(3R-trans)-3-ethyl-4,5-dihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-thiophenone | 117707-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3R-trans)-3-ethyl-4,5-dihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-thiophenone
• 英文别名: 3-Ethyl-4-(3-methyl-3H-imidazol-4-ylmethyl)-dihydro-thiophen-2-one；(3R,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]thiolan-2-one
• CAS: 117707-50-3
• 化学式: C₁₁H₁₆N₂OS
• 分子量: 224.327
• InChiKey: JEKWFJIPBJGBJT-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R-trans)-3-ethyl-4,5-dihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-thiophenone 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以2.33 g的产率得到(2RS,3S,4S)-2-hydroxy-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]tetrahydrothiophene
  参考文献：
  名称：

  Muscarinic activity of the thiolactone, lactam, lactol, and thiolactol analogs of pilocarpine and a hypothetical model for the binding of agonists to the M1 receptor

  摘要：

  Pilocarpine isosteres have been synthesized and characterized with regard to their in vitro muscarinic properties. The results indicate that the carbonyl oxygen of the lactone function of pilocarpine is of primary importance for agonist activity with the ether oxygen being of lesser or secondary importance. An X-ray structure determination for the hydrogen O,O'-ditoluoyltartrate salt of thiolactone pilocarpine isostere 2a has been performed. This compound has an unusual pharmacological profile exhibiting M1-agonist selectivity as well as presynaptic antagonism. As a result this compound is also viewed as having therapeutic potential for Alzheimer's disease. A model for the binding of pilocarpine and other muscarinic agonists to the third transmembrane helix of the human m1 muscarinic receptor has been developed.

  DOI：

  10.1021/jm00079a002
• 作为产物：
  描述：

  毛果芸香碱 生成 (3R-trans)-3-ethyl-4,5-dihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-thiophenone
  参考文献：
  名称：

  AMSTUTZ, RENE;BOLLIGER, GEORG;SHAPIRO, GIDEON

  摘要：

  DOI：

文献信息

• US4835174A
  申请人：——

  公开号：US4835174A

  公开（公告）日：1989-05-30
• US4977176A
  申请人：——

  公开号：US4977176A

  公开（公告）日：1990-12-11
• Muscarinic activity of the thiolactone, lactam, lactol, and thiolactol analogs of pilocarpine and a hypothetical model for the binding of agonists to the M1 receptor
  作者：Gideon Shapiro、P. Floersheim、J. Boelsterli、R. Amstutz、G. Bolliger、H. Gammenthaler、G. Gmelin、P. Supavilai、M. Walkinshaw

  DOI：10.1021/jm00079a002

  日期：1992.1

  Pilocarpine isosteres have been synthesized and characterized with regard to their in vitro muscarinic properties. The results indicate that the carbonyl oxygen of the lactone function of pilocarpine is of primary importance for agonist activity with the ether oxygen being of lesser or secondary importance. An X-ray structure determination for the hydrogen O,O'-ditoluoyltartrate salt of thiolactone pilocarpine isostere 2a has been performed. This compound has an unusual pharmacological profile exhibiting M1-agonist selectivity as well as presynaptic antagonism. As a result this compound is also viewed as having therapeutic potential for Alzheimer's disease. A model for the binding of pilocarpine and other muscarinic agonists to the third transmembrane helix of the human m1 muscarinic receptor has been developed.
• AMSTUTZ, RENE;BOLLIGER, GEORG;SHAPIRO, GIDEON
  作者：AMSTUTZ, RENE、BOLLIGER, GEORG、SHAPIRO, GIDEON

  DOI：——

  日期：——