title: Synthesis of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-ones and their 2-methylene derivatives as potential spermicidal and microbicidal agents.
abstract: A series of twenty two derivatives of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-one and their 2-methylene derivatives were synthesized from naturally abundant cinchonine (I). Tartarate salts of these compounds were prepared and evaluated for spermicidal activity. The most active compounds (24, 27, 34, 36, and 38) showing potent spermicidal activity were further evaluated against different strains of Trichomonas vaginalis, for antimicrobial activity, in HeLa cell lines for cytotoxicity and against Lactobacillus jensenii for eco-safety. The tartarate of 3-(1-pentyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-one (27) was found to be more active than N-9 in spermicidal activity.
authors: Pharmaceutics Division, CSIR-Central Drug Research Institute, PO Box 173, MG Road, Lucknow 226001, India.
authors: Rishi Ranjan
authors: RR
authors: Pandey
authors: Akansha
authors: A
authors: Srivastava
authors: Richa
authors: R
authors: Malasoni
authors: Arshi
authors: A
authors: Naqvi
authors: Ashish
authors: A
authors: Jain
authors: Jagdamba Prasad
authors: JP
authors: Maikhuri
authors: Sarvesh
authors: S
authors: Paliwal
authors: Gopal
authors: G
authors: Gupta
authors: Anil Kumar
authors: AK
authors: Dwivedi
mesh_terms: D000977:Antiparasitic Agents / Q000737:chemistry* / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D002930:Cinchona Alkaloids / Q000737:chemistry* / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D007778:Lactobacillus / Q000187:drug effects; D008297:Male; D013089:Spermatocidal Agents / Q000737:chemistry* / Q000494:pharmacology*; D013094:Spermatozoa / Q000187:drug effects; D014245:Trichomonas Infections / Q000188:drug therapy; D014246:Trichomonas vaginalis / Q000187:drug effects*
chemical_list: D000977:Antiparasitic Agents; D002930:Cinchona Alkaloids; D013089:Spermatocidal Agents; C010086:cinchonine