N-(benzo[d]thiazol-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene-3-carboxamide | 1588534-85-3

• 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: N-(benzo[d]thiazol-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene-3-carboxamide
• CAS: 1588534-85-3
• 化学式: C₂₂H₂₁BN₂O₃S₂
• 分子量: 436.363
• InChiKey: ITYORJBKIVZKAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.45
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-溴-2-吡啶羧酸 、 N-(benzo[d]thiazol-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene-3-carboxamide 在 bis-triphenylphosphine-palladium(II) chloride 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.08h， 以33%的产率得到6-(3-(benzo[d]thiazol-2-ylcarbamoyl)benzo[b]thiophen-5-yl)picolinic acid
  参考文献：
  名称：

  Structure-Guided Rescaffolding of Selective Antagonists of BCL-X_L

  摘要：

  Because of the promise of BCL-2 antagonists in combating chronic lymphocytic leukemia (CLL) and non-Hodgkin's lymphoma (NHL), interest in additional selective antagonists of antiapoptotic proteins has grown. Beginning with a series of selective, potent BCL-X-L antagonists containing an undesirable hydrazone functionality, in silico design and X-ray crystallography were utilized to develop alternative scaffolds that retained the selectivity and potency of the starting compounds.

  DOI：

  10.1021/ml500030p
• 作为产物：
  描述：

  2-氨基苯并噻唑 在 4-二甲氨基吡啶 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成 N-(benzo[d]thiazol-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene-3-carboxamide
  参考文献：
  名称：

  Structure-Guided Rescaffolding of Selective Antagonists of BCL-X_L

  摘要：

  Because of the promise of BCL-2 antagonists in combating chronic lymphocytic leukemia (CLL) and non-Hodgkin's lymphoma (NHL), interest in additional selective antagonists of antiapoptotic proteins has grown. Beginning with a series of selective, potent BCL-X-L antagonists containing an undesirable hydrazone functionality, in silico design and X-ray crystallography were utilized to develop alternative scaffolds that retained the selectivity and potency of the starting compounds.

  DOI：

  10.1021/ml500030p