(2S,5S)-(-)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one | 124623-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,5S)-(-)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one
• 英文别名: (2S,5S)-5-(4-chlorophenyl)-3-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one
• CAS: 124623-51-4
• 化学式: C₁₅H₁₃ClN₂OS
• 分子量: 304.8
• InChiKey: LHRGTGYAWYACEG-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,5S)-(-)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以39 mg的产率得到(2S,5R)-(-)-cis-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one
  参考文献：
  名称：

  Tanabe, Yoo; Yamamoto, Hitomi; Murakami, Masanari, Journal of the Chemical Society. Perkin transactions I, 1995, # 7, p. 935 - 948

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,5R)-(-)-cis-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以40 mg的产率得到(2S,5S)-(-)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one
  参考文献：
  名称：

  Tanabe, Yoo; Yamamoto, Hitomi; Murakami, Masanari, Journal of the Chemical Society. Perkin transactions I, 1995, # 7, p. 935 - 948

  摘要：

  DOI：

文献信息

• Stereoselective synthesis of anti-PAF active thiazolidin-4-ones via cyclo-condensation of alkyl α-mercaptocarboxylates with arylimines
  作者：Yoo Tanabe、Yoshi-no Kubota、Yuzuru Sanemitsu、Nobushige Itaya、Gohfu Suzukamo

  DOI：10.1016/s0040-4039(00)92634-0

  日期：1991.1

  Two distinctive methods for the synthesis of cis- and trans-2, 5-disubstituted-thiazolidin-4-ones via stereoselective cyclo-condensation between α-mercaptocarboxylic esters and arylimines have been developed. With the new reaction used as the key step, two sets of optically active anti-PAF active thiazolidin-4-ones were synthesized.

  已经开发出两种独特的方法，其通过α-巯基羧酸酯和芳胺的立体选择性环缩合合成顺式和反式-2，5-二取代-噻唑烷-4-酮。以新的反应为关键步骤，合成了两套光学活性的抗PAF活性噻唑烷酮-4-酮。
• Certain pyridyl-thiazolidin-4-one having anti-ulcer activity
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：US05021435A1

  公开（公告）日：1991-06-04

  A 2-pyridyl-thiazolidin-4-one derivative represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each a hydrogen atom, an C.sub.1 -C.sub.20 alkyl group, an C.sub.2 -C.sub.20 alkenyl group, an C.sub.2 -C.sub.20 alkynyl group, an aryl group, a C.sub.3 -C.sub.8 cycloalkyl group or an aralkyl group which may have a substituent, R.sub.3 is a hydrogen atom, an C.sub.1 -C.sub.20 alkyl group, an C.sub.2 -C.sub.20 alkenyl group, an C.sub.2 -C.sub.20 alkynyl group, a C.sub.3 -C.sub.8 cycloalkyl group or an aralkyl group which may have a substituent, P is a pyridyl group or its N-substituted pyridinium salt which may have a substituent, said substituent being selected from the group consisting of halogen atom, cyano group, hydroxy group, amino group, lower alkyl group, lower alkoxy group, lower alkylamino group, halogenated lower alkyl group, acyl group, acyloxy group, acylthio group, acylamino group, carboxyl group, lower alkoxycarbonyl group, carbamoyl group, lower alkyl substituted carbamoyl group, heterocyclic group, and lower cycloalkyl group, and n represents an integer of 0, 1 or 2, or a pharmaceutically acceptable salts thereof and an anti-ulcer agent which contains, as an effective ingredient, said 2-pyridyl-thiazolidine-4-one derivative or a pharmaceutically acceptable salt thereof.

