Synthesis of disulfide esters of dialkylaminocarbothioic acid as potent, non-detergent spermicidal agents.
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.
Dwivedi
Anil Kumar
AK
Division of Pharmaceutics, CDRI, Lucknow, India. a_k_dwivedi@yahoo.com
Sharma
Vishnu Lal
VL
Kumaria
Niharika
N
Kiran Kumar
S T V S
ST
Srivastava
Pradeep Kumar
PK
Ansari
Abdul Haq
AH
Maikhuri
Jagdamba Prasad
JP
Gupta
Gopal
G
Dhar
Janak Dulari
JD
Roy
Raja
R
Joshi
Bhawani Shankar
BS
Shukla
Praveen Kumar
PK
Kumar
Manish
M
Singh
Satyawan
S
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004220:Disulfides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005021:Ethylamines / Q000737:chemistry*; D006801:Humans; D008297:Male; D012661:Semen / Q000187:drug effects*; D013076:Sperm Count; D013081:Sperm Motility / Q000187:drug effects; D013089:Spermatocidal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000935:Antifungal Agents; D004220:Disulfides; D005021:Ethylamines; D013089:Spermatocidal Agents; D013438:Sulfhydryl Compounds