Open AccessEfficient Synthesis and Spectroscopic Characterization of Biologically Relevant Pregnane Derivatives, and its Glycoside
Author(s) -
Arun Sethi,
Ranvijay Pratap Singh,
Akriti Bhatia,
Priyanka Yadav
Publication year - 2021
Publication title -
current chinese chemistry
Language(s) - English
Resource type - Journals
eISSN - 2666-0016
pISSN - 2666-0008
DOI - 10.2174/2666001601999201029204603
Subject(s) - chemistry , oxime , pregnane , ene reaction , glycoside , derivative (finance) , epoxide , stereochemistry , medicinal chemistry , organic chemistry , catalysis , financial economics , economics
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 NSAIDsIbuprofen and naproxen, respectively. Methods: The epoxide derivative 3β-hydroxy-16α, 17α-epoxypregn-5-ene-20-one (4) was opened byBF3.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.