3-bromo-5-bromomethyl-2,1-benzisothiazole | 566194-21-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-bromo-5-bromomethyl-2,1-benzisothiazole
• 英文别名: 3-Bromo-5-(bromomethyl)-2,1-benzothiazole
• CAS: 566194-21-6
• 化学式: C₈H₅Br₂NS
• 分子量: 307.008
• InChiKey: DITBPVDCSQHSNI-UHFFFAOYSA-N

物化性质

• 沸点：
  366.5±27.0 °C(Predicted)
• 密度：
  2.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-5-bromomethyl-2,1-benzisothiazole 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 6-(3-Bromo-benzo[c]isothiazol-5-ylmethylsulfanyl)-7-butyl-7H-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) 、 正丁基锂 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 为溶剂， 反应 12.0h， 生成 3-bromo-5-bromomethyl-2,1-benzisothiazole
  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。
• Analogs of nitrobenzylthioinosine
  申请人：Puetz Claudia

  公开号：US20050096293A1

  公开（公告）日：2005-05-05

  Analogs or derivatives of nitrobenzylthioinosine compounds. The use of these new analogs of nitrobenzylthioinosine and methods for the treatment of pain and various other indications using these analogs of nitrobenzylthioinosine as well as pharmaceutical compositions including analogs of nitrobenzylthioinosine.

  硝基苯基硫代核苷类似物或衍生物。使用这些新的硝基苯基硫代核苷类似物的方法，治疗疼痛和其他各种适应症，以及包括硝基苯基硫代核苷类似物的制药组合物。
• NEW ANALOGS OF NITROBENZYLTHIOINOSINE
  申请人：Grünenthal GmbH

  公开号：EP1492803A1

  公开（公告）日：2005-01-05
• US7358235B2
  申请人：——

  公开号：US7358235B2

  公开（公告）日：2008-04-15
• [EN] NEW ANALOGS OF NITROBENZYLTHIOINOSINE<br/>[FR] NOUVEAUX ANALOGUES DE LA NITROBENZYLTHIOINOSINE
  申请人：GRUENENTHAL GMBH

  公开号：WO2003084975A1

  公开（公告）日：2003-10-16

  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.