[(2R,3S,5R)-5-[2,6-bis(methylsulfanyl)purin-9-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate | 127472-46-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [(2R,3S,5R)-5-[2,6-bis(methylsulfanyl)purin-9-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 127472-46-2
• 化学式: C₂₈H₂₈N₄O₅S₂
• 分子量: 564.686
• InChiKey: SXNASGLNLPDCOQ-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-[2,6-bis(methylsulfanyl)purin-9-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate 在 氨 作用下， 反应 20.0h， 以32%的产率得到4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Synthesis and cytotoxicity of deoxyadenosine analogs: isomer distribution in the sodium salt glycosylation of 2,6-disubstituted purines

  摘要：

  Several 2-substituted deoxyadenosine derivatives were synthesized and screened for cytotoxicity toward hematopoietic cells in culture. To prepare intermediates for these syntheses, the sodium salts of 2,6-dibromopurine and 2,6-bis(methylthio)purine were reacted with 1-chloro-3,5-di-p-toluyl-alpha-D-erythro-pentofuranose in acetonitrile. Similar reactions using 6-chloropurines have been reported to give only 9-beta and 7-beta nucleosides as major and minor products, respectively. 2,6-Dibromopurine, however, gave 9-beta and 9-alpha isomers as major and minor products, along with a lesser amount of the 7-beta isomer. 2,6-Bis(methylthio)purine, in contrast, produced 9-beta and 7-beta isomers as major and minor products. These results are discussed in terms of sugar anomerization and possible steric and kinetic effects of base substituents in the sodium salt glycosylation reaction. Reactions of the 9-beta nucleoside isomers with ammonia and alkylamines produced several 2-bromo, 2-methylthio, and 2-amino deoxyadenosines. All of the compounds showed weaker cytotoxic activity than 2-bromodeoxyadenosine against hematopoietic cells in culture, when [14C]leucine incorporation into cellular proteins was measured.

  DOI：

  10.1021/jm00168a023
• 作为产物：
  描述：

  2,6-双(甲基硫代)-9H-嘌呤 、 1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 生成 [(2R,3S,5R)-5-[2,6-bis(methylsulfanyl)purin-9-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
  参考文献：
  名称：

  KAZIMIERCZUK, ZYGMUNT;VILPO, JUHANI;HILDEBRAND, CATHERINE;WRIGHT, GEORGE, J. MED. CHEM., 33,(1990) N, C. 1683-1687

  摘要：

  DOI：

文献信息

• KAZIMIERCZUK, ZYGMUNT;VILPO, JUHANI;HILDEBRAND, CATHERINE;WRIGHT, GEORGE, J. MED. CHEM., 33,(1990) N, C. 1683-1687
  作者：KAZIMIERCZUK, ZYGMUNT、VILPO, JUHANI、HILDEBRAND, CATHERINE、WRIGHT, GEORGE

  DOI：——

  日期：——
• Synthesis and cytotoxicity of deoxyadenosine analogs: isomer distribution in the sodium salt glycosylation of 2,6-disubstituted purines
  作者：Zygmunt Kazimierczuk、Juhani Vilpo、Catherine Hildebrand、George Wright

  DOI：10.1021/jm00168a023

  日期：1990.6

  Several 2-substituted deoxyadenosine derivatives were synthesized and screened for cytotoxicity toward hematopoietic cells in culture. To prepare intermediates for these syntheses, the sodium salts of 2,6-dibromopurine and 2,6-bis(methylthio)purine were reacted with 1-chloro-3,5-di-p-toluyl-alpha-D-erythro-pentofuranose in acetonitrile. Similar reactions using 6-chloropurines have been reported to give only 9-beta and 7-beta nucleosides as major and minor products, respectively. 2,6-Dibromopurine, however, gave 9-beta and 9-alpha isomers as major and minor products, along with a lesser amount of the 7-beta isomer. 2,6-Bis(methylthio)purine, in contrast, produced 9-beta and 7-beta isomers as major and minor products. These results are discussed in terms of sugar anomerization and possible steric and kinetic effects of base substituents in the sodium salt glycosylation reaction. Reactions of the 9-beta nucleoside isomers with ammonia and alkylamines produced several 2-bromo, 2-methylthio, and 2-amino deoxyadenosines. All of the compounds showed weaker cytotoxic activity than 2-bromodeoxyadenosine against hematopoietic cells in culture, when [14C]leucine incorporation into cellular proteins was measured.