{5-[1-Allylamino-meth-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid | 98984-33-9

• 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: {5-[1-Allylamino-meth-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid
• 英文别名: 2-[4-oxo-5-[(prop-2-enylamino)methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
• CAS: 98984-33-9
• 化学式: C₉H₁₀N₂O₃S₂
• 分子量: 258.322
• InChiKey: ZQBFFLPAIOUIFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-羧甲基绕丹宁 以 乙醇 、 乙酸酐 为溶剂， 反应 5.5h， 生成 {5-[1-Allylamino-meth-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid
  参考文献：
  名称：

  Preparations of 5-alkylmethylidene-3-carboxymethylrhodanine derivatives and their aldose reductase inhibitory activity.

  摘要：

  3-羧甲基罗丹宁（1）与醛（2a-u）反应，选择性地生成了5-单烷亚甲基-3-羧甲基罗丹宁（3a-u）。通过X射线结构分析，确认5-单烷亚甲基-3-羧甲基罗丹宁（3k）的构型为Z型。讨论了立体选择性反应途径。还合成了几种5-二烷亚甲基-3-羧甲基罗丹宁（15a-f）和3-羧甲基罗丹宁的烷基氨基衍生物（18a-o）。这些产物被评估了醛糖还原酶抑制活性，其中一半显示出了有价值的抑制活性。

  DOI：

  10.1248/cpb.38.1911

文献信息

• Rhodanines useful as a therapeutic agent for diabetic complications
  申请人：Kaken Pharmaceutical Co., Ltd.

  公开号：US04606860A1

  公开（公告）日：1986-08-19

  A rhodanine derivative having the following general formula (I): ##STR1## wherein R is a mono- or di-alkylamino group having 1 to 6 carbon atoms which may be substituted by a hydroxyl group; an alkenylamino group having 3 to 6 carbon atoms; a phenylamino group, the benzene ring of which may be substituted by a lower alkyl group, a lower alkoxyl group, phenyl group or a halogen atom; or a cyclic amino group which may contain in the ring an oxygen atom or a nitrogen atom to which a lower alkyl group is attached; or a nontoxic salt thereof. The rhodanine derivative has potent platelet aggregation inhibiting activity and aldose reductase inhibiting activity and therefore is useful as a therapeutic agent for diabetic complications.

  一种罗丹明衍生物，具有以下通式（I）：##STR1## 其中R是具有1至6个碳原子的单烷基或双烷基氨基基团，可以被羟基取代; 具有3至6个碳原子的烯基氨基基团; 苯胺基团，其苯环可以被较低的烷基、较低的烷氧基、苯基或卤素原子取代; 或者是一个环状氨基基团，该环中可能含有一个氧原子或一个氮原子，该原子上附有一个较低的烷基; 或者是其无毒盐。该罗丹明衍生物具有强效的血小板聚集抑制活性和醛固酮还原酶抑制活性，因此可用作糖尿病并发症的治疗剂。
• Preparations of 5-alkylmethylidene-3-carboxymethylrhodanine derivatives and their aldose reductase inhibitory activity.
  作者：Yoshitaka OHISHI、Teruo MUKAI、Michiko NAGAHARA、Motoyuki YAJIMA、Norio KAJIKAWA、Kazumoto MIYAHARA、Tsunehiro TAKANO

  DOI：10.1248/cpb.38.1911

  日期：——

  Reactions of 3-carboxymethylrhodanine (1) with aldehydes (2a-u) afforded stereoselectively the 5-monoalkymethylidene-3-carboxymethylrhodanines (3a-u). The configuration of the 5-monoalkylmethylidene-3-carboxymethylrhodanine (3k) were examined by X-ray structure analysis and confirmed to be Z-configuration. The stereoselective reaction path was discussed. Several 5-dialkylmethylidene-3-carboxymethylrhodanines (15a-f) and alkyl-amino derivatives of 3-carboxymethylrhodanines (18a-o) were also prepared.These products were evaluated for aldose reductase-inhibitory potency and half of them exhibited valuable inhibitory potency.

  3-羧甲基罗丹宁（1）与醛（2a-u）反应，选择性地生成了5-单烷亚甲基-3-羧甲基罗丹宁（3a-u）。通过X射线结构分析，确认5-单烷亚甲基-3-羧甲基罗丹宁（3k）的构型为Z型。讨论了立体选择性反应途径。还合成了几种5-二烷亚甲基-3-羧甲基罗丹宁（15a-f）和3-羧甲基罗丹宁的烷基氨基衍生物（18a-o）。这些产物被评估了醛糖还原酶抑制活性，其中一半显示出了有价值的抑制活性。