(2E)-1-(1',3'-benzodioxol-5-yl)-3-(2-chloro-6-methoxyquinolin-3-yl)-2-propen-1-one | 1352444-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (2E)-1-(1',3'-benzodioxol-5-yl)-3-(2-chloro-6-methoxyquinolin-3-yl)-2-propen-1-one
• 英文别名: (2E)-1-(1,3-benzodioxol-5-yl)-3-(2-chloro-5-methoxyquinolin-3-yl)-2-propen-1-one；(E)-1-(1,3-benzodioxol-5-yl)-3-(2-chloro-6-methoxy-3-quinolyl)prop-2-en-1-one；(E)-1-(1,3-benzodioxol-5-yl)-3-(2-chloro-6-methoxyquinolin-3-yl)prop-2-en-1-one
• CAS: 1352444-88-2
• 化学式: C₂₀H₁₄ClNO₄
• 分子量: 367.788
• InChiKey: HXTLFKYUBOQMTH-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 、 2-氯-6-甲氧基喹啉-3-甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以95%的产率得到(2E)-1-(1',3'-benzodioxol-5-yl)-3-(2-chloro-6-methoxyquinolin-3-yl)-2-propen-1-one
  参考文献：
  名称：

  Antibacterial activity of chalcones, hydrazones and oxadiazoles against methicillin-resistant Staphylococcus aureus

  摘要：

  The increase in antibiotic resistance due to multiple factors has encouraged the search for new compounds which are active against multidrug-resistant pathogens. In this context, chalcones, dihydrochalcones, hydrazones and oxadiazoles were tested against Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus (MRSA) isolates, which were obtained from clinical laboratories and were characterized as MRSA using traditional and molecular methods. Among 65 tested compounds, two chalcones, one dihydrochalcone and two hydrazones were active against MRSA. Based on the minimal inhibitory concentration and cytotoxicity, hydrazones provided a better selectivity index than chalcones. Active hydrazones are promising antibiotic-like substances and they should be the subject of further microbiological studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.059

文献信息

• Synthesis, Biological Evaluation, And Molecular Modeling of Chalcone Derivatives As Potent Inhibitors of Mycobacterium tuberculosis Protein Tyrosine Phosphatases (PtpA and PtpB)
  作者：Louise Domeneghini Chiaradia、Priscila Graziela Alves Martins、Marlon Norberto Sechini Cordeiro、Rafael Victorio Carvalho Guido、Gabriela Ecco、Adriano Defini Andricopulo、Rosendo Augusto Yunes、Javier Vernal、Ricardo José Nunes、Hernán Terenzi

  DOI：10.1021/jm2012062

  日期：2012.1.12

  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.