(3S,6R)-6-phthalimido-3-(2-thienyl)perhydro-1,4-thiazepin-5-one | 102090-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3S,6R)-6-phthalimido-3-(2-thienyl)perhydro-1,4-thiazepin-5-one
• 英文别名: 5-oxo-6(R)-phthalimido-3(S)-(2-thienyl)perhydro-1,4-thiazepine；2-[(3S,6R)-5-oxo-3-thiophen-2-yl-1,4-thiazepan-6-yl]isoindole-1,3-dione
• CAS: 102090-01-7
• 化学式: C₁₇H₁₄N₂O₃S₂
• 分子量: 358.442
• InChiKey: AIULRAOXNRZXRU-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,6R)-6-phthalimido-3-(2-thienyl)perhydro-1,4-thiazepin-5-one 在 盐酸 、 sodium hydroxide 、 sodium hydride 、 一水合肼 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 93.0h， 生成 (S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. Perhydro-1,4-thiazepin-5-one derivatives

  摘要：

  alpha-[6-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-5-oxoperhydro -1,4-thiazepin-4-yl]acetic acids (monoester monoacids) and their dicarboxylic acids having the hydrophobic substituents at the 2- or 3-position of the thiazepinone ring were prepared and assayed for angiotensin-converting enzyme (ACE) inhibitory activity. The dicarboxylic acids having the pseudoequatorial amino groups at the 6-position and the pseudoequatorial hydrophobic substituents at the 2- or 3-position of the chair conformation of the thiazepinone ring had potent in vitro inhibitory activity. The monoester monoacids having the hydrophobic substituents at the 2-position suppressed pressor response to angiotensin I for a longer duration than those having the substituents at the 3-position when administered orally. The structure-activity relationship was studied by conformational energy calculations of the thiazepinone ring.

  DOI：

  10.1021/jm00394a009
• 作为产物：
  描述：

  (2S)-3-[(2S)-2-amino-2-thiophen-2-ylethyl]sulfanyl-2-(1,3-dioxoisoindol-2-yl)propanoic acid;2,2,2-trifluoroacetic acid 、 N-甲基吗啉 以24%的产率得到
  参考文献：
  名称：

  YANAGISAWA, HIROAKI;ISHIHARA, SADAO;ANDO, AKIKO;KANAZAKI, TAKURO;MIYAMOTO+, J. MED. CHEM., 30,(1987) N 11, 1984-1991

  摘要：

  DOI：

文献信息

• Perhydrothiazepine derivatives, their preparation and their therapeutic
  申请人：Sankyo Company, Limited

  公开号：US04699905A1

  公开（公告）日：1987-10-13

  Compounds of formula (I): ##STR1## (wherein: R.sup.1 represents an optionally substituted alkyl, cycloalkyl, aryl, partially hydrogenated aryl or heterocyclic group; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 represent hydrogen or an optionally substituted alkyl, cycloalkyl, aralkyl, aryl, heterocyclic or heterocyclic-alkyl group or any adjacent pair thereof form a cyclic structure, at least one not being hydrogen; A represents a bond, or a methylene, ethylene, oxymethyl or thiomethyl group; B represents an alkylene, alkylidene, cycloalkylene or cycloalkylidene group; and n is 0, 1 or 2) and salts and esters thereof are hypotensive agents.

  式(I)的化合物：##STR1##（其中：R.sup.1代表一个可选择取代的烷基、环烷基、芳基、部分氢化的芳基或杂环基；R.sup.2、R.sup.3、R.sup.4和R.sup.5代表氢或一个可选择取代的烷基、环烷基、芳基、芳基烷基、杂环基或杂环烷基，或者其中任意相邻的一对形成一个环结构，至少有一个不是氢；A代表一个键或一个亚甲基、乙烯基、氧甲基或硫甲基基团；B代表一个烷基、烷基亚甲基、环烷基或环烷基亚甲基基团；n为0、1或2）及其盐和酯是降压药。
• Perhydrothiazepine derivatives, their preparation and their therapeutic use
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0161801B1

  公开（公告）日：1990-11-07
• YANAGISAWA, HIROAKI;ISHIHARA, SADAO;ANDO, AKIKO;KANAZAKI, TAKURO;MIYAMOTO+, J. MED. CHEM., 30,(1987) N 11, 1984-1991
  作者：YANAGISAWA, HIROAKI、ISHIHARA, SADAO、ANDO, AKIKO、KANAZAKI, TAKURO、MIYAMOTO+

  DOI：——

  日期：——
• US4699905A
  申请人：——

  公开号：US4699905A

  公开（公告）日：1987-10-13
• Angiotensin-converting enzyme inhibitors. Perhydro-1,4-thiazepin-5-one derivatives
  作者：Hiroaki Yanagisawa、Sadao Ishihara、Akiko Ando、Takuro Kanazaki、Shuichi Miyamoto、Hiroyuki Koike、Yasuteru Iijima、Kiyoshi Oizumi、Yoichi Matsushita、Tadashi Hata

  DOI：10.1021/jm00394a009

  日期：1987.11

  alpha-[6-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-5-oxoperhydro -1,4-thiazepin-4-yl]acetic acids (monoester monoacids) and their dicarboxylic acids having the hydrophobic substituents at the 2- or 3-position of the thiazepinone ring were prepared and assayed for angiotensin-converting enzyme (ACE) inhibitory activity. The dicarboxylic acids having the pseudoequatorial amino groups at the 6-position and the pseudoequatorial hydrophobic substituents at the 2- or 3-position of the chair conformation of the thiazepinone ring had potent in vitro inhibitory activity. The monoester monoacids having the hydrophobic substituents at the 2-position suppressed pressor response to angiotensin I for a longer duration than those having the substituents at the 3-position when administered orally. The structure-activity relationship was studied by conformational energy calculations of the thiazepinone ring.