Synthesis and Pharmacological Evaluation of New 16-Methyl Pregnane Derivatives
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概要
- 論文の詳細を見る
The pharmacological activity of several new pregnane derivatives 15-19 were determined on gonadectomized male hamster flank organs, seminal vesicles and in vitro conversion of testosterone(T)to dihydrotestosterone(DHT)as 5α-reductase inhibitors. Steroids 15-19 decreased the diameter of the pigmented spot in the flank organs as compared to the T treated animals; in this model, steroids 16 and 19 showed a higher activity than the commercially available finasteride 3. Injection of T increased the weight of the seminal vesicles. Compounds 15-19 when injected together with T decreased the weight of the seminal vesicles thus showing an antiandrogenic effect. The trienone 19 exhibited a considerably higher activity than finasteride. Steroids 15-19 inhibited the in vitro metabolism of [^3H]T to [^3H]DHT in seminal vesicles homogenates of gonadectomized male hamsters. Compounds 18 and 19 showed a much higher antiandrogenic effect than finasteride. This cnhancement of the biological activity could probably be attributed to the coplanarity of the steroidal skeleton as previously observed by our group. The high antiandrogenic activity of the epoxy compound 16 is probably the result of the ring opening of the oxiran ring with the nucleophilic part of the enzyme 5α-reductase thus leading to a stable adduct with concomitant deactivation of this enzyme.
- 公益社団法人日本薬学会の論文
- 2002-01-01
著者
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Ramirez Elena
Department Of Pharmacy Faculty Of Chemistry National University Of Mexico City
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BRATOEFF Eugene
Departamento de Farmacia, Facultad de Quimica, UNAM, Ciudad Universitaria
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CABEZA Marisa
Departamento de Farmacia, Facultad de Quimica, UNAM, Ciudad Universitaria
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Bratoeff Eugene
Department Of Pharmacy Faculty Of Chemistry National University Of Mexico City
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Cabeza M
Departments Of Biological Systems And Animal Production Metropolitan University-xochimilco
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Cabeza Marisa
Departamento De Farmacia Facultad De Quimica Unam Ciudad Universitaria
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HEUZE Ivonne
Departments of Biological Systems and Animal Production, Metropolitan University-Xochimilco
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GUTIERREZ Edgar
Department of Biological Systems and Animal Production, Metropolitan University
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MEMBRILLO Marisol
Department of Pharmacy, Faculty or Chemistry UNAM, Ciudad Universitaria
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LIRA Alfonso
Department of Pharmacy, Faculty or Chemistry UNAM, Ciudad Universitaria
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Murillo M
Department Of Pharmacy Faculty Or Chemistry Unam Ciudad Universitaria
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Heuze Ivonne
Departments Of Biological Systems And Animal Production Metropolitan University-xochimilco
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Ramirez Elena
Departamento De Farmacia Facultad De Quimica Unam Ciudad Universitaria
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Lira Aifonso
Department Of Pharmacy Faculty Or Chemistry Unam Ciudad Universitaria
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Bratoeff Eugene
Departamento De Farmacia Facultad De Quimica Unam Ciudad Universitaria
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Gutierrez Edgar
Department Of Biological Systems And Animal Production Metropolitan University
関連論文
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- Crystal Structure and Synthesis of 17α-(5-Bromovalerayloxy)-16β-methylpregna-4,6-diene-3,20-dione
- Crystal Structure of 17-β-Benzoyloxy-16-β-methylpregna-4,6-diene-3,20-dione
- Crystal Stucture of 17α-Acetoxy-6-chloro-16β-methyl-4, 6-pregnadiene-3, 20-dione
- Synthesis and Pharmacological Evaluation of New Progesterone Esters as 5α-Reductase Inhibitors
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- Molecular Interactions of New Pregnenedione Derivatives
- 5α-Reductase Inhibitory and Antiandrogenic Activities of Novel Steroids in Hamster Seminal Vesicles
- Synthesis and Pharmacological Evaluation of New 16-Methyl Pregnane Derivatives
- New Progesterone Esters as 5α-Reductase Inhibitors
- Evaluation of New Pregnane Derivatives as 5α-Reductase Inhibitor
- Synthesis and Pharmacological Evaluation of 4-Halo Progesterone Derivatives as Antiandrogen
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