4-(4-Chloroanilino)-5,7-dimethylchromen-2-one | 1258700-79-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-(4-Chloroanilino)-5,7-dimethylchromen-2-one
• CAS: 1258700-79-6
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: CGDPVWPSHDGWBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-hydroxy-5,7-imethylcoumarin 、 对氯苯胺 生成 4-(4-Chloroanilino)-5,7-dimethylchromen-2-one
  参考文献：
  名称：

  Screening for In Vitro Antimycobacterial Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of 4-(arylamino)coumarin Derivatives

  摘要：

  The resurgence of tuberculosis and the emergence of multidrug‐resistant strains of Mycobacteria necessitate the search for new classes of antimycobacterial agents. We have synthesized a small library of 50 analogues of 4‐(arylamino)coumarins with various aromatic amines at the C4‐ position of the coumarin scaffold. The compounds were evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Rv with rifampicin as the standard. Of the molecules synthesized, compound 9 was found to be most potent with a minimum inhibitory concentration >6.25 μg/mL for 100% inhibition. In an effort to develop new and more effective molecules in this series, the relationship between structure and activity was investigated by comparative molecular field analysis. Various models were generated using comparative molecular field analysis alone and comparative molecular field analysis plus a hydropathy field (HINT). In all, eight models were generated with atom‐fit and field‐fit alignment strategies. The comparative molecular field analysis models (Models 3a and 4a) based on field‐fit alignment were the best with statistically good correlation coefficients (r2) and cross‐validated q2. The values of r2pred for the validation set were 0.469 and 0.516. Based on the comparative molecular field analysis contours, some insights into the structure–activity relationship of the compounds could be gained.

  DOI：

  10.1111/j.1747-0285.2010.00997.x

文献信息

• Screening for In Vitro Antimycobacterial Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of 4-(arylamino)coumarin Derivatives
  作者：Vijay Virsdoia、Mushtaque S. Shaikh、Atul Manvar、Bhavik Desai、Alpesh Parecha、Raju Loriya、Kinnari Dholariya、Gautam Patel、Vipul Vora、Kuldip Upadhyay、Karia Denish、Anamik Shah、Evans C. Coutinho

  DOI：10.1111/j.1747-0285.2010.00997.x

  日期：2010.11

  The resurgence of tuberculosis and the emergence of multidrug‐resistant strains of Mycobacteria necessitate the search for new classes of antimycobacterial agents. We have synthesized a small library of 50 analogues of 4‐(arylamino)coumarins with various aromatic amines at the C4‐ position of the coumarin scaffold. The compounds were evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Rv with rifampicin as the standard. Of the molecules synthesized, compound 9 was found to be most potent with a minimum inhibitory concentration >6.25 μg/mL for 100% inhibition. In an effort to develop new and more effective molecules in this series, the relationship between structure and activity was investigated by comparative molecular field analysis. Various models were generated using comparative molecular field analysis alone and comparative molecular field analysis plus a hydropathy field (HINT). In all, eight models were generated with atom‐fit and field‐fit alignment strategies. The comparative molecular field analysis models (Models 3a and 4a) based on field‐fit alignment were the best with statistically good correlation coefficients (r2) and cross‐validated q2. The values of r2pred for the validation set were 0.469 and 0.516. Based on the comparative molecular field analysis contours, some insights into the structure–activity relationship of the compounds could be gained.