5-(2-pyridylethynyl)-2'-deoxyuridine | 78824-48-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-(2-pyridylethynyl)-2'-deoxyuridine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-pyridin-2-ylethynyl)pyrimidine-2,4-dione
• CAS: 78824-48-3
• 化学式: C₁₆H₁₅N₃O₅
• 分子量: 329.312
• InChiKey: UWFIOOITHCODEX-BFHYXJOUSA-N

物化性质

• 熔点：
  193-195 °C (decomp)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  di-O-trimethylsilyl-5-iodo-2'-deoxyuridine 在 TEA 、 水 作用下， 生成 5-(2-pyridylethynyl)-2'-deoxyuridine
  参考文献：
  名称：

  Alcynyl-5脱氧2'尿苷与有机锌的偶合产物，碘代-s 0-3'，5'-双（三甲基甲硅烷基）脱氧尿苷，催化有机物和镍的配合物

  摘要：

  通过炔基锌试剂与0-3'，5'-双（三甲基甲硅烷基）脱氧尿苷的钯和镍催化反应，可以低至中等的产率获得5-炔基2'-脱氧尿苷

  DOI：

  10.1016/0040-4039(81)89015-6

文献信息

• 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.
• Alcynyl-5 desoxy-2′ uridines par couplages d'organozinciques acetyleniques avec l'iodo-s 0-3′, 5′-bis(trimethylsilyl) desoxyuridine, catalyses par des complexes organopalladies et de nickel
  作者：Patrice Vincent、Jean-Pierre Beaucourt、Louis Pichat

  DOI：10.1016/0040-4039(81)89015-6

  日期：1981.1

  5-Alkynyl 2′-deoxyuridines are obtained in low to modest yields by the palladium and Nickel catalyzed reaction of alkynylzinc reagents with 0-3′, 5′-bis(trimethylsilyl) deoxyuridine in T.H.F.

  通过炔基锌试剂与0-3'，5'-双（三甲基甲硅烷基）脱氧尿苷的钯和镍催化反应，可以低至中等的产率获得5-炔基2'-脱氧尿苷