6-[[(3-bromo-benzo-[2,1]-isothiazol-5-yl)methyl]sulfanyl]-9H-purine | 566194-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-[[(3-bromo-benzo-[2,1]-isothiazol-5-yl)methyl]sulfanyl]-9H-purine
• 英文别名: 3-bromo-5-(7H-purin-6-ylsulfanylmethyl)-2,1-benzothiazole
• CAS: 566194-55-6
• 化学式: C₁₃H₈BrN₅S₂
• 分子量: 378.276
• InChiKey: WGHLEASCVMLUNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 6-[[(3-bromo-benzo-[2,1]-isothiazol-5-yl)methyl]sulfanyl]-9H-purine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以69%的产率得到6-(3-Bromo-benzo[c]isothiazol-5-ylmethylsulfanyl)-9-butyl-9H-purine
  参考文献：
  名称：

  Inhibition of nucleoside transport By new analogues of nitrobenzylthioinosine

  摘要：

  Nitrobenzylthioinosine (NBTI, 1) was systematically modified by attachment of substituents at positions C6 and N9, and also by substitution of N1 with C. These modifications were chosen to reduce the polarity of the new compounds. Incorporation of the nitro functionality into a benzoxadiazole ring system was considered first. These new nucleosides showed high affinity (1.5-10 nM) towards the nucleoside transport protein as present on human erythrocyte ghosts. Next, modification of this benzoxadiazole ring system with C, S and O in different positions produced a number of less polar nucleosides with affinity in the higher nanomolar range. Modification of N9 was achieved with different alkyl and alcohol substituents. An n-butyl substituent proved best, although all variations yielded substantial decreases in affinity. Replacement of N1 by a carbon atom in combination with a 2-Cl substituent also resulted in a relatively potent NBTI derivative (47 nM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00544-8
• 作为产物：
  描述：

  3-bromo-5-methyl-2,1-benzisothiazole 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 6-[[(3-bromo-benzo-[2,1]-isothiazol-5-yl)methyl]sulfanyl]-9H-purine
  参考文献：
  名称：

  Inhibition of nucleoside transport By new analogues of nitrobenzylthioinosine

  摘要：

  Nitrobenzylthioinosine (NBTI, 1) was systematically modified by attachment of substituents at positions C6 and N9, and also by substitution of N1 with C. These modifications were chosen to reduce the polarity of the new compounds. Incorporation of the nitro functionality into a benzoxadiazole ring system was considered first. These new nucleosides showed high affinity (1.5-10 nM) towards the nucleoside transport protein as present on human erythrocyte ghosts. Next, modification of this benzoxadiazole ring system with C, S and O in different positions produced a number of less polar nucleosides with affinity in the higher nanomolar range. Modification of N9 was achieved with different alkyl and alcohol substituents. An n-butyl substituent proved best, although all variations yielded substantial decreases in affinity. Replacement of N1 by a carbon atom in combination with a 2-Cl substituent also resulted in a relatively potent NBTI derivative (47 nM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00544-8