3(S)-amino-5-methyl-2-hexanone hydrochloride | 123768-64-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3(S)-amino-5-methyl-2-hexanone hydrochloride
• 英文别名: (3S)-3-amino-5-methylhexan-2-one;hydrochloride
• CAS: 123768-64-9
• 化学式: C₇H₁₅NO*ClH
• 分子量: 165.663
• InChiKey: SUACQQMTWXXZEZ-FJXQXJEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(tert-Butyloxycarbonyl)-3-amino-5-methyl-2-hexanone 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 3(S)-amino-5-methyl-2-hexanone hydrochloride
  参考文献：
  名称：

  .alpha.-Keto amide inhibitors of aminopeptidases

  摘要：

  The design and synthesis of 3-amino-2-oxo-4-phenylbutanoic acid amides (alpha-keto amides), a new class of aminopeptidase inhibitor, are described. These compounds, illustrated by the Phe-Leu analogue 2, are effective inhibitors of arginyl aminopeptidase (K(i) = 1.5-mu-M), cytosol aminopeptidase (K(i) = 1.0-mu-M), and microsomal aminopeptidase (K(i) = 2.5-mu-M). The ketone carbonyl of the alpha-keto amide was found to hydrate readily in an aqueous DMSO solution, due to the electron-withdrawing effect of the neighboring amide group. A mechanism of inhibition is proposed for the alpha-keto amides that is similar to that proposed for the structurally related aminopeptidase inhibitor bestatin and its analogues, wherein the inhibitor may interact with the S1'-S2' subsite of the enzyme rather than the S1-S1' subsite. Like bestatin, the alpha-keto amides are slow-binding inhibitors of all three enzymes.

  DOI：

  10.1021/jm00081a005

文献信息

• 17$g(b)-SUBSTITUTED 4-AZA-5$g(a)-ANDROSTAN-3-ONE DERIVATIVES
  申请人：FARMITALIA CARLO ERBA S.p.A.

  公开号：EP0611374A1

  公开（公告）日：1994-08-24
• 17-BETA-SUBSTITUTED 4-AZA-5-ALPHA-ANDROSTAN-3-ONE DERIVATIVES
  申请人：PHARMACIA & UPJOHN S.p.A.

  公开号：EP0611374B1

  公开（公告）日：1997-10-22
• US5418238A
  申请人：——

  公开号：US5418238A

  公开（公告）日：1995-05-23
• [EN] 17 beta -SUBSTITUTED 4-AZA-5 alpha -ANDROSTAN-3-ONE DERIVATIVES<br/>[FR] DERIVES DE 4-AZA-5 alpha -ANDROSTAN-3-ONE A SUBSTITUTION EN POSITION 17 beta
  申请人：FARMITALIA CARLO ERBA S.R.L.

  公开号：WO1994003476A1

  公开（公告）日：1994-02-17

  (EN) A compound of formula (I), wherein R is a hydrogen atom or a C1-C4 alkyl group; A is a single bond or a straight or branched C1-C6 alkylene chain; R1 is a hydrogen atom or a C1-C6 alkyl group; R2 is a C1-C6 alkyl group, a C5-C7 cycloalkyl or a C6-C10 cycloalkylalkyl group, aryl or a C7-C10 arylalkyl group, or a C6-C10 heterocycloalkyl group; R3 is hydrogen, a C1-C4 alkyl group or an aryl or a C7-C10 arylalkyl group; Z is a C1-C6 alkyl group, an -OR5 group wherein R5 is a C1-C6 alkyl group, a (a) group wherein each of R6 and R7 is hydrogen, C1-C6 alkyl, C5-C7 cycloalkyl, phenyl or R6 and R7 taken together with the nitrogen to which they are linked form a pentatomic or hexatomic saturated heteromonocyclic ring; and the symbol .^_.^_.^_.^_ represents a single or a double bond, is a testosterone 5$g(a)-reductase inhibitor and is therapeutically useful in benign prostatic hyperplasia, prostatic and breast cancers, seborrhoea, female hirsutism and male pattern baldness.(FR) Composé de formule (I) dans laquelle R représente un atome d'hydrogène ou un groupe alkyle C1-C4; A représente une liaison simple ou une chaîne alkylène C1-C6 droite ou ramifiée; R1 représente un atome d'hydrogène ou un groupe alkyle C1-C6; R2 représente un groupe alkyle C1-C6, un groupe cycloalkyle C5-C7 ou un groupe cycloalkylalkyle C6-C10, aryle ou un groupe arylalkyle C7-C10, ou un groupe hétérocycloalkyle C6-C10; R3 représente hydrogène, un groupe alkyle C1-C4 ou un groupe aryle ou bien un groupe arylalkyle C7-C10; Z représente un groupe alkyle C1-C6, un groupe-OR5 dans lequel R5 représente un groupe alkyle C1-C6, un groupe (a) dans lequel R6 et R7 représentent chacun hydrogène, alkyle C1-C6, cycloalkyle C5-C7, phényle, ou R6 ainsi que R7 pris ensemble avec l'atome d'azote auquel ils sont liés forment un cycle pentatomique ou hexatomique hétéromonocyclique saturé, le symbole .^_.^_.^_.^_ représentant une liaison simple ou double. Ledit composé constitue un inhibiteur de 5$g(a)-réductase de testostérone, il présente une utilité thérapeutique dans le traitement de l'adénome prostatique, des cancers de la prostate et du sein, de la séborrhée, de l'hirsutisme féminin, et de la calvitie hypocratique.
• .alpha.-Keto amide inhibitors of aminopeptidases
  作者：Timothy D. Ocain、Daniel H. Rich

  DOI：10.1021/jm00081a005

  日期：1992.2

  The design and synthesis of 3-amino-2-oxo-4-phenylbutanoic acid amides (alpha-keto amides), a new class of aminopeptidase inhibitor, are described. These compounds, illustrated by the Phe-Leu analogue 2, are effective inhibitors of arginyl aminopeptidase (K(i) = 1.5-mu-M), cytosol aminopeptidase (K(i) = 1.0-mu-M), and microsomal aminopeptidase (K(i) = 2.5-mu-M). The ketone carbonyl of the alpha-keto amide was found to hydrate readily in an aqueous DMSO solution, due to the electron-withdrawing effect of the neighboring amide group. A mechanism of inhibition is proposed for the alpha-keto amides that is similar to that proposed for the structurally related aminopeptidase inhibitor bestatin and its analogues, wherein the inhibitor may interact with the S1'-S2' subsite of the enzyme rather than the S1-S1' subsite. Like bestatin, the alpha-keto amides are slow-binding inhibitors of all three enzymes.