N-(3-bromo-4-chloro-phenyl)-5-chloro-2-hydroxy-benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-bromo-4-chloro-phenyl)-5-chloro-2-hydroxy-benzamide
• 英文别名: N-(3-bromo-4-chlorophenyl)-5-chloro-2-hydroxybenzamide
• 化学式: C₁₃H₈BrCl₂NO₂
• 分子量: 361.022
• InChiKey: YACBPAJKSOVDHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯代水杨酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-(3-bromo-4-chloro-phenyl)-5-chloro-2-hydroxy-benzamide
  参考文献：
  名称：

  SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway

  摘要：

  Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. We describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochemical properties relative to previously described derivatives of naphthol AS-E phosphate.

  DOI：

  10.1016/j.bmcl.2019.06.023

文献信息

• SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway
  作者：Hee-Don Chae、Nick Cox、Samanta Capolicchio、Jae Wook Lee、Naoki Horikoshi、Sharon Kam、Andrew A. Ng、Jeffrey Edwards、Tae-León Butler、Justin Chan、Yvonne Lee、Garrett Potter、Mark C. Capece、Corey W. Liu、Soichi Wakatsuki、Mark Smith、Kathleen M. Sakamoto

  DOI：10.1016/j.bmcl.2019.06.023

  日期：2019.8

  Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. We describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochemical properties relative to previously described derivatives of naphthol AS-E phosphate.