2,2-Dichloro-14-phenylsulfonyl-tetradecanoic acid ethyl ester | 178671-38-0

• 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: 2,2-Dichloro-14-phenylsulfonyl-tetradecanoic acid ethyl ester
• 英文别名: Ethyl 14-(benzenesulfonyl)-2,2-dichlorotetradecanoate
• CAS: 178671-38-0
• 化学式: C₂₂H₃₄Cl₂O₄S
• 分子量: 465.482
• InChiKey: BBSOGBLBTFMLAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-Dichloro-14-phenylsulfonyl-tetradecanoic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以97%的产率得到14-Benzenesulfonyl-2,2-dichloro-tetradecanoic 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
• 作为产物：
  描述：

  2,2-Dichloro-14-phenylsulfenyl-tetradecanoic acid ethyl ester 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以77%的产率得到2,2-Dichloro-14-phenylsulfonyl-tetradecanoic acid ethyl ester
  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.