Rapid microwave assisted synthesis and antimicrobial bioevaluation of novel steroidal chalcones

Steroids

Volumn 78, Issue 3, 2013, Pages 321-326

  Kakati, Dwipen ^a   Sarma, Rupak K ^a   Saikia, Ratul ^a   Barua, Nabin C ^a   Sarma, Jadab C ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Antibacterial; Antifungal; Chalcone; Claisen Schmidt condensation; Pregnenolone

Indexed keywords

1 (3BETA) 3 (ACETYLOXY) ANDROST 5 EN 17 YL] 3 (4 HYDROXY 3 METHOXYPHENYL) 2 PROPEN 1 ONE; 1 (3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (2,4 DICHLOROPHENYL) 2 PROPEN 1 ONE; 1 (3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (2,4 DIMETHOXYPHENYL) 2 PROPEN 1 ONE; 1 (3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (4 BROMOPHENYL) 2 PROPEN 1 ONE; 1 (3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (4 METHYLPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (2 BROMOPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (2 NITROPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (2,3,5 TRIFLUOROPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (2,4 DIFLUOROPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (3,4 DIHYDROXYPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (4 CHLOROPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (4 FLUOROPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (4 HYDROXYPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (4 METHOXYPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 (4 NITROPHENYL) 2 PROPEN 1 ONE; 1 [(3BETA) 3 (ACETYLOXY)ANDROST 5 EN 17 YL] 3 PHENYL 2 PROPEN 1 ONE; ANTIINFECTIVE AGENT; CHALCONE DERIVATIVE; FLUCONAZOLE; KANAMYCIN; PREGNENOLONE ACETATE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BACILLUS SUBTILIS; BACTERIAL STRAIN; CANDIDA ALBICANS; CHEMICAL REACTION; CLAISEN SCHMIDT CONDENSATION; DRUG SCREENING; DRUG SYNTHESIS; EPOXIDATION; ESCHERICHIA COLI; FUNGAL STRAIN; MICROWAVE RADIATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ASPERGILLUS NIGER; BACILLUS SUBTILIS; CANDIDA ALBICANS; CHALCONES; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; MICROWAVES; PREGNENOLONE; STRUCTURE-ACTIVITY RELATIONSHIP;

ASPERGILLUS NIGER; BACILLUS SUBTILIS; BACTERIA (MICROORGANISMS); CANDIDA ALBICANS; ESCHERICHIA COLI;

EID: 84872528200     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2012.12.003     Document Type: Article

References (17)

1. A. Cammarata, S.K. Upadhyay, B.S. Jursic, and D.M. Neumann Antifungal activity of 2α,3β-functionalized steroids stereoselectively increases with the addition of oligosaccharides Bioorg Med Chem Lett 21 2001 7379 7386
2. S.A. Khan Synthesis, characterization and in vitro antibacterial activity of new steroidal 5-en-3-oxazolo and thiazoloquinoxaline Eur J Med Chem 43 2008 2040 2044
3. L.-H. Shan, H.-M. Liu, K.-X. Huang, G.-F. Dai, C. Cao, and R.-J. Dong Synthesis of 3β, 7α, 11α-trihydroxy-pregn-21-benzylidene-5-en- 20-one derivatives and their cytotoxic activities Bioorg Med Chem Lett 19 2009 6637 6639
4. A.H. Banday, B.P. Mir, I.H. Lone, K.A. Suri, and H.M.S. Kumar Studies on novel d-ring substituted steroidal pyrazolines as potential anticancer agents Steroids 75 2010 805 809
5. Z. Nowakowska A review of anti-infective and anti-inflammatory chalcones Eur J Med Chem 42 2007 125 137
6. D. Kakati, and J.C. Sarma Microwave assisted solvent free synthesis of 1,3-diphenylpropenones Chem Cent J 5 2011 8 [references cited therein]
7. S. Cheenpracha, C. Karalai, C. Ponglimanont, S. Subhdhirasakul, and S. Tewtrakul Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata Bioorg Med Chem 14 2006 1710 1714
8. H.N. ElSohly, A.S. Joshi, A.C. Nimrod, L.A. Walker, and A.M. Clark Antifungal chalcones from Maclura tinctoria Planta Med 67 2001 87 89
9. B.A. Bhat, K.L. Dhar, S.C. Puri, A.K. Saxena, M. Shanmugavel, and G.N. Qazi Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents Bioorg Med Chem Lett 15 2005 3177 3180
10. E.E. Baulieu, and P. Robel Neurosteroids: a new brain function? J Steroid Biochem Mol Biol 37 1990 395 403
11. M.I. Choudhary, M.S. Alam, A.-U. Rahman, S. Yousuf, Y.-C. Wu, and A.-S. Lin Pregnenolone derivatives as potential anticancer agents Steroids 76 2011 1554 1559
12. M. Bianchi, and E.E. Baulieu 3β-Methoxy pregnenolone (MAP-4343) as an innovative therapeutic approach for depressive disorders Proc Natl Acad Sci USA 109 2012 1713 1718
13. V. Pérez-Ornelas, M. Cabeza, E. Bratoeff, I. Heuze, M. Sánchez, and E. Ramírez New 5alpha-reductase inhibitors: in vitro and in vivo effects Steroids 70 2005 217 224
14. A. Magyar, J. Wölfling, M. Kubas, J.A.C. Seijo, M. Sevvana, R. Herbst-Irmer, P. Forgó, and G. Schneider Synthesis of novel steroid-tetrahydroquinoline hybrid molecules and d-homosteroids by intramolecular cyclization reactions Steroids 69 2004 301 312
15. G. Mehta, and V. Singh Hybrid systems through natural product leads: an approach towards new molecular entities Chem Soc Rev 31 2002 324 334
16. S. Pal, Y.K. Tak, and J.M. Song Does the antibacterial activity of silver nanoparticles depend on the shape of the nanoparticle? A study of the Gram-negative bacterium Escherichia coli Appl Environ Microbiol 73 2007 1712 1720
17. U. Schillinger, and F.K. Lücke Antimicrobial activity of Lactobacillus sake isolated from meat Appl Environ Microbiol 55 1989 1901 1906