2-(4-chlorophenyl)-5-nitrobenzo[d]thiazole | 1215113-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(4-chlorophenyl)-5-nitrobenzo[d]thiazole
• 英文别名: 5-nitro-2-(4-chlorophenyl)-benzothiazole；2-(4-Chlorophenyl)-5-nitro-1,3-benzothiazole
• CAS: 1215113-39-5
• 化学式: C₁₃H₇ClN₂O₂S
• 分子量: 290.73
• InChiKey: UFNQSHWWUWBECC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-5-nitrobenzo[d]thiazole 在 铁粉 、 氯化铵 作用下， 以 industrial methylated spirit 、 水 为溶剂， 反应 2.5h， 以32%的产率得到5-Amino-2-(4-chlor-phenyl)-benzothiazol
  参考文献：
  名称：

  Discovery of 2-Arylbenzoxazoles as Upregulators of Utrophin Production for the Treatment of Duchenne Muscular Dystrophy

  摘要：

  A series of novel 2-arylbenzoxazoles that upregulate the production of utrophin in murine H2K cells, as assessed using a luciferase reporter linked assay, have been identified. This compound class appears to hold considerable promise as a potential treatment for Duchenne muscular dystrophy. Following the delineation of structure-activity relationships in the series, a number of potent upregulators were identified, and preliminary ADME evaluation is described. These studies have resulted in the identification of 1, a compound that has been progressed to clinical trials.

  DOI：

  10.1021/jm200135z
• 作为产物：
  描述：

  2-氟-5-硝基苯胺 在 甲烷磺酸 、 sodiumsulfide nonahydrate 、 四磷十氧化物 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 0.25h， 生成 2-(4-chlorophenyl)-5-nitrobenzo[d]thiazole
  参考文献：
  名称：

  Discovery of 2-Arylbenzoxazoles as Upregulators of Utrophin Production for the Treatment of Duchenne Muscular Dystrophy

  摘要：

  A series of novel 2-arylbenzoxazoles that upregulate the production of utrophin in murine H2K cells, as assessed using a luciferase reporter linked assay, have been identified. This compound class appears to hold considerable promise as a potential treatment for Duchenne muscular dystrophy. Following the delineation of structure-activity relationships in the series, a number of potent upregulators were identified, and preliminary ADME evaluation is described. These studies have resulted in the identification of 1, a compound that has been progressed to clinical trials.

  DOI：

  10.1021/jm200135z

文献信息

• Syntheses and reactivity of alkyl 1-[<i>N</i>-(2-chloro-5-nitro-phenyl)-benzimidoyl] thioureas
  作者：Walid Fathalla、Ibrahim. A.I. Ali、Jaromir Marek、Pavel Pazdera

  DOI：10.1080/17415993.2011.629094

  日期：2012.2.1

  series of new alkyl 1-[N-(2-chloro-5-nitro-phenyl)-benzimidoyl] thioureas 3a–h were prepared from benzamides 1a–c. Benzimidoyl thioureas 3a–e afforded 5-nitro-2-phenyl-benzothiazole 5a–c under basic conditions via thiourea–isothiourea rearrangement and SNAr. A mechanistic rationalization supported by the direct formation of benzothioamide 8 and bis-benzimidoyl sulfide 9 derivatives from the reaction

  从苯甲酰胺 1a-c 制备了一系列新的烷基 1-[N-​​(2-氯-5-硝基-苯基)-苯并亚氨基] 硫脲 3a-h。苯甲酰硫脲 3a-e 在碱性条件下通过硫脲-异硫脲重排和 SNAr 得到 5-硝基-2-苯基-苯并噻唑 5a-c。支持由亚氨基异硫氰酸酯 2 与大体积胺反应直接形成苯并硫代酰胺 8 和双苯并亚氨基硫醚 9 衍生物所支持的机械合理化。