2-[(3S)-3-(2,3-dihydro-1-benzofuran-5-ylsulfonylamino)-2-oxoazepan-1-yl]-N-[[4-(N'-hydroxycarbamimidoyl)phenyl]methyl]acetamide | 368426-31-7

• 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: 2-[(3S)-3-(2,3-dihydro-1-benzofuran-5-ylsulfonylamino)-2-oxoazepan-1-yl]-N-[[4-(N'-hydroxycarbamimidoyl)phenyl]methyl]acetamide
• CAS: 368426-31-7
• 化学式: C₂₄H₂₉N₅O₆S
• 分子量: 515.59
• InChiKey: AXLUJDSTPPLMRB-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[(3S)-3-(2,3-dihydro-1-benzofuran-5-ylsulfonylamino)-2-oxoazepan-1-yl]-N-[[4-(N'-hydroxycarbamimidoyl)phenyl]methyl]acetamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 N-[(4-carbamimidoylphenyl)methyl]-2-[(3S)-3-(2,3-dihydro-1-benzofuran-5-ylsulfonylamino)-2-oxoazepan-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：

  (S)-3-氨基-2-己内酰胺 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 氢气 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 35.0 ℃ 、310.26 kPa 条件下， 反应 33.0h， 生成 2-[(3S)-3-(2,3-dihydro-1-benzofuran-5-ylsulfonylamino)-2-oxoazepan-1-yl]-N-[[4-(N'-hydroxycarbamimidoyl)phenyl]methyl]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

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.