Methyl 3-(adamantan-1-yl)-2-hydroxypropanoate | 1033777-75-1

• 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: Methyl 3-(adamantan-1-yl)-2-hydroxypropanoate
• 英文别名: methyl 3-(1-adamantyl)-2-hydroxypropanoate
• CAS: 1033777-75-1
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: QTAZOSNCQGDJFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 3-(adamantan-1-yl)-2-hydroxypropanoate 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 rac-3-(1-adamantyl)-lactic acid
  参考文献：
  名称：

  Non-urea functionality as the primary pharmacophore in soluble epoxide hydrolase inhibitors

  摘要：

  Inhibition of soluble epoxide hydrolase has been proposed as a promising new pharmaceutical target for diseases involving hypertension and vascular inflammation. The most potent sEH inhibitors reported to date contain a urea or amide moiety as the central or 'primary' pharmacophore. We evaluated replacing the urea pharmacophore with other functional groups such as thiourea, sulfonamide, sulfonylurea, aminomethylene amide, hydroxyamide, and ketoamide to identify novel and potent inhibitors. The hydroxyamide moiety was identified as a novel pharmacophore affording potency comparable to urea. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.013
• 作为产物：
  描述：

  甲醇 、 3-(Adamant-1-yl)-2-hydroxypropionitril 在 盐酸 作用下， 反应 4.0h， 以61%的产率得到Methyl 3-(adamantan-1-yl)-2-hydroxypropanoate
  参考文献：
  名称：

  WO2008/73623

  摘要：

  公开号：

文献信息

• SOLUBLE EPOXIDE HYDROLASE INHIBITORS
  申请人：Patel Dinesh

  公开号：US20080200467A1

  公开（公告）日：2008-08-21

  Disclosed are alpha keto amide and alpha hydroxy amide compounds and compositions that inhibit soluble epoxide hydrolase (sEH), methods for preparing the compounds and compositions, and methods for treating patients with such compounds and compositions. The compounds, compositions, and methods are useful for treating a variety of sEH mediated diseases, including hypertensive, cardiovascular, inflammatory, pulmonary, and diabetic-related diseases.

  本发明涉及抑制可溶性环氧水解酶（sEH）的α酮酰胺和α羟基酰胺化合物和组合物，制备这些化合物和组合物的方法，以及使用这些化合物和组合物治疗患者的方法。这些化合物、组合物和方法可用于治疗各种sEH介导的疾病，包括高血压、心血管、炎症、肺部和糖尿病相关疾病。
• WO2008/73623
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] SOLUBLE EPOXIDE HYDROLASE INHIBITORS<br/>[FR] INHIBITEURS D'HYDROLASE EPOXYDE SOLUBLE
  申请人：ARETE THERAPEUTICS INC

  公开号：WO2008073623A2

  公开（公告）日：2008-06-19

  [EN] Disclosed are alpha keto amide and alpha hydroxy amide compounds and compositions that inhibit soluble epoxide hydrolase (sEH), methods for preparing the compounds and compositions, and methods for treating patients with such compounds and compositions. The compounds, compositions, and methods are useful for treating a variety of sEH mediated diseases, including hypertensive, cardiovascular, inflammatory, pulmonary, and diabetic-related diseases.
  [FR] L'invention concerne des composés alpha-céto amides et alpha-hydroxy amides ainsi que des compositions inhibant l'hydrolase époxyde soluble (sEH), des procédés de préparation de ces composés et compositions, ainsi que des méthodes de traitement de patients mettant en uvre ces composés et compositions. Les composés, compositions et méthodes selon l'invention sont utiles dans le traitement de diverses maladies induites par sEH, notamment les maladies hypertensives, cardiovasculaires, inflammatoires, pulmonaires et les maladies liées au diabète.
• Non-urea functionality as the primary pharmacophore in soluble epoxide hydrolase inhibitors
  作者：Sampath-Kumar Anandan、Zung N. Do、Heather K. Webb、Dinesh V. Patel、Richard D. Gless

  DOI：10.1016/j.bmcl.2009.01.013

  日期：2009.2

  Inhibition of soluble epoxide hydrolase has been proposed as a promising new pharmaceutical target for diseases involving hypertension and vascular inflammation. The most potent sEH inhibitors reported to date contain a urea or amide moiety as the central or 'primary' pharmacophore. We evaluated replacing the urea pharmacophore with other functional groups such as thiourea, sulfonamide, sulfonylurea, aminomethylene amide, hydroxyamide, and ketoamide to identify novel and potent inhibitors. The hydroxyamide moiety was identified as a novel pharmacophore affording potency comparable to urea. (C) 2009 Elsevier Ltd. All rights reserved.