C-N bond formation under Cu-catalysis: Synthesis and in vitro evaluation of N-aryl substituted thieno[2,3-d]pyrimidin-4(3H)-ones against chorismate mutase

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 17, 2012, Pages 5127-5138

  Adepu, Raju ^a   Shiva Kumar, K ^a   Sandra, Sandhya ^a   Rambabu, D ^a   Rama Krishna, G ^b   Malla Reddy, C ^b   Kandale, Ajit ^a   Misra, Parimal ^a   Pal, Manojit ^a  

^a INSTITUTE OF LIFE SCIENCES   (India)

^b INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA   (India)

Author keywords

Chorismate mutase; Copper; Coupling; Thienopyrimidinone

Indexed keywords

3 (3 CHLOROPHENYL) 5,6,7,8 TETRAHYDROBENZO[B]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 3 (3 METHOXYPHENYL) 5,6,7,8 TETRAHYDROBENZO[B]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 3 (4 FLUOROPHENYL) 5 METHYLTHIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 3 (4 FLUOROPHENYL) 5,6,7,8 TETRAHYDROBENZO[B]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 3 (4 FLUOROPHENYL) 6,7 DIHYDRO 5H CYCLOPENTA[4,5]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 3 (4 FLUOROPHENYL) 6,7,8,9 TETRAHYDRO 5H CYCLOHEPTA[4,5]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 3 (4 OXO 5,6,7,8 TETRAHYDROBENZO[B]THIENO[2,3 D]PYRIMIDIN 3(4H) YL) BENZALDEHYDE; 3 (NAPHTHALEN 2 YL) 5,6,7,8 TETRAHYDROBENZO[B]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 3 PHENYL 3,4,5,6,7,8 HEXAHYDROPYRIDO[4',3':4,5]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 3 PHENYL 5,6,7,8 TETRAHYDROBENZO[B]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 3 PHENYL 6,7,8,9 TETRAHYDRO 5H CYCLOHEPTA[4,5]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 7 (2 IODOBENZOYL) 3 PHENYL 3,4,5,6,7,8 HEXAHYDROPYRIDO[4',3':4,5]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; BORONIC ACID DERIVATIVE; CARBON; CHORISMATE MUTASE; COPPER; NITROGEN; PYRIMIDINE DERIVATIVE; TERT BUTYL 3 (4 FLUORPHENYL) 4 OXO 3,4,5,6,7,8 HEXAHYDROPYRIDO[4',3':4,5]THIENO[2,3 D]PYRIMIDINE 7 CARBOXYLATE; TERT BUTYL 3 (4 FORMYLPHENYL) 4 OXO 3,4,5,6,7,8 HEXAHYDROPYRIDO[4',3':4,5]THIENO[2,3 D]PYRIMIDINE 7 CARBOXYLATE; TERT BUTYL 3 (NAPHTHALEN 2 YL) 4 OXO 3,4,5,6,7,8 HEXAHYDROPYRIDO[4',3':4,5]THIENO[2,3 D]PYRIMIDINE 7 CARBOXYLATE; TERT BUTYL 3 PARA TOLYL 4 OXO 3,4,5,6,7,8 HEXAHYDROPYRIDO[4',3':4,5]THIENO[2,3 D]PYRIMIDINE 7 CARBOXYLATE; TERT BUTYL 3 PHENYL 4 OXO 3,4,5,6,7,8 HEXAHYDROPYRIDO[4',3':4,5]THIENO[2,3 D]PYRIMIDINE 7 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC MOISTURE; CARBON NITROGEN BOND; CATALYSIS; CHEMICAL BOND; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; NONHUMAN; X RAY DIFFRACTION;

CATALYSIS; CHORISMATE MUTASE; COPPER; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; ORGANOMETALLIC COMPOUNDS; PYRIMIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84864974738     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.07.011     Document Type: Article

References (47)

