5,8-Dichlor-4-hydroxy-carbostyril | 1900-42-1

• 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: 5,8-Dichlor-4-hydroxy-carbostyril
• 英文别名: 5,8-dichloro-4-hydroxy-1H-quinolin-2-one；5,8-Dichloroquinoline-2,4-diol；5,8-dichloro-4-hydroxy-1H-quinolin-2-one
• CAS: 1900-42-1
• 化学式: C₉H₅Cl₂NO₂
• 分子量: 230.05
• InChiKey: XFJWQXAGOXFCIL-UHFFFAOYSA-N

物化性质

• 熔点：
  >360 °C
• 沸点：
  448.7±45.0 °C(Predicted)
• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  0
• 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

• 作为反应物：
  描述：

  5,8-Dichlor-4-hydroxy-carbostyril 、 2-甲基-4-甲氧基苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 为溶剂， 反应 1.5h， 以52%的产率得到5,8-dichloro-3-[2-(4-methoxy-2-methylphenyl)hydrazono]quinoline-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and binary QSAR study of antitubercular quinolylhydrazides

  摘要：

  In continuation with our previous work in anti-TB research area, in the present study we have demonstrated the structural diversity of quinolylhydrazides as potent anti-tuberculars. The compound library was synthesized by molecular hybridization approach and tested in vitro against Mycobacterium tuberculosis H(37)Rv strains. Among the designed conjugates, the most promising molecules were found to exhibit 100% Growth Inhibition (GI) at MIC <6.25 mu g/mL. Moreover, several analogs in the designed series were also turned out as excellent anti-tuberculars. To probe the structural characteristics influencing on the SAR, the classification model was generated using a binary QSAR approach termed recursive partitioning (RP) analysis. The significant features outlined by the RP model act as a guide in order to design the 'lead' compound. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.076
• 作为产物：
  描述：

  5,8-dichloro-4-(2,5-dichloro-anilino)-quinolin-2-ol 在 盐酸 作用下， 生成 5,8-Dichlor-4-hydroxy-carbostyril
  参考文献：
  名称：

  Eine neue Synthese des 4-Hydroxy-carbostyrils

  摘要：

  DOI：

  10.1007/bf00917842

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.
• Kappe, Thomas; Karem, Abdel S.; Stadlbauer, Wolfgang, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 857 - 862
  作者：Kappe, Thomas、Karem, Abdel S.、Stadlbauer, Wolfgang

  DOI：——

  日期：——
• KAPPE, THOMAS;KAREM, ABDEL S.;STADLBAUER, WOLFGANG, J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 857-862
  作者：KAPPE, THOMAS、KAREM, ABDEL S.、STADLBAUER, WOLFGANG

  DOI：——

  日期：——