(3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ((S)-1-carbamimidoyl-2-hydroxy-piperidin-3-yl)-amide

• 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: (3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ((S)-1-carbamimidoyl-2-hydroxy-piperidin-3-yl)-amide
• 英文别名: (3R,6S,8aS)-6-(benzylsulfonylamino)-N-[(3S)-1-carbamimidoyl-2-hydroxypiperidin-3-yl]-5-oxo-2,3,6,7,8,8a-hexahydro-[1,3]thiazolo[3,2-a]pyridine-3-carboxamide
• 化学式: C₂₁H₃₀N₆O₅S₂
• 分子量: 510.638
• InChiKey: XYHQRSYCQQCWPT-JVTNLNQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  203
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 1-甲酯 在 palladium on activated charcoal N-甲基吗啉 、 吡啶 、 2,3,5-三甲基吡啶 、 盐酸 、 三乙基硅烷 、 4-二甲氨基吡啶 、 sodium hydroxide 、 4 A molecular sieve 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 105.0h， 生成 (3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ((S)-1-carbamimidoyl-2-hydroxy-piperidin-3-yl)-amide
  参考文献：
  名称：

  Rational design, synthesis, and serine protease inhibitory activity of a novel P1-argininal derivative featuring a conformationally constrained P2–P3 bicyclic lactam moiety

  摘要：

  Based on molecular modeling and judicious combination of the salient topographic features of the recently discovered P-3-lactam derivative 1 with the P-2-prolyl derivatives 2a,b, the novel thrombin inhibitor 3a was designed. Inhibitor 3a incorporates a fused bicyclic lactam as a novel type of P-2-P-3 dipeptide surrogate. The synthesis and biological activity of this potent serine protease inhibitor is presented. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00004-8

文献信息

• Rational design, synthesis, and serine protease inhibitory activity of a novel P1-argininal derivative featuring a conformationally constrained P2–P3 bicyclic lactam moiety
  作者：Susan Y. Tamura、Erick A. Goldman、Terence K. Brunck、William C. Ripka、J. Edward Semple

  DOI：10.1016/s0960-894x(97)00004-8

  日期：1997.2

  Based on molecular modeling and judicious combination of the salient topographic features of the recently discovered P-3-lactam derivative 1 with the P-2-prolyl derivatives 2a,b, the novel thrombin inhibitor 3a was designed. Inhibitor 3a incorporates a fused bicyclic lactam as a novel type of P-2-P-3 dipeptide surrogate. The synthesis and biological activity of this potent serine protease inhibitor is presented. (C) 1997, Elsevier Science Ltd.