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Synthesis and Characterization of Furo[3,2-h]Quinoliniums as Potent Non-Detergent Spermicides

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Title Synthesis and Characterization of Furo[3,2-h]Quinoliniums as Potent Non-Detergent Spermicides
 
Creator Banerjee, Maitreyee
Kumar, Shrabanti
Paira, Rupankar
Ghosh, Soma
Karmakar, Sanmoy
Mondal, Nirup B
 
Subject Chemistry
 
Description 7-Aryl substituted furo[3,2-h]quinoliniums have been synthesised in two steps from 5-chloro-8-hydroxy-7-
iodo-quinoline through a tandem Sonogashira alkynylation-cyclization pathway using aryl acetylenes followed by quaternisation reaction with alkyl halides under microwave irradiation. The compounds have been characterized spectroscopically and assessed for their sperm-immobilizing efficacy in vitro by modified Sander–Cramer test. Most of the derivatives showed potent spermicidal effect with minimum effective concentration (MEC) ranging from 125�g/ml – 1mg/ml. The results were further confirmed by double fluoroprobe staining with syber14/PI (Propidium Iodide). The mode of spermicidal action was assessed by (a) Hypo-osmotic swelling tests and (b) Scanning electron microscopy. The compounds have been found to be nontoxic to lactobacillus in 36 hours of culture whereas mild to moderately effective on common vaginal pathogens. Taken together it can be inferred that the water-soluble salts prepared from facile technique are potential candidates
for spermicides and could further be utilized for the preparation of vaginal contraceptives.
 
Publisher Bentham Science Publishers
 
Date 2014
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/2028/1/LETTERS_IN_DRUG_DESIGN_%26_DISCOVERY__V_11(_1)104%2D113;2014(37).pdf
Banerjee, Maitreyee and Kumar, Shrabanti and Paira, Rupankar and Ghosh, Soma and Karmakar, Sanmoy and Mondal, Nirup B (2014) Synthesis and Characterization of Furo[3,2-h]Quinoliniums as Potent Non-Detergent Spermicides. Letters in Drug Design & Discovery, 11 (1). pp. 104-113.
 
Relation http://www.eprints.iicb.res.in/2028/