cis-4-Oxo-1,2-cyclopentanedicarboxylic acid diethyl ester | 156293-34-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-4-Oxo-1,2-cyclopentanedicarboxylic acid diethyl ester
• 英文别名: diethyl (1R,2S)-4-oxocyclopentane-1,2-dicarboxylate
• CAS: 156293-34-4
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: GRPKMLGYFVVOJS-DTORHVGOSA-N

物化性质

• 沸点：
  328.4±42.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-4-Oxo-1,2-cyclopentanedicarboxylic acid diethyl ester 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Novel carbocyclic nucleoside analogs suppress glomerular mesangial cells proliferation and matrix protein accumulation through ROS-dependent mechanism in the diabetic milieu

  摘要：

  The synthesis of a series of novel 3,4-cis- and 3,4-trans-substituted carbocyclic nucleoside analogs from protected uracil and thymine is described. The key reaction in the followed synthetic protocols utilized the Mitsunobu reaction to couple 3,4-substituted cyclopentanols to N-3-benzoyl uracil or N-3-benzoyl thymine. These molecules were evaluated with regard to their ability to treat diabetic nephropathy. Our results show that two analogs significantly reduced high-glucose induced glomerular mesangial cells proliferation and matrix protein accumulation in vitro and, more interestingly, exhibited an anti-oxidative effect suggesting that the activity may be mediated through ROS-dependent mechanism. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.122
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 potassium permanganate 、 sodium acetate 、 乙酸酐 、 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 51.0h， 生成 cis-4-Oxo-1,2-cyclopentanedicarboxylic acid diethyl ester
  参考文献：
  名称：

  Novel carbocyclic nucleoside analogs suppress glomerular mesangial cells proliferation and matrix protein accumulation through ROS-dependent mechanism in the diabetic milieu

  摘要：

  The synthesis of a series of novel 3,4-cis- and 3,4-trans-substituted carbocyclic nucleoside analogs from protected uracil and thymine is described. The key reaction in the followed synthetic protocols utilized the Mitsunobu reaction to couple 3,4-substituted cyclopentanols to N-3-benzoyl uracil or N-3-benzoyl thymine. These molecules were evaluated with regard to their ability to treat diabetic nephropathy. Our results show that two analogs significantly reduced high-glucose induced glomerular mesangial cells proliferation and matrix protein accumulation in vitro and, more interestingly, exhibited an anti-oxidative effect suggesting that the activity may be mediated through ROS-dependent mechanism. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.122

文献信息

• Novel carbocyclic nucleoside analogs suppress glomerular mesangial cells proliferation and matrix protein accumulation through ROS-dependent mechanism in the diabetic milieu. II. Acylhydrazone-functionalized pyrimidines
  作者：Kamal H. Bouhadir、Ali Koubeissi、Fatima A. Mohsen、Mira Diab El-Harakeh、Rouba Cheaib、Joan Younes、Georges Azzi、Assaad A. Eid

  DOI：10.1016/j.bmcl.2015.12.042

  日期：2016.2

  We report herein the synthesis of a novel series of carbocyclic acylhydrazone derivatives of uracil, thymine and cytosine from the corresponding nucleic bases and their biological activity to treat diabetic nephropathy. Intriguingly, five derivatives significantly reduced high-glucose induced glomerular mesangial cells proliferation and matrix protein accumulation in vitro. The anti-oxidative effects displayed by these molecules suggest that their activity might involve a ROS-dependent mechanism. (C) 2015 Elsevier Ltd. All rights reserved.