4-[3-[3-[2-(1-羟基环己基)乙基]-4-氧代-1,3-噻唑烷-2-基]丙基]苯甲酸 | 72313-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[3-[3-[2-(1-羟基环己基)乙基]-4-氧代-1,3-噻唑烷-2-基]丙基]苯甲酸
• 中文别名: 苯甲酸,加合2-氨基-2-甲基-1-丙醇(1:1)
• 英文名称: 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl} benzoic acid
• 英文别名: benzoic acid, 4-[3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl]；Benzoic acid, 4-(3-(3-(2-(1-hydroxycyclohexyl)ethyl)-4-oxo-2-thiazolidinyl)propyl)-；4-[3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-1,3-thiazolidin-2-yl]propyl]benzoic acid
• CAS: 72313-44-1
• 化学式: C₂₁H₂₉NO₄S
• 分子量: 391.532
• InChiKey: BCZCFHAXZSPKAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[3-[3-[2-(1-羟基环己基)乙基]-4-氧代-1,3-噻唑烷-2-基]丙基]苯甲酸 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.5h， 生成 (-)-methyl 4-<3-<3-<2-<1-<(1S)-ω-camphanyloxy>cyclohexyl>ethyl>-4-oxo-2-thiazolidinyl>propyl>benzoate
  参考文献：
  名称：

  Prostaglandin isosteres. 2. Chain-modified thiazolidinone prostaglandin analogs as renal vasodilators

  摘要：

  Chain modification of a thiazolidinone prostaglandin isostere has led to the production of 4-[3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl] benzoic acid (5b) which at 1 mg/kg po in the conscious dog causes a 70% increase in renal blood flow over control values with a duration of action exceeding 5 h. Preliminary testing indicates that 5b has a relatively specific action on the vasculature of the kidney. The enantiomers of 5b have been separated and the renal vasodilatory activity has been found to be entirely a property of the R-(+) enantiomer.

  DOI：

  10.1021/jm00357a006
• 作为产物：
  描述：

  4-(3-甲酰基丙基)苯甲酸乙酯 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 38.0h， 生成 4-[3-[3-[2-(1-羟基环己基)乙基]-4-氧代-1,3-噻唑烷-2-基]丙基]苯甲酸
  参考文献：
  名称：

  Prostaglandin isosteres. 2. Chain-modified thiazolidinone prostaglandin analogs as renal vasodilators

  摘要：

  Chain modification of a thiazolidinone prostaglandin isostere has led to the production of 4-[3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl] benzoic acid (5b) which at 1 mg/kg po in the conscious dog causes a 70% increase in renal blood flow over control values with a duration of action exceeding 5 h. Preliminary testing indicates that 5b has a relatively specific action on the vasculature of the kidney. The enantiomers of 5b have been separated and the renal vasodilatory activity has been found to be entirely a property of the R-(+) enantiomer.

  DOI：

  10.1021/jm00357a006

文献信息

• Interphenylene 9-thia-11-oxo-12-aza-prostanoic acids
  申请人：Merck & Co., Inc.

  公开号：US04225609A1

  公开（公告）日：1980-09-30

  This invention relates to novel interphenylene 9-thia-11-oxo-12-azaprostanoic acid compounds, salts, and derivatives thereof. These compounds are exceptionally potent renal vasodilators and antihypertensives which are active when administered orally but which have a more specific type of biological activity than that of many of the natural prostaglandins and their synthetic analogs or derivatives.

  这项发明涉及新型的间苯二酚9-硫-11-酮-12-氮代前列腺酸化合物、盐和衍生物。这些化合物在口服后表现出异常强大的肾脏扩血管作用和降压作用，但其生物活性比许多天然前列腺素及其合成类似物或衍生物具有更特定的类型。
• Antihypertensive composition
  申请人：Merck & Co., Inc.

  公开号：US04472384A1

  公开（公告）日：1984-09-18

  A pharmaceutical composition is disclosed which comprises the combination of interphenylene 9-thia-11-oxo-12-aza prostanoic acid derivatives and carboxyalkyl dipeptide derivatives.

  揭示了一种药物组合物，其中包括间苯二酚9-硫-11-酮-12-氮代前列腺酸衍生物和羧基烷基二肽衍生物的组合。
• Anti-inflammatory composition
  申请人：Merck & Co., Inc.

  公开号：US04379792A1

  公开（公告）日：1983-04-12

  A pharmaceutical composition containing an interphenylene 9-thia-11-oxo-12-aza prostanoic acid type renal vasodilator and a non-steroidal anti-inflammatory agent and its use are disclosed.

  本发明揭示了一种含有间苯乙烯9-硫代-11-酮-12-氮杂前列腺酸类肾脏血管扩张剂和非甾体抗炎药的制药组合物及其使用方法。
• Intermediates for the resolution of some
  申请人：Merck & Co., Inc.

  公开号：US04390703A1

  公开（公告）日：1983-06-28

  Some derivatives of interphenylene-9-thia-11-oxo-12-azaprostanoic acid which are active renal vasodilator agents are resolved via diastereomeric camphanyl or camphorcarbonyl esters. Upon hydrolysis, the separated diastereoisomers yield optically pure enantiomers.

  一些间苯二酚-9-硫-11-氧-12-氮-前列腺酸的衍生物是活性肾血管扩张剂，通过对映异构的莰基或莰酮酰酯分离。在水解后，分离的对映异构体产生光学纯的对映体。
• Interphenylene 9-thia-11-oxo-12-azaprostanoic acid compounds
  申请人：Merck & Co., Inc.

  公开号：US04260771A1

  公开（公告）日：1981-04-07

  This invention relates to novel interphenylene 9-thia-11-oxo-12-azaprostanoic acid compounds, salts, and derivatives thereof. These compounds have prostaglandin-like biological activity and are particularly useful as renal vasodilators, as platelet aggregation inhibitors, and for the treatment of certain autoimmune diseases.

  该发明涉及新型的间苯基9-硫-11-酮-12-氮杂-前列腺酸类化合物、盐及其衍生物。这些化合物具有类前列腺素的生物活性，特别适用于作为肾血管扩张剂、血小板聚集抑制剂，并用于治疗某些自身免疫性疾病。