2,4-二溴-6-硝基喹啉 | 437708-86-6

• 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
• 中文名称: 2,4-二溴-6-硝基喹啉
• 英文名称: 2,4-dibromo-6-nitroquinoline
• CAS: 437708-86-6
• 化学式: C₉H₄Br₂N₂O₂
• 分子量: 331.951
• InChiKey: OQHTYRLFDROPPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2,4-二溴-6-硝基喹啉 在 四(三苯基膦)钯 硼烷四氢呋喃络合物 、 硫酸 、 四丁基氢氧化铵 、 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 15.5h， 生成 4-(3-fluoropropyl)-6-nitroquipazine
  参考文献：
  名称：

  Lee, B. S.; Lee, B. C.; Choe, Y. S., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S207 - S209

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-喹啉二醇 在 硫酸 、 硝酸 、 三溴氧磷 作用下， 反应 2.0h， 生成 2,4-二溴-6-硝基喹啉
  参考文献：
  名称：

  喹啉衍生物作为 NF-κB 诱导激酶 (NIK) 抑制剂的发现，具有体外抗炎作用、对 T 细胞生长的低毒性

  摘要：

  NIK是非经典NF-kB通路的关键调节蛋白，其激活失调已被证明是多种自身免疫性疾病和炎症性疾病的致病因素之一。然而，其相应的抑制剂开发面临诸多障碍，包括已知抑制剂结构类型的缺乏、化合物体外活性评价方法不成熟等。本研究通过合理设计和化学合成得到了一系列喹啉衍生物。其中，代表性化合物17c和24c对LPS诱导的巨噬细胞（J774）一氧化氮释放和抗Con A刺激的原代T细胞增殖具有优异的抑制活性。该评价方法具有良好的普适性，在一定程度上克服了当前抑制剂研究面临的上述障碍。此外，首次评估了该化合物在非应激条件下对T细胞生长的毒性，作为研究的指标，以避免潜在的安全风险。对毒性较小的化合物24c的药代动力学性质评价证实了其良好的代谢行为（尤其是口服性质，F% = 21.7%）以及后续的开发价值。

  DOI：

  10.1016/j.bmc.2020.115856

文献信息

• Quinoline derivatives, their preparation and pharmaceutical compositions comprising the same
  申请人：Chi Dae-Yoon

  公开号：US20050165006A1

  公开（公告）日：2005-07-28

  Novel quinoline derivatives were prepared and evaluated their pharmaceutical activities. The quinoline derivatives according to the present invention effectively bind serotonin transporter (SERT) which is called serotonin reuptake site. Serotonin is one of the neurotransmitter and the lack of its concentration in synapse cause the depression. The quinoline derivatives in this invention can interrupt reuptake of serotonin into presynaptic neuron resulting the increasement of concentration of serotonin in synapse as well as stimulating the signal through the binding with serotonin recepter. Thus, they can be used for the prevention and treatment of mental disorder, especially depression, caused by the deficiency of serotonin concentration in synapse.

  通过本发明制备了新型喹啉衍生物，并评估了它们的药物活性。本发明的喹啉衍生物能够有效地结合血清素转运体（SERT），也称为血清素再摄取位点。血清素是一种神经递质，如果突触中缺乏其浓度，则会导致抑郁症。本发明中的喹啉衍生物可以中断血清素重新摄取到突触前神经元中，从而增加突触中血清素的浓度，并通过与血清素受体结合刺激信号。因此，它们可以用于预防和治疗由突触中血清素浓度不足引起的心理障碍，特别是抑郁症。
• Looking for new antileishmanial derivatives in 8-nitroquinolin-2(1H)-one series
  作者：Charline Kieffer、Anita Cohen、Pierre Verhaeghe、Sébastien Hutter、Caroline Castera-Ducros、Michèle Laget、Vincent Remusat、Manel Kraiem M'Rabet、Sylvain Rault、Pascal Rathelot、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.ejmech.2014.12.056

