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Current Chinese Chemistry

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ISSN (Print): 2666-0016
ISSN (Online): 2666-0008

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Research Article

Efficient Synthesis and Spectroscopic Characterization of Biologically Relevant Pregnane Derivatives, and its Glycoside

Author(s): Arun Sethi*, Ranvijay Pratap Singh, Akriti Bhatia and Priyanka Yadav

Volume 1, Issue 1, 2021

Published on: 29 October, 2020

Page: [72 - 79] Pages: 8

DOI: 10.2174/2666001601999201029204603

Abstract

Objective: In the present research article, we synthesized novel pregnane derivatives from 16- dehydropregnenolone acetate (1) obtained by the degradation of naturally occurring plant productdiosgenin. The oxime esters, 3β-acetoxy-pregn-5,16-diene, 20-one O-(2-(6-methoxynaphthalene-2yl) propionyl) oxime (5) and 3β-hydroxy-pregn-5, 16-diene, 20-one O-(2-(4-isobutyl phenyl) propionyl) oxime (6) have been synthesized by reaction of 3β-acetoxy-5,16-pregnadien-20-oxime (3) with NSAIDs Ibuprofen and naproxen, respectively.

Methods: The epoxide derivative 3β-hydroxy-16α, 17α-epoxypregn-5-ene-20-one (4) was opened by BF3.Et2O and yielding product 3,16-di-hydroxy pregn-5-ene-20-one (7) and 3,16,17-tri-hydroxy pregn-5- ene-20-one (8), both the synthesized compounds underwent esterification with Ibuprofen affording 3,16- di-(2-(4-isobutyl phenyl) propionoxy) pregn-5-ene-20-one (9) and 3,16-di-(2-(4-isobutyl phenyl) propionoxy) 17-hydroxy pregn-5-ene-20-one (10), respectively.

Results: A one novel pregnane glycoside 3β-[2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopy-ranosyl]-Oxy-20β- hydroxy-16α-methoxy-pregn-5-ene (15) has also been synthesized from 3β, 20β-dihydroxy-16α-methoxypregn- 5-ene (12).

Conclusion: After the synthesis, all the compounds have been characterized by modern spectroscopic techniques.

Keywords: Pregnane, NSAIDs, oxime, steglich esterification, glycoside, spectroscopic characterization, steroids.

Graphical Abstract

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