phthaloyl cysteine | 48165-80-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phthaloyl cysteine
• 英文别名: (2R)-2-(1,3-dioxoisoindol-2-yl)-3-sulfanylpropanoic acid
• CAS: 48165-80-6
• 化学式: C₁₁H₉NO₄S
• 分子量: 251.263
• InChiKey: KHYKDXCOERMWAJ-QMMMGPOBSA-N

物化性质

• 熔点：
  185-186 °C
• 沸点：
  444.6±40.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  75.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phthaloyl cysteine 在 potassium fluoride 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 S-<(S)-2-<(tert-butoxycarbonyl)amino>-2-(2-thienyl)ethyl>-N-phthaloyl-L-cysteine diphenylmethyl ester
  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：

  N,N-diphthaloyl-L,L-cystine 生成 phthaloyl cysteine
  参考文献：
  名称：

  KARANEWSKY, DONALD S.

  摘要：

  DOI：

文献信息

• Photochemistry of phthaloylcysteine, its methyl ester and C-unprotected S-alkyl derivatives
  作者：Axel G. Griesbeck、Joachim Hirt、Wolfgang Kramer、Paul Dallakian

  DOI：10.1016/s0040-4020(98)00063-5

  日期：1998.3

  cysteine derivatives 1a-d were photochemically transformed by elimination, decarboxylation, and via electron transfer cyclization to the products 2,3,4 and 6–8. The spin selectivities of singlet and triplet pathways were investigated in acetonitrile and acetone. The excited singlets were prone to elimination and γ-H abstractions (e.g. formation of 5) whereas the triplets cyclized to thiazinoisoindoles

  N-邻苯二甲酰基半胱氨酸衍生物1a-d通过消除，脱羧和通过电子转移环化而光化学转化为产物2,3,4和6-8。在乙腈和丙酮中研究了单重态和三重态途径的自旋选择性。激发的单线态易于消除和γ-H提取（例如形成5），而三联体环化成噻嗪基异吲哚。该行为可以与正向和返回电子转移步骤相对于均质氢提取的效率相关，如半胱氨酸底物9所证明的。
• Chiral sensors for determining the absolute configurations of α-amino acid derivatives
  作者：Zhongxiang Chen、Hongjun Fan、Shiwei Yang、Guangling Bian、Ling Song

  DOI：10.1039/c8ob01933a

  日期：——

  A simple strategy for configurational assignments of alpha-amino acids has been developed by comparison of the proton NMR chemical shift values of the alpha hydrogens of N-phthaloyl protected alpha-amino acids in the presence of (R)-CSA 1 and (S)-CSA 1, respectively. Highly resolved NMR spectra can be obtained directly on the mixed solution of the chiral solvating agents with N-phthaloyl protected

  通过比较在（R）-CSA 1和（S）存在下N-邻苯二甲酰基保护的α-氨基酸的α氢的质子NMR化学位移值，开发了一种简单的α-氨基酸构型分配策略-CSA 1。可以在NMR管中直接在手性溶剂化剂与N-邻苯二甲酰基保护的α-氨基酸的混合溶液上获得高分辨的NMR光谱，从而给出可明显区分的质子信号而不会产生干扰，从而显着提高了分配的准确性并加快了分配过程。该策略广泛适用于各种天然和非天然氨基酸。
• Thiazine and thiazepine containing compounds
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0120728A1

  公开（公告）日：1984-10-03

  This invention is directed to compounds of the formula wherein X is a thiazine or thiazepine selected from These compounds possess angiotensin converting anzyme inhibition activity and are thus useful as hypotensive agents.

  本发明涉及如下式的化合物 其中 X 是选自下列化合物的噻嗪或硫氮杂卓 这些化合物具有血管紧张素转换酶抑制活性，因此可用作降压药。
• Acylamino oxo or hydroxy substituted alkylamino thiazines and thiazepines
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0154904A1

  公开（公告）日：1985-09-18

  New compounds, possessing angiotensin converting enzyme inhibition activity and thus useful as hypotensive agents, have the formula wherein R is or X is an oxo substituted thiazine or thiazepine, and R,, R2, R3 and R4 are as defined herein.

  具有血管紧张素转换酶抑制活性从而可用作降血压剂的新化合物具有如下式子 其中 R 是或 X 是氧代取代的噻嗪或硫氮杂卓，R、R2、R3 和 R4 如本文所定义。
• 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