2-methoxy-8-nitroquinoline | 90771-32-7

• 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-methoxy-8-nitroquinoline
• CAS: 90771-32-7
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: RLQXMCGBGSCICR-UHFFFAOYSA-N

物化性质

• 沸点：
  336.3±27.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-8-nitroquinoline 在 盐酸 、 tin(ll) chloride 作用下， 生成 8-氨基-6-甲氧基喹啉
  参考文献：
  名称：

  DE486079

  摘要：

  公开号：
• 作为产物：
  描述：

  2-三氯甲基喹啉 在 硫酸 、 硝酸 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 2-methoxy-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

• Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study
  作者：Julien Pedron、Clotilde Boudot、Sébastien Hutter、Sandra Bourgeade-Delmas、Jean-Luc Stigliani、Alix Sournia-Saquet、Alain Moreau、Elisa Boutet-Robinet、Lucie Paloque、Emmanuelle Mothes、Michèle Laget、Laure Vendier、Geneviève Pratviel、Susan Wyllie、Alan Fairlamb、Nadine Azas、Bertrand Courtioux、Alexis Valentin、Pierre Verhaeghe

  DOI：10.1016/j.ejmech.2018.06.001

  日期：2018.7

  important shift of the redox potential (+0.3 V in comparison with 8-nitroquinoline). With the assistance of computational chemistry, a set of derivatives presenting a large range of redox potentials (from −1.1 to −0.45 V) was designed and provided a list of suitable molecules to be synthesized and tested. This approach highlighted that, in this series, only substrates with a redox potential above −0.6 V

  为了研究抗寄生虫8-硝基喹啉-2（1 H）-一药效基团，以1-5个步骤合成了一系列31种衍生物，并在体外针对婴儿利什曼原虫和布鲁氏锥虫进行了评估。。并行地，通过循环伏安法测量所有分子的还原电势。构效关系首先表明，抗菌活性取决于内酰胺官能团与硝基之间的分子内氢键（通过X射线衍射描述），这是氧化还原电势（+0.3 V与氧化还原电势相比重要的变化）的重要原因。 8-硝基喹啉）。在计算化学的帮助下，设计了一组表现出大范围氧化还原电势（从-1.1至-0.45 V）的衍生物，并提供了一系列适合合成和测试的分子。该方法强调了在该系列中，只有氧化还原电势高于-0.6 V的底物才对婴儿乳杆菌具有活性。。然而，在T中未观察到氧化还原电势与体外抗寄生虫活性之间的这种关系。b。布鲁西。化合物22是该系列中的一种新型命中化合物，对人类HepG2细胞系既显示出抗疟原虫活性又具有抗锥虫活性，并且具有较低的细胞毒性。化合物22被L
• Inhibitors of prenyl-protein transferase
  申请人：Merck & Co., Inc.

  公开号：US06441017B1

  公开（公告）日：2002-08-27

  The present invention is directed to macrocyclic compounds which inhibit prenyl-protein transferase (FTase) and the prenylation of the oncogene protein Ras. The invention is further directed to chemothera-peutic compositions containing the compounds of this invention and methods for inhibiting prenyl-protein transferase and the prenylation of the oncogene protein Ras.

  本发明涉及抑制萜基-蛋白转移酶（FTase）和致癌基因蛋白Ras的大环化合物。该发明还涉及含有本发明化合物的化疗组合物以及抑制萜基-蛋白转移酶和致癌基因蛋白Ras的方法。
• Structure–Activity Relationship of Anti-<i>Mycobacterium abscessus</i> Piperidine-4-carboxamides, a New Class of NBTI DNA Gyrase Inhibitors
  作者：Andreas Beuchel、Dina Robaa、Dereje A. Negatu、Abdeldjalil Madani、Nadine Alvarez、Matthew D. Zimmerman、Adrian Richter、Lea Mann、Sophie Hoenke、René Csuk、Thomas Dick、Peter Imming

  DOI：10.1021/acsmedchemlett.1c00549

  日期：2022.3.10

  evidence suggesting that P4Cs display a similar binding mode to DNA gyrase as gepotidacin. Gepotidacin is a member of the Novel Bacterial Topoisomerase Inhibitors (NBTIs), a new class of nonfluoroquinolone DNA gyrase poisons. Thus, our work suggests that P4Cs present a novel structural subclass of NBTI. We describe structure–activity relationship studies of 844 leading to analogues showing increased

