4-hydroxy-5-hexynamide | 118800-12-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-hydroxy-5-hexynamide
• 英文别名: 4-Hydroxyhex-5-ynamide
• CAS: 118800-12-7
• 化学式: C₆H₉NO₂
• mdl: MFCD19211896
• 分子量: 127.143
• InChiKey: PPPYWDIVYDAKFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5-hexynamide 在 吡啶 、 4-二甲氨基吡啶 、 copper(l) chloride 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 28.0h， 生成 1-methyl-5-(3-pyrrolidino-1-propynyl)-2-pyrrolidone
  参考文献：
  名称：

  Conformationally restricted analogs of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide

  摘要：

  Conformationally restricted analogues of the selective partial muscarinic agonist N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM 5; 2) were synthesized. The compounds were tested for muscarinic and antimuscarinic activity in the isolated guinea pig ileum and in intact mice. They were found to be moderately potent muscarinic antagonists or weak partial agonists. The new compounds were less potent than 2 in inhibiting (-)-[3H]-N-methylscopolamine binding in the rate cerebral cortex. Thus, structural modifications of 2 in which part of the amide moiety has been connected with the methyl group in the butynyl chain to form a five-membered ring decrease affinity and in most cases abolish efficacy.

  DOI：

  10.1021/jm00124a022
• 作为产物：
  描述：

  methyl 4-oxo-6-(trimethylsilyl)hex-5-ynoate 在 sodium tetrahydroborate 、 氨 作用下， 以 甲醇 为溶剂， 反应 88.0h， 生成 4-hydroxy-5-hexynamide
  参考文献：
  名称：

  Conformationally restricted analogs of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide

  摘要：

  Conformationally restricted analogues of the selective partial muscarinic agonist N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM 5; 2) were synthesized. The compounds were tested for muscarinic and antimuscarinic activity in the isolated guinea pig ileum and in intact mice. They were found to be moderately potent muscarinic antagonists or weak partial agonists. The new compounds were less potent than 2 in inhibiting (-)-[3H]-N-methylscopolamine binding in the rate cerebral cortex. Thus, structural modifications of 2 in which part of the amide moiety has been connected with the methyl group in the butynyl chain to form a five-membered ring decrease affinity and in most cases abolish efficacy.

  DOI：

  10.1021/jm00124a022

文献信息

• LUNDKVIST, J. R. MICHAEL;RINGDAHL, BJORN;HACKSELL, ULI, J. MED. CHEM., 32,(1989) N, C. 863-869
  作者：LUNDKVIST, J. R. MICHAEL、RINGDAHL, BJORN、HACKSELL, ULI

  DOI：——

  日期：——
• Conformationally restricted analogs of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide
  作者：J. R. Michael Lundkvist、Bjorn Ringdahl、Uli Hacksell

  DOI：10.1021/jm00124a022

  日期：1989.4

  Conformationally restricted analogues of the selective partial muscarinic agonist N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM 5; 2) were synthesized. The compounds were tested for muscarinic and antimuscarinic activity in the isolated guinea pig ileum and in intact mice. They were found to be moderately potent muscarinic antagonists or weak partial agonists. The new compounds were less potent than 2 in inhibiting (-)-[3H]-N-methylscopolamine binding in the rate cerebral cortex. Thus, structural modifications of 2 in which part of the amide moiety has been connected with the methyl group in the butynyl chain to form a five-membered ring decrease affinity and in most cases abolish efficacy.