(2R,3R)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid | 42399-50-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R,3R)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid
• 英文别名: (R-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acid；(2R,3R)-3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoic acid
• CAS: 42399-50-8；42399-55-3
• 化学式: C₁₆H₁₇NO₄S
• 分子量: 319.381
• InChiKey: KHQWPNQLSKDWAR-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid 以 solid 为溶剂， 反应 1.5h， 生成 cis-(+)-2-(4'-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepine-4(5H)-one
  参考文献：
  名称：

  Structural Study of the Solid-State Ring-Closure Reaction of (2R,3R)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionic Acid.

  摘要：

  The crystal structure of the (2R,3R)-(-)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid has been determined from single-crystal X-ray diffraction data in order to study the solid state ring closure reaction between the carboxylic acid and the amino substituent. This reaction occurs only in the optically active crystals, whereas the racemate reacts only in melt or solution. (2R,3R)-(-)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid (C16H17NO4S) crystallizes in the monoclinic space group P2(1) with a = 14.240(2), b = 5.3154(11), c = 19.535(6) Angstrom, beta = 91.93(2)degrees, V = 1477.8(6) Angstrom(3), Z = 4, D-x = 1.435 g cm(-3), mu = 20.63 cm(-1). The two independent molecules differ in their protonization: one is a cation and the other is an anion. A very short hydrogen bond [O ... O = 2.480(6) Angstrom] links the carboxylic acid and the carboxylate groups. The two molecules adopt different conformations: one has an extended structure whereas the other has the amino group close to the carboxylate group. The latter molecule requires only minor changes for the solid-state reaction to take place forming the seven-membered ring. From the analysis of the hydrogen-bonding pattern a reaction mechanism for the ring closure reaction is proposed.

  DOI：

  10.3891/acta.chem.scand.50-0899
• 作为产物：
  描述：

  (2R,3R)-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)propionic acid methyl ester 生成 (2R,3R)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid
  参考文献：
  名称：

  NAGAO, SUSUMU;KURABAYASHI, KATSUHIKO;FUTAMURA, NOBUYUKI;KINOSHITA, HIDEFU+

  摘要：

  DOI：

文献信息

• Myocardial protection during ischemia and reperfusion
  申请人：Universite de Montreal

  公开号：US05580867A1

  公开（公告）日：1996-12-03

  Myocardial protection is achieved by administering to a patient an effective amount of a benzothiazepine derivative. The benzothiazepine derivatives have the following general chemical formula: ##STR1## wherein R.sub.1 represents hydrogen or methyl, R.sub.2 represents hydrogen or acetyl, R.sub.3 represents hydrogen or methyl, and R.sub.4 represents hydrogen or a halogen, with the proviso that R.sub.1 cannot be methyl when R.sub.2 =acetyl, R.sub.3 =methyl and R.sub.4 =hydrogen. The above compounds may also be used in other clinical conditions such as treatment of stable and unstable angina, non-Q-wave myocardial infarction, cerebral trauma ischemia and reperfusion, organ graft preservation, etc.

  心肌保护是通过向患者施用有效量的苯并噻吩衍生物实现的。苯并噻吩衍生物具有以下一般化学式：##STR1##其中R.sub.1代表氢或甲基，R.sub.2代表氢或乙酰基，R.sub.3代表氢或甲基，R.sub.4代表氢或卤素，但有一项限制，即当R.sub.2 =乙酰基，R.sub.3 =甲基且R.sub.4 =氢时，R.sub.1不能为甲基。上述化合物还可以用于其他临床情况，如稳定性和不稳定性心绞痛、非Q波心肌梗死、脑外伤缺血和再灌注、器官移植保存等。
• Studies of the resolution of racemates in the Synthesis of Diltiazem
  作者：Tibor Gizur、K�lm�n Hars�nyi、Elem�r Fogassy

  DOI：10.1002/prac.19943360715

  日期：——
• PROCESS FOR THE RECYCLE OF A WASTE PRODUCT OF DILTIAZEM SYNTHESIS
  申请人：ZAMBON GROUP S.p.A.

  公开号：EP1025080B1

  公开（公告）日：2003-01-08
• Process for the resolution of intermediates useful in the preparation of 1,5-benzothiazepines
  申请人：ZAMBON GROUP S.p.A.

  公开号：EP0392543B1

  公开（公告）日：1997-08-06
• NAGAO, SUSUMU;KURABAYASHI, KATSUHIKO;FUTAMURA, NOBUYUKI;KINOSHITA, HIDEFU+
  作者：NAGAO, SUSUMU、KURABAYASHI, KATSUHIKO、FUTAMURA, NOBUYUKI、KINOSHITA, HIDEFU+

  DOI：——

  日期：——