Stereoselective synthesis of hexahydro-3-methyl-1-arylchromeno[3,4-b] pyrrole and its annulated heterocycles as potent antimicrobial agents for human pathogens

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 24, 2010, Pages 7288-7291

  Purushothaman, S ^a   Prasanna, R ^a   Niranjana, P ^a   Raghunathan, R ^a   Nagaraj, S ^a   Rengasamy, R ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

1,3 DC reaction; Antimicrobial; Azomethine ylide; Chromenopyrrole; Heterocycles; Intramolecular reaction

Indexed keywords

ALDEHYDE; AMINO ACID; ANTIINFECTIVE AGENT; AZOMETHINE YLIDE; CARBENDAZIM; HEXAHYDRO 3 METHYL 1 ARYLCHROMENO[3,4 B]PYRROLE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIUM; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGUS; NONHUMAN; STEREOCHEMISTRY;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; AZO COMPOUNDS; BENZOPYRANS; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; PYRROLES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THIOSEMICARBAZONES;

BACTERIA (MICROORGANISMS); FUNGI;

EID: 78449272053     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.10.073     Document Type: Article

References (35)

1. J.R. Liddell Nat. Prod. Rep. 13 1996 187
2. J.P. Michael Nat. Prod. Rep. 12 1995 535
3. D. Robins J. Nat. Prod. Rep. 12 1995 413
4. P. Gupta, P. Butler, N.B. Shepperson, and A. McHarg Eur. J. Pharmacol. 398 2000 73
5. E. Ramesh, R. Rathna Durga, R. Raghunathan, S. Sainath, and R. Malathi Bioorg. Med. Chem. 17 2009 660
6. G. Periyasami, R. Raghunathan, G. Surendiran, and N. Mathivanan Bioorg. Med. Chem. Lett. 18 2008 2342
7. N. Jain, R.M. Kanojia, J. Xu, G. Jian-Zhong, E. Pacia, M.T. Lai, F. Du, A. Musto, G. Allan, D.W. Hahn, S. Lundeen, and Z. Sui J. Med. Chem. 49 2006 3056
8. D. Amantini, F. Fringuelli, and F. Pizzo J. Org. Chem. 67 2002 7238
9. M. Poornachandran, and R. Raghunathan Tetrahedron Lett. 46 2005 7197
10. E. Ramesh, and R. Raghunathan Tetrahedron Lett. 49 2008 1125
11. S. Purushothaman, and R. Raghunathan Tetrahedron Lett. 50 2009 6848
12. R. Prasanna, S. Purushothaman, and R. Raghunathan Tetrahedron Lett. 51 2010 4538
13. A. Padwa, and M.D. Weingarten Chem. Rev. 96 1996 223
14. K.V. Gothelf, and K.A. Jorgensen Chem. Rev. 98 1998 863
15. P.N. Confalone, and E.M. Huie J. Org. Chem. 48 1983 2994
16. P.N. Confalone, and E.M. Huie J. Am. Chem. Soc. 106 1984 7175
17. R. Grigg, M.F. Aly, V. Sridharan, and S. Thianpatanagul J. Chem. Soc., Chem. Commun. 1984 182
18. R. Grigg, G. Donegan, H.Q.N. Gunaratne, D.A. Kennedy, J.F. Malone, V. Sridharan, and S. Thianpatanagul Tetrahedron 45 1989 1723
19. S.F. Martin, and T.H. Cheavens Tetrahedron Lett. 30 1989 7017
20. H. Ardill, R. Grigg, V. Sridharan, and S. Surendrakumar Tetrahedron 44 1988 4953
21. P. Armstrong, R. Grigg, M.W. Jordan, and J.F. Malone Tetrahedron 41 1985 3547
22. S. Najdi, K.-H. Park, M.M. Olmstead, and M.J. Kurth Tetrahedron Lett. 39 1998 1685
23. Y.D. Gong, S. Najdi, M.M. Olmstead, and M.J. Kurth J. Org. Chem. 63 1998 3081
24. M.S. Novikov, A.F. Khlebnikov, O.V. Besedina, and R.R. Kostikov Tetrahedron Lett. 42 2001 533
25. A. Padwa, and H. Ku J. Org. Chem. 44 1979 255
26. P. DeShong, D.A. Kell, and D.R. Sidler J. Org. Chem. 50 1985 2309
27. R.J. Andersen, D.J. Faulkner, H. Cun-Heng, G.D. Van Duyne, and J. Clardy J. Am. Chem. Soc. 107 1985 5492
28. A.R. Quesada, M.D.G. Gravalos, and J.L.F. Puentes Br. J. Cancer 74 1996 677
29. M.V.R. Reddy, M.R. Rao, D. Rhodes, M.S.T. Hansen, K. Rubins, F.D. Bushman, Y. Venkateswarlu, and D.J. Faulkner J. Med. Chem. 42 1999 1901
30. J. He, J. Zheng, J. Liu, X. She, and X. Pan Org. Lett. 8 2006 4637
31. 2: C, 79.97; H, 6.71; N, 4.05. Found: C, 80.12; H, 6.91; N, 4.02.
32. The detailed X-ray crystallographic data for 4 (CCDC numbers: 752538) is available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
33. The detailed X-ray crystallographic data for 10 (CCDC numbers: 770455) is available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
34. J. Parekh, and V.S. Chanda Turk. J. Biol. 31 2007 53
35. J.N. Eloff Planta Med. 64 1998 711