cis-methyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate | 445389-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: cis-methyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate
• 英文别名: methyl 5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylate；methyl (3aR,6aS)-5-oxo-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate
• CAS: 445389-19-5
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: GEWLIOWDXKMKLP-KNVOCYPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  维格列汀杂质57 、 cis-methyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate 在 甲醇 、 三乙酰氧基硼氢化钠 作用下， 反应 3.0h， 以41%的产率得到cis-5-[2-(2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  DICYCLOAZAALKANE DERIVATES, PREPARATION PROCESSES AND MEDICAL USES THEREOF

  摘要：

  公开号：

  EP2246347B1
• 作为产物：
  描述：

  顺式-5-氧代六氢环戊二烯并[c]吡咯-2(1H)-羧酸叔丁酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 cis-methyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate
  参考文献：
  名称：

  Scaffold hopping approach towards various AFQ-056 analogs as potent metabotropic glutamate receptor 5 negative allosteric modulators

  摘要：

  The metabotropic glutamate receptor subtype 5 has evolved into a promising target for the treatment of various diseases of the central nervous system, such as Fragile X and L-DOPA induced dyskinesia. One of the most advanced clinical compound is Novartis' AFQ-056 (Mavoglurant), which served us as a template for a scaffold hopping approach, generating a structurally diverse set of potent analogs. Both the limited aqueous solubility and the relatively poor metabolic stability of AFQ-056 were improved with hexahydrocyclopenta[c]pyrrole derivative 54a, which proved to be a valuable candidate for further development. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.059

文献信息

• DICYCLOAZAALKANE DERIVATIVES, PREPARATION PROCESSES AND MEDICAL USES THEREOF
  申请人：Tang Peng Cho

  公开号：US20130012705A1

  公开（公告）日：2013-01-10

  Disclosed are new dicycloazaalkane derivates represented by general formula (I), preparation processes and pharmaceutical compositions containing them, and the uses for treatment especially for dipeptidyl peptidase inhibitor (DPP-IV), in which each substitute group of general formula (I) is as defined in specification.

  本发明涉及一种新的二环氮烷衍生物，其通式为（I），以及其制备方法、含有它们的制药组合物以及用于治疗特别是二肽基肽酶抑制剂（DPP-IV）的用途，其中通式（I）的每个取代基如规范中所定义。
• Synthesis and biological evaluation of azobicyclo[3.3.0] octane derivatives as dipeptidyl peptidase 4 inhibitors for the treatment of type 2 diabetes
  作者：Tang Peng Cho、Yang Fang Long、Lin Zhi Gang、Wang Yang、Lu He Jun、Shen Guang Yuan、Fu Jian Hong、Wang Lin、Guan Dong Liang、Zhang Lei、Luo Jing Jing、Gong Ai Shen、She Gao Hong、Wang Dan、Feng Ying、Yan Pang Ke、Leng Ying、Feng Jun、Mong Xian Tai

  DOI：10.1016/j.bmcl.2010.04.120

  日期：2010.6

  A series of novel azobicyclo[3.3.0]octane derivatives were synthesized and evaluated as dipeptidyl peptidase 4 (DPP-4) inhibitors. The effort resulted in the discovery of inhibitor 2a, which exhibited excellent efficacies in an oral glucose tolerance test. Introduction of methyl group (2j) could prolong the inhibition of serum DPP-4 activity. (C) 2010 Elsevier Ltd. All rights reserved.
• US8304411B2
  申请人：——

  公开号：US8304411B2

  公开（公告）日：2012-11-06
• US8415349B2
  申请人：——

  公开号：US8415349B2

  公开（公告）日：2013-04-09