1. D.J. Brown A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry Vol. 3 1984 Pergamon Press Oxford 443
2. B. Roth, and C. Cheng G.P. Ellis, G.B. West, Progress in Medicinal Chemistry Vol. 19 1982 Elsevier Biomedical Press New York 267
3. C.R. Petrie, H.B. Cottam, P.A. Mckernan, R.K. Robins, and G.R. Revankar J. Med. Chem. 28 1985 1010
4. B.V. Ashalatha, B. Narayana, K.K.V. Raj, and N.S. Kumari Eur. J. Med. Chem. 42 2007 719
5. M.A. Elsherbeny, M.B. Elashmawy, H.I. Elsubbagh, A.A. Elemam, and F.A. Badria Eur. J. Med. Chem. 30 1995 445
6. V. Alagarsamy, S. Meena, K.V. Ramseshu, V.R. Solomon, K. Thirumurugan, K. Dhanabal, and M. Murugan Eur. J. Med. Chem. 41 2006 1293
7. J.F. Deng, L. Peng, G.C. Zhang, X.B. Lan, C.F. Li, F.X. Chen, Y.Y. Zhou, Z.X. Lin, L. Chen, R.K. Dai, H.J. Xu, L. Yang, X.Q. Zhang, and W.H. Hu Eur. J. Med. Chem. 46 2011 71
8. T. Horiuchi, M. Nagata, M. Kitagawa, K.B. Akahane, and K. Uoto Bioorg. Med. Chem. 17 2009 7850
9. M. Modica, M. Santagati, S. Guccione, F. Russo, A. Cagnotto, M. Goegan, and T. Mennini Eur. J. Med. Chem. 35 2000 1065
10. M. Modica, G. Romeo, L. Materia, F. Russo, A. Cagnotto, T. Mennini, R. Gaspar, G. Falkay, and F. Fulop Bioorg. Med. Chem. 12 2004 3891
11. Alinakhi, B. Prasad, R.M. Rao, U. Reddy, S. Sandra, R. Kapavarapu, D. Rambabu, G.R. Krishna, C.M. Reddy, R. Kishore, P. Misra, J. Iqbal, and M. Pal Med. Chem. Commun. 2 2011 1006
12. T.R. Reddy, L.S. Reddy, G.R. Reddy, N.V. Subbaiah, Y. Lingappa, S. Sandra, R. Kapavarapu, P. Misra, and M. Pal Bioorg. Med. Chem. Lett. 21 2011 6433
13. K.S. Kumar, D. Rambabu, S. Sandra, R. Kapavarapu, G.R. Krishna, M.V.B. Rao, K. Chatti, C.M. Reddy, P. Misra, and M. Pal Bioorg. Med. Chem. 20 2012 1711
14. K.S. Kumar, R. Adepu, S. Sandra, D. Rambabu, G.R. Krishna, C.M. Reddy, P. Misra, and M. Pal Bioorg. Med. Chem. Lett. 22 2012 1146
15. T.R. Reddy, L.S. Reddy, G.R. Reddy, K. Yarbagi, Y. Lingappa, D. Rambabu, G.R. Krishna, C.M. Reddy, K.S. Kumar, and M. Pal Green Chem. 2012 1870 14
16. For selected references, see H. Agarwal, A. Kumar, N.C. Bal, M.I. Siddiqi, and A. Arora Bioorg. Med. Chem. Lett. 17 2007 3053
17. M.E. Hediger Bioorg. Med. Chem. 12 2004 4995
18. P.A. Bartlett, Y. Nakagawa, C.R. Johnson, S.H. Reich, and A. Luis J. Org. Chem. 53 1988 3195
19. H. Maeda, Yoo Heejin, and N. Dudareva N. Nat. Chem. Biol. 7 2011 19
20. F. Claeyssens, K.E. Ranaghan, N. Lawan, S.J. Macrae, F.R. Manby, J.N. Harvey, and A. Mulholland J. Org. Biomol. Chem. 9 2011 1578
