6-(Benzo[c]isothiazol-5-ylmethylsulfanyl)-9H-purine | 566194-53-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(Benzo[c]isothiazol-5-ylmethylsulfanyl)-9H-purine
• 英文别名: 5-(7H-purin-6-ylsulfanylmethyl)-2,1-benzothiazole
• CAS: 566194-53-4
• 化学式: C₁₃H₉N₅S₂
• 分子量: 299.38
• InChiKey: ODIPLJJUKOFJRB-UHFFFAOYSA-N

物化性质

• 熔点：
  93-94 °C
• 沸点：
  626.0±50.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.35
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 6-(Benzo[c]isothiazol-5-ylmethylsulfanyl)-9H-purine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到6-(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：

  5-甲基苯并[c]异噻唑 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 15.0h， 生成 6-(Benzo[c]isothiazol-5-ylmethylsulfanyl)-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

文献信息

• New analogs of nitrobenzylthioinosine
  申请人：Grünenthal GmbH

  公开号：EP1352910A1

  公开（公告）日：2003-10-15

  This invention relates to new analogs or derivatives of nitrobenzylthioinosine, use of these new analogs of nitrobenzylthioinosine for the treatment of pain and various other diseases as well as pharmaceuticals comprising at least on new analog of nitrobenzylthioinosine.

  这项发明涉及新的硝基苯基硫基核苷类似物或衍生物，以及利用这些新的硝基苯基硫基核苷类似物治疗疼痛和其他各种疾病，以及包含至少一种新的硝基苯基硫基核苷类似物的药品。