5-heptynyluridine

• 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-heptynyluridine
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hept-1-ynylpyrimidine-2,4-dione
• 化学式: C₁₆H₂₂N₂O₆
• 分子量: 338.36
• InChiKey: KSMZSVWYSFYRTI-RGCMKSIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-heptynyluridine 在 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 3-(β-D-ribofuranosyl)-6-pentyl-2,3-dihydrofurano[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  呋喃和吡咯 [2,3-D] 嘧啶核苷及其 5'-O-三磷酸酯：合成和酶活性

  摘要：

  合成了一系列双环 [2,3-d] 呋喃和吡咯并嘧啶核糖核苷，并将其化学转化为相应的 5'-O-三磷酸。报道了三磷酸盐对某些 RNA 和 DNA 聚合酶的底物特性

  DOI：

  10.1080/15257770701516250
• 作为产物：
  描述：

  1-庚炔 、 5-碘尿苷 在 palladium on activated charcoal copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 5-heptynyluridine
  参考文献：
  名称：

  呋喃和吡咯 [2,3-D] 嘧啶核苷及其 5'-O-三磷酸酯：合成和酶活性

  摘要：

  合成了一系列双环 [2,3-d] 呋喃和吡咯并嘧啶核糖核苷，并将其化学转化为相应的 5'-O-三磷酸。报道了三磷酸盐对某些 RNA 和 DNA 聚合酶的底物特性

  DOI：

  10.1080/15257770701516250

文献信息

• Design and Studies of Novel 5-Substituted Alkynylpyrimidine Nucleosides as Potent Inhibitors of Mycobacteria
  作者：Dinesh Rai、Monika Johar、Tracey Manning、B. Agrawal、Dennis Y. Kunimoto、Rakesh Kumar

  DOI：10.1021/jm058167w

  日期：2005.11.1

  We herein report a new category of 5-substituted pyrimidine nucleosides as potent inhibitors of mycobacteria. A series of 5-alkynyl derivatives of 2'-deoxyuridine (1-8), 2'-deoxycytidine (9-14), uridine (15-17), and 2'-O-methyluridine (18, 19) were synthesized and evaluated for their antimycobacterial activity in vitro. 5-Decynyl, 5-dodecynyl, and 5-tetradecynyl derivatives showed the highest antimycobacterial potency against M. bovis and M. avium, with the 2'-deoxyribose derivatives being more effective than the ribose analogues. Nucleosides bearing short alkynyl side chains 5-ethynyl, 5-propynyl, 5-pentynyl, and 5-heptynyl were mostly not inhibitory. Incorporation of a phenylethynyl function at the 5-position diminished the antimicrobial effect. Furthermore, related bicyclic analogues (20-24) were devoid of antimycobacterial activity, indicating that an acyclic side chain at the C-5 position of the pyrimidine ring is essential for potent activity. Compounds 1-17 were synthesized by the Pd-catalyzed coupling reactions of respective alkynes with 5-iodo derivatives of 2'-deoxyuridine, 2'-deoxycytidine, and uridine. Intramolecular cyclization of 1 and 3-6 in the presence of Cu afforded the corresponding bicyclic compounds 20-24. The investigated nucleosides are recognized here for the first time to be potent inhibitors of mycobacteria. This class of compounds could be of interest for lead optimization as antimycobacterial agents.