Issue 20, 2008
From the journal:

Organic & Biomolecular Chemistry

Synthesis and biological evaluation of bile acid dimers linked with 1,2,3-triazole and bis-β-lactam†

Namdev S. Vatmurge,a   Braja G. Hazra,*a   Vandana S. Pore,a   Fazal Shirazi,b   Mukund V. Deshpande,b   Sreenath Kadreppa,c   Samit Chattopadhyayc  and  Rajesh G. Gonnaded  

* Corresponding authors

a Division of Organic Chemistry, National Chemical Laboratory, Pune, India
E-mail: bg.hazra@ncl.res.in
Fax: 91-20-25902629/2624
Tel: 91-20-25902336

b Biochemical Sciences Division, National Chemical Laboratory, Pune, India

c National Centre for Cell Science, Pune, India

d Centre for Materials Characterization, National Chemical Laboratory, Pune, India

Abstract

We report herein the synthesis and biological evaluation of bile acid dimers 11–18 linked through 1,2,3-triazole and bis-β-lactam. The dimers 11–18 were synthesized using 1,3-dipolar cycloaddition reaction of diazido bis-β-lactams 3, 4 and terminal alkynes 7–10 derived from cholic acid/deoxycholic acid in the presence of Cu(I) catalyst (click chemistry). These novel molecules were evaluated in vitro for their antifungal and antibacterial activity. Most of the compounds exhibited significant antifungal as well as antibacterial activity against all the tested fungal and bacterial strains. Moreover, their in vitro cytotoxicities towards HEK-293 and MCF-7 cells were also established.

Graphical abstract: Synthesis and biological evaluation of bile acid dimers linked with 1,2,3-triazole and bis-β-lactam

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Article information

DOI
https://doi.org/10.1039/B809221D
Article type
Paper
Submitted
30 May 2008
Accepted
18 Jul 2008
First published
29 Aug 2008

Org. Biomol. Chem., 2008,6, 3823-3830

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Synthesis and biological evaluation of bile acid dimers linked with 1,2,3-triazole and bis-β-lactam

N. S. Vatmurge, B. G. Hazra, V. S. Pore, F. Shirazi, M. V. Deshpande, S. Kadreppa, S. Chattopadhyay and R. G. Gonnade, Org. Biomol. Chem., 2008, 6, 3823 DOI: 10.1039/B809221D

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