Carbocyclodipeptides as modified nucleosides: synthesis and anti-HIV activities

Author:

Chhikara Bhupender S.1,Rao M. Sudershan2,Rao V. Kameshwara2,Kumar Anil2,Buckheit Karen W.3,Buckheit Jr. Robert W.3,Parang Keykavous124

Affiliation:

1. Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, 7 Greenhouse Road, Kingston, RI 02881, USA.

2. Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031 Rajasthan, India.

3. ImQuest BioSciences Inc., 7340 Executive Way, Suite R, Frederick, MD 21704, USA.

4. Chapman University School of Pharmacy, Harry and Diane Rinker Health Science Campus, 9401 Jeronimo Road, Irvine, CA 92618, USA.

Abstract

A new class of nucleoside analogues were synthesized using cyclic dipeptides and modified 2′-deoxyfuranoribose sugars to introduce flexibility by peptides in place of common nucleoside bases and to determine their biological properties. The synthesis was carried out by coupling of a protected ribose sugar with synthesized dipeptides in the presence of hexamethyldisilazane and trimethylsilyltriflate. The final products were characterized by NMR and high-resolution MS-TOF spectroscopy. The compounds were evaluated for anti-HIV activities. 1-(4-Azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,6-diisopropylpiperazine-2,5-dione (compound 14) containing 3- and 6-isopropyl groups in the base and 3′-azide (EC50 = 1.96 μmol/L) was the most potent compound among all of the synthesized analogs.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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