2015
DOI: 10.5155/eurjchem.6.1.1-7.1139
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Exploration of new 3α-pregnenolone ester analogues via Mitsunobu reaction, their anti-HIV activity and molecular modeling study

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 1 H, 13 C 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 n… Show more

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Cited by 8 publications
(2 citation statements)
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“…Recently, we have synthesized a new series of 3a-pregnenolone ester derivatives including (5-pregnen-20-on-3a-yl)-3,4,5-trihydroxybenzoate (33) and acrylate analogues 34-36 from b-pregnenolone (4) [35] by applying Mitsunobu reaction (Scheme 2) with evaluation of their anti-HIV activity.…”
Section: Chemistrymentioning
confidence: 99%
“…Recently, we have synthesized a new series of 3a-pregnenolone ester derivatives including (5-pregnen-20-on-3a-yl)-3,4,5-trihydroxybenzoate (33) and acrylate analogues 34-36 from b-pregnenolone (4) [35] by applying Mitsunobu reaction (Scheme 2) with evaluation of their anti-HIV activity.…”
Section: Chemistrymentioning
confidence: 99%
“…Analytical silica gel TLC plates 60F254 were purchased from Merck. All reagents were obtained from commercial suppliers and were used without further purification [25].…”
Section: Instrumentationmentioning
confidence: 99%