N-butyl-4-(9H-fluoren-9-yl)piperazine-1-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-butyl-4-(9H-fluoren-9-yl)piperazine-1-carboxamide
• 化学式: C₂₂H₂₇N₃O
• 分子量: 349.476
• InChiKey: JHMANYWHUFGGHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-溴芴 在 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 生成 N-butyl-4-(9H-fluoren-9-yl)piperazine-1-carboxamide
  参考文献：
  名称：

  Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

  摘要：

  A series of fluorene-based derivatives was synthesized and evaluated for inhibiting both InhA and Mycobacterium tuberculosis growth. These compounds were inspired by the previously reported Genz-10850 molecule, a good InhA inhibitor, but with a poor activity against M. tuberculosis growth. Structure activity relationships were performed by introducing the following chemical modifications: 1) the piperazine ring; 2) the amide group; 3) the aryl moiety; and 4) the fluorene moiety. Among these new derivatives, one of them was more effective against both the InhA activity and mycobacterial growth, compared to the hit compound. Docking studies were also performed to rationalize activities of these derivatives. Furthermore, we showed for the first time that efflux pump inhibitors potentiated the efficacy of Genz-10850 (GEQ) derivatives against M. tuberculosis growth, demonstrating that these compounds could be substrates of some efflux pumps. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.035

文献信息

• Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth
  作者：Aurélien Chollet、Giorgia Mori、Christophe Menendez、Frédéric Rodriguez、Isabelle Fabing、Maria Rosalia Pasca、Jan Madacki、Jana Korduláková、Patricia Constant、Annaïk Quémard、Vania Bernardes-Génisson、Christian Lherbet、Michel Baltas

  DOI：10.1016/j.ejmech.2015.06.035

  日期：2015.8

  A series of fluorene-based derivatives was synthesized and evaluated for inhibiting both InhA and Mycobacterium tuberculosis growth. These compounds were inspired by the previously reported Genz-10850 molecule, a good InhA inhibitor, but with a poor activity against M. tuberculosis growth. Structure activity relationships were performed by introducing the following chemical modifications: 1) the piperazine ring; 2) the amide group; 3) the aryl moiety; and 4) the fluorene moiety. Among these new derivatives, one of them was more effective against both the InhA activity and mycobacterial growth, compared to the hit compound. Docking studies were also performed to rationalize activities of these derivatives. Furthermore, we showed for the first time that efflux pump inhibitors potentiated the efficacy of Genz-10850 (GEQ) derivatives against M. tuberculosis growth, demonstrating that these compounds could be substrates of some efflux pumps. (C) 2015 Elsevier Masson SAS. All rights reserved.