7-{3-[2-(1-Hydroxy-cyclohexyl)-ethyl]-4-oxo-thiazolidin-2-yl}-heptanoic acid methyl ester | 64250-45-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7-{3-[2-(1-Hydroxy-cyclohexyl)-ethyl]-4-oxo-thiazolidin-2-yl}-heptanoic acid methyl ester
• 英文别名: Methyl 7-{3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl}heptanoate；methyl 7-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-1,3-thiazolidin-2-yl]heptanoate
• CAS: 64250-45-9
• 化学式: C₁₉H₃₃NO₄S
• 分子量: 371.541
• InChiKey: JZWJVWVGOILYJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-{3-[2-(1-Hydroxy-cyclohexyl)-ethyl]-4-oxo-thiazolidin-2-yl}-heptanoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以18%的产率得到7-{3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl}heptanoic acid
  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：

  1-羟基环己烷乙腈 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 7-{3-[2-(1-Hydroxy-cyclohexyl)-ethyl]-4-oxo-thiazolidin-2-yl}-heptanoic acid methyl ester
  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

• Novel analogs of prostaglandins with 4-oxo-thiazolidinyl nucleus and
  申请人：Merck & Co., Inc.

  公开号：US04022794A1

  公开（公告）日：1977-05-10

  This invention relates to novel 9-thia-, 9-oxothia-, and 9-dioxothia-11-oxo-12-azaprostanoic acid compounds, salts, and derivatives thereof and also to processes for the preparation of such compounds. 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.

  本发明涉及新型9-硫代、9-氧代硫代和9-二氧代硫代-11-氧代-12-氮杂前列腺酸化合物、盐及其衍生物，以及制备这样的化合物的方法。这些化合物具有类似前列腺素的生物活性，特别适用于作为肾脏血管扩张剂、血小板聚集抑制剂以及治疗某些自身免疫性疾病。
• US4022794A
  申请人：——

  公开号：US4022794A

  公开（公告）日：1977-05-10