喹啉-2-甲酰肼 | 5382-44-5

• 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: 喹啉-2-甲酰肼
• 中文别名: 喹啉-2-卡巴肼；2-喹啉甲酸,肼；2-喹啉卡巴肼
• 英文名称: quinoline-2-carboxylic acid hydrazide
• 英文别名: quinoline-2-carbohydrazide；Chinolin-2-carbonsaeure-hydrazid；2-quinoloyl hydrazide
• CAS: 5382-44-5
• 化学式: C₁₀H₉N₃O
• mdl: MFCD00614750
• 分子量: 187.201
• InChiKey: JTDPJYXDDYUJBS-UHFFFAOYSA-N

物化性质

• 溶解度：
  17.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 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：
  68
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P264,P270,P301+P312,P330,P501
• 危险性描述：
  H302
• 储存条件：
  存储条件：2-8°C，密封保存，并确保环境干燥。

反应信息

• 作为反应物：
  描述：

  喹啉-2-甲酰肼 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3-[(3-Chloroanilino)methyl]-5-quinolin-2-yl-1,3,4-oxadiazole-2-thione
  参考文献：
  名称：

  Synthesis, molecular modeling and biological evaluation of 2-aminomethyl-5-(quinolin-2-yl)-1,3,4-oxadiazole-2(3H)-thione quinolone derivatives as novel anticancer agent

  摘要：

  A series of quinoline derivatives (4a-4o) have been synthesized and their biological activities were also evaluated as potential telomerase inhibitors. Bioassay tests demonstrated that most of the compounds exhibited substantial broad-spectrum antitumor activity against the three cancer cell lines (HepG2, SGC-7901 and MCF-7). Moreover, all the title compounds were assayed for telomerase inhibition using the TRAP-PCR-ELISA assay. Compounds 4d and 4i displayed the most potent anticancer activities, which were comparable to the positive control. Docking simulation was performed to position compounds 4d and 4i into the telomerase structure active site to determine the probable binding model. Compounds 4d and 4i with potent inhibitory activity in tumor growth inhibition may be potential anticancer agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.039
• 作为产物：
  描述：

  喹醛酰氯 在 hydrazine hydrate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以63%的产率得到喹啉-2-甲酰肼
  参考文献：
  名称：

  基于喹啉席夫氏碱及其细胞成像的高选择性和高灵敏度的铝（III）开启探针。

  摘要：

  设计，合成和评估了基于喹啉衍生物的Al3 +（3,5-二氯-2-羟基亚苄基）喹啉-2-碳酰肼（QC）的可逆Schiff碱性荧光探针。通过与Al3 +形成1：1的络合物，QC对EtOH-H2O（v / v = 1：9，pH = 6）中的Al3 +具有高灵敏度和选择性，QC对Al3 +的检出限低至0.012μM 。此外，这些结果表明，QCAl3 +的结合被F-破坏，因此该系统将来可用于监测F-。QC的增强荧光可能归因于对PET和ESIPT的抑制以及Al3 +诱导的CHEF进程的紧急性。更重要的是，质控不仅成功地用于自来水和人血清中微量Al3 +的测定，

  DOI：

  10.1016/j.saa.2017.09.007

文献信息

• Stereoselective, solvent free, highly efficient synthesis of aldo- and keto-N-acylhydrazones applying grindstone chemistry
  作者：José Maurício dos Santos Filho、Savio Moita Pinheiro

  DOI：10.1039/c7gc00730b

  日期：——

  A mild and efficient synthesis of N-acylhydrazones has been developed, applying a simple grindstone procedure, leading to a library of 51 examples exhibiting a broad variety of structural features, 21 of them described for the first time in this paper. This methodology works without any organic solvent under the catalysis of acetic acid at room temperature, promotes the formation of essentially pure

  已经开发出了温和而有效的N-酰基hydr酮合成方法，该方法采用了简单的磨石程序，从而产生了51个实例，这些实例均显示出多种结构特征，其中21个实例首次在本文中进行了描述。该方法在室温下在乙酸催化下无需任何有机溶剂即可工作，可促进形成基本纯净的粗产物，并避免繁琐的后处理和有害溶剂的使用以及能耗。另外，如NMR分析所支持的，其导致N-酰基hydr的立体选择性形成。
• Dual-action inhibitors of HIF prolyl hydroxylases that induce binding of a second iron ion
  作者：Kar Kheng Yeoh、Mun Chiang Chan、Armin Thalhammer、Marina Demetriades、Rasheduzzaman Chowdhury、Ya-Min Tian、Ineke Stolze、Luke A. McNeill、Myung Kyu Lee、Esther C. Y. Woon、Mukram M. Mackeen、Akane Kawamura、Peter J. Ratcliffe、Jasmin Mecinović、Christopher J. Schofield

  DOI：10.1039/c2ob26648b

  日期：——

  Inhibition of the hypoxia-inducible factor (HIF) prolyl hydroxylases (PHD or EGLN enzymes) is of interest for the treatment of anemia and ischemia-related diseases. Most PHD inhibitors work by binding to the single ferrous ion and competing with 2-oxoglutarate (2OG) co-substrate for binding at the PHD active site. Non-specific iron chelators also inhibit the PHDs, both in vitro and in cells. We report the identification of dual action PHD inhibitors, which bind to the active site iron and also induce the binding of a second iron ion at the active site. Following analysis of small-molecule iron complexes and application of non-denaturing protein mass spectrometry to assess PHD2·iron·inhibitor stoichiometry, selected diacylhydrazines were identified as PHD2 inhibitors that induce the binding of a second iron ion. Some compounds were shown to inhibit the HIF hydroxylases in human hepatoma and renal carcinoma cell lines.

