trans-(4R,5R)-5-{4-[amino(benzyloxycarbonylimino)methyl]benzylaminocarbonyl}-1,3-dioxolane-4-carboxylic acid ethyl ester | 439860-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-(4R,5R)-5-{4-[amino(benzyloxycarbonylimino)methyl]benzylaminocarbonyl}-1,3-dioxolane-4-carboxylic acid ethyl ester
• CAS: 439860-08-9
• 化学式: C₂₃H₂₅N₃O₇
• 分子量: 455.467
• InChiKey: HCAMXCFPRVDODR-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  138.54
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  trans-(4R,5R)-5-{4-[amino(benzyloxycarbonylimino)methyl]benzylaminocarbonyl}-1,3-dioxolane-4-carboxylic acid ethyl ester 在 palladium on activated charcoal sodium hydroxide 、 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 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.91h， 生成 trans-(4R,5R,2'R)-N¹-{4-[amino(imino)methyl]benzyl}-N²-(2'-carboxybenzyl)-1,3-dioxolane-4,5-dicarboxamide acetate
  参考文献：
  名称：

  Synthesis of Potential Thrombin Inhibitors. Incorporation of Tartaric Acid Templates as P2 Proline Mimetics

  摘要：

  With the objective to prepare novel non-peptidic thrombin inhibitors, bioisosteres of the inhibitory tripeptide D-Phe-Pro-Arg chain have been examined. Thus, the P1 Arg was replaced with p-amidinobenzylamine, an elongated homologue of the same and with 2,5-dichloro benzylamine. The P2-P3, D-Phe-Pro, was replaced with a novel tartaric acid template coupled to a series of readily available, mainly lipophilic, amines. Some,of these compounds exhibit promising thrombin inhibition activity in vitro, IC50 similar to5.9 muM. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00426-6
• 作为产物：
  描述：

  trans-(4R,5R)-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester 在 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 trans-(4R,5R)-5-{4-[amino(benzyloxycarbonylimino)methyl]benzylaminocarbonyl}-1,3-dioxolane-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Potential Thrombin Inhibitors. Incorporation of Tartaric Acid Templates as P2 Proline Mimetics

  摘要：

  With the objective to prepare novel non-peptidic thrombin inhibitors, bioisosteres of the inhibitory tripeptide D-Phe-Pro-Arg chain have been examined. Thus, the P1 Arg was replaced with p-amidinobenzylamine, an elongated homologue of the same and with 2,5-dichloro benzylamine. The P2-P3, D-Phe-Pro, was replaced with a novel tartaric acid template coupled to a series of readily available, mainly lipophilic, amines. Some,of these compounds exhibit promising thrombin inhibition activity in vitro, IC50 similar to5.9 muM. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00426-6