3-[4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)phenyl]acrylic acid ethyl ester | 1044504-37-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-[4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)phenyl]acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-[4-[(5-methyl-2,4-dioxopyrimidin-1-yl)methyl]phenyl]prop-2-enoate
• CAS: 1044504-37-1
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: VNUSEMHXHVHVJS-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)phenyl]acrylic acid ethyl ester 在 ammonium hydroxide 作用下， 以84%的产率得到(E)-3-[4-[(5-methyl-2,4-dioxo-pyrimidin-1-yl)methyl]phenyl]prop-2-enamide
  参考文献：
  名称：

  Substituted benzyl-pyrimidines targeting thymidine monophosphate kinase of Mycobacterium tuberculosis: Synthesis and in vitro anti-mycobacterial activity

  摘要：

  A series of N(1)-(4-substituted-benzyl)-pyrimidines were synthesized as potential inhibitors of thymidine monophosphate kinase of Mycobacterium tuberculosis (TMPKmt). Key SAR parameters included the chain length substitution in para position of the benzyl ring, the functional group terminating the alkyl chain, and the substituent on the C-5 pyrimidine ring. Synthesized molecules were assayed against both recombinant enzyme and mycobacteria cultures. The most potent compounds have K(i) values in the micromolar range and an MIC(50) of 50 mu g/mL against Mycobacterium bovis. These results will guide the design of a new generation of lead compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.045
• 作为产物：
  描述：

  5-methyl-1-(4-iodobenzyl)-1H-pyrimidine-2,4-dione 、 丙烯酸乙酯 在 palladium diacetate 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以97%的产率得到3-[4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)phenyl]acrylic acid ethyl ester
  参考文献：
  名称：

  Substituted benzyl-pyrimidines targeting thymidine monophosphate kinase of Mycobacterium tuberculosis: Synthesis and in vitro anti-mycobacterial activity

  摘要：

  A series of N(1)-(4-substituted-benzyl)-pyrimidines were synthesized as potential inhibitors of thymidine monophosphate kinase of Mycobacterium tuberculosis (TMPKmt). Key SAR parameters included the chain length substitution in para position of the benzyl ring, the functional group terminating the alkyl chain, and the substituent on the C-5 pyrimidine ring. Synthesized molecules were assayed against both recombinant enzyme and mycobacteria cultures. The most potent compounds have K(i) values in the micromolar range and an MIC(50) of 50 mu g/mL against Mycobacterium bovis. These results will guide the design of a new generation of lead compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.045

文献信息

• Aryl, Pyrimidyl Compounds, Pharmaceutical Compositions Comprising them, Their Use as Antimicrobial Agents
  申请人：Munier-Lehmann Helene

  公开号：US20080096907A1

  公开（公告）日：2008-04-24

  Substituted aryl pyrimidyl compounds responding to formula (I) and their use for the preparation of a medicament for the prevention and/or treatment of a pathology caused by a mycobacteria.

  本发明涉及哒嗪苯基取代化合物，其符合以下式子（I），以及其用于制备预防和/或治疗由分枝杆菌引起的病理的药物。
• Substituted benzyl-pyrimidines targeting thymidine monophosphate kinase of Mycobacterium tuberculosis: Synthesis and in vitro anti-mycobacterial activity
  作者：Cécile Gasse、Dominique Douguet、Valérie Huteau、Gilles Marchal、Hélène Munier-Lehmann、Sylvie Pochet

  DOI：10.1016/j.bmc.2008.04.045

  日期：2008.6

  A series of N(1)-(4-substituted-benzyl)-pyrimidines were synthesized as potential inhibitors of thymidine monophosphate kinase of Mycobacterium tuberculosis (TMPKmt). Key SAR parameters included the chain length substitution in para position of the benzyl ring, the functional group terminating the alkyl chain, and the substituent on the C-5 pyrimidine ring. Synthesized molecules were assayed against both recombinant enzyme and mycobacteria cultures. The most potent compounds have K(i) values in the micromolar range and an MIC(50) of 50 mu g/mL against Mycobacterium bovis. These results will guide the design of a new generation of lead compounds. (C) 2008 Elsevier Ltd. All rights reserved.