Issue 38, 2013
From the journal:

RSC Advances

Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties

Udaya Pratap Singh,*ad   Hans Raj Bhat,a   Amita Verma,a   Mukesh Kumar Kumawat,b   Rajinder Kaur,c   S. K. Guptac  and  Ramendra K. Singh*d  

* Corresponding authors

a Department of Pharmaceutical Sciences, Sam Higginbottom Institute of Agriculture, Technology & Sciences, Allahabad 211007, India
E-mail: udaysingh98@gmail.com

b Anand College of Pharmacy, Agra 282007, India

c National Institute of Immunology, Aruna Asaf Ali Marg, New Delhi 110067, India

d Nucleic Acids and Antiviral Research Laboratory, Department of Chemistry, University of Allahabad, Allahabad 211002, India
E-mail: singhramk@rediffmail.com

Abstract

A novel series of phenyl hydrazone bearing pyrazole and pyrimidine hybrid compounds has been designed using the molinspiration toolkit based on Lipinski's rule of five and developed via sequential reactions starting from the diazotization of different anilines and further active methylation with acetyl acetone, ethyl acetoacetate and ethyl cyanoacetate to generate hydrazono derivatives. The target hybrid compounds were synthesized on cyclisation of the resulting hydrazono derivatives with hydrazine, phenyl hydrazine and urea. These molecules have been subsequently tested for anti-HIV activity using TZM-bl cell lines. The MTT assay was also carried out for the cytotoxicity determination of the active compounds. Further, to exemplify the key structural features of the molecules, a molecular docking analysis of the most active compounds was performed at the NNIBP of the HIV-RT protein. The antibacterial activity of the target compounds was also determined against a panel of four Gram-positive and four Gram-negative human pathogens. All molecules showed a potent anti-HIV activity along with a prominent inhibition of bacterial organisms.

Graphical abstract: Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/C3RA41604F
Article type
Paper
Submitted
04 Apr 2013
Accepted
15 Jul 2013
First published
16 Jul 2013

RSC Adv., 2013,3, 17335-17348

Permissions

Request permissions

Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties

U. P. Singh, H. R. Bhat, A. Verma, M. K. Kumawat, R. Kaur, S. K. Gupta and R. K. Singh, RSC Adv., 2013, 3, 17335 DOI: 10.1039/C3RA41604F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements