6-溴-8-硝基喹啉 | 68527-67-3

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 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: 6-溴-8-硝基喹啉
• 中文别名: 二苯甲基硫代乙酰胺
• 英文名称: 6-bromo-8-nitroquinoline
• 英文别名: 6-bromo-8-nitro-quinoline；6-Brom-8-nitro-chinolin
• CAS: 68527-67-3
• 化学式: C₉H₅BrN₂O₂
• 分子量: 253.055
• InChiKey: IANZBVIZZQFJPI-UHFFFAOYSA-N

物化性质

• 熔点：
  170-177 °C
• 沸点：
  365.8±27.0 °C(Predicted)
• 密度：
  1.747±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 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

• 海关编码：
  2933499090
• 储存条件：
  室温和干燥环境下使用。

反应信息

• 作为反应物：
  描述：

  6-溴-8-硝基喹啉 在 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 6-甲基-8-喹啉胺
  参考文献：
  名称：

  Synthesis and in vitro evaluation of novel 8-aminoquinoline–pyrazolopyrimidine hybrids as potent antimalarial agents

  摘要：

  In the search of novel chemotherapeutic agents for emerging drug resistant parasites, the hybridization approaches have successfully emerged as an efficient tool in malarial chemotherapy. Herein, a rational design and synthesis of novel 8-aminoquinoline and pyrazolopyrimidine hybrids and their antimalarial activity against wild type Plasmodium falciparum (Pf_NF54) and resistant strain (Pf_K1) is reported. The medicinal chemistry approach to expand the scope of this series resulted in an identification of potent compounds with nanomolar potency (best IC50 5-10 nM). Systematic structure activity relationship (SAR) studies revealed that pyrazolopyrimidine and 8-aminoquinoline ring are essential for achieving good P. falciparum potency. The docking study revealed that the compound 6 can retain some of the critical interactions within pfDHODH drug target. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.003
• 作为产物：
  描述：

  6-溴喹啉 在 硝酸 作用下， 生成 6-溴-8-硝基喹啉
  参考文献：
  名称：

  Claus; Reinhard, Journal fur praktische Chemie (Leipzig 1954), 1894, vol. <2> 49, p. 534,539

  摘要：

  DOI：

文献信息

• [EN] QUINOLINYL-PYRAZINE-CARBOXAMIDE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE QUINOLINYL-PYRAZINE-CARBOXAMIDE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2020132459A1

  公开（公告）日：2020-06-25

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quinolinyl-pyrazine-carboxamide (or similar) structure which function as activators of the cholesterol biosynthesis pathway within cancer cells and/or immune cells, which function as activators of the cell cycle regulation pathway within cancer cells and/or immune cells, and which function as up-regulators of HMGCS1 protein expression within cancer cells and/or immune cells, and which function as effective therapeutic agents for treating, ameliorating, and preventing various forms of cancer and other inflammatory disease.

  这项发明属于药物化学领域。具体来说，该发明涉及一类新型小分子，其具有喹啉基-吡嗪-羧酰胺（或类似）结构，其在癌细胞和/或免疫细胞内作为胆固醇生物合成途径的激活剂，作为癌细胞和/或免疫细胞内细胞周期调控途径的激活剂，作为癌细胞和/或免疫细胞内HMGCS1蛋白表达的上调剂，以及作为治疗、改善和预防各种癌症和其他炎症性疾病的有效治疗剂。
• Metal-Binding Pharmacophore Library Yields the Discovery of a Glyoxalase 1 Inhibitor
  作者：Christian Perez、Amanda M. Barkley-Levenson、Benjamin L. Dick、Peter F. Glatt、Yadira Martinez、Dionicio Siegel、Jeremiah D. Momper、Abraham A. Palmer、Seth M. Cohen

  DOI：10.1021/acs.jmedchem.8b01868

  日期：2019.2.14

  8-(methylsulfonylamino)quinoline (8-MSQ) was identified as a hit. Through computational modeling and synthetic elaboration, a potent GLO1 inhibitor was developed with a novel sulfonamide core pharmacophore. A lead compound was demonstrated to penetrate the blood-brain barrier, elevate levels of methylglyoxal in the brain, and reduce depression-like behavior in mice. These findings provide the basis

  焦虑和抑郁是常见的高度共病的精神疾病，占全世界医学残疾的很大比例。乙二醛酶1（GLO1）已被确定为治疗焦虑症和抑郁症的可能靶标。GLO1是一种Zn2 +依赖性酶，可将由谷胱甘肽和甲基乙二醛形成的半硫缩醛异构化为乳酸硫酯。为了开发GLO1的活性抑制剂，基于片段的药物发现被用于鉴定可用作铅开发核心支架的片段。在筛选了聚焦于金属结合药效基团的文库后，鉴定出了8-（甲基磺酰基氨基）喹啉（8-MSQ）。通过计算建模和合成，开发了一种具有新型磺酰胺核心药效基团的有效GLO1抑制剂。铅化合物被证明可以穿透血脑屏障，提高大脑中甲基乙二醛的水平，并减少小鼠的抑郁样行为。这些发现为GLO1抑制剂治疗抑郁症和相关的精神疾病提供了依据。
• Influence of Functionalized Substituents on the Electron‐Transfer Abilities of Copper Guanidinoquinoline Complexes
  作者：Julia Stanek、Marc Konrad、Johannes Mannsperger、Alexander Hoffmann、Sonja Herres‐Pawlis

  DOI：10.1002/ejic.201801078

  日期：2018.12.13

  The influence of functionalized ligands on the electron‐transfer abilities of copper guanidinoquinoline complexes as entatic state models has been examined. An electron donating group (OCH3) or electron withdrawing group (Br) was introduced in 6‐position of the quinoline unit of the ligands TMGqu and DMEGqu. The electron self‐exchange rates k11 of the copper complexes with these ligands were determined

  考察了功能化配体对铜胍基喹啉络合物作为电子态模型的电子传递能力的影响。在配体TMGqu和DMEGqu的喹啉单元的6位引入了一个给电子基团（OCH 3）或一个吸电子基团（Br）。具有这些配体的铜配合物的电子自交换率k 11是使用马库斯（Marcus）交叉关系确定的。该ķ 11官能化的配合物的值小于或等于其未取代形式的值。通过Eyring理论和DFT计算检查电子转移的重组能，可以补充这些结果。[Cu（DMEG6Xqu）2 ] + / 2 +（X = H，Br，OCH 3）系统的更高重组能与其减速的电子传输速度相对应。此外，计算出的分子静电势还显示了官能团对电子转移的影响。加入取代基后，CH 3上的电荷进一步分布O- / Br-基团导致氧化反应期间需要更大的重组。配体功能化对[Cu（GUA6Xqu）2 ] + / 2 +阳离子电子转移的影响揭示了对络合物电子结构及其对电子转移能力的影响的更深入的认识。
• Increasing the Activity of Copper Guanidine Quinoline Catalysts: Substitution at the Quinoline Backbone Leads to Highly Active Complexes for ATRP
  作者：Konstantin W. Kröckert、Johannes S. Mannsperger、Thomas Rösener、Alexander Hoffmann、Sonja Herres‐Pawlis

  DOI：10.1002/zaac.202000461

  日期：2021.4.26

  to increase the solubility in apolar monomers like styrene. CuI and CuII bromide complexes were crystallised and the structural data correlated to the different substituents and the catalyst activity. The electrochemical potentials E1/2, the equilibrium constants KATRP and rate constants kact and kdeact were determined. Polymerizations of styrene were conducted in solution whereas the catalyst based

  研究了溴化铜与配体TMG6NO 2 qu，TMG6Brqu，TMG6Methoxyqu，TMG6NMe 2 qu，TMG6EHOqu和TMG6dBAqu的配合物在原子转移自由基聚合（ATRP）中的活性。配体受1,1,3,3-四甲基-2-（喹啉-8-基）胍（TMGqu）的启发，并且取代基的选择范围介于吸电子能力和供电能力之间。可以极大地影响配体的供体性质，并且可以基于这些体系获得进一步的高活性催化剂。此外，具有强供体基团的配体还通过烷基进行了改性，以增加其在非极性单体（如苯乙烯）中的溶解度。铜I和铜II溴化物配合物结晶，结构数据与不同的取代基和催化剂活性相关。确定电化学势E 1/2，平衡常数K ATRP和速率常数k act和k deact。苯乙烯的聚合是在溶液中进行的，而基于TMG6EHOqu的催化剂显示出良好的溶解性和整体性能。
• Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression
  申请人：American Home Products Corporation

  公开号：US20020045628A1

  公开（公告）日：2002-04-18

  Compounds are provided which are useful for the treatment of serotonin-affected neurological disorders which comprise 1 Wherein: R 1 , R 2 and R 3 are each, independently, hydrogen, halogen, CF 3 , alkyl, alkoxy, MeSO 2 , or together can form a 5-7 membered carbocyclic or heterocyclic ring; R 4 is hydrogen, halogen, or alkyl; R 5 is hydrogen, alkyl, alkylaryl, or aryl; R 6 is hydrogen, halogen, CF 3 , CN, carbamide, or alkoxy; X 1 , X 2 and X 3 are each carbon or one of X 1 , X 2 or X 3 may be nitrogen; Y is carbon or nitrogen; and Z is carbon or nitrogen; or pharmaceutically acceptable salts thereof;

  提供了化合物，用于治疗受血清素影响的神经系统疾病，其中包括：1。其中：R1、R2和R3各自独立地为氢、卤素、CF3、烷基、烷氧基、MeSO2，或共同形成5-7个成员的碳环或杂环；R4为氢、卤素或烷基；R5为氢、烷基、烷基芳基或芳基；R6为氢、卤素、 、CN、碳酰胺或烷氧基；X1、X2和X3各自为碳或其中一个为氮；Y为碳或氮；Z为碳或氮；或其药物可接受的盐。