5-[1-(2-bromoethoxy)-2-iodoethyl]-1H-pyrimidine-2,4-dione | 609810-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-[1-(2-bromoethoxy)-2-iodoethyl]-1H-pyrimidine-2,4-dione
• CAS: 609810-26-6
• 化学式: C₈H₁₀BrIN₂O₃
• 分子量: 388.987
• InChiKey: JOFAODXIRVGEBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-乙烯尿嘧啶 、 2-溴乙醇 在 一氯化碘 作用下， 生成 5-[1-(2-bromoethoxy)-2-iodoethyl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Inhibition of Mycobacterial Replication by Pyrimidines Possessing Various C-5 Functionalities and Related 2′-Deoxynucleoside Analogues Using in Vitro and in Vivo Models

  摘要：

  Tuberculosis (TB) has become an increasing problem since the emergence of human immunodeficiency virus and increasing appearance of drug-resistant strains. There is an urgent need to advance our knowledge and discover a new class of agents that are distinct than current therapies. Antimycobacterial activities of several 5-alkyl, 5-alkynyl, furanopyrimiclines and related 2'-deoxynucleosides were investigated against Mycobacterium tuberculosis. Compounds with 5-arylalkynyl substituents (23-26,33, 35) displayed potent in vitro antitubercular activity against Mycobacterium bovis and Mycobacterium tuberculosis. The in vivo activity of 5-(2-pyridylethyny1)-uracil (26) and its 2'-deoxycytidine analogue, 5-(2-pyridylethynyI)-2'-deoxycytidine (35), was assessed in BA LB/c mice infected with M. tuberculosis (H 37 Ra). Both compounds 26 and 35 given at a dose of 50 mg/kg for 5 weeks showed promising in vivo efficacy in a mouse model, with the 2'-deoxycytidine derivative being more effective than the uracil analogue and a reference drug o-cycloserine. These data indicated that there is a significant potential in this class of compounds.

  DOI：

  10.1021/jm100568q