[(S)-3-(2,3-Dihydro-benzofuran-5-sulfonylamino)-2-oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-acetic acid | 368426-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: [(S)-3-(2,3-Dihydro-benzofuran-5-sulfonylamino)-2-oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-acetic acid
• 英文别名: 2-[(3S)-3-(2,3-dihydro-1-benzofuran-5-ylsulfonylamino)-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid
• CAS: 368426-48-6
• 化学式: C₂₀H₂₀N₂O₆S
• 分子量: 416.455
• InChiKey: QRONJMPRMKNEDQ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(S)-3-(2,3-Dihydro-benzofuran-5-sulfonylamino)-2-oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-acetic acid 在 palladium on activated charcoal N-甲基吗啉 、 盐酸羟胺 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 反应 58.0h， 生成 N-(4-Carbamimidoyl-benzyl)-2-[(S)-3-(2,3-dihydro-benzofuran-5-sulfonylamino)-2-oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-acetamide
  参考文献：
  名称：

  Novel, Potent Non-Covalent Thrombin Inhibitors Incorporating P3-Lactam Scaffolds

  摘要：

  Evolution of P-1-argininal inhibitor prototypes led to a series of non-covalent P-3-7-membered lactam inhibitors 1a-w, featuring novel peptidomimetic units that probe each of the S-1, S-2, and S-3 specificity pockets of thrombin. Rigid P-1-arginine surrogates possessing a wide range of basicity (calcd pK(a)'ssimilar toneutral-14) were surveyed. The design, synthesis, and biological activity of these targets are presented. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00010-0
• 作为产物：
  描述：

  1,3,4,5-四氢-2H-1-苯并氮杂卓-2-酮 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 四甲基乙二胺 、 氨 、 氢气 、 碘 、 sodium carbonate 、 sodium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -5.0~70.0 ℃ 、310.26 kPa 条件下， 反应 69.0h， 生成 [(S)-3-(2,3-Dihydro-benzofuran-5-sulfonylamino)-2-oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-acetic acid
  参考文献：
  名称：

  Novel, Potent Non-Covalent Thrombin Inhibitors Incorporating P3-Lactam Scaffolds

  摘要：

  Evolution of P-1-argininal inhibitor prototypes led to a series of non-covalent P-3-7-membered lactam inhibitors 1a-w, featuring novel peptidomimetic units that probe each of the S-1, S-2, and S-3 specificity pockets of thrombin. Rigid P-1-arginine surrogates possessing a wide range of basicity (calcd pK(a)'ssimilar toneutral-14) were surveyed. The design, synthesis, and biological activity of these targets are presented. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00010-0

文献信息

• Novel, Potent Non-Covalent Thrombin Inhibitors Incorporating P3-Lactam Scaffolds
  作者：Jonathan Z Ho、Tony S Gibson、J.Edward Semple

  DOI：10.1016/s0960-894x(02)00010-0

  日期：2002.3

  Evolution of P-1-argininal inhibitor prototypes led to a series of non-covalent P-3-7-membered lactam inhibitors 1a-w, featuring novel peptidomimetic units that probe each of the S-1, S-2, and S-3 specificity pockets of thrombin. Rigid P-1-arginine surrogates possessing a wide range of basicity (calcd pK(a)'ssimilar toneutral-14) were surveyed. The design, synthesis, and biological activity of these targets are presented. (C) 2002 Elsevier Science Ltd. All rights reserved.