaction of Malononitrile with Aldehydes and Thiols. J. Org. Chem. 2007, 72, 3443-3453.
19. Safaei-Ghomi, J., Kiani, M., Ziarati, A., Shahbazi-Alavi, H. Highly efficient synthesis of benzopyranopyridines via ZrP2O7 nanoparticles catalyzed multicomponent reactions of salicylaldehydes with malononitrile and thiols. J. Sulfur Chem. 2014, 35, 450-457.
20. Safaei-Ghomi, J., Shahbazi-Alavi, H., Heidari-Baghbahadorani, E. SnO nanoparticles as an efficient catalyst for the one-pot synthesis of chromeno[2, 3-b]pyridines and 2-Amino-3, 5-dicyano-6-sulfanyl pyridines. RSC Adv. 2014, 4, 50668-50677.
21. Chen, J., Ahn, S., Wang, J., Lu, Y., Dalton, J.T., Miller, D.D., Li, W. Discovery of novel 2-Aryl-4-benzoyl-imidazole (ABI-III) analogues targeting tubulin polymerization as antiproliferative agents. J. Med. Chem. 2012, 55, 7285-7289.
22. Wang, Z., Chen, J., Wang, J., Ahn, S., Li, C.M., Lu, Y., Loveless, V.S., Dalton, J.T., Miller, D.D., Li, W. Novel tubulin polymerization inhibitors overcome multidrug resistance and reduce melanoma lung metastasis. Pharm. Res. 2012, 29, 3040-3052.