Thieno[3,2-c]pyran-4-one based novel small molecules: Their synthesis, crystal structure analysis and in vitro evaluation as potential anticancer agents

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 13, 2012, Pages 4418-4427

  Nakhi, Ali ^a   Adepu, Raju ^a   Rambabu, D ^a   Kishore, Ravada ^b   Vanaja, G R ^b   Kalle, Arunasree M ^b   Pal, Manojit ^a  

^a INSTITUTE OF LIFE SCIENCES   (India)

^b UNIVERSITY OF HYDERABAD   (India)

Author keywords

Alkynylation; Heck; Iodocyclization; Sonogashira; Suzuki; Thienopyranone

Indexed keywords

ANTINEOPLASTIC AGENT; THIENO[3,2 C]PYRAN 4 ONE; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CANCER INHIBITION; CHEMICAL BOND; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; IN VITRO STUDY; IODINATION; SANDMEYER REACTION; SONOGASHIRA REACTION; STRUCTURE ANALYSIS;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HEK293 CELLS; HEP G2 CELLS; HUMANS; HYDROGEN BONDING; MOLECULAR CONFORMATION; PYRANS; SMALL MOLECULE LIBRARIES; THIOPHENES;

EID: 84862190429     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.04.109     Document Type: Article

References (37)

1. H.B. El-Serag, and K.L. Rudolph Gastroenterology 132 2007 2557
2. B.J. Druker Cancer Cell 1 2002 31
3. A.M. Kalle, A. Mallika, J. Badiger, Alinakhi, P. Talukdar, and Sachchidanand Biochem. Biophys. Res. Commun. 401 2010 13
4. N. Mulakayala, D. Rambabu, M.R. Raja, M. Chaitanya, C.S. Kumar, A.M. Kalle, G.R. Krishna, C.M. Reddy, M.V.B. Rao, and M. Pal Bioorg. Med. Chem. 20 2012 759
5. C.M. Grozinger, E.D. Chao, H.E. Blackwell, D. Moazed, and S.L. Schreiber J. Biol. Chem. 276 2001 38837
6. For a review, see: S. Pal, V. Chatare, and M. Pal Curr. Org. Chem. 15 2011 782
7. T. Oikawa, M. Sasaki, M. Inose, M. Shimamura, H. Kuboki, S.-I. Hirano, H. Kumagai, M. Ishizuka, and T. Takeuchi Anticancer Res. 1997 1881 17
8. E. Campaigne, and A.R. Katritzky Comprehensive Heterocyclic Chemistry 1984 Pergamon New York, NY Vol. 4, p 911
9. V.J. Ram, A. Goel, P.K. Shukla, and A. Kapil Bioorg. Med. Chem. Lett. 7 1997 3101
10. S. Raju, V.R. Batchu, N.K. Swamy, R.V. Dev, B.R. Sreekanth, J.M. Babu, K. Vyas, P.R. Kumar, K. Mukkanti, P. Annamalai, and M. Pal Tetrahedron 62 2006 955
11. S. Raju, V.R. Batchu, N.K. Swamy, R.V. Dev, J.M. Babu, P.R. Kumar, K. Mukkanti, and M. Pal Tetrahedron Lett. 47 2006 83
12. K. Gewald, E. Schinke, and H. Böttcher Chem. Ber. 99 1966 94
13. K.S. Kumar, C. Srinivas, P. Vishweshwar, J. Iqbal, and M. Pal Tetrahedron Lett. 51 2010 3269
14. T. Wang, X.-G. Huang, J. Liu, B. Li, J.-J. Wu, K.-X. Chen, W.-L. Zhu, X.-Y. Xu, and B.-B. Zeng Synlett 2010 1351
15. M. Sridhar, R.M. Rao, N.H.K. Baba, and R.M. Kumbhare Tetrahedron Lett 48 2007 3171
16. M. Gütschow, L. Kuerschner, U. Neumann, M. Pietsch, R. Löser, N. Koglin, and K. Eger J. Med. Chem 42 1999 5437
17. (a) Z. Puterová, A. Andicsová, J. Moncol, C. Rabong, and D. Végh Tetrahedron Lett 50 2009 4670
18. Perrior, T. R.; Tapolczay, D. J.; Whittle. A. J. US Patent No. 5077297, 31 Dec 1991.
19. M. Pal Synlett 2009 2896
20. J.S. Yadav, B.V.S. Reddy, and S.R. Hashim J. Chem. Soc., Perkin Trans. 1 2000 3025
21. J.S. Yadav, B.V.S. Reddy, K. Premalatha, and T. Swamy Tetrahedron Lett. 46 2005 2687
22. J.S. Yadav, B.V.S. Reddy, C.V. Rao, P.K. Chand, and A.R. Prasad Synlett 2001 1638
23. D. Bandyopadhyay, S. Mukherjee, and B.K. Banik Molecules 15 2010 2520
24. For a review, see: M.J. Mphahlele Molecules 14 2009 5308
25. N. Mulakayala, P.V.N.S. Murthy, D. Rambabu, M. Aeluri, R. Adepu, G.R.C. Krishna, M. Reddy, K.R.S. Prasad, M. Chaitanya, C.S. Kumar, M.V.B. Rao, and M. Pal Bioorg. Med. Chem. Lett. 22 2012 2186
26. R. Reddy, T.R. Reddy, S.C. Joseph, K.S. Reddy, L.S. Reddy, P.M. Kumar, and M. Pal RSC Advances 2 2012 3387
27. D.K. Barange, V.R. Batchu, D. Gorja, V.R. Pattabiraman, L.K. Tatini, J.M. Babu, and M. Pal Tetrahedron 63 2007 1775
28. For recent and leading examples, see: R. Mancuso, S. Mehta, B. Gabriele, G. Salerno, W.S. Jenks, and R.C. Larock J. Org. Chem. 75 2010 897
29. A.K. Verma, T. Aggarwal, V. Rustagi, and R.C. Larock Chem. Commun. 46 2010 4064
30. S. Mehta, and R.C. Larock J. Org. Chem. 75 2010 1652
31. C.-H. Cho, B. Neuenswander, and R.C. Larock J. Comb. Chem. 12 2010 278
32. -3 respectively. Goodness of fit = 1.060. Crystallographic data (excluding structure factors) for 5d have been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 867625. (b) Bondi, A. J. Phys. Chem. 1964, 68, 441.
33. S. Michan, and D. Sinclair Biochem. J. 404 2007 1
34. A.A. Sauve, C. Wolberger, V.L. Schramm, and J.D. Boeke Annu. Rev. Biochem. 75 2006 435
35. L.R. Saunders, and E. Verdin Oncogene 26 2007 5489
36. W. Zhao, J.P. Kruse, Y. Tang, S.Y. Jung, J. Qin, and W. Gu Nature 451 2008 587
37. M. Layek, Y.S. Kumar, A. Islam, R. Karavarapu, A. Sengupta, D. Halder, K. Mukkanti, and M. Pal Med. Chem. Commun. 2 2011 478