(+)-3R,4R,5S-cisneoclausenamidone | 608122-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-3R,4R,5S-cisneoclausenamidone
• 英文别名: (3R,4R,5S)-5-Benzoyl-3-hydroxy-1-methyl-4-phenylpyrrolidin-2-one
• CAS: 608122-70-9
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: XBQHNXLCOAIENZ-HLLBOEOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-3R,4R,5S-cisneoclausenamidone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (3R,4R,5S,6R)-cis-neoclausenamide 、 (3R,4R,5S,6S)-epi-cis-neoclausenamide
  参考文献：
  名称：

  Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers

  摘要：

  Clausenamide, isolated from aqueous extract of dry leaves of Clausena lansium, a Chinese folk medicine, was found to have potent activity in enhancing LTP and show nootropic activity in animal tests. In order to discovery more potent stereoisomers and to analyze the relationship of structure-activity, the synthesis of 16 (8 pairs) optically pure stereoisomers of clausenamide with four chiral centers was achieved. The results of LTP assay showed that the nootropic activity of the stereoisomers of clausenamide is closely related to the configuration of stereoisomers. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.018
• 作为产物：
  描述：

  (3R,4R,5R)-cis-clausenamidone 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以90%的产率得到(+)-3R,4R,5S-cisneoclausenamidone
  参考文献：
  名称：

  Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers

  摘要：

  Clausenamide, isolated from aqueous extract of dry leaves of Clausena lansium, a Chinese folk medicine, was found to have potent activity in enhancing LTP and show nootropic activity in animal tests. In order to discovery more potent stereoisomers and to analyze the relationship of structure-activity, the synthesis of 16 (8 pairs) optically pure stereoisomers of clausenamide with four chiral centers was achieved. The results of LTP assay showed that the nootropic activity of the stereoisomers of clausenamide is closely related to the configuration of stereoisomers. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.018

文献信息

• Optically active clausenamides, process of the preparation thereof, pharmaceutical composition containing the same and their medical use
  申请人：INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：EP1348696A1

  公开（公告）日：2003-10-01

  The present invention relates to some new optically active clausenamide derivatives, process of the preparation thereof, a pharmaceutical composition containing the same and their medical use, particularly their use in the respects of hypoxia protective, nootropic and neurodegenerative disease such as cerebral ischemia, Alzheimer disease and vascular dementia.

  本发明涉及一些新的光学活性克劳烯酰胺衍生物、其制备工艺、含有这些衍生物的药物组合物及其医疗用途，特别是它们在缺氧保护、神经营养和神经退行性疾病（如脑缺血、阿尔茨海默病和血管性痴呆）方面的用途。
• Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers
  作者：Zhiqiang Feng、Xingzhou Li、Guojun Zheng、Liang Huang

  DOI：10.1016/j.bmcl.2009.03.018

  日期：2009.4

  Clausenamide, isolated from aqueous extract of dry leaves of Clausena lansium, a Chinese folk medicine, was found to have potent activity in enhancing LTP and show nootropic activity in animal tests. In order to discovery more potent stereoisomers and to analyze the relationship of structure-activity, the synthesis of 16 (8 pairs) optically pure stereoisomers of clausenamide with four chiral centers was achieved. The results of LTP assay showed that the nootropic activity of the stereoisomers of clausenamide is closely related to the configuration of stereoisomers. (C) 2009 Elsevier Ltd. All rights reserved.