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Volume 1, Issue 1
  • ISSN: 2666-0016
  • E-ISSN: 2666-0008

Abstract

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

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

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 has also been synthesized from 3β, 20β-dihydroxy-16α-methoxy-pregn-5-ene .

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

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/content/journals/ccchem/10.2174/2666001601999201029204603
2021-03-01
2024-11-26

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/content/journals/ccchem/10.2174/2666001601999201029204603
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Efficient Synthesis and Spectroscopic Characterization of Biologically Relevant Pregnane Derivatives, and its Glycoside
Curr Chin Chem 1, 72 (2021); https://doi.org/10.2174/2666001601999201029204603
/content/journals/ccchem/10.2174/2666001601999201029204603
/content/journals/ccchem/10.2174/2666001601999201029204603
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  • Article Type:     Research Article
Keyword(s): glycoside; NSAIDs; oxime; Pregnane; spectroscopic characterization; steglich esterification; steroids

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