1-(3,5-dichlorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde | 347331-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(3,5-dichlorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde
• 英文别名: 1-(3,5-dichlorophenyl)-2,5-dimethylpyrrole-3-carbaldehyde
• CAS: 347331-67-3
• 化学式: C₁₃H₁₁Cl₂NO
• mdl: MFCD02904625
• 分子量: 268.142
• InChiKey: KVBRPHMQEKHDLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3,5-dichlorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde 、 苄胺 在 溶剂黄146 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 18.33h， 生成 N-[[1-(3,5-dichlorophenyl)-2,5-dimethylpyrrol-3-yl]methyl]-1-phenylmethanamine
  参考文献：
  名称：

  Improving the Potency of N-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria

  摘要：

  A series of N-phenyl-2,5-dimethylpyrrole derivatives, designed as hybrids of the antitubercular agents BM212 and SQ109, have been synthesized and evaluated against susceptible and drug-resistant mycobacteria strains. Compound 5d, bearing a cyclohexylmethylene side chain, showed high potency against M. tuberculosis including MDR-TB strains at submicromolar concentrations. The new compound shows bacteriostatic activity and low toxicity and proved to be effective against intracellular mycobacteria too, showing an activity profile similar to isoniazid.

  DOI：

  10.1021/acsmedchemlett.9b00515
• 作为产物：
  描述：

  2,5-己二酮 在 对甲苯磺酸 、 三氯氧磷 作用下， 生成 1-(3,5-dichlorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde
  参考文献：
  名称：

  Improving the Potency of N-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria

  摘要：

  A series of N-phenyl-2,5-dimethylpyrrole derivatives, designed as hybrids of the antitubercular agents BM212 and SQ109, have been synthesized and evaluated against susceptible and drug-resistant mycobacteria strains. Compound 5d, bearing a cyclohexylmethylene side chain, showed high potency against M. tuberculosis including MDR-TB strains at submicromolar concentrations. The new compound shows bacteriostatic activity and low toxicity and proved to be effective against intracellular mycobacteria too, showing an activity profile similar to isoniazid.

  DOI：

  10.1021/acsmedchemlett.9b00515

文献信息

• Improving the Potency of <i>N</i>-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria
  作者：Meir Touitou、Fabrizio Manetti、Camila Maringolo Ribeiro、Fernando Rogerio Pavan、Nicolò Scalacci、Katarina Zrebna、Neelu Begum、Dorothy Semenya、Antima Gupta、Sanjib Bhakta、Timothy D. McHugh、Hanoch Senderowitz、Melina Kyriazi、Daniele Castagnolo

  DOI：10.1021/acsmedchemlett.9b00515

  日期：2020.5.14

  A series of N-phenyl-2,5-dimethylpyrrole derivatives, designed as hybrids of the antitubercular agents BM212 and SQ109, have been synthesized and evaluated against susceptible and drug-resistant mycobacteria strains. Compound 5d, bearing a cyclohexylmethylene side chain, showed high potency against M. tuberculosis including MDR-TB strains at submicromolar concentrations. The new compound shows bacteriostatic activity and low toxicity and proved to be effective against intracellular mycobacteria too, showing an activity profile similar to isoniazid.