(E)-3-cycloheptyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid | 345635-22-5

• 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: (E)-3-cycloheptyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid
• 英文别名: (E)-3-cycloheptyl-2-(4-methylsulfonylphenyl)prop-2-enoic acid
• CAS: 345635-22-5
• 化学式: C₁₇H₂₂O₄S
• 分子量: 322.425
• InChiKey: QEOLDQLQQMMLEX-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-cycloheptyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  2,3-Disubstituted acrylamides as potent glucokinase activators

  摘要：

  The phenylacetamide 1 represents the archtypical glucokinase activator (GKA) in which only the R-isomer is active. In order to probe whether the chiral center could be replaced, we prepared a series of olefins 2 and show in the present work that these compounds represent a new class of GKAs. Surprisingly, the SAR of the new series paralleled that of the saturated derivatives with the exception that there was greater tolerance for larger alkyl and cycloalkyl groups at R-2 region in comparison to the phenylacetamides. In normal Wistar rats, the 2,3-disubstituted acrylamide analog 10 was well absorbed and demonstrated robust glucose lowering effects. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.029
• 作为产物：
  描述：

  (E)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-acrylic acid methyl ester 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 以86%的产率得到(E)-3-cycloheptyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid
  参考文献：
  名称：

  Trans olefinic glucokinase activators

  摘要：

  具有2,3-二取代的反式烯烃性N-杂环芳基或尿嘧啶丙酰胺，其中2-位取代为取代苯基，3-位取代为环烷基环，这些丙酰胺是葡萄糖激酶激活剂，可以增加胰岛素分泌，用于治疗2型糖尿病。

  公开号：

  US06353111B1

文献信息

• Trans olefinic glucokinase activators
  申请人：Hoffmann-La Roche Inc.

  公开号：US06353111B1

  公开（公告）日：2002-03-05

  2,3-Di-substituted trans olefinic N-heteroaromatic or urido propionamides with said substitution at the 2-position being a substituted phenyl group and at the 3-position being a cycloalkyl ring, said propionamides being glucokinase activators which increase insulin secretion in the treatment of type II diabetes.

  具有2,3-二取代的反式烯烃性N-杂环芳基或尿嘧啶丙酰胺，其中2-位取代为取代苯基，3-位取代为环烷基环，这些丙酰胺是葡萄糖激酶激活剂，可以增加胰岛素分泌，用于治疗2型糖尿病。
• TRANS OLEFINIC GLUCOKINASE ACTIVATORS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1242397A1

  公开（公告）日：2002-09-25
• US6353111B1
  申请人：——

  公开号：US6353111B1

  公开（公告）日：2002-03-05
• [EN] TRANS OLEFINIC GLUCOKINASE ACTIVATORS<br/>[FR] ACTIVATEURS TRANSOLEFINIQUES DE GLUCOKINASE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2001044216A1

  公开（公告）日：2001-06-21

  2,3-Di-substituted trans olefinic N-heteroaromatic or urido proprionamides of formula (I) with said substitution at the 2-position being a substituted phenyl group and at the 3-position being a cycloalkyl ring, said proprionamides being glucokinase activators which increase insulin secretion in the treatment of type II diabetes.
• 2,3-Disubstituted acrylamides as potent glucokinase activators
  作者：Achyutharao Sidduri、Joseph S. Grimsby、Wendy L. Corbett、Ramakanth Sarabu、Joseph F. Grippo、Jianping Lou、Robert F. Kester、Mark Dvorozniak、Linda Marcus、Cheryl Spence、Jagdish K. Racha、David J. Moore

  DOI：10.1016/j.bmcl.2010.08.029

  日期：2010.10

  The phenylacetamide 1 represents the archtypical glucokinase activator (GKA) in which only the R-isomer is active. In order to probe whether the chiral center could be replaced, we prepared a series of olefins 2 and show in the present work that these compounds represent a new class of GKAs. Surprisingly, the SAR of the new series paralleled that of the saturated derivatives with the exception that there was greater tolerance for larger alkyl and cycloalkyl groups at R-2 region in comparison to the phenylacetamides. In normal Wistar rats, the 2,3-disubstituted acrylamide analog 10 was well absorbed and demonstrated robust glucose lowering effects. (C) 2010 Elsevier Ltd. All rights reserved.