  一种由以下式表示的2-吡啶基噻唑啉-4-酮衍生物：其中R.sub.1和R.sub.2分别为氢原子、C.sub.1-C.sub.20烷基、C.sub.2-C.sub.20烯基、C.sub.2-C.sub.20炔基、芳基、C.sub.3-C.sub.8环烷基或可能具有取代基的芳基烷基，R.sub.3为氢原子、C.sub.1-C.sub.20烷基、C.sub.2-C.sub.20烯基、C.sub.2-C.sub.20炔基、C.sub.3-C.sub.8环烷基或可能具有取代基的芳基烷基，P为吡啶基或其可能具有取代基的N-取代吡啶盐基，所述取代基选自卤原子、氰基、羟基、氨基、低烷基、低烷氧基、低烷基氨基、卤代低烷基、酰基、酰氧基、硫代酰基、酰胺基、羧基、低烷氧羰基、氨基甲酰基、低烷基取代的氨基甲酰基、杂环基和低环烷基，n表示0、1或2的整数，或其药学上可接受的盐，以及作为有效成分的抗溃疡药物，包含上述2-吡啶基噻唑啉-4-酮衍生物或其药学上可接受的盐。
• Structure-activity relationship of optically active 2-(3-pyridyl)thiazolidin-4-ones as a PAF antagonists
  作者：Y. Tanabe、G. Suzukamo、Y. Komuro、N. Imanishi、S. Morooka、M. Enomoto、A. Kojima、Y. Sanemitsu、M. Mizutani

  DOI：10.1016/s0040-4039(00)92633-9

  日期：1991.1

  Two sets of optically active 5-substituted-2-(3-pyridyl)thiazolidin-4-ones, highly potent and selective antagonists of platelet activating factor (PAF), displayed apparently different anti-PAF activities between their enantiomers, wherein these activities depend markedly on the absolute configuration of the 2-position in the thiazolidin-4-ones.

  两组光学活性5-取代的-2-（3-吡啶基）噻唑烷酮-4-酮是血小板活化因子（PAF）的强效和选择性拮抗剂，它们的对映异构体之间表现出明显不同的抗PAF活性，其中这些活性取决于明显地位于噻唑烷-4-酮中2-位的绝对构型上。
• 2-Pyridyl thiazolidin-4-one derivatives as anti-ulcer agents
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0325496A1

  公开（公告）日：1989-07-26

  A 2-pyridyl-thiazolidin-4-one derivative represented by the formula: wherein Ri and R2 are each a hydrogen atom, a C1-C20 alkyl group, a C2-C2o alkenyl group, a C2-C20 alkynyl group, an aryl group, a C3-C8 cycloalkyl group or an aralkyl group which may have a substituent, Rs is a hydrogen atom, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C2o alkynyl group, a C3-C8 cycloalkyl group or an aralkyl group which may have a substituent, P is a pyridyl group or its N-substituted pyridinium salt which may have a substituent, said substituent being selected from the group consisting of halogen atom, cyano group, hydroxy group, amino group, lower alkyl group, lower alkoxy group, lower alkylamino group, halogenated lower alkyl group, acyl group, acyloxy group, acylthio group, acylamino group, carboxyl group, lower alkoxycarbonyl group, carbamoyl group, lower alkyl substituted carbamoyl group, heterocyclic group, and lower cycloalkyl group, and n represents an integer of 0, 1 or 2, or a pharmaceutically acceptable salt thereof is an anti-ulcer agent effective against stress induced ulcers. Some of these compounds are novel.

  一种2-吡啶基噻唑烷-4-酮衍生物，由式表示： 其中 Ri 和 R2 各为氢原子、C1-C20 烷基、C2-C2o 烯基、C2-C20 炔基、芳基、C3-C8 环烷基或可带有取代基的芳烷基，Rs 为氢原子、C1-C20 烷基、C2-C20 烯基、C2-C2o 炔基、C3-C8 环烷基或可带有取代基的芳烷基、C2-C2o 烷基、C3-C8 环烷基或可带有取代基的芳基，P 是吡啶基或其 N-取代的吡啶鎓盐，可带有取代基，所述取代基可选 自卤素原子组成的组、氰基、羟基、氨基、低级烷基、低级烷氧基、低级烷基氨基、卤代低级烷基、酰基、酰氧基、酰硫基、酰氨基、羧基、低级烷氧基羰基、氨基甲酰基、低级烷基取代的氨基甲酰基、杂环基和低级环烷基，且 n 代表 0、1 或 2 的整数，或其药学上可接受的盐。其中一些化合物是新型的。
• US5021435A
  申请人：——

  公开号：US5021435A

  公开（公告）日：1991-06-04