Methanesulfonic acid 2-amino-5-(3,4,5-trimethoxy-phenyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl ester | 178551-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: Methanesulfonic acid 2-amino-5-(3,4,5-trimethoxy-phenyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl ester
• CAS: 178551-71-8
• 化学式: C₁₆H₂₀N₄O₆S
• 分子量: 396.424
• InChiKey: GHYCFYQNLSAKPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  134.89
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 2-amino-5-(3,4,5-trimethoxy-phenyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 18.0h， 以20 mg的产率得到5-(3,4,5-Trimethoxy-phenyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-2-ylamine
  参考文献：
  名称：

  Pyrrolo[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines as conformationally restricted analogues of the antibacterial agent trimethoprim

  摘要：

  Conformationally restricted analogues of the antibacterial agent trimethoprim (TMP) were designed to mimic the conformation of drug observed in its complex with bacterial dihydrofolate reductase (DHFR). This conformation of TMP was achieved by linking the 4-amino function to the methylene group by one-land two-carbon bridges. A pyrrolo[2,3-d]pyrimidine, a dihydro analogue, and a tetrahydropyrido[2,3-d]pyrimidine were synthesized and tested as inhibitors of DHFR. One analogue showed activity equivalent to that of TMP against DHFR from three species of bacteria. An X-ray crystal structure of this inhibitor bound to Escherichia coli DHFR was determined to evaluate the structural consequences of the conformational restriction. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00045-4
• 作为产物：
  描述：

  2-Ethoxy-4-(3,4,5-trimethoxy-phenyl)-4,5-dihydro-3H-pyrrole-3-carboxylic acid ethyl ester 在 吡啶 、 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 Methanesulfonic acid 2-amino-5-(3,4,5-trimethoxy-phenyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl ester
  参考文献：
  名称：

  Pyrrolo[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines as conformationally restricted analogues of the antibacterial agent trimethoprim

  摘要：

  Conformationally restricted analogues of the antibacterial agent trimethoprim (TMP) were designed to mimic the conformation of drug observed in its complex with bacterial dihydrofolate reductase (DHFR). This conformation of TMP was achieved by linking the 4-amino function to the methylene group by one-land two-carbon bridges. A pyrrolo[2,3-d]pyrimidine, a dihydro analogue, and a tetrahydropyrido[2,3-d]pyrimidine were synthesized and tested as inhibitors of DHFR. One analogue showed activity equivalent to that of TMP against DHFR from three species of bacteria. An X-ray crystal structure of this inhibitor bound to Escherichia coli DHFR was determined to evaluate the structural consequences of the conformational restriction. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00045-4

文献信息

• Pyrrolo[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines as conformationally restricted analogues of the antibacterial agent trimethoprim
  作者：Lee F Kuyper、Janice M Garvey、David P Baccanari、John N Champness、David K Stammers、Christopher R Beddell

  DOI：10.1016/0968-0896(96)00045-4

  日期：1996.4

  Conformationally restricted analogues of the antibacterial agent trimethoprim (TMP) were designed to mimic the conformation of drug observed in its complex with bacterial dihydrofolate reductase (DHFR). This conformation of TMP was achieved by linking the 4-amino function to the methylene group by one-land two-carbon bridges. A pyrrolo[2,3-d]pyrimidine, a dihydro analogue, and a tetrahydropyrido[2,3-d]pyrimidine were synthesized and tested as inhibitors of DHFR. One analogue showed activity equivalent to that of TMP against DHFR from three species of bacteria. An X-ray crystal structure of this inhibitor bound to Escherichia coli DHFR was determined to evaluate the structural consequences of the conformational restriction. Copyright (C) 1996 Elsevier Science Ltd