2',3'-dideoxy-3'-(2-tetrazolyl)thymidine | 158868-17-8

• 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: 2',3'-dideoxy-3'-(2-tetrazolyl)thymidine
• 英文别名: 3'-(tetrazole-2''-yl)-3'-deoxythymidine；3'-(tetrazol-2''-yl)-3'-deoxythymidine；3'-(2-tetrazolyl)-2',3'-dideoxythymidine；1-[(2R,4S,5S)-5-(hydroxymethyl)-4-(tetrazol-2-yl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 158868-17-8
• 化学式: C₁₁H₁₄N₆O₄
• 分子量: 294.27
• InChiKey: NFNLNGUVUTUNNM-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2',3'-dideoxy-3'-(2-tetrazolyl)thymidine 在 1H-1,2,3-三氮唑 、 三丁基焦磷酸铵 、 三乙胺 、 三氯氧磷 作用下， 生成 3'-(tetrazole-2''-yl)-3'-deoxythymidine 5'-triphosphate
  参考文献：
  名称：

  Synthesis, Conformation of 3′-(Tetrazole-2″-yl)-3′-deoxythymidine and its 5″-Derivatives. Substrate Properties of 3′-(Tetrazole-2″-yl)-3′-deoxythymidine 5′-Triphosphate

  摘要：

  5'-O-Benzoyl-3'-(tetrazole-2 ''-yl)-3'-deoxythymidine and its 5 ''-substituted derivatives were obtained by the reaction of 5'-O-benzoyl-2,3'-anhydrothymidine with triethylammonium salts of either tetrazole or 5-substituted tetrazoles. Debenzoylation of these compounds yielded 3'-(tetrazole-2 ''-yl)-3'-deoxythymidine and its 5 ''-derivatives. Structures of two of them were confirmed by X-ray analysis. Both 3'-(tetrazole-2 ''-yl)-3'-deoxythymidine and 3'-(5 ''-methyltetrazole-2 ''-yl)-3'-deoxythymidine have anti-conformation with respect to the glycosidic bond, and 2'-endo-3'-exo-conformation of the sugar residue with gauche(+) orientation relative to the C4'-C5' bond. 3'-(Tetrazole-2 ''-yl)-3'-deoxythymidine 5'-triphosphate exhibited poor termination substrate properties towards avian myeloblastosis virus reverse transcriptase and did not serve as a substrate for other employed DNA polymerases.

  DOI：

  10.1080/15257779508010691
• 作为产物：
  描述：

  2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine 在 二甲胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.83h， 生成 2',3'-dideoxy-3'-(2-tetrazolyl)thymidine
  参考文献：
  名称：

  Ostrovskii, V. A.; Studentsov, E. P.; Poplavskii, V. S., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 1, p. 42 - 47

  摘要：

  DOI：

文献信息

• Ostrovskii, V. A.; Ivanova, N. V.; Malin, A. A., Russian Journal of Organic Chemistry, 1993, vol. 29, # 11.2, p. 1947 - 1948
  作者：Ostrovskii, V. A.、Ivanova, N. V.、Malin, A. A.、Shcherbinin, M. B.、Poplavskii, V. S.、Studentsov, E. P.

  DOI：——

  日期：——
• Synthesis, Conformation of 3′-(Tetrazole-2″-yl)-3′-deoxythymidine and its 5″-Derivatives. Substrate Properties of 3′-(Tetrazole-2″-yl)-3′-deoxythymidine 5′-Triphosphate
  作者：V. A. Ostrovskii、E. P. Studentsov、V. S. Poplavskii、N. V. Ivanova、G. V. Gurskaya、V. E. Zavodnik、M. V. Jasko、D. G. Semizarov、A. A. Krayevsky

  DOI：10.1080/15257779508010691

  日期：1995.8

  5'-O-Benzoyl-3'-(tetrazole-2 ''-yl)-3'-deoxythymidine and its 5 ''-substituted derivatives were obtained by the reaction of 5'-O-benzoyl-2,3'-anhydrothymidine with triethylammonium salts of either tetrazole or 5-substituted tetrazoles. Debenzoylation of these compounds yielded 3'-(tetrazole-2 ''-yl)-3'-deoxythymidine and its 5 ''-derivatives. Structures of two of them were confirmed by X-ray analysis. Both 3'-(tetrazole-2 ''-yl)-3'-deoxythymidine and 3'-(5 ''-methyltetrazole-2 ''-yl)-3'-deoxythymidine have anti-conformation with respect to the glycosidic bond, and 2'-endo-3'-exo-conformation of the sugar residue with gauche(+) orientation relative to the C4'-C5' bond. 3'-(Tetrazole-2 ''-yl)-3'-deoxythymidine 5'-triphosphate exhibited poor termination substrate properties towards avian myeloblastosis virus reverse transcriptase and did not serve as a substrate for other employed DNA polymerases.
• METALLOENZYME INHIBITOR COMPOUNDS
  申请人：Hoekstra William J.

  公开号：US20120309800A1

  公开（公告）日：2012-12-06

  The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
• US8987315B2
  申请人：——

  公开号：US8987315B2

  公开（公告）日：2015-03-24
• [EN] METALLOENZYME INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE MÉTALLO-ENZYME
  申请人：VIAMET PHARMACEUTICALS INC

  公开号：WO2011082245A2

  公开（公告）日：2011-07-07

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