2-chloromethyl-8-nitroquinoline | 76253-78-6

• 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-chloromethyl-8-nitroquinoline
• 英文别名: 2-(Chloromethyl)-8-nitroquinoline
• CAS: 76253-78-6
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: MWFFNNKFHNIXCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-8-nitroquinoline 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成 2-(2-methylprop-1-enyl)-8-nitroquinoline
  参考文献：
  名称：

  Nishikawa, Makoto; Saeki, Seitaro; Hamana, Masatomo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 8, p. 2436 - 2442

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(氯甲基)喹啉 在 硫酸 、 potassium nitrate 作用下， 反应 2.0h， 以42%的产率得到2-chloromethyl-8-nitroquinoline
  参考文献：
  名称：

  Nishikawa, Makoto; Saeki, Seitaro; Hamana, Masatomo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 8, p. 2436 - 2442

  摘要：

  DOI：

文献信息

• Novel quinoline-based metal chelators as antiviral agents
  申请人：Rajagopalan Raghavan

  公开号：US20060094755A1

  公开（公告）日：2006-05-04

  This invention relates to novel quinoline-based divalent metal ion chelating ligands of Formula I, wherein A or B are independently —CR 7 R 8 , or —CH(R 9 )CH(R 10 ). X is hydrogen, C 1 -C 10 alkyl; —OH, or —NR 11 R 12 . R 1 to R 12 are various substituents selected to optimize the physicochemical and biological properties such as enzyme binding, tissue penetration, lipophilicity, toxicity, bioavailability, and pharmacokinetics of compounds of Formula 13. R 1 to R 12 may include, but are not limited to hydrogen, alkyl, acyl, hydroxyl, hydroxyalkyl, substituted or unsubstituted aryl, amino, aminoalkyl, alkoxyl, aryloxyl, carboxyl, halogen, alkoxycarbonyl, cyano, and other suitable electron donating or electron withdrawing groups. The compounds of the present invention are useful for inhibiting the activity of viral enzymes responsible for the proliferation of human immunodeficiency virus (HIV).

  该发明涉及一种新型喹啉基二价金属离子螯合配体，其化学式为I，其中A或B分别独立地为—CR7R8或—CH(R9)CH(R10)。X为氢、C1-C10烷基；—OH或—NR11R12。R1至R12为各种取代基，选定以优化化合物13的生理化学和生物学性质，如酶结合、组织渗透性、亲脂性、毒性、生物利用度和药代动力学。R1至R12可能包括但不限于氢、烷基、酰基、羟基、羟基烷基、取代或未取代芳基、氨基、氨基烷基、烷氧基、芳氧基、羧基、卤素、烷氧羰基、氰基和其他适当的电子给体或电子提取基团。本发明的化合物可用于抑制与人类免疫缺陷病毒（HIV）增殖相关的病毒酶的活性。
• 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.
• 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：——
• 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：——