1-(4-isopropylphenyl)-2,5-dimethyl-1H-pyrrole

• 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-(4-isopropylphenyl)-2,5-dimethyl-1H-pyrrole
• 英文别名: 2,5-Dimethyl-1-(4-propan-2-ylphenyl)pyrrole
• 化学式: C₁₅H₁₉N
• mdl: MFCD07429175
• 分子量: 213.323
• InChiKey: QFZYWPFCCYTUGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(4-isopropylphenyl)-2,5-dimethyl-1H-pyrrole 在 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 18.33h， 生成 N-[[1-(4-isopropylphenyl)-2,5-dimethylpyrrol-3-yl]methyl]cyclohexanamine
  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：

  4-异丙基苯胺 、 2,5-己二酮 在 amidosulfonic acid-graphitic carbon nitride nanocomposite 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以75%的产率得到1-(4-isopropylphenyl)-2,5-dimethyl-1H-pyrrole
  参考文献：
  名称：

  Amidosulfonic acid supported on graphitic carbon nitride: novel and straightforward catalyst for Paal–Knorr pyrrole reaction under mild conditions

  摘要：

  DOI：

  10.1007/s00706-021-02771-1

文献信息

• New 2,5-Dimethylpyrrole Derivatives
  作者：W. S. Bishop

  DOI：10.1021/ja01228a502

  日期：1945.12
• Indium-mediated one-pot pyrrole synthesis from nitrobenzenes and 1,4-diketones
  作者：Hyunseung Lee、Byeong Hyo Kim

  DOI：10.1016/j.tet.2013.05.113

  日期：2013.8

  One-pot reduction-triggered heterocyclizations of nitrobenzene derivatives with 1,4-diketones were investigated. In the presence of indium/AcOH in toluene at 80 degrees C, reaction of nitrobenzenes with 2,5-hexadione produced moderate to excellent yields (40-98%) of the corresponding pyrroles within 1.5-24 h depending on the substituents of the starting materials. Similarly, the reaction of nitrobenzenes with 1-phenyl-1,4-pantanedione in the presence of indium/AcOH in toluene at reflux afforded the corresponding pyrroles within 0.5-24 h with 60-98% yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Design and Synthesis of 1-((1,5-Bis(4-chlorophenyl)-2-methyl-1<i>H</i>-pyrrol-3-yl)methyl)-4-methylpiperazine (BM212) and <i>N</i>-Adamantan-2-yl-<i>N</i>′-((<i>E</i>)-3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine (SQ109) Pyrrole Hybrid Derivatives: Discovery of Potent Antitubercular Agents Effective against Multidrug-Resistant Mycobacteria
  作者：Sanjib Bhakta、Nicolò Scalacci、Arundhati Maitra、Alistair K. Brown、Saiprasad Dasugari、Dimitrios Evangelopoulos、Timothy D. McHugh、Parisa N. Mortazavi、Alexander Twist、Elena Petricci、Fabrizio Manetti、Daniele Castagnolo

  DOI：10.1021/acs.jmedchem.6b00031

  日期：2016.3.24

  Novel pyrroles have been designed, synthesized, and evaluated against mycobacterial strains. The pyrroles have originally been designed as hybrids of the antitubercular drugs BM212 (1) and SQ109 (2), which showed common chemical features with very similar topological distribution. A perfect superposition of the structures of 1 and 2 revealed by computational studies suggested the introduction of bulky substituents at the terminal portion of the pyrrole C3 side chain and the removal of the CS aryl moiety. Five compounds showed high activity toward Mycobacterium tuberculosis, while 9b and 9c were highly active also against multidrug-resistant clinical isolates. Compound 9c showed low eukaryotic cell toxicity, turning out to be an excellent lead candidate for preclinical trials. In addition, four compounds showed potent inhibition (comparable to that of verapamil) toward the whole-cell drug efflux pump activity of mycobacteria, thus turning out to be promising multidrug-resistance-reversing agents.
• US7652023B2
  申请人：——

  公开号：US7652023B2

  公开（公告）日：2010-01-26
• 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.