(1R,2R)-2-[[4-[[(苯基氨基)羰基]氨基][1,1-联苯]-4-基]羰基]-环戊烷羧酸甲酯 | 959122-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2R)-2-[[4-[[(苯基氨基)羰基]氨基][1,1-联苯]-4-基]羰基]-环戊烷羧酸甲酯
• 英文名称: (1R,2R)-2-({4'-[(anilinocarbonyl)amino]-1,1'-biphenyl-4-yl}carbonyl)cyclopentanecarboxylic acid methyl ester
• 英文别名: methyl (1R,2R)-2-({4'-[(anilinocarbonyl)amino]-1,1'-biphenyl-4-yl}carbonyl)cyclopentanecarboxylate；Cyclopentanecarboxylic acid, 2-[[4'-[[(phenylamino)carbonyl]amino][1,1'-biphenyl]-4-yl]carbonyl]-, methyl ester, (1R,2R)-；methyl (1R,2R)-2-[4-[4-(phenylcarbamoylamino)phenyl]benzoyl]cyclopentane-1-carboxylate
• CAS: 959122-10-2
• 化学式: C₂₇H₂₆N₂O₄
• 分子量: 442.514
• InChiKey: NDIRKROHIMEFOI-DNQXCXABSA-N

物化性质

• 沸点：
  538.6±50.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-[[4-[[(苯基氨基)羰基]氨基][1,1-联苯]-4-基]羰基]-环戊烷羧酸甲酯 在 lithium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2R)-2-[[4-[[(苯基氨基)羰基]氨基][1,1-联苯]-4-基]甲酰基]环戊烷羧酸
  参考文献：
  名称：

  Inhibitors of diacylglycerol O-acyltransferase type 1 enzyme

  摘要：

  本发明涉及式(I)的化合物。其中R1、R2、R3、R4、R5、R6、m、n、p和q在此处定义。还公开了用于治疗DGAT-1相关疾病或症状的药物组合物和方法。

  公开号：

  US20080015227A1
• 作为产物：
  描述：

  (1S,2R)-2-Chlorocarbonyl-cyclopentanecarboxylic acid methyl ester 在 aluminum (III) chloride 、 potassium fluoride 、 四(三苯基膦)钯 、 (S)-(-)-N-甲基-1-苯基乙胺 、 铁粉 、 碳酸氢钠 、 氯化铵 、 sodium hydroxide 作用下， 以 乙醇 、 醋酸异丙酯 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (1R,2R)-2-[[4-[[(苯基氨基)羰基]氨基][1,1-联苯]-4-基]羰基]-环戊烷羧酸甲酯
  参考文献：
  名称：

  Process Development of a Diacyl Glycerolacyltransferase-1 Inhibitor

  摘要：

  A synthesis of a selective diacyl glycerolacyltransferase-1 (DGAT-1) inhibitor, 1, is described. The synthesis illustrates a diketone Favorskii reaction on 9 in place of the more common ketoester variant for generation of the dicarboxycyclopentane core, the development of an efficient classical resolution of a key cyclopentyl ketoacid intermediate 4, and an ambient temperature Suzuki-Miyaura coupling which avoids epimerization of the labile aryl ketone of 1.

  DOI：

  10.1021/op900310v

文献信息

• WO2007/137107
  申请人：——

  公开号：——

  公开（公告）日：——
• Validation of Diacyl Glycerolacyltransferase I as a Novel Target for the Treatment of Obesity and Dyslipidemia Using a Potent and Selective Small Molecule Inhibitor
  作者：Gang Zhao、Andrew J. Souers、Martin Voorbach、H. Doug Falls、Brian Droz、Sevan Brodjian、Yau Yi Lau、Rajesh R. Iyengar、Ju Gao、Andrew S. Judd、Seble H. Wagaw、Matthew M. Ravn、Kenneth M. Engstrom、John K. Lynch、Mathew M. Mulhern、Jennifer Freeman、Brian D. Dayton、Xiaojun Wang、Nelson Grihalde、Dennis Fry、David W. A. Beno、Kennan C. Marsh、Zhi Su、Gilbert J. Diaz、Christine A. Collins、Hing Sham、Regina M. Reilly、Michael E. Brune、Philip R. Kym

  DOI：10.1021/jm7013887

  日期：2008.2.1

  A highly potent and selective DGAT-1 inhibitor was identified and used in rodent models of obesity and postprandial chylomicron excursion to validate DGAT-1 inhibition as a novel approach for the treatment of metabolic diseases. Specifically, compound 4a conferred weight loss and a reduction in liver triglycerides when dosed chronically in DIO mice and depleted serum triglycerides following a lipid challenge in a dose-dependent manner, thus, reproducing major phenotypical characteristics of DGAT-1(-/-) mice.
• Process Development of a Diacyl Glycerolacyltransferase-1 Inhibitor
  作者：Matthew M. Ravn、Seble H. Wagaw、Kenneth M. Engstrom、Jianzhang Mei、Brian Kotecki、Andrew J. Souers、Philip R. Kym、Andrew S. Judd、Gang Zhao

  DOI：10.1021/op900310v

  日期：2010.3.19

  A synthesis of a selective diacyl glycerolacyltransferase-1 (DGAT-1) inhibitor, 1, is described. The synthesis illustrates a diketone Favorskii reaction on 9 in place of the more common ketoester variant for generation of the dicarboxycyclopentane core, the development of an efficient classical resolution of a key cyclopentyl ketoacid intermediate 4, and an ambient temperature Suzuki-Miyaura coupling which avoids epimerization of the labile aryl ketone of 1.
• Inhibitors of diacylglycerol O-acyltransferase type 1 enzyme
  申请人：Kym R. Philip

  公开号：US20080015227A1

  公开（公告）日：2008-01-17

  The present invention relates to compounds of formula (I). wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , m, n, p and q are defined herein Pharmaceutical compositions and methods for treating DGAT-1 related diseases or conditions are also disclosed.

  本发明涉及式(I)的化合物。其中R1、R2、R3、R4、R5、R6、m、n、p和q在此处定义。还公开了用于治疗DGAT-1相关疾病或症状的药物组合物和方法。