Synthesis of benzenepropanamine analogues as non-detergent spermicides with antitrichomonas and anticandida activities

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 19, 2006, Pages 6593-6600

  Kiran Kumar, S T V S ^a   Sharma, Vishnu Lal ^a   Kumar, Manish ^a   Shukla, Praveen Kumar ^a   Tiwari, Pratibha ^a   Jain, Rajeev Kumar ^a   Maikhuri, Jagdamba Prasad ^a   Singh, Divya ^a   Gupta, Gopal ^a   Singh, Man Mohan ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Anticandida agents; Antitrichomonas; Benzenepropanamines; Spermicides

Indexed keywords

1 (3 CHLOROPHENYL) 4 [3 PHENYL 3 (4 TRIFLUOROMETHYLPHENOXY)PROPYL] PIPERAZINE; 1 [3 PHENYL 3 (4 TRIFLUOROMETHYLPHENOXY)PROPYL] 4 (3 TRIFLUOROMETHYLPHENYL) PIPERAZINE; 1 [3 PHENYL 3 (4 TRIFLUOROMETHYLPHENOXY)PROPYL] 4 PYRIDIN 2 YLPIPERAZINE; 1 METHYL 4 [3 PHENYL 3 (4 TRIFLUOROMETHYLPHENOXY)PROPYL]PIPERAZINE; 1 PHENYL 3 (4 PYRIDIN 2 YLPIPERAZIN 1 YL)PROPAN 1 OL; 1 PHENYL 3 (4 PYRIDIN 2 YLPIPERAZIN 1 YL)PROPAN 1 ONE; 1 PHENYL 3 (4 PYRIMIDIN 2 YLPIPERAZIN 1 YL)PROPAN 1 OL; 1 PHENYL 3 (4 PYRIMIDIN 2 YLPIPERAZIN 1 YL)PROPAN 1 ONE; 1 PHENYL 3 [4 (3 TRIFLUOROMETHYLPHENYL)PIPERAZIN 1 YL]PROPAN 1 OL; 1 PHENYL 3 [4 (3 TRIFLUOROMETHYLPHENYL)PIPERAZIN 1 YL]PROPAN 1 ONE; 2 [4 [3 PHENYL 3 (4 TRIFLUOROMETHYLPHENOXY)PROPYL]PIPERAZIN 1 YL]PYRIMIDINE; 3 (4 METHYLPIPERAZIN 1 YL) 1 PHENYLPROPAN 1 OL; 3 (4 METHYLPIPERAZIN 1 YL) 1 PHENYLPROPAN 1 ONE; 3 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL] 1 PHENYLPROPAN 1 OL; 3 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL] 1 PHENYLPROPAN 1 ONE; AMINE; ANTIFUNGAL AGENT; ANTITRICHOMONAL AGENT; METRONIDAZOLE; SPERMICIDAL AGENT; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STRUCTURE ACTIVITY RELATION; TRICHOMONAS VAGINALIS;

ADULT; AMINES; ANIMALS; ANTIFUNGAL AGENTS; ANTITRICHOMONAL AGENTS; BENZENE DERIVATIVES; CANDIDA ALBICANS; CELL SURVIVAL; CHEMISTRY, PHYSICAL; HUMANS; MALE; MICROBIAL SENSITIVITY TESTS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SPERMATOCIDAL AGENTS; SPERMATOZOA; STRUCTURE-ACTIVITY RELATIONSHIP; TRICHOMONAS VAGINALIS;

CANDIDA; TRICHOMONAS VAGINALIS;

EID: 33747169667     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.06.003     Document Type: Article

References (34)

