Synthesis, stereochemistry, and antimicrobial activity of 2,6-diaryl-3-(arylthio)piperidin-4-ones

Chemical and Pharmaceutical Bulletin

Volumn 54, Issue 6, 2006, Pages 795-801

  Srinivasan, Murugesan ^a   Perumal, Subbu ^a   Selvaraj, Sangavanaicker ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

Antibacterial activity; Antifungal activity; NMR; Piperidin 4 one; Stereochemistry

Indexed keywords

ACETONE; ALDEHYDE; AMMONIUM ACETATE; METHYLAMINE; NYSTATIN; PIPERIDIN 4 ONE DERIVATIVE; PIPERIDINE DERIVATIVE; STREPTOMYCIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SALMONELLA TYPHI; STAPHYLOCOCCUS AUREUS; STEREOCHEMISTRY; VIBRIO CHOLERAE;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; DRUG EVALUATION, PRECLINICAL; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PIPERIDONES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33744732434     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.54.795     Document Type: Article

References (25)

1. Dimmock J. R., Arora V., Quail J. K. W., Pugazhenthi V., Allen T. M., Kao G. Y., Declercq E., J. Pharm. Sci., 83, 1124-1130 (1994).
2. Dimmock J. R., Arora V. K., Semple H. A., Lee J. S., Allen T. M., Kao G. Y., Pharmazie, 47, 246-248 (1992).
3. Mobio I. G., Soldatankov A. T., Fedorov V. O., Khim-Farm. Zh., 23, 421-427 (1989).
4. Barondi M., Robert J., Luu-Duc C., J. Steroid Biochem. Mol. Biol., 57, 73-77 (1996).
5. Dimmock J. R., Padmanilayam M. P., Puthucode R. N., Nazarali A. J., Motaganahalli N. L., Zello G. A., Quail J. W., Oloo E. O., Kraatz H. B., Prisciak J. S., Allen T. M., Santos C. L., Balzarini J., De Clercq E., Manavathu E. K., J. Med. Chem., 44, 586-593 (2001).
6. El-Subbagh H. I., Abu-Zaid S. M., Mahran M. A., Badria F. A., Al-Obaid A. M., J. Med. Chem., 43, 2915-2921 (2000).
7. Miyoshi N., Mishik V., Fukuda M., Riesz P., Radiat. Res., 143, 194-202 (1995).
8. Dzwigaj S., Pezerart H., Free Rad. Res., 23, 103-115 (1995).
9. Bagrov F. V., Matveeva T. M., Nikolaev V. N., Chem. Tech. Fuels Oil., 27, 543-545 (1991).
10. Shintani R., Tokunaga N., Doi H., Hayashi T., J. Am. Chem. Soc., 126, 6240-6241 (2004).
11. Lee H. K., Chun J. S., Pak C. S., Tetrahedron Lett., 42, 3483-3486 (2001).
12. Fleet G. W. J., Ramsden N. G., Witty D. R., Tetrahedron, 45, 319-326 (1990).
13. Winkler D. A., Holan G., J. Med. Chem., 32, 2084-2089 (1989).
14. Fleet G. W. J., Ramsden N. G., Dwek R. A., Rademacher T. W., Fellows L. E., Nash R. J., Green D. S. C., Winchester B., J. Chem. Soc. Chem. Commun., 7, 483-485 (1988).
15. Reddy P. A., Woodward K. E., Mllhoran S. M., Hsiang B. C., Latifi N., Hill M. W., Rothman S. M., Ferrendelli J. A., Covey D. F., J. Med. Chem., 40, 44-49 (1997).
16. Garcia M., del Rio X., Sivestre S., Rubiralta M., Lozoya E., Segarra V., Fernandez D., Miralpeix M., Aparici M., Diez A., Org. Biomol. Chem., 2, 1633-1642 (2004).
17. Piro J., Rubiralta H., Giralt E., Diez A., Tetrahedron Lett., 42, 871-873 (2001).
18. Piro J., Rubiralta H., Giralt E., Diez A., Tetrahedron Lett., 40, 4865-4868 (1999).
19. Takeuchi Y., Azuma K., Takakura K., Abe H., Harayama T., Chem. Commun., 2000, 1643-1644 (2000).
20. Khanum S. A., Shashikanth S., Sudha S. B., Science Asia, 29, 383-392 (2003).
21. Gnanadeepam M., Selvaraj S., Perumal S., Renuga S., Tetrahedron, 58, 2227-2230 (2002).
22. Renuga S., Selvaraj S., Perumal S., Hewlins M. J. E., Tetrahedron, 55, 9309-9316 (1999).
23. Baliah V., Ekambaram A., Govindarajan T. S., Curr. Sci., 23, 264 (1954).
24. Faria L. E., Donnici C. L., Lopes J. C. D., Int. J. Quantum Chem., 95, 313-321 (2003).
25. Bauer A. M., Kirby W. M. M., Sherris J. C., Turck M., Am. J. Clin. Pathol., 45, 493-496 (1966).