1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-5-pent-1-ynyl-1H-pyrimidine-2,4-dione | 77887-18-4

• 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: 1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-5-pent-1-ynyl-1H-pyrimidine-2,4-dione
• 英文别名: 5-pentynyluridine；2'-Deoxy-5-(1-pentynyl)uridine；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-pent-1-ynylpyrimidine-2,4-dione
• CAS: 77887-18-4
• 化学式: C₁₄H₁₈N₂O₆
• 分子量: 310.307
• InChiKey: MEFIIULDYGIAQV-PRULPYPASA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-戊炔 、 5-碘尿苷 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以88%的产率得到1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-5-pent-1-ynyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Efficient coupling of low boiling point alkynes and 5-iodonucleosides

  摘要：

  The coupling of unprotected 5-iodonucleosides and low boiling point alkynes has been achieved in a high yield for the first time. The coupling is highly dependent on concentration and can be carried out at low temperature and pressure conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.047

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.
• PROBES COMPRISING FLUORESCENT ARTIFICIAL NUCLEOBASES AND USE THEREOF FOR DETECTION OF SINGLE BASE ALTERATION
  申请人：Humboldt Universität zu Berlin

  公开号：EP2475674B1

  公开（公告）日：2017-01-25
• Efficient coupling of low boiling point alkynes and 5-iodonucleosides
  作者：Stephanos Ghilagaber、William N. Hunter、Rodolfo Marquez

  DOI：10.1016/j.tetlet.2006.11.047

  日期：2007.1

  The coupling of unprotected 5-iodonucleosides and low boiling point alkynes has been achieved in a high yield for the first time. The coupling is highly dependent on concentration and can be carried out at low temperature and pressure conditions. (c) 2006 Elsevier Ltd. All rights reserved.