1. United Nations Population Division (2003) World population prospects. The 2002 revision. Available from http://www.un.org/esa/population/publications/wpp2002/WPP2002-HIGHLIGHTSrev1.PDF.
2. Gupta G. Eur. J. Contrcept. Reprod. Health Care 10 (2005) 212
3. Sugarman B., and Mummaw N. Antimicrob. Agents Chemother. 32 (1988) 1323
4. Jones B.M., and Willcox L.M. Genitourin. Med. 67 (1991) 475
5. Kirkman R., and Chantler E. Br. Med. Bull. 49 (1993) 171
6. Stephenson J. JAMA 284 (2000) 949
7. Roddy R.E., Zekeng L., Ryan K.A., Tamoufe U., and Tweedy K.G. JAMA 287 (2002) 1117
8. Van Damme, L.; Ramjee, G.; Alary, M.; Vuylsteke, B.; Chandeying, V.; Rees, H.; Sirivongrangson, P.; Mukenge-Tshibaka, L.; Ettiegne-Traore, V.; Uaheowitchai, C.; Karim, S. S.; Masse, B.; Perriens, J.; Laga, M.; COL-1492 Study Group. Lancet 2002, 360, 971.
9. D'Cruz O.J., and Uckun F.M. Contraception 64 (2001) 113
10. Srivastava S., Bajpai L.K., Batra S., Bhaduri A.P., Maikhuri J.P., Gupta G., and Dhar J.D. Bioorg. Med. Chem. 7 (1999) 2607
11. Garg A., Anderson R.A., Zaneveld L.J.D., and Garg S. J. Androl. 26 (2005) 414
12. Salve P.S., Doncel G.F., Bryant S.D., Hubieki M.P., Robinette R.G., and Gandour R.D. Bioorg. Med. Chem. Lett. 9 (1999) 2545
13. D'Cruz O.J., Venkatchalam T.K., and Uckun F.M. Biol. Reprod. 62 (2000) 37
14. Belec L., Tevi-Benissan C., Bianchi A., Cotigni S., Beumont-mauviel M., and Si-Mohammad A. J. Antimicrob. Chemother. 46 (2000) 685
15. D'Cruz O.J., Venkatchalam T.K., and Uckun F.M. Biol. Reprod. 63 (2000) 196
16. Weber J., Nunn A., O'Conner T., Jeffries D., Kitchen V., McCormac S., Stott J., Almond N., Stone A., and Darbyshire J. AIDS 15 (2001) 1563
17. Raghuvanshi P., Bagga R., Malhotra D., Gopalan S., and Talwar G.P. Indian J. Med. Res. 113 (2001) 135
18. Wong Y.-L., Curfmann C.L., Doncel G.F., Patricia Hubieki M., Dudding T.C., Salve P.S., and Gandour R.D. Tetrahedron 58 (2002) 45
19. Maikhuri J.P., Dwivedi A.K., Dhar J.D., Setty B.S., and Gupta G. Contraception 67 (2003) 403
20. Windsor D.P., White I.G., Selly M.L., and Swan M.A. J. Reprod. Fertil. 99 (1993) 359
21. Wolf W.A., and Kuhn D.M. J. Biol. Chem. 267 (1992) 20820
22. Solanki, S.; Potter, W. D.; Anderson, L. Spermicides. US Patent US 2005131238, 2005.
23. Kiran Kumar S.T.V.S., Sharma V.L., Tiwari P., Singh D., Maikhuri J.P., Gupta G., and Singh M.M. Bioorg. Med. Chem. Lett. 16 (2006) 2509
24. Tseng, C.-Y.; Wang, J.; Hudson, M.; Liu, J.-Ch. Spermicidal antiviral lubricant composition and method of using same. US Patent US 5512289, 1996.
25. Batra S., Gupta P., Bose K., Bhaduri A.P., and Setty B.S. Indian J. Chem. B (1996) 36
26. Hatcher R.A., Rinehart W., Blackburn R., and Geller J.S. Sexually Transmitted Diseases Including HIV/AIDS. The Essentials of Contraceptive Technology-A Handbook for Clinic Staff (1997), Population Information Program, Baltimore 16
27. Sonurlikar U.A., Shankar B., Kirke P.A., and Bhide M.B. Bull. Hoffkine 5 (1977) 94
28. Romero D.L., Morge R.A., Genin M.J., Biles C., Busso M., Resnick L., Althaus I.W., Reusser F., Thomas R.C., and Tarpley W.G. J. Med. Chem. 36 (1993) 1505
29. Nivsarkar M., Cherian B., and Patel S. Biochem. Biophys. Res. Commun. 247 (1998) 716
30. Gupta G., Jain R.K., Maikhuri J.P., Shukla P.K., Kumar M., Roy A.K., Patra A., Singh V., and Batra S. Hum. Reprod. 20 (2005) 2301
31. National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of yeasts. Approved standard M27-A. National Committee for Clinical Laboratory Standards, Wayne, PA, USA, 1997.
32. National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of conidium-forming filamentous fungi: proposed standard. Document M 38-P. National Committee for Clinical Laboratory Standards, Wayne, PA, USA, 1998.
33. Diamond L.S., Harlow D.R., and Cunnick A.C. Trans. R. Soc. Trop. Med. Hyg. 72 (1978) 431
34. Upcroft J.A., and Upcroft P. Antimicrob. Agents Chemother. 45 (2001) 1810