4-[4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)phenyl]butanoic acid tert-butyl ester | 886836-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)phenyl]butanoic acid tert-butyl ester
• 英文别名: Tert-butyl 4-[4-[(2,4-dioxopyrimidin-1-yl)methyl]phenyl]butanoate
• CAS: 886836-89-1
• 化学式: C₁₉H₂₄N₂O₄
• 分子量: 344.411
• InChiKey: RRLACZHIRHTGPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  4-[4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)phenyl]butanoic acid tert-butyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以80%的产率得到4-[4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)phenyl]butanoic acid sodium salt
  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：

  1-[4-(4-hydroxybutyl)benzyl]-1H-pyrimidine-2,4-dione 、 叔丁醇 在 重铬酸吡啶 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以70%的产率得到4-[4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)phenyl]butanoic acid tert-butyl 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