Synthesis of disulfide esters of dialkylaminocarbothioic acid as potent, non-detergent spermicidal agents

被引：24
作者：
Dwivedi, Anil Kumar [1 ]
Sharma, Vishnu Lal
Kumaria, Niharika
Kumar, S. T. V. S. Kiran
Srivastava, Pradeep Kumar
Ansari, Abdul Haq
Maikhuri, Jagdamba Prasad
Gupta, Gopal
Dhar, Janak Dulari
Roy, Raja
Joshi, Bhawani Shankar
Shukla, Praveen Kumar
Kumar, Manish
Singh, Satyawan
机构：
[1] Cent Drug Res Inst, Div Pharmaceut, Lucknow 226001, Uttar Pradesh, India
[2] Cent Drug Res Inst, Div Med & Proc Chem, Lucknow 226001, Uttar Pradesh, India
[3] Cent Drug Res Inst, Div Endocrinol, Lucknow 226001, Uttar Pradesh, India
[4] Cent Drug Res Inst, Reg Sophisticated Instruments Ctr, Lucknow 226001, Uttar Pradesh, India
[5] Cent Drug Res Inst, Div Fermentat Technol, Lucknow 226001, Uttar Pradesh, India
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 21期
关键词：
disulfide esters; dialkylaminocarbothioic acid; non-detergent spermicide; spermicidal activity; antifungal activity;
D O I：
10.1016/j.bmc.2007.08.024
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
S,S'-[disulfanediylbis(dialkylaminopropane-2,1-diyl)]bis- (dialkylaminothiocarbamate) (14-31) were prepared and evaluated for the spermicidal activity and antifungal activity. Dialkyldithiocarbamates (1-5) were reacted with epichlorohydrin to give 1-dialkylaminocarbothioic acid S-[(2,3-epithio)propyl]ester (7-11), these on further reaction with a secondary amine gave S,S'-[disulfanediylbis(dialkylaminopropane-2,1-diyl)]bis- (dialkylaminothiocarbamate) (14-31). Some of these compounds (16, 19-21, 23 30 31) were found to be very potent spermicidal agents with marginal antifungal activity. Two compounds (20, 21) were 25 times more active than nonoxynol-9 (N-9), the spermicide currently in the market. (C) 2007 Published by Elsevier Ltd.
引用
收藏
页码：6642 / 6648
页数：7
相关论文
共 34 条
[1]  
Anderson RA, 2002, J ANDROL, V23, P426
[2]  
Andreu D, 1998, BIOPOLYMERS, V47, P415, DOI 10.1002/(SICI)1097-0282(1998)47:6<415::AID-BIP2>3.0.CO
[3]  
2-D
[4]  
Balzarini J, 2007, LANCET, V369, P787, DOI 10.1016/S0140-6736(07)60202-5
[5]  
CLAYPOOL LE, 1994, CONTRACEPTIVE RES DE, P461
[6]   Short-term (13-week) toxicity study of 5-bromo-6-methoxy-5,6-dihydro-3′-azidothymidine-5′-(p-bromophenyl) methoxyalaninyl phosphate (WHI-07), a novel anti-HIV and contraceptive agent, in B6C3F1 mice [J].
D'Cruz, OJ ;
Uckun, FM .
TOXICOLOGICAL SCIENCES, 2001, 60 (02) :373-378
[7]   Exploiting common targets in human fertilization and HIV infection: development of novel contraceptive microbicides [J].
Doncel, GF .
HUMAN REPRODUCTION UPDATE, 2006, 12 (02) :103-117
[8]   Anti-human immunodeficiency virus type 1 microbicide cellulose acetate 1,2-benzenedicarboxylate in a human in vitro model of vaginal inflammation [J].
Fichorova, RN ;
Zhou, F ;
Ratnam, V ;
Atanassova, V ;
Jiang, S ;
Strick, N ;
Neurath, AR .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2005, 49 (01) :323-335
[9]   Microbicidal spermicide or spermicidal microbicide? [J].
Gupta, G .
EUROPEAN JOURNAL OF CONTRACEPTION AND REPRODUCTIVE HEALTH CARE, 2005, 10 (04) :212-218
[10]  
GUPTA RC, 1981, INDIAN J CHEM B, V20, P303
1234