4-Bromomethyl-7-methyl-6,8-dinitrocoumarin | 1245797-67-4

• 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-Bromomethyl-7-methyl-6,8-dinitrocoumarin
• 英文别名: 4-(bromomethyl)-7-methyl-6,8-dinitrochromen-2-one
• CAS: 1245797-67-4
• 化学式: C₁₁H₇BrN₂O₆
• 分子量: 343.09
• InChiKey: HGIUUHQDEOUCAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Bromomethyl-7-methyl-6,8-dinitrocoumarin 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 10.25h， 生成 7-Methyl-4-[[4-[(4-methyl-2-oxo-chromen-7-yl)oxymethyl]triazol-1-yl]methyl]-6,8-dinitro-chromen-2-one
  参考文献：
  名称：

  Click Chemistry Approach for Bis-Chromenyl Triazole Hybrids and Their Antitubercular Activity

  摘要：

  1,4‐Disubstituted bis‐chromenyl triazole hybrids 5a–m have been synthesized in a three‐step reaction sequence from 4‐(bromomethyl)‐2H‐chromen‐2‐ones 3a–m. The intermediate azides 4a–m underwent a regioselective 1,3‐dipolar cycloaddition with a 2H‐chromen‐2‐one linked acetylenic dipolarophile in the presence of Cu (II)/ascorbate/water/n‐butanol reaction medium. Three compounds 5h–j exhibited 6.25 μg/mL MIC against M. tuberculosis. Among the compounds screened for antifungal activity, lowest MIC of 6.25 μg/mL was observed for 5c against A. niger that also exhibited DNA cleavage observed by agarose gel electrophoresis. All the compounds were moderately active against both Gram‐positive and Gram‐negative bacterial strains. The cytotoxic effect of potent compounds on normal cells (V79 and HBL100) was assessed by MTT assay.

  DOI：

  10.1111/j.1747-0285.2012.01441.x
• 作为产物：
  描述：

  4-溴乙酰乙酸乙酯 、 3-甲基-2,4-二硝基苯酚 在 硫酸 作用下， 生成 4-Bromomethyl-7-methyl-6,8-dinitrocoumarin
  参考文献：
  名称：

  Click Chemistry Approach for Bis-Chromenyl Triazole Hybrids and Their Antitubercular Activity

  摘要：

  1,4‐Disubstituted bis‐chromenyl triazole hybrids 5a–m have been synthesized in a three‐step reaction sequence from 4‐(bromomethyl)‐2H‐chromen‐2‐ones 3a–m. The intermediate azides 4a–m underwent a regioselective 1,3‐dipolar cycloaddition with a 2H‐chromen‐2‐one linked acetylenic dipolarophile in the presence of Cu (II)/ascorbate/water/n‐butanol reaction medium. Three compounds 5h–j exhibited 6.25 μg/mL MIC against M. tuberculosis. Among the compounds screened for antifungal activity, lowest MIC of 6.25 μg/mL was observed for 5c against A. niger that also exhibited DNA cleavage observed by agarose gel electrophoresis. All the compounds were moderately active against both Gram‐positive and Gram‐negative bacterial strains. The cytotoxic effect of potent compounds on normal cells (V79 and HBL100) was assessed by MTT assay.

  DOI：

  10.1111/j.1747-0285.2012.01441.x

文献信息

• Novel One-Pot Synthesis for 2,5-Diaryl and 5-Aryl-pyridazin-3(<i>2H</i>)-ones
  作者：Mahantesha Basanagouda、Manohar V. Kulkarni

  DOI：10.1080/00397911.2010.515330

  日期：2011.9.1

  A novel method for the synthesis of 2-phenyl-5-(o-hydroxyphenyl)-pyridazin-3(2H)-ones and 5-(o-hydroxyphenyl)-pyridazin-3(2H)-ones has been found during the reaction of 4-bromomethylcoumarins with phenylhydrazine and hydrazinehydrate, respectively, under controlled alkaline conditions.
• Click Chemistry Approach for Bis-Chromenyl Triazole Hybrids and Their Antitubercular Activity
  作者：Reshma J. Naik、Manohar V. Kulkarni、K. Sreedhara Ranganath Pai、Pawan G. Nayak

  DOI：10.1111/j.1747-0285.2012.01441.x

  日期：2012.10

  1,4‐Disubstituted bis‐chromenyl triazole hybrids 5a–m have been synthesized in a three‐step reaction sequence from 4‐(bromomethyl)‐2H‐chromen‐2‐ones 3a–m. The intermediate azides 4a–m underwent a regioselective 1,3‐dipolar cycloaddition with a 2H‐chromen‐2‐one linked acetylenic dipolarophile in the presence of Cu (II)/ascorbate/water/n‐butanol reaction medium. Three compounds 5h–j exhibited 6.25 μg/mL MIC against M. tuberculosis. Among the compounds screened for antifungal activity, lowest MIC of 6.25 μg/mL was observed for 5c against A. niger that also exhibited DNA cleavage observed by agarose gel electrophoresis. All the compounds were moderately active against both Gram‐positive and Gram‐negative bacterial strains. The cytotoxic effect of potent compounds on normal cells (V79 and HBL100) was assessed by MTT assay.