5-nitro-2-quinolinecarboxyaldehyde | 59394-31-9

• 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: 5-nitro-2-quinolinecarboxyaldehyde
• 英文别名: 5-nitro-quinoline-2-carbaldehyde；5-Nitrochinolin-2-carboxaldehyd；Chinolinaldehyd；5-Nitroquinoline-2-carbaldehyde
• CAS: 59394-31-9
• 化学式: C₁₀H₆N₂O₃
• 分子量: 202.169
• InChiKey: QRNHAJDHLIRMED-UHFFFAOYSA-N

物化性质

• 熔点：
  179-180 °C (decomp)
• 沸点：
  398.4±27.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitro-2-quinolinecarboxyaldehyde 以70%的产率得到
  参考文献：
  名称：

  TADROS W. M.; SHOEB H. A.; KIRA M. A.; YOUSIF F.; EKLADIOS E. M.; IBRAHIM+, INDIAN J. CHEM. , 1975, 13, NO 12, 1366-1368

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-5-硝基喹啉1-氧化物 在 sodium ethanolate 、 对甲苯磺酰氯 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.33h， 生成 5-nitro-2-quinolinecarboxyaldehyde
  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

• Phenanthro[9,10-<i>d</i>]imidazole-quinoline Boron Difluoride Dyes with Solid-State Red Fluorescence
  作者：Weiling Li、Weiying Lin、Jiaoliang Wang、Xiaoyu Guan

  DOI：10.1021/ol400605x

  日期：2013.4.5

  A new family of boron difluoride-rigidified dyes, phenanthro[9,10-d]imidazole-quinoline boron difluoride (PQBD), with solid-state fluorescence has been designed and synthesized. The novel series of PQBD are advantageous over the typical boron difluoride-rigidified dyes such as BODIPYs in terms of large Stokes shift and red fluorescence in the solid state.

  设计并合成了一种新的二氟化硼刚性染料家族，即菲咯啉[ 9,10 - d ]咪唑-喹啉二氟化硼（PQBD），具有固态荧光。就大的斯托克斯频移和固态红色荧光而言，新颖的PQBD系列优于典型的二氟化硼刚性化染料（如BODIPYs）。
• Quinoline and isoquinoline derivatives, a process for their production and their use as inflammation inhibitors
  申请人：Schering AG

  公开号：US20040116694A1

  公开（公告）日：2004-06-17

  The invention relates to quinoline and isoquinoline derivatives of general formula I 1 a process for their production and their use as inflammation inhibitors.

  本发明涉及通式I的喹啉和异喹啉衍生物，以及其制备方法和作为抗炎药物的用途。
• 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：——
• SHOEB H. A.; KORKOR M. I.; TAMMAM G. H., PHARMAZIE, 1978, 33, NO 9, 581-583
  作者：SHOEB H. A.、 KORKOR M. I.、 TAMMAM G. H.

  DOI：——

  日期：——