21. H.F. Zohdi, W.W. Wardakhan, S.H. Doss, and R.M. Mohareb J. Chem. Res. (M) 10 1996 2526
22. M. Schellhase, R. Boehm, and R. Pech Pharmazie 34 1984 19
23. S. Kanwar, and S.D. Sharma Indian J. Chem., Sec B 44 2005 2367
24. P.Y.S. Lam, C.G. Clark, S. Saubern, J. Adams, K. Averill, D.M.T. Chan, and A.P. Combs Synlett 2000 674
25. P.Y.S. Lam, C.G. Clark, S. Saubern, J. Adams, M.P. Winters, D.M.T. Chan, and A. Combs Tetrahedron Lett. 39 1998 2941
26. P.Y.S. Lam, S. Deudon, K.M. Averil, R. Li, M. He, P. DeShong, and C.G. Clark J. Am. Chem. Soc. 122 2000 7600
27. P.Y.S. Lam, G. Vincent, D. Bonne, and C.G. Clark Tetrahedron Lett. 43 2002 3091
28. D.M.T. Chan, K.L. Monaco, R. Li, D. Bonne, C.G. Clark, and P.Y.S. Lam Tetrahedron Lett. 44 2003 3863
29. D.A. Evans, J.L. Katz, G.S. Peterson, and T. Hinterman J. Am. Chem. Soc. 123 2001 12411
30. J.P. Collman, M. Zhong, C. Zhang, and S. Costanzo Org. Lett. 66 2001 7892
31. C. Savarin, J. Srogl, and L.S. Liebeskind Org. Lett. 4 2002 4309
32. A.K. Bakkestuen, and L.-L. Gundersen Tetrahedron Lett. 44 2003 3359
33. J.J. Strouse, M. Jeselnik, F. Tapaha, C.B. Jonsson, W.B. Parker, and J.B. Arterburn Tetrahedron Lett. 46 2005 5699
34. S. Benard, L. Neuville, and J. Zhu J. Org. Chem. 73 2008 6441
35. C.S. Guy, and T.C. Jones Synlett 2009 2253
36. K. Sreeramamurthy, E. Ashok, V. Mahendar, G. Santoshkumar, and P. Das Synlett 2010 721
37. K.S. Kumar, S. Chamakuri, P. Vishweshwar, J. Iqbal, and M. Pal Tetrahedron Lett. 51 2010 3269
38. Zhang, C.; Sidhu, K.; Lobell, M.; Ladouceur, G.; Zhao, Q.; Liu, Z.; Allegue, K.; Darne, C.; Newcom, J. US patent application US 2010/0298297 A1.
39. D.R. Gorja, K.S. Kumar, and M. Pal Beilstein J. Org. Chem 7 2011 338
40. Crystallographic data (excluding structure factors) for 3m have been deposited with the Cambridge Crystallographic Data Center as Supplementary publication number CCDC 875760.
41. M. Jithunsa, M. Ueda, and O. Miyata Org. Lett. 13 2011 518
42. K. Takagi Chem. Lett. 3 1993 469
43. For a similar mechanism proposed for the coupling of phenols with arylboronic acids, see: D.A. Evans, J.L. Katz, and T.R. West Tetrahedron Lett. 39 1998 2937
44. S.K. Kim, S.K. Reddy, B.C. Nelson, G.B. Vasquez, A. Davis, A.J. Howard, S. Patterson, G.L. Gilliland, J.E. Ladner, and P.T. Reddy J. Bacteriol. 188 2006 8638
45. S. Sasso, C. Ramakrishnan, M. Gamper, D. Hilvert, and P. Kast FEBS J. 272 2005 375
46. Bruker SADABS V2008-1, Bruker AXS.: Madison, WI, USA, 2008.
47. G.M. Sheldrick SHELX-97 1997 University of Göttingen Program for Crystal Structure Determination