2,2-Dichloro-12-cyclohexyl-dodecanoic acid

• 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: 2,2-Dichloro-12-cyclohexyl-dodecanoic acid
• 英文别名: 2,2-Dichloro-12-cyclohexyldodecanoic acid
• 化学式: C₁₈H₃₂Cl₂O₂
• 分子量: 351.357
• InChiKey: KDQCWPVSVOLUJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二氯乙酸 、 1-Bromo-10-cyclohexyldecane 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以46%的产率得到2,2-Dichloro-12-cyclohexyl-dodecanoic acid
  参考文献：
  名称：

  ω-Substituted alkyl carboxylic acids as antidiabetic and lipid-lowering agents

  摘要：

  In screening experiments certain omega-substituted alkyl carboxylic acids were found to produce an increase in insulin-stimulated C-14-acetate incorporation into triglycerides, which may indicate an improvement in the action of insulin. Antidiabetic and lipid-lowering properties in genetically diabetic ob/ob mice demonstrated the in vivo relevance of the insulin-potentiating effects seen in vitro. The chemical structures of the w-substituted alkyl carboxylic acids with insulin-potentiating effects correspond to the general formula ring-spacer-COOH. A close structure-activity relationship was observed. The most potent compound in ob/ob mice was 3e, which normalized blood glucose as well as hyperinsulinaemia and lowered serum triglycerides and cholesterol by 52% and 37%, respectively. On the basis of these results, omega-substituted alkyl carboxylic acids are interesting as a new class of oral antidiabetic agents with insulin-sensitizing and lipid-lowering activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80029-4

文献信息

• 2,2-DICHLORALKANCARBONSÄUREN, VERFAHREN ZU IHRER HERSTELLUNG DIESE ENTHALTENDE ARZNEIMITTEL, UND IHRE VERWENDUNG ZUR BEHANDLUNG DER INSULINRESISTENZ
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0790824A1

  公开（公告）日：1997-08-27
• US5968982A
  申请人：——

  公开号：US5968982A

  公开（公告）日：1999-10-19
• [DE] 2,2-DICHLORALKANCARBONSÄUREN, VERFAHREN ZU IHRER HERSTELLUNG DIESE ENTHALTENDE ARZNEIMITTEL, UND IHRE VERWENDUNG ZUR BEHANDLUNG DER INSULINRESISTENZ<br/>[EN] 2,2-DICHLOROALKANE CARBOXYLIC ACIDS, PROCESS FOR PREPARING THE SAME, MEDICAMENT CONTAINING THE SAME, AND USE THEREOF FOR TREATING INSULIN RESISTANCE<br/>[FR] ACIDES 2,2-DICHLOROALCANECARBOXYLIQUES, LEUR PROCEDE DE PREPARATION, MEDICAMENTS LES CONTENANT, ET LEUR UTILISATION DANS LE TRAITEMENT DE LA RESISTANCE INSULINIQUE
  申请人：——

  公开号：WO1996015784A2

  公开（公告）日：1996-05-30

  [EN] A medicament for the treatment of diabetes mellitus contains as active substance a compound having the formula (I), in which A, B, A' and W have the meanings given in the description. Also disclosed are new compounds having the formula (I) and a process for preparing the same.
  [FR] L'invention concerne un médicament de traitement du diabète sucré qui contient comme principe actif un composé ayant la formule (I), dans laquelle A, B, A' et W ont la notation donnée dans les revendications, de nouveaux composés ayant la formule (I) et leur procédé de préparation.
  [DE] Arzneimittel zur Behandlung des Diabetes mellitus, die als Wirkstoff eine Verbindung der Formel (I) enthalten in der A, B, A' und W die in den Ansprüchen angegebene Bedeutung haben, neue Verbindungen der Formel (I) sowie Verfahren zu ihrer Herstellung.
• ω-Substituted alkyl carboxylic acids as antidiabetic and lipid-lowering agents
  作者：Kirstin Meyer、Edgar Voss、Richard Neidlein、Hans-Frieder Kühnle、Johannes Pill

  DOI：10.1016/s0223-5234(99)80029-4

  日期：1998.10

  In screening experiments certain omega-substituted alkyl carboxylic acids were found to produce an increase in insulin-stimulated C-14-acetate incorporation into triglycerides, which may indicate an improvement in the action of insulin. Antidiabetic and lipid-lowering properties in genetically diabetic ob/ob mice demonstrated the in vivo relevance of the insulin-potentiating effects seen in vitro. The chemical structures of the w-substituted alkyl carboxylic acids with insulin-potentiating effects correspond to the general formula ring-spacer-COOH. A close structure-activity relationship was observed. The most potent compound in ob/ob mice was 3e, which normalized blood glucose as well as hyperinsulinaemia and lowered serum triglycerides and cholesterol by 52% and 37%, respectively. On the basis of these results, omega-substituted alkyl carboxylic acids are interesting as a new class of oral antidiabetic agents with insulin-sensitizing and lipid-lowering activity. (C) Elsevier, Paris.