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RISS 인기검색어
- 검색키워드
- 저자 : Norman J. Doorenbos (검색결과 1 건)
- 무료
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김정균,이억석,두렌보스,Jack C. Kim,Lee Euk-suk,Charles C. Chang,Norman J. Doorenbos Korean Chemical Society 1975 대한화학회지 Vol.19 No.3
The intermediate, 17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(Ⅸ) required for the synthesis of 4-(${\beta}$-guanidinoethyl)-17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(V) was obtained through a reaction of 17${\alpha}$-methyl-3,5-seco-4-norandrostan-17${\beta}$-ol-5-on-3-oic acid(VI) with ammonium hydroxide followed by two reductions(platinum dioxide with hydrogen and lithium aluminium hydride). Condensation of Ⅸ with chloroacetonitrile under anhydrous condition, followed by reduction of the nitrile with lithium aluminium hydride gave 4-(${\beta}$-aminoethyl)-17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(XI). The reaction of XI with 2-methyl-2-thiopseudourea or 3,5-dimethylpyrazole-1-carboxamidine, or cyanamide provided the title compound, V. Relaxation of the nictitating membrane, in the absence of mydriasis, is considered to be evidence of adrenergic neurone blockade. Thus the test compound(V) resembles that of the classical adrenergic neurone blocking agents. 4-(${\beta}$-Guanidinoethyl)-17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(V)을 합성하는데에 필요한 중간화합물인 17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(IX)은 4단계를 거쳐 합성하였으며 IX을 chloroacetonitrile과 축합반응을 한후 $LiAlH_4$로서 환원하여 4-(${\beta}$-aminoethyl)-17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(XI)을 얻었다. Tktle compound인 V은 3가지의 시약, 2-methyl-2-thiopseudourea,3,5-dimethylpyrazole-1-carboxamidine, cyanamide를 각각 XI와 반응시켜 좋은 수득률을 얻었다. 약리작용의 실험결과 V은 classical한 adrenergic neurone blocking agents와 유사하며 혈압강하제로서의 전망은 좋다고 예상된다.
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