<2R-<2α,3α(R^*)>>-1-<(1,1-dimethylethoxy)carbonyl>-3-<<<1-(methoxycarbonyl)-3-methylbutyl>amino>methyl>-2-pyrrolidinecarboxylic acid ethyl ester | 143267-38-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: <2R-<2α,3α(R^*)>>-1-<(1,1-dimethylethoxy)carbonyl>-3-<<<1-(methoxycarbonyl)-3-methylbutyl>amino>methyl>-2-pyrrolidinecarboxylic acid ethyl ester
• 英文别名: 1-O-tert-butyl 2-O-ethyl (2R,3R)-3-[[[(2R)-1-methoxy-4-methyl-1-oxopentan-2-yl]amino]methyl]pyrrolidine-1,2-dicarboxylate
• CAS: 143267-38-3
• 化学式: C₂₀H₃₆N₂O₆
• 分子量: 400.516
• InChiKey: KSVWHTPDBXIAPI-BZUAXINKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-leucine methyl ester hydrochloride 在 Rh/Al₂O₃ 、 镍 4-二甲氨基吡啶 、 氢气 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 72.0h， 生成 <2R-<2α,3α(R^*)>>-1-<(1,1-dimethylethoxy)carbonyl>-3-<<<1-(methoxycarbonyl)-3-methylbutyl>amino>methyl>-2-pyrrolidinecarboxylic acid ethyl ester
  参考文献：
  名称：

  Conformationally constrained tachykinin analogs: potent and highly selective neurokinin NK-2 receptor agonists

  摘要：

  The design and synthesis of potent and seleCtive neurokinin NK-2 receptor agonists 12 (GR64349) and 31 are described, together with structure-activity relationships for related analogues. Compound 12 (EC50 = 3.7 nM at NK-2 receptors in the rat colon; selectivity > 1000- and > 300-fold with respect to NK-1 and NK-3 receptors. respectively) was derived by incorporation of a Gly-Leu gamma-lactam conformational constraint into the C-terminal region of the neurokinin A. octapeptide analogue [Lys3]-NKA(3-10). Compound 31 (EC50 = 15 nM in rat colon) contains a novel fused-bicyclic constraint at the corresponding site in the substance P hexapeptide analogue [Ava6]-SP(6-11).

  DOI：

  10.1021/jm00100a027

文献信息

• Conformationally constrained tachykinin analogs: potent and highly selective neurokinin NK-2 receptor agonists
  作者：Martyn J. Deal、Russell M. Hagan、Simon J. Ireland、Christopher C. Jordan、Andrew B. McElroy、Barry Porter、Barry C. Ross、Michaela Stephens-Smith、Peter Ward

  DOI：10.1021/jm00100a027

  日期：1992.10

  The design and synthesis of potent and seleCtive neurokinin NK-2 receptor agonists 12 (GR64349) and 31 are described, together with structure-activity relationships for related analogues. Compound 12 (EC50 = 3.7 nM at NK-2 receptors in the rat colon; selectivity > 1000- and > 300-fold with respect to NK-1 and NK-3 receptors. respectively) was derived by incorporation of a Gly-Leu gamma-lactam conformational constraint into the C-terminal region of the neurokinin A. octapeptide analogue [Lys3]-NKA(3-10). Compound 31 (EC50 = 15 nM in rat colon) contains a novel fused-bicyclic constraint at the corresponding site in the substance P hexapeptide analogue [Ava6]-SP(6-11).