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Phase Transfer Catalyzed Synthesis of Bis-Quinolines: Antileishmanial Activity in Experimental Visceral Leishmaniasis and in Vitro Antibacterial Evaluation

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Title Phase Transfer Catalyzed Synthesis of Bis-Quinolines: Antileishmanial Activity in Experimental Visceral Leishmaniasis and in Vitro Antibacterial Evaluation
 
Creator Palit, Partha
Paira, Priyankar
Hazra, Abhijit
Banerjee, Sukdeb
Das Gupta, Asish
Dastidar, Sujata G
Mondal, Nirup B
 
Subject Chemistry
 
Description A one-pot synthesis of some novel bis-quinolines has been achieved under phase transfer catalyzed conditions using 8-hydroxy quinoline
derivatives as substrates. The synthesized analogues were evaluated for antileishmanial activity against Leishmania donovani promastigotes
and amastigotes. The entire bis-quinolines showed efficacy in both in vitro and in vivo studies. Compound 5 (1,1-bis-[(5-chloro-8-quinolyl)oxy]
methane) exhibited the most significant activity. Compounds 4 (1,1-bis-[(8-quinolyl)oxy]methane) and 9 (1,5-bis-[(2-methyl-8-quinolyl)oxy]
pentane) also demonstrated significant leishmanicidal efficacy against established visceral leishmaniasis in BALB/c model. Ultrastructural studies
of promastigotes treated with compound 5, demonstrated membrane blebbing, chromatin condensation and vacuolization in the parasites and
the flagellated parasites became round shaped after treatment. Moreover, in vitro antibacterial activity of compound 5 against several bacterial
strains revealed its promising efficacy. The findings suggested that 1,1-bis-[(5-chloro-8-quinolyl)oxy]methane (5) is a bright candidate to be
considered as lead compound for leishmanicidal drug.
 
Publisher Elsevier
 
Date 2009
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/1362/1/EUROPEAN_JOURNAL_OF_MEDICINAL_CHEMISTRY__Volume_44___Issue_2___Pages_845%2D853;2009[109].pdf
Palit, Partha and Paira, Priyankar and Hazra, Abhijit and Banerjee, Sukdeb and Das Gupta, Asish and Dastidar, Sujata G and Mondal, Nirup B (2009) Phase Transfer Catalyzed Synthesis of Bis-Quinolines: Antileishmanial Activity in Experimental Visceral Leishmaniasis and in Vitro Antibacterial Evaluation. European Journal of Medicinal Chemistry, 44 (2). pp. 845-853.
 
Relation http://dx.doi.org/10.1016/j.ejmech.2008.04.014
http://www.eprints.iicb.res.in/1362/