1-<3-(1,2,3-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl>thymine | 122370-58-5

• 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-(1,2,3-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl>thymine
• 英文别名: 3'-(1,2,3-triazol-1-yl)-3'-deoxy-β-D-thymidine；3'-(1,2,3-triazol-1-yl)-2',3'-dideoxythymidine；3'-(1,2,3-triazol-1-yl)-3'-deoxythymidine；1-[3-(1,2,3-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine；3'-Deoxy-3'-(1,2,3-triazol-1-yl)thymidine；1-[(2R,4S,5S)-5-(hydroxymethyl)-4-(triazol-1-yl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 122370-58-5
• 化学式: C₁₂H₁₅N₅O₄
• 分子量: 293.282
• InChiKey: CPWUCLYZTKEZPT-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3'-(4-trimethylsilyl-1,2,3-triazol-1-yl)-2',3'-dideoxythymidine 在 甲醇 、 溶剂黄146 作用下， 反应 2.0h， 以52%的产率得到1-<3-(1,2,3-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl>thymine
  参考文献：
  名称：

  3'-（1,2,3-三唑-1-基）-2'，3'-二脱氧胸苷和3'-（1,2,3-三唑-1-基）-2'，3'-二脱氧尿苷

  摘要：

  不同炔属化合物的环加成对3'-azido-2'，3'-二脱氧胸苷和3'-azido-2'，3'-二脱氧尿苷的叠氮基官能团提供具有1,2,3-三唑-1-基的产物在3'-位上的取代基。与母体化合物相反，这些三唑基衍生物对人免疫缺陷病毒（HIV-1）没有明显的活性。

  DOI：

  10.1002/jhet.5570260624

文献信息

• 3′-[4-Aryl-(1,2,3-triazol-1-yl)]-3′-deoxythymidine Analogues as Potent and Selective Inhibitors of Human Mitochondrial Thymidine Kinase
  作者：Sara Van Poecke、Ana Negri、Federico Gago、Ineke Van Daele、Nicola Solaroli、Anna Karlsson、Jan Balzarini、Serge Van Calenbergh

  DOI：10.1021/jm901532h

  日期：2010.4.8

  In an effort to increase the potency and selectivity of earlier identified substrate-based inhibitors of mitochondrial thymidine kinase 2 (TK-2), we now describe the synthesis of new thymidine analogues containing a 4- or 5-substituted 1,2,3-triazol-1-yl substituent at the 3'-position of the 2'-deoxyribofuranosyl ring. These analogues were prepared by Cu- and Ru-catalyzed cycloadditions of 3'-azido-3'-deoxythymidine and the appropriate alkynes, which produced the 1,4- and 1,5-triazoles, respectively. Selected analogues showed nanomolar inhibitory activity for TK-2, while virtually not affecting the TK-1 counterpart. Enzyme kinetics indicated a competitive and uncompetitive inhibition profile against thymidine and the cosubstrate ATP, respectively. This behavior is rationalized by suggesting that the inhibitors occupy the substrate-binding site in a TK-2 ATP complex that maintains the enzyme's active site in a closed conformation through the stabilization of a small lid domain.
• 1,3-Dipolar cycloaddition of alkenes to 3’-azido-3’-deoxythymidine as a route to 3’-deoxythymidin-3’-yl derivatives
  作者：Pavel N. Solyev、Roman A. Novikov、Marina K. Kukhanova、Maxim V. Jasko

  DOI：10.1016/j.mencom.2014.06.005

  日期：2014.7

  1,3-Cycloaddition of acrylonitrile, acrylamide, vinyl acetate and allyl alcohol to azido group of 3'-azido-3'-deoxythymidine under mild conditions afforded the corresponding adducts which were tested as inhibitors of HIV reverse transcriptase.
• HABICH, DIETER;BARTH, WOLFGANG;ROSNER, MANFRED, HETEROCYCLES, 29,(1989) N1, C. 2083-2088
  作者：HABICH, DIETER、BARTH, WOLFGANG、ROSNER, MANFRED

  DOI：——

  日期：——
• WIGERINCK, PIET;VAN, AERSCHOT ARTHUR;CLAES, PAUL;BALZARINI, JAN;DE, CLERC+, J. HETEROCYCL. CHEM., 26,(1989) N, C. 1635-1642
  作者：WIGERINCK, PIET、VAN, AERSCHOT ARTHUR、CLAES, PAUL、BALZARINI, JAN、DE, CLERC+

  DOI：——

  日期：——
• [EN] METALLOENZYME INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE MÉTALLOENZYME
  申请人：VIAMET PHARMACEUTICALS INC

  公开号：WO2012082746A2

  公开（公告）日：2012-06-21

  The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.