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Open Access Highly Accessed Research article

Three-component synthesis of pyrano[2,3-d]-pyrimidine dione derivatives facilitated by sulfonic acid nanoporous silica (SBA-Pr-SO3H) and their docking and urease inhibitory activity

Ghodsi Mohammadi Ziarani1*, Sakineh Faramarzi1, Shima Asadi1, Alireza Badiei2, Roya Bazl3 and Massoud Amanlou3*

Author Affiliations

1 Department of Chemistry, Alzahra University, Vanak Square, P.O. Box 19938939973, Tehran, Iran

2 School of Chemistry, College of Science, University of Tehran, Tehran, Iran

3 Drug Design and Development Research Center and Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

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DARU Journal of Pharmaceutical Sciences 2013, 21:3  doi:10.1186/2008-2231-21-3

Published: 5 January 2013

Abstract

Background

A straightforward and efficient method for the synthesis of pyrano[2,3-d]pyrimidine diones derivatives from the reaction of barbituric acid, malononitrile and various aromatic aldehydes using SBA-Pr-SO3H as a nanocatalyst is reported.

Results

Reactions proceed with high efficiency under solvent free conditions. Urease inhibitory activity of pyrano[2,3-d]pyrimidine diones derivatives were tested against Jack bean urease using phenol red method. Three compounds of 4a, 4d and 4l were not active in urease inhibition test, but compound 4a displayed slight urease activation properties. Compounds 4b, 4k, 4f, 4e, 4j, 4g and 4c with hydrophobic substitutes on phenyl ring, showed good inhibitory activity (19.45-279.14 μM).

Discussion

The compounds with electron donating group and higher hydrophobic interaction with active site of enzyme prevents hydrolysis of substrate. Electron withdrawing groups such as nitro at different position and meta-methoxy reduced urease inhibitory activity. Substitution of both hydrogen of barbituric acid with methyl group will convert inhibitor to activator.

Keywords:
SBA-Pr-SO3H; Barbituric acid; Pyrano[2,3-d]pyrimidine diones; Multicomponent reaction (MCRs); Urease inhibitory