2-(4-fluorophenyl)-1-nitroindolizine-3-carbonitrile | 1260393-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(4-fluorophenyl)-1-nitroindolizine-3-carbonitrile
• CAS: 1260393-83-6
• 化学式: C₁₅H₈FN₃O₂
• 分子量: 281.246
• InChiKey: CDSIBJAMVNDRHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吡啶 、 1-(4-氟苯基)-2-硝基乙烯 、 溴乙腈 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以53%的产率得到2-(4-fluorophenyl)-1-nitroindolizine-3-carbonitrile
  参考文献：
  名称：

  Facile three-component domino reactions in the regioselective synthesis and antimycobacterial evaluation of novel indolizines and pyrrolo[2,1-a]isoquinolines

  摘要：

  The domino reactions of pyridine/isoquinoline, bromoacetonitrile/ethyl bromoacetate and a series of beta-nitrostyrenes in the presence of triethylamine afforded novel tri-/disubstituted indolizines and pyrrolo [2,1-a]isoquinolines regioselectively, presumably via substitution-dipole generation-1,3-dipolar cycloaddition-elimination and/or aromatisation sequence. In vitro screening of all the seventeen compounds synthesized against Mycobacterium tuberculosis H37Rv discloses that ethyl 2-(4-fluorophenyl)pyrrolo [2,1-a]isoquinoline-3-carboxylate displays maximum potency with minimum inhibitory concentration (MIC) of 1.0 mu M, being 7.6 and 4.7 times more potent than the standard first line TB drugs, ethambutol and ciprofloxacin, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.128

文献信息

• Facile three-component domino reactions in the regioselective synthesis and antimycobacterial evaluation of novel indolizines and pyrrolo[2,1-a]isoquinolines
  作者：Sivasubramanian Muthusaravanan、Subbu Perumal、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.tetlet.2010.09.128

  日期：2010.12

  The domino reactions of pyridine/isoquinoline, bromoacetonitrile/ethyl bromoacetate and a series of beta-nitrostyrenes in the presence of triethylamine afforded novel tri-/disubstituted indolizines and pyrrolo [2,1-a]isoquinolines regioselectively, presumably via substitution-dipole generation-1,3-dipolar cycloaddition-elimination and/or aromatisation sequence. In vitro screening of all the seventeen compounds synthesized against Mycobacterium tuberculosis H37Rv discloses that ethyl 2-(4-fluorophenyl)pyrrolo [2,1-a]isoquinoline-3-carboxylate displays maximum potency with minimum inhibitory concentration (MIC) of 1.0 mu M, being 7.6 and 4.7 times more potent than the standard first line TB drugs, ethambutol and ciprofloxacin, respectively. (C) 2010 Elsevier Ltd. All rights reserved.