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INTERNATIONAL JOURNAL OF PHARMACEUTICAL RESEARCH

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IJPR included in UGC-Approved List of Journals - Ref. No. is SL. No. 4812 & J. No. 63703

Published by : Advanced Scientific Research
ISSN
0975-2366
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IJPR 9[3] July - September 2017 Special Issue

July - September 9[3] 2017

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Synthesis and Pharmacological Evaluation of Furan, Pyrrole and 2, 3-Dimethyl 1, 3-Butadiene Adducts of Methandrostenolone in Rats

Author: UPLOADED BY-ADMIN, FAZEL SHAMSA, MOHAMMAD SHARIFZADEH, HASHIM SHAMSA
Abstract: In present study the reactivity of methandrostenolone (compound A) or [(17?)-17-methylandrosta-1, 4-diene-3-one], as a dienophil in a Diels-Alder type cycloaddition reaction was investigated. The purpose of this approach was to investigate whether the 1-dehydro position of compound A undergoes a cycloaddition reaction with dienes, such as pyrrole, furan or dimethyl butadiene and to investigate the biological outcome of this approach. The results indicated that the cycloaddition reaction did not proceed under the usual circumstances of high pressure and temperature, but successfully proceeded in the presence of a Lewis acid (AlCl3). The structures of 3 novel compounds B, C and D were confirmed by spectroscopic methods. The androgenic behavior of compounds B, C and D in comparison to compound A in the apomorphine test indicated that they were almost devoid of androgenic activity. But C and D prevented apomorphine mediated penile erection in male rats in a similar manner as the anti-androgen cyproterone acetate, but with lower potencies.
Keyword: Methandrostenolone; pyrrole; furan; 2, 3-dimethyl 1, 3-butadiene; anti-androgenic effects.
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0.12
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