  脓肿分枝杆菌会导致难以治愈的肺部感染。该细菌对大多数抗感染药物具有耐药性，包括一线抗结核（抗结核）药物。MMV688844 ( 844 ) 是一种哌啶-4-甲酰胺 (P4C)，对脓肿分枝杆菌具有杀菌特性。我们最近将 DNA 促旋酶鉴定为844的分子靶标。在这里，我们展示了计算机对接和遗传证据表明 P4C 与 DNA 促旋酶显示出与 gepotidacin 相似的结合模式。Gepotidacin 是新型细菌拓扑异构酶抑制剂 (NBTI) 的成员，NBTI 是一类新的非氟喹诺酮类 DNA 促旋酶毒物。因此，我们的工作表明 P4Cs 是 NBTI 的一个新的结构子类。我们描述了844的结构-活性关系研究，导致类似物显示出增强的抗菌活性。测试了所选衍生物对重组脓肿分枝杆菌DNA 促旋酶的抑制活性。先导结构的进一步优化提高了小鼠血浆中的稳定性并提高了口服生物利用度。
• Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
  作者：Aleksandar R. Todorov、Santeri Aikonen、Mikko Muuronen、Juho Helaja

  DOI：10.1021/acs.orglett.9b01205

  日期：2019.5.17

  A photoreductive protocol utilizing [Ru(bpy)3]2+ photocatalyst, blue light LEDs, and ascorbic acid (AscH2) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH2, photocatalyst, and the nitro N-heteroaryl. The method

  已经开发出一种利用[Ru（bpy）3 ] 2+光催化剂，蓝光LED和抗坏血酸（AscH 2）的光还原方案，以将硝基N-杂芳基还原为相应的苯胺。根据实验和计算结果以及先前的研究，我们建议反应通过质子偶联的电子在AscH 2，光催化剂和硝基N-杂芳基之间转移而进行。该方法提供了一种绿色的催化程序，可以将例如4- / 8-硝基喹啉还原为相应的氨基喹啉，而后者是重要的抗疟疾药物中存在的亚结构。
• A Preparative and Preliminary Spectroscopic Study of Analogues of a Zinquin-Related Fluorophore
  作者：Marc C. Kimber、Jason P. Geue、Stephen F. Lincoln、A. David Ward、Edward R. T. Tiekink

  DOI：10.1071/ch01071

  日期：——

  The syntheses of the 4- and 5-methoxy isomers of 4-N-(6-methoxy-2-methyl-8-quinolyl)-4-methylbenzenesulfon-amide and of N-(2-methoxy-8-quinolyl)-4-methylbenzenesulfonamide are described. The 6-methoxy compound is a precursor of Zinquin ester, a specific fluorophore for Zn(II). The 2-methoxy analogue was synthesized by nitration of 2-chloroquinoline and subsequent functional group manipulation. The 4-methoxy isomer was synthesized from a 4-quinolone derivative, and the 5-methoxy isomer was synthesized by a standard Skraup quinoline synthesis. The structures of the 4- and 5-methoxy isomers were determined by single-crystal X-ray analysis. All of these compounds showed a bathochromic shift in their ultraviolet/visible spectra upon addition of Zn(II) to the solution. These compounds are all weakly or non-fluorescent in solution. All form fluorescent complexes with Zn(II) except the 5-methoxy compound. The 4-methoxy compound forms a significantly more fluorescent complex than those of the 6-methoxy compound and Zinquin ester and has a higher quantum yield than the others.

  介绍了 4-N-(6-甲氧基-2-甲基-8-喹啉基)-4-甲基苯磺酰胺和 N-(2-甲氧基-8-喹啉基)-4-甲基苯磺酰胺的 4-和 5-甲氧基异构体的合成。6- 甲氧基化合物是 Zinquin 酯的前体，是 Zn（II）的特异性荧光团。2-甲氧基类似物是通过 2-氯喹啉的硝化和随后的官能团操作合成的。4-甲氧基异构体是由 4-喹啉酮衍生物合成的，而 5-甲氧基异构体则是通过标准的 Skraup 喹啉合成法合成的。4- 和 5-甲氧基异构体的结构是通过单晶 X 射线分析确定的。在溶液中加入 Zn（II）后，所有这些化合物的紫外/可见光谱都出现了浴色偏移。这些化合物在溶液中都是弱荧光或无荧光。除 5-甲氧基化合物外，所有化合物都会与 Zn（II）形成荧光络合物。与 6-甲氧基化合物和锌喹酯相比，4-甲氧基化合物形成的荧光络合物明显更强，量子产率也更高。