2-(2-methylprop-1-enyl)-8-nitroquinoline | 76253-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(2-methylprop-1-enyl)-8-nitroquinoline
• CAS: 76253-88-8
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: LDJZIZJDQGERPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-8-硝基喹啉 在 N-氯代丁二酰亚胺 、 偶氮二异丁腈 、 四丁基氢氧化铵 作用下， 以 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 2-(2-methylprop-1-enyl)-8-nitroquinoline
  参考文献：
  名称：

  Discovery of a new antileishmanial hit in 8-nitroquinoline series

  摘要：

  A series of nitrated 2-substituted-quinolines was synthesized and evaluated in vitro toward Leishmania donovani promastigotes. In parallel, the in vitro cytotoxicity of these molecules was assessed on the murine J774 and human HepG2 cell lines. Thus, a very promising antileishmanial hit molecule was identified (compound 21), displaying an IC50 value of 6.6 mu M and CC50 values >= 100 mu M, conferring quite good selectivity index to this molecule, in comparison with 3 drug-compounds of reference (amphotericin B, miltefosine and pentamidine). Compound 21 also appears as an efficient in vitro antileishmanial molecule against both Leishmania infantum promastigotes and the intracellular L. donovani amastigotes (respective IC50 = 7.6 and 6.5 mu M). Moreover, hit quinoline 21 does not show neither significant antiplasmodial nor antitoxoplasmic in vitro activity and though, presents a selective antileishmanial activity. Finally, a structure activity relationships study enabled to define precisely the antileishmanial pharmacophore based on this nitroquinoline scaffold: 2-hydroxy-8-nitroquinoline. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.029

文献信息

• Nishikawa, Makoto; Saeki, Seitaro; Hamana, Masatomo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 8, p. 2436 - 2442
  作者：Nishikawa, Makoto、Saeki, Seitaro、Hamana, Masatomo、Noda, Hiroshi

  DOI：——

  日期：——
• Quinoline derivatives: potential antiparasitic and antiviral agents
  作者：Jana Sopková-de Oliveira Santos、Pierre Verhaeghe、Jean-François Lohier、Pascal Rathelot、Patrice Vanelle、Sylvain Rault

  DOI：10.1107/s0108270107046550

  日期：2007.11.15

  The crystal structures of closely related quinoline compounds substituted at the 2-position by a vinyl group, either including a Cl atom [2-(1-chloro-2-methylprop-1-enyl)-8-nitroquinoline, C13H11ClN2O2, (I)] or not[2-(2-methylprop-1-enyl)-8-nitroquinoline, C13H12N2O2, (II)], show an important deviation of the vinyl group from coplanarity with the quinoline ring system if the Cl atom is present. The nitro group is perpendicular [in (II)] or nearly so [in (I)] to the quinoline ring system. In (II), all non-H atoms except the nitro O atoms are located on a crystallographic mirror plane.
• NISHIKAWA MAKOTO; SAEKI SEITARO; HAMANA MASATOMO; NODA HIROSHI, CHEM. AND PHARM. BULL., 1980, 28 NO 8, 2436-2442
  作者：NISHIKAWA MAKOTO、 SAEKI SEITARO、 HAMANA MASATOMO、 NODA HIROSHI

  DOI：——

  日期：——
• Discovery of a new antileishmanial hit in 8-nitroquinoline series
  作者：Lucie Paloque、Pierre Verhaeghe、Magali Casanova、Caroline Castera-Ducros、Aurélien Dumètre、Litaty Mbatchi、Sébastien Hutter、Manel Kraiem-M'Rabet、Michèle Laget、Vincent Remusat、Sylvain Rault、Pascal Rathelot、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.ejmech.2012.04.029

  日期：2012.8

  A series of nitrated 2-substituted-quinolines was synthesized and evaluated in vitro toward Leishmania donovani promastigotes. In parallel, the in vitro cytotoxicity of these molecules was assessed on the murine J774 and human HepG2 cell lines. Thus, a very promising antileishmanial hit molecule was identified (compound 21), displaying an IC50 value of 6.6 mu M and CC50 values >= 100 mu M, conferring quite good selectivity index to this molecule, in comparison with 3 drug-compounds of reference (amphotericin B, miltefosine and pentamidine). Compound 21 also appears as an efficient in vitro antileishmanial molecule against both Leishmania infantum promastigotes and the intracellular L. donovani amastigotes (respective IC50 = 7.6 and 6.5 mu M). Moreover, hit quinoline 21 does not show neither significant antiplasmodial nor antitoxoplasmic in vitro activity and though, presents a selective antileishmanial activity. Finally, a structure activity relationships study enabled to define precisely the antileishmanial pharmacophore based on this nitroquinoline scaffold: 2-hydroxy-8-nitroquinoline. (C) 2012 Elsevier Masson SAS. All rights reserved.