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

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

Journal Name: Current Chinese Chemistry

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Abstract:

Objective: In present research article, we synthesized novel pregnane derivatives from 16-dehydropregnenolone acetate (1) which has been 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 (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-pregna-dien-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 undergoes esterification with Ibuprofen afforded 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 and Conclusion: A one novel pregnane glycoside 3β-[2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl]-Oxy-20β-hy-droxy-16α-methoxy-pregn-5-ene (15) has also been synthesized from 3β, 20β-dihydroxy-16α-methoxy-pregn-5-ene (12). After the synthesis all the compounds have been characterized by modern spectroscopic techniques.

Keywords: Pregnane, NSAIDs, oxime, Steglich Esterification, glycoside, spectroscopic characterization, Steroids.

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(E-pub Ahead of Print)
DOI: 10.2174/2666001601999201029204603