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Information Journal Paper

Title

SYNTHESIS AND PHARMACOLOGICAL EFFECTS OF BUTADIENE AND CYCLOPENTADIENE ADDUCTS OF METHANDROSTENOLONE IN RATS

Pages

  151-154

Abstract

 In this study the reactivity of METHANDROSTENOLONE or [(17β)-17-hydroxy-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 METHANDROSTENOLONE 1 undergoes a cycloaddition reaction with dienes, such as 1, 3 BUTADIENE or CYCLOPENTADIENE, and to investigate the biological behavior of the reaction adducts, i.e, compound 3 {(17β)-17-hydroxy-17-methyl androsta [1α, 2 α] cyclohex 3’, 4-diene-3-one} and compound 4 {(17β)-17-hydroxy-17-methyl androsta [1 α, 2 α] cyclohex (2’,5’ methylene) 3’, 4-diene-3-one}, relative to compound 1. The results indicated that thedDiels-Alder reactionddid notpproceed under the usual circumstances of high pressure and temperature, but could proceed in the presence of a Lewis acid (AlCl3). The structures of compounds 3 and 4 were confirmed by spectroscopic methods. The androgenic behavior of compounds 3 and 4 in comparison to compound 1 in the apomorphine test indicated that both compounds were almost devoid of androgenic activity, but prevented apomorphine mediated penile erection in male rats in a similar manner as cyproterone acetate.  

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    APA: Copy

    SHAMSA, F., SHARIFZADEH, M., & MIRZAEE, S.. (2006). SYNTHESIS AND PHARMACOLOGICAL EFFECTS OF BUTADIENE AND CYCLOPENTADIENE ADDUCTS OF METHANDROSTENOLONE IN RATS. DARU JOURNAL OF PHARMACEUTICAL SCIENCE, 14(3), 151-154. SID. https://sid.ir/paper/275358/en

    Vancouver: Copy

    SHAMSA F., SHARIFZADEH M., MIRZAEE S.. SYNTHESIS AND PHARMACOLOGICAL EFFECTS OF BUTADIENE AND CYCLOPENTADIENE ADDUCTS OF METHANDROSTENOLONE IN RATS. DARU JOURNAL OF PHARMACEUTICAL SCIENCE[Internet]. 2006;14(3):151-154. Available from: https://sid.ir/paper/275358/en

    IEEE: Copy

    F. SHAMSA, M. SHARIFZADEH, and S. MIRZAEE, “SYNTHESIS AND PHARMACOLOGICAL EFFECTS OF BUTADIENE AND CYCLOPENTADIENE ADDUCTS OF METHANDROSTENOLONE IN RATS,” DARU JOURNAL OF PHARMACEUTICAL SCIENCE, vol. 14, no. 3, pp. 151–154, 2006, [Online]. Available: https://sid.ir/paper/275358/en

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