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Synthesis and Pharmacological Evaluation of Furan, Pyrrole and 2, 3-Dimethyl 1, 3-Butadiene Adducts of Methandrostenolone in Rats
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| Author:
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UPLOADED BY-ADMIN, FAZEL SHAMSA, MOHAMMAD SHARIFZADEH, HASHIM SHAMSA
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| Abstract:
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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.
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| Keyword:
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Methandrostenolone; pyrrole; furan; 2, 3-dimethyl 1, 3-butadiene; anti-androgenic effects.
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| EOI:
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| DOI:
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