5-<1-(2,2,2-trifluoroethoxy)-2-iodoethyl>uracil | 133787-38-9

• 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-(2,2,2-trifluoroethoxy)-2-iodoethyl>uracil
• 英文别名: 5-[2-iodo-1-(2,2,2-trifluoroethoxy)ethyl]-1H-pyrimidine-2,4-dione
• CAS: 133787-38-9
• 化学式: C₈H₈F₃IN₂O₃
• 分子量: 364.063
• InChiKey: MKLKZBQJCAPIHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 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：
  6

反应信息

• 作为产物：
  描述：

  5-乙烯尿嘧啶 、 2,2,2-三氟乙醇 在 一氯化碘 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以38%的产率得到5-<1-(2,2,2-trifluoroethoxy)-2-iodoethyl>uracil
  参考文献：
  名称：

  5-（1-烷氧基-2-卤代乙基）-2'-脱氧尿苷及相关尿嘧啶类似物的合成及生物学评价

  摘要：

  通过C-5乙烯基取代基与一氯化碘和一价碘的对映体特异性反应，合成了2'-脱氧尿苷和尿嘧啶的一类新的5- [1-烷氧基-2-碘（或2，2-二碘代）乙基]衍生物。酒精。这些化合物是弱的或无活性的抗病毒和无活性的细胞毒剂。

  DOI：

  10.1002/jhet.5570280206

文献信息

• Synthesis and biological evaluation of 5-(1-alkoxy-2-haloethyl)-2′-deoxyuridines and related uracil analogues
  作者：Rakesh Kumar、Leonard I. Wiebe、E. E. Knaus、Mark L. Tempest

  DOI：10.1002/jhet.5570280206

  日期：1991.2

  A new class of 5-[1-alkoxy-2-iodo(or 2,2-diiodo)ethyl] derivatives of 2′-deoxyuridine and uracil were synthesized by a regiospecific reaction of the C-5 vinyl substituent with iodine monochloride and an alcohol. These compounds were either weak or inactive antiviral and inactive cytotoxic agents.

  通过C-5乙烯基取代基与一氯化碘和一价碘的对映体特异性反应，合成了2'-脱氧尿苷和尿嘧啶的一类新的5- [1-烷氧基-2-碘（或2，2-二碘代）乙基]衍生物。酒精。这些化合物是弱的或无活性的抗病毒和无活性的细胞毒剂。
• KUMAR, RAKESH;WIEBE, LEONARD I.;KNAUS, E. E.;TEMPEST, MARK L., J. HETEROCYCL. CHEM., 28,(1991) N, C. 237-240
  作者：KUMAR, RAKESH、WIEBE, LEONARD I.、KNAUS, E. E.、TEMPEST, MARK L.

  DOI：——

  日期：——
• Inhibition of Mycobacterial Replication by Pyrimidines Possessing Various C-5 Functionalities and Related 2′-Deoxynucleoside Analogues Using in Vitro and in Vivo Models
  作者：Naveen C. Srivastav、Dinesh Rai、Christopher Tse、B. Agrawal、Dennis Y. Kunimoto、Rakesh Kumar

  DOI：10.1021/jm100568q

  日期：2010.8.26

  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.