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

被引：18

作者：

Pandey, Rishi Ranjan ^{[1
]}

Srivastava, Akansha ^{[1
]}

Malasoni, Richa ^{[1
]}

Naqvi, Arshi ^{[1
]}

Jain, Ashish ^{[2
]}

Maikhuri, Jagdamba Prasad ^{[2
]}

Paliwal, Sarvesh ^{[3
]}

Gupta, Gopal ^{[2
]}

Dwivedi, Anil Kumar ^{[1
]}

机构：

[1] CSIR Cent Drug Res Inst, Div Pharmaceut, Lucknow 226001, Uttar Pradesh, India

[2] CSIR Cent Drug Res Inst, Div Endocrinol, Lucknow 226001, Uttar Pradesh, India

[3] Banasthali Vidyapeeth, Dept Pharm, Banasthali, Rajasthan, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 17期

关键词：

Spermicides; Cinchotoxin derivatives; Microbicides; HeLa cells; Trichomonas vaginalis; IN-VITRO; BENZALKONIUM CHLORIDE; SULFHYDRYL-GROUPS; DISULFIDE ESTERS; SPERM; ACRYLOPHENONES; SPERMATOZOA; SEARCH; VIRUS; ACID;

D O I：

10.1016/j.bmcl.2012.06.062

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5735 / 5738

页数：4

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