3-(2,5-dioxo-1-pyrrolidinyl)-1-<2(S)->-1-propyne | 130419-39-5

• 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: 3-(2,5-dioxo-1-pyrrolidinyl)-1-<2(S)->-1-propyne
• CAS: 130419-39-5
• 化学式: C₁₆H₂₂N₂O₄
• 分子量: 306.362
• InChiKey: KYSDSGBGBZPRQW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  66.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(2,5-dioxo-1-pyrrolidinyl)-1-<2(S)->-1-propyne 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 3-(5-hydroxy-2-oxo-1-pyrrolidinyl)-1-<2(R)-N-(tert-butoxycarbonyl)pyrrolidinyl>-1-propyne
  参考文献：
  名称：

  Synthesis and in vitro characterization of novel amino terminally modified oxotremorine derivatives for brain muscarinic receptors

  摘要：

  A series of novel 2-substituted acetylenic pyrrolidines and piperidines related to oxotremorine (1) were prepared and evaluated in vitro as muscarinic cholinergic agents at brain M1 and M2 receptors. One analogue, 3-(2-oxo-1-pyrrolidinyl)-1-[2 (R)-pyrrolidinyl]-1-propyne hydrogen oxalate (6a), was found to be a partial agonist producing a PI hydrolysis response at cortical M1 receptors approximately 3-fold larger than that produced by 1. The intrinsic activity profile of 6a at brain muscarinic receptors is similar to those of azetidine oxo analogue 2 and dimethylamino oxo analogue (3). All three compounds are partial M1 agonists and full M2 agonists; however, the profile of 6a in binding studies is significantly different. While 2 and 3 exhibit large M2 selectivities ranging between 8-fold to several hundred-fold, the binding profile of 6a shows almost no subtype selectivity.

  DOI：

  10.1021/jm00087a008
• 作为产物：
  描述：

  丁二酰亚胺 、 3-hydroxy-1-<2(S)->-1-propyne 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 3-(2,5-dioxo-1-pyrrolidinyl)-1-<2(S)->-1-propyne
  参考文献：
  名称：

  Synthesis of chiral α-acetylenic cyclic amines from α-amino acids: Applications to differentially constrained oxotremorine analogues as muscarinic agents

  摘要：

  DOI：

  10.1016/s0040-4039(00)94471-x