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。
• Discovery of 2-Arylbenzoxazoles as Upregulators of Utrophin Production for the Treatment of Duchenne Muscular Dystrophy
  作者：Daniel R. Chancellor、Kay E. Davies、Olivier De Moor、Colin R. Dorgan、Peter D. Johnson、Adam G. Lambert、Daniel Lawrence、Cristina Lecci、Carole Maillol、Penny J. Middleton、Gary Nugent、Séverine D. Poignant、Allyson C. Potter、Paul D. Price、Richard J. Pye、Richard Storer、Jonathon M. Tinsley、Renate van Well、Richard Vickers、Julia Vile、Fraser J. Wilkes、Francis X. Wilson、Stephen P. Wren、Graham M. Wynne

  DOI：10.1021/jm200135z

  日期：2011.5.12

  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.