Ethyl (6S,8aS)-4-oxooctahydropyrrolo[1,2-a]pyrazine-6-carboxylate | 473923-54-5

• 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: Ethyl (6S,8aS)-4-oxooctahydropyrrolo[1,2-a]pyrazine-6-carboxylate
• 英文别名: ethyl (6S,8aS)-4-oxo-2,3,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine-6-carboxylate
• CAS: 473923-54-5
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: LMNSDABWIORHPT-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二苯基重氮甲烷 、 Ethyl (6S,8aS)-4-oxooctahydropyrrolo[1,2-a]pyrazine-6-carboxylate 在 二氧化硫 作用下， 以 乙醚 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  Novel bicyclic lactam inhibitors of thrombin: highly potent and selective inhibitors

  摘要：

  The potency and selectivity of a previous series of low molecular weight thrombin inhibitors were improved through modifications of the P1 and P3 residues. Introduction of diphenyl substituted sulfonamides in the P3 moiety led to highly efficacious compounds. By correctly selecting the combination of P1 and P3 residues, high levels of potency, selectivity and in vivo efficacy were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00131-2
• 作为产物：
  描述：

  L-焦谷氨酸乙酯 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 4-二甲氨基吡啶 、 copper(I) bromide dimethylsulfide complex 、 二甲基硫 、 三氟化硼乙醚 、 氢气 、 sodium cyanoborohydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 对甲苯磺酸 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl (6S,8aS)-4-oxooctahydropyrrolo[1,2-a]pyrazine-6-carboxylate
  参考文献：
  名称：

  Potent bicyclic lactam inhibitors of thrombin: Part I: P3 modifications

  摘要：

  Peptidomimetic inhibitors of general structure 1 have been prepared. Optimization of the binding affinities of these compounds through variation of the P3 hydrophobic residue is described. Selected substituted bicylic lactams displayed interesting pharmacological profiles both in vitro and in vivo. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00550-2

文献信息

• Novel bicyclic lactam inhibitors of thrombin: highly potent and selective inhibitors
  作者：Yves St-Denis、Sophie Lévesque、Benoit Bachand、Jeremy J Edmunds、Lorraine Leblond、Patrice Préville、Micheline Tarazi、Peter D Winocour、M.Arshad Siddiqui

  DOI：10.1016/s0960-894x(02)00131-2

  日期：2002.4

  The potency and selectivity of a previous series of low molecular weight thrombin inhibitors were improved through modifications of the P1 and P3 residues. Introduction of diphenyl substituted sulfonamides in the P3 moiety led to highly efficacious compounds. By correctly selecting the combination of P1 and P3 residues, high levels of potency, selectivity and in vivo efficacy were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Potent bicyclic lactam inhibitors of thrombin: Part I: P3 modifications
  作者：Yves St-Denis、Corinne E. Augelli-Szafran、Benoit Bachand、Kent A. Berryman、John DiMaio、Annette M. Doherty、Jeremy J. Edmunds、Lorraine Leblond、Sophie Lévesque、Lakshmi S. Narasimhan、Jan R. Penvose-Yi、J.Ronald Rubin、Micheline Tarazi、Peter D. Winocour、M.Arshad Siddiqui

  DOI：10.1016/s0960-894x(98)00550-2

  日期：1998.11

  Peptidomimetic inhibitors of general structure 1 have been prepared. Optimization of the binding affinities of these compounds through variation of the P3 hydrophobic residue is described. Selected substituted bicylic lactams displayed interesting pharmacological profiles both in vitro and in vivo. (C) 1998 Elsevier Science Ltd. All rights reserved.