5'-O-benzoyl-3'-(2-tetrazolyl)-2',3'-dideoxythymidine | 158868-16-7

• 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'-O-benzoyl-3'-(2-tetrazolyl)-2',3'-dideoxythymidine
• 英文别名: [(2S,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-(tetrazol-2-yl)oxolan-2-yl]methyl benzoate
• CAS: 158868-16-7
• 化学式: C₁₈H₁₈N₆O₅
• 分子量: 398.378
• InChiKey: CRCUZXJRIIIMED-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-benzoyl-3'-(2-tetrazolyl)-2',3'-dideoxythymidine 在 二甲胺 作用下， 以 甲醇 为溶剂， 以57%的产率得到2',3'-dideoxy-3'-(2-tetrazolyl)thymidine
  参考文献：
  名称：

  Malin, A. A.; Ostrovskii, V. A.; Yas'ko, M. V., Russian Journal of Organic Chemistry, 1995, vol. 31, # 4, p. 581 - 582

  摘要：

  DOI：
• 作为产物：
  描述：

  四氮唑 、 2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以45%的产率得到5'-O-benzoyl-3'-(2-tetrazolyl)-2',3'-dideoxythymidine
  参考文献：
  名称：

  Malin, A. A.; Ostrovskii, V. A.; Yas'ko, M. V., Russian Journal of Organic Chemistry, 1995, vol. 31, # 4, p. 581 - 582

  摘要：

  DOI：

文献信息

• Ostrovskii, V. A.; Studentsov, E. P.; Poplavskii, V. S., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 1, p. 42 - 47
  作者：Ostrovskii, V. A.、Studentsov, E. P.、Poplavskii, V. S.、Ivanova, N. V.、Gurskaya, G. V.、et al.

  DOI：——

  日期：——
• 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：——
• ——
  作者：A. A. Malin、E. V. Korchevskaya、M. B. Shcherbinin、V. A. Ostrovskii

  DOI：10.1023/a:1013995011933

  日期：——

  The reaction of 5'-O-benzoyl-2,3'-anhydrothymidine with triethylammonium tetrazolide in DMF at 100-120degreesC is described by a second-order kinetic equation, following-the first-order kinetics in each of the reactants. On the basis of the experimental activatin parameters, DeltaH(298)(not equal) = 80 kJ/mol, DeltaS(not equal) = -116 J x mol(-1) K-1, a mechanism was proposed, according to which in the rate-determining stage of S(N)2 reaction triethylammonium tetrazolide attacks the C-3 atom of 5'-O-benzoyl-2,3'-anhydrothymidine with simultaneous loosening of the C-3 -O-2 anhydro bond.
• 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.