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oai:ojs.www.eurjchem.com:article/1139 2015-03-31T07:18:02Z eurjchem:ART driver

Exploration of new 3α-pregnenolone ester analogues via Mitsunobu reaction, their anti-HIV activity and molecular modeling study Mahdi, Kuthair Mohammed Abdul-Reda, Nabeel Abed Al-Masoudi, Najim Aboud Steriods Pregnenolone Anti-HIV activity Mitsunobu reaction Molecular modeling study 17α-Hydroxylase/C17 20-lyase 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. Atlanta Publishing House LLC 2015-03-31 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion application/pdf https://www.eurjchem.com/index.php/eurjchem/article/view/1139 10.5155/eurjchem.6.1.1-7.1139 European Journal of Chemistry; Vol. 6 No. 1 (2015): March 2015; 1-7 2153-2257 2153-2249 eng https://www.eurjchem.com/index.php/eurjchem/article/view/1139/pdf_1139