Bioorganic & Medicinal Chemistry Letters 2012-09-01

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.

Rishi Ranjan Pandey, Akansha Srivastava, Richa Malasoni, Arshi Naqvi, Ashish Jain, Jagdamba Prasad Maikhuri, Sarvesh Paliwal, Gopal Gupta, Anil Kumar Dwivedi

Index: Bioorg. Med. Chem. Lett. 22(17) , 5735-8, (2012)

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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.Copyright © 2012 Elsevier Ltd. All rights reserved.

Related Compounds

  • Cinchonine
  • (9S)-Cinchonan-9-...

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