  日期：2015.3

  From a recently identified antileishmanial pharmacophore, a structure activity relationship study was conducted by introducing various aminated, phenoxy or thiophenoxy moieties at position 4 of the 8-nitroquinolin-2(1H)-one scaffold, using SNAr reactions. Thus a series of 47 derivatives was synthesized and evaluated in vitro on the promastigote stage of Leishmania donovani. In parallel, the cytotoxicity of the active molecules was tested on the human HepG2 cell line. The results we obtained showed that the introduction of a substituent at position 4 of the antileishmanial pharmacophore can either lead to inactive or active derivatives, depending on the nature of the substituent. Aminated moieties appear as very unfavorable toward antileishmanial activity, while phenoxy or thiophenoxy moieties were shown to maintain the in vitro antileishmanial profile, especially when the phenyl ring of these moieties was substituted at the para or ortho position by a halogen atom (except fluorine), a trifluoromethyl group or a methyl group. Most of these derivatives showed a lack of solubility in the culture media which hindered the in vitro determination of both their cytotoxicity and activity against the intracellular amastigoste stage of L. donovani. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. part 2: 4-Substituted 6-nitroquipazines
  作者：Byoung Se Lee、Soyoung Chu、Bon-Su Lee、Dae Yoon Chi、Yun Seon Song、Changbae Jin

  DOI：10.1016/s0960-894x(02)00028-8

  日期：2002.3

  Eleven 4-substituted derivatives of 6-nitroquipazine were synthesized and evaluated for their abilities to displace [H-3]citalopram binding to the rat cortical synaptic membranes. Among them, 4-chloro-6-nitroquipazine was shown to possess the highest binding affinity (K-i - 0.03 nM) which was approximately 6 times higher than that of 6-nitroquipazine (K-i = 0.17 nM) itself. In this paper, we describe the syntheses of 4-substituted 6-nitroquipazine derivatives, the results of corresponding biological evaluation and the SAR study. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines
  作者：Byung Seok Moon、Byoung Se Lee、Dae Yoon Chi

  DOI：10.1016/j.bmc.2005.05.031

  日期：2005.8

  On the basis of the structure activity relationship (SAR) of 4-chloro-6-nitroquipazine (K-i = 0.03 nM) and 3-fluoropropyl-6-nitroquipazine (K-i = 0.32 nM), 3-alkyl-4-halo-6-nitroquipazines were synthesized and tested for their potential abilities in vitro to displace [H-3]citalopram binding to the rat cortical membranes. Binding affinities of 3h and 4d were K-i = 2.70 +/- 0.32 and 2.23 +/- 0.46 nM. respectively. The syntheses of 3-alkyl-4-halo-6-nitroquipazine. their in vitro binding affinitics. and the SAR of C3, C4 position in 6-nitroquipazine are described. (c) 2005 Elsevier Ltd. All rights reserved.
• [EN] QUINOLINE DERIVATIVES, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME<br/>[FR] DERIVES DE QUINOLINE, PREPARATIONS DE CES DERIVES ET COMPOSITIONS PHARMACEUTIQUES COMPRENANT CES DERIVES
  申请人：CHEMON INC

  公开号：WO2003082286A1

  公开（公告）日：2003-10-09

  Novel quinoline derivatives were prepared and evaluated their pharmaceutical activities. The quinoline derivatives according to the present invention effectively bind serotonin transporter (SERT) which is called serotonin reuptake site. Serotonin is one of the neurotransmitter and the lack of its concentration in synapse cause the depression. The quinoline derivatives in this invention can interrupt reuptake of serotonin into presynaptic neuron resulting the increasement of concentration of serotonin in synapse as well as stimulating the signal through the binding with serotonin recepter. Thus, they can be used for the prevention and treatment of mental disorder, especially depression, caused by the deficiency of serotonin concentration in synapse.