European Journal of Chemistry

Exploration of new 3α-pregnenolone ester analogues via Mitsunobu reaction, their anti-HIV activity and molecular modeling study

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Published: Mar 31, 2015
DOI: https://doi.org/10.5155/eurjchem.6.1.1-7.1139
Keywords:
Steriods, Pregnenolone, Anti-HIV activity, Mitsunobu reaction, Molecular modeling study, 17α-Hydroxylase/C17, 20-lyase
Section
Research Article
Issue
Vol. 6 No. 1 (2015): March 2015
Dates
Received 2014-08-31
Accepted 2014-10-29
Published 2015-03-31


Main Article Content

Kuthair Mohammed Mahdi
Department of Chemistry, College of Education, University of Qadisiya, Qadisiya, 58002, Iraq
Nabeel Abed Abdul-Reda
Department of Chemistry, College of Education, University of Qadisiya, Qadisiya, 58002, Iraq
Najim Aboud Al-Masoudi
Department of Chemistry, College of Science, University of Basrah, Basrah, 61004, Iraq

Abstract

A new series of (5-pregnen-20-on-3α-yl)-substituted-benzoate analogues (10-13), (5-pregnene-20-on-3α-yl)-3-(substituted)acrylate derivatives (17-19) as well as the (17-(2-acetoxyacetyl)pregen-3α-yl)-3,4,5-trihydroxybenzoate (21) were synthesized from the β-pregenenolone scaffolds, by applying Mitsunobu reaction. All new compounds were characterized by 1H, 13C and 2D NMR spectroscopy. The inversion in configuration at C-3 during the formation of α-ester analogues was confirmed by NOESY NMR spectroscopy. The new compounds were evaluated for their in vitro antiviral activity against the replication of HIV-1 and HIV-2 in MT-4 cells. Compounds 18 showed an EC50 value of >1.95 mg/mL. In addition, preliminary structure-activity relationship and molecular modeling of compound 18 has been studied.


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Mahdi, K. M.; Abdul-Reda, N. A.; Al-Masoudi, N. A. Exploration of New 3α-Pregnenolone Ester Analogues via Mitsunobu Reaction, Their Anti-HIV Activity and Molecular Modeling Study. Eur. J. Chem. 2015, 6, 1-7.

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