Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents

Bioorganic and Medicinal Chemistry Letters

Volumn 25, Issue 20, 2015, Pages 4580-4586

  Reddy, Chada Narsimha ^a   Nayak, V Lakshma ^a   Mani, Geeta Sai ^a,c   Kapure, Jeevak Sopanrao ^a,c   Adiyala, Praveen Reddy ^a   Maurya, Ram Awatar ^a   Kamal, Ahmed ^a,b,c  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

^c NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Anticancer agents; Cyclopropane; Spirooxindoles; Structure activity relationship (SAR)

Indexed keywords

ANTINEOPLASTIC AGENT; CASPASE 3; CYCLOPROPANE DERIVATIVE; INDOLE DERIVATIVE; SPIRO[CYCLOPROPANE 1,3' INDOLIN] 2' ONE DERIVATIVE; UNCLASSIFIED DRUG; SPIRO(CYCLOPROPANE-1,3'-INDOLIN)-2'-ONE;

A549 CELL LINE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; G1 PHASE CELL CYCLE CHECKPOINT; HELA CELL LINE; HT 29 CELL LINE; HUMAN; HUMAN CELL; MCF 7 CELL LINE; MITOCHONDRIAL MEMBRANE POTENTIAL; PHARMACOPHORE; PROSTATE CANCER CELL LINE; STRUCTURE ACTIVITY RELATION; CELL CYCLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CYCLOPROPANES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84942827582     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2015.08.056     Document Type: Article

References (33)

1. A. Jordan, J.A. Hadfield, N.J. Lawrence, and A.T. Mcgown Med. Res. Rev. 18 1998 259
2. P. Giannakakou, D. Sackett, and T. Fojo J. Natl. Cancer Inst. 92 2000 182
3. P.M. Checchi, J.H. Nettles, J. Zhou, J.P. Snyder, and H.C. Joshi Trends Pharmacol. Sci. 24 2003 361
4. A. Thorburn, D.H. Thamm, and D.L. Gustafson Mol. Pharmacol. 85 2014 830
5. Q. Wu, Z. Yang, Y. Nie, Y. Shi, and D. Fan Cancer Lett. 347 2014 159
6. Y. Wang, C.E. Kaiser, B. Frett, and H.-Y. Li J. Med. Chem. 56 2013 5219
7. G. Gasser, I. Ott, and N. Metzler-Nolte J. Med. Chem. 54 2011 3
8. D. Garg, S. Henrich, O.M.H. Salo-Ahen, H. Myllykallio, M.P. Costi, and R.C. Wade J. Med. Chem. 53 2010 6539
9. J.R. Pollard, and M. Mortimore J. Med. Chem. 52 2009 2629
10. N. Mahindroo, C. Punchihewa, and N. Fujii J. Med. Chem. 52 2009 3829
11. J. Wang, T. Luo, S. Li, Y. Zhang, C. Wang, and J. Zhao Curr. Med. Chem. 20 2013 4070
12. C.S. Matos, L.M.B. de Carvalho, R.P. Lopes, and M.P.M. Marques Curr. Med. Chem. 19 2012 4678
13. A. Kumar, S. Sharma, R.A. Maurya, and J. Sarkar J. Comb. Chem. 12 2010 20
14. J.S. Kapure, C.N. Reddy, P.R. Adiyala, R. Nayak, V.L. Nayak, J.B. Nanubolu, K.K. Singarapu, and R.A. Maurya RSC Adv. 4 2014 38425
15. A. Bertamino, M. Soprano, S. Musella, M.R. Rusciano, M. Sala, E. Vernieri, V.D. Sarno, A. Limatola, A. Carotenuto, S. Cosconati, P. Grieco, E. Novellino, M. Illario, P. Campiglia, and I. Gomez-Monterrey J. Med. Chem. 56 2013 5407
16. I. Gomez-Monterrey, A. Bertamino, A. Porta, A. Carotenuto, S. Musella, C. Aquino, I. Granata, M. Sala, D. Brancaccio, D. Picone, C. Ercole, P. Stiuso, P. Campiglia, P. Grieco, P. Ianelli, B. Maresca, and E. Novellino J. Med. Chem. 53 2010 8319
17. K. Arya, P. Tomar, and J. Singh RSC Adv. 4 2014 3060
18. Y. Arun, G. Bhaskar, C. Balachandran, S. Ignacimuthu, and P.T. Perumal Bioorg. Med. Chem. Lett. 2013 1839 23
19. S.R. Yong, A.T. Ung, S.G. Pyne, B.W. Skelton, and A.H. White Tetrahedron 63 2007 5579
20. D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, A. Gzella, and R. Lesyk J. Med. Chem. 55 2012 8630
21. R.A. Maurya, J.S. Kapure, P.R. Adiyala, P. S. S., D. Chandrasekhar, and A. Kamal RSC Adv. 3 2013 15600
22. R.A. Maurya, C.N. Reddy, G.S. Mani, J.S. Kapure, P.R. Adiyala, J.B. Nanubolu, K.K. Singarapu, and A. Kamal Tetrahedron 70 2014 4709
23. A. Kamal, K.N.V. Sastry, D. Chandrasekhar, G.S. Mani, P.R. Adiyala, J.B. Nanubolu, K.K. Singarapu, and R.A. Maurya J. Org. Chem. 80 2015 4325
24. G. Faita, M. Mella, P.P. Righetti, and G. Tacconi Tetrahedron 50 1994 10955
25. M. Botta, S. Armaroli, D. Castagnolo, G. Fontana, P. Perad, and E. Bombardelli Bioorg. Med. Chem. Lett. 17 2007 1579
26. K.T. Chan, F.Y. Meng, Q. Li, C.Y. Ho, T.S. Lam, Y. To, W.H. Lee, M. Li, K.H. Chu, and M. Toh Cancer Lett. 294 2010 118
27. J.K. Shen, H.P. Du, M. Yang, Y.G. Wang, and J. Jin Ann. Hematol. 88 2009 52
28. M.A. Hotz, J. Gong, F. Traganos, and Z. Darzynkiewicz Cytometry 15 1994 237
29. K. Gonda, H. Tsuchiya, T. Sakabe, Y. Akechi, R. Ikeda, R. Nishio, K. Terabayashi, K. Ishii, Y. Matsumi, A.A. Ashla, H. kamoto, K. Takubo, S. Matsuoka, Y. Watanabe, Y. Hoshikawa, A. Kurimasa, and G. Shiota Biochem. Biophys. Res. Commun. 370 2008 629
30. H. Zhu, J. Zhang, N. Xue, Y. Hu, B. Yang, and Q. He Invest. New Drugs 28 2010 493
31. L.H. Zhang, L. Wu, H.K. Raymon, R.S. Chen, L. Corral, M.A. Shirley, R.K. Narla, J. Gamez, G.W. Muller, D.I. Stirling, B.J. Bartlett, P.H. Schafer, and F. Payvandi Cancer Res. 66 2006 951
32. S. Kumar Cell Death Differ. 14 2007 32
33. N.A. Thornberry Chem. Biol. 5 1998 97