methyl 4-oxooctahydroquinoline-1(2H)-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉类
• 英文名称: methyl 4-oxooctahydroquinoline-1(2H)-carboxylate
• 英文别名: (rac)-methyl 4-oxooctahydroquinoline-1(2H)-carboxylate；Methyl 4-oxo-2,3,4a,5,6,7,8,8a-octahydroquinoline-1-carboxylate；methyl 4-oxo-2,3,4a,5,6,7,8,8a-octahydroquinoline-1-carboxylate
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: VXGCVDQEWWZDCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  methyl 4-oxooctahydroquinoline-1(2H)-carboxylate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以195 mg的产率得到(rac)-cis-methyl 4-oxooctahydroquinoline-1(2H)-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
• 作为产物：
  描述：

  八氢对苯二酚-4(1H)-酮 、 氯甲酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以94%的产率得到methyl 4-oxooctahydroquinoline-1(2H)-carboxylate
  参考文献：
  名称：

  Heterocyclic derivatives as metabotropic glutamate receptor modulators

  摘要：

  这项发明涉及公式I的杂环衍生物及其药学上可接受的盐。该发明还涉及制备这类化合物的方法。该发明的化合物是mGluR5调节剂，因此对于控制和预防急性和/或慢性神经系统疾病是有用的。

  公开号：

  EP2650284A1

文献信息

• Heterocyclic derivatives as metabotropic glutamate receptor modulators
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：EP2650284A1

  公开（公告）日：2013-10-16

  The invention relates to heterocyclic derivatives of formula I as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are mGluR5 modulators and are therefore useful for the control and prevention of acute and/or chronic neurological disorders.

  这项发明涉及公式I的杂环衍生物及其药学上可接受的盐。该发明还涉及制备这类化合物的方法。该发明的化合物是mGluR5调节剂，因此对于控制和预防急性和/或慢性神经系统疾病是有用的。
• Scaffold hopping approach towards various AFQ-056 analogs as potent metabotropic glutamate receptor 5 negative allosteric modulators
  作者：Holger Kubas、Udo Meyer、Mirko Hechenberger、Kai-Uwe Klein、Patrick Plitt、Ronalds Zemribo、Harm W. Spexgoor、Sander G.A. van Assema、Ulrich Abel

  DOI：10.1016/j.bmcl.2013.09.059

  日期：2013.12

  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.