(2E)-1-(1,3-benzodioxol-5-yl)-3-(2,4-dichlorophenyl)-2-propen-1-one | 1003449-35-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-1-(1,3-benzodioxol-5-yl)-3-(2,4-dichlorophenyl)-2-propen-1-one
• 英文别名: (E)-1-(1,3-benzodioxol-5-yl)-3-(2,4-dichlorophenyl)prop-2-en-1-one
• CAS: 1003449-35-1
• 化学式: C₁₆H₁₀Cl₂O₃
• 分子量: 321.16
• InChiKey: GNIQFIOQLFKKCU-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 、 2,4-二氯苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以84%的产率得到(2E)-1-(1,3-benzodioxol-5-yl)-3-(2,4-dichlorophenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis, Biological Evaluation, And Molecular Modeling of Chalcone Derivatives As Potent Inhibitors of Mycobacterium tuberculosis Protein Tyrosine Phosphatases (PtpA and PtpB)

  摘要：

  Tuberculosis (TB) is a major infectious disease caused by Mycobacterium tuberculosis (Mtb). According to the World Health Organization (WHO), about 1.8 million people die from TB and 10 million new cases are recorded each year. Recently, a new series of naphthylchalcones has been identified as inhibitors of Mtb protein tyrosine phosphatases (PTPs). In this work, 100 chalcones were designed, synthesized, and investigated for their inhibitory properties against MtbPtps. Structure-activity relationships (SAR) were developed, leading to the discovery of new potent inhibitors with IC50 values in the low-micromolar range. Kinetic studies revealed competitive inhibition and high selectivity toward the Mtb enzymes. Molecular modeling investigations were carried out with the aim of revealing the most relevant structural requirements underlying the binding affinity and selectivity of this series of inhibitors as potential anti-TB drugs.

  DOI：

  10.1021/jm2012062