  翻译结果： 对缺氧诱导因子（HIF）脯氨酰羟化酶（PHD或EGLN酶）的抑制在治疗贫血和缺血相关疾病方面备受关注。大多数PHD抑制剂通过结合单个亚铁离子并与2-氧代戊二酸（2OG）共底物竞争结合PHD活性位点来发挥作用。非特异性铁螯合剂也能在体外和细胞内抑制PHD。我们报告了双作用PHD抑制剂的鉴定，这些抑制剂不仅与活性位点的铁结合，还能诱导在活性位点上结合第二个铁离子。通过对小分子铁络合物的分析并在非变性蛋白质谱法中评估PHD2·铁·抑制剂的比例后，鉴定出某些二酰基联氨为诱导第二个铁离子结合的PHD2抑制剂。有些化合物被证明能抑制人类肝癌和肾癌细胞系中的HIF羟化酶。
• 4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors
  作者：Laurent Gavara、Alice Legru、Federica Verdirosa、Laurent Sevaille、Lionel Nauton、Giuseppina Corsica、Paola Sandra Mercuri、Filomena Sannio、Georges Feller、Rémi Coulon、Filomena De Luca、Giulia Cerboni、Silvia Tanfoni、Giulia Chelini、Moreno Galleni、Jean-Denis Docquier、Jean-François Hernandez

  DOI：10.1016/j.bioorg.2021.105024

  日期：2021.8

  (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs

  在革兰氏阴性菌中，对 β-内酰胺类抗生素产生耐药性的主要机制是产生一种或多种 β-内酰胺酶 (BLs)，包括令人担忧的碳青霉烯酶。尽管这些酶的抑制剂最近上市，但它们仅针对丝氨酸-碳青霉烯酶（例如 KPC 型），尚无临床上有用的抑制剂来中和金属-β-内酰胺酶 (MBL) 类。我们正在开发基于 1,2,4-三唑-3-硫酮支架的化合物，该支架以原始方式与 MBL 的二锌催化位点结合，我们之前报道了其产生广谱抑制剂的潜力。然而，到目前为止，在微生物测定中只能观察到适度的抗生素增强作用，需要进一步探索以改善外膜渗透。这里，我们合成并表征了一系列在杂环的 4 位具有不同官能化烷基链的化合物。我们发现在烷基链末端存在羧基会产生有效的 VIM 型酶抑制剂K i值在 μM 到亚 μM 范围内，并且该烷基链必须更长或等于丙基链。该结果证实了羧基官能团对 1,2,4-三唑-3-硫酮杂环的 4-取代基的重要性。如
• Synthesis of Dihydrothienopyridine Derivatives Fused with Triazole Rings
  作者：Péter Ábrányi-Balogh、Mátyás Milen、András Dancsó、Dávid Frigyes、László Pongó、György Keglevich

  DOI：10.1002/hc.21087

  日期：2013.5

  New dihydro[3,2-c][1,2,4]triazolo[4,3-a]pyridines were synthesized by the reaction of 4-(methylsulfanyl)-6,7-dihydrothieno[3,2-c]pyridine with acid hydrazides. One bis(dihydrothienotriazolo-pyridine) was also prepared. In a few cases, the corresponding intermediate could be detected by LC-MS. The bromophenyl derivative was involved in Suzuki and Sonogashira cross-coupling reactions. © 2013 Wiley Periodicals

  4-(甲基硫烷基)-6,7-二氢噻吩并[3,2-c]吡啶反应合成了新型二氢[3,2-c][1,2,4]三唑并[4,3-a]吡啶与酸酰肼。还制备了一种双(二氢噻吩并三唑并吡啶)。在少数情况下，可以通过 LC-MS 检测到相应的中间体。溴苯基衍生物参与 Suzuki 和 Sonogashira 交叉偶联反应。© 2013 Wiley Periodicals, Inc. 杂原子化学 24:226–233, 2013; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.21087
• Design and Discovery of Novel Antifungal Quinoline Derivatives with Acylhydrazide as a Promising Pharmacophore
  作者：Yu-Dong Yang、Ying-Hui He、Kun-Yuan Ma、Hu Li、Zhi-Jun Zhang、Yu Sun、Yu-Ling Wang、Guan-Fang Hu、Ren-Xuan Wang、Ying-Qian Liu

  DOI：10.1021/acs.jafc.1c00670

  日期：2021.8.4

  were synthesized and evaluated for their fungicidal activity. Most of these compounds exhibited excellent fungicidal activity in vitro. Significantly, compound 2e displayed the superior in vitro antifungal activity against Sclerotinia sclerotiorum, Rhizoctonia solani, Botrytis cinerea, and Fusarium graminearum with the EC50 values of 0.39, 0.46, 0.19, and 0.18 μg/mL, respectively, and were more potent

  受天然 2-喹啉羧酸衍生物的启发，合成了一系列含有酰肼、酰腙、磺酰肼、恶二唑、噻二唑或三唑部分的喹啉化合物，并评估了它们的杀菌活性。大多数这些化合物在体外表现出极好的杀真菌活性。值得注意的是，化合物2e对核盘菌、立枯丝核菌、灰葡萄孢和禾谷镰刀菌显示出优异的体外抗真菌活性，EC 50值分别为 0.39、0.46、0.19 和 0.18 μg/mL，并且更有效。多菌灵（EC50，0.68，0.14，> 100，和0.65微克/毫升，分别地）。此外，化合物2e可以抑制禾谷镰刀菌的孢子萌发。初步机理研究表明，化合物2e可引起细胞壁和液泡形态异常、线粒体丢失、膜通透性增加和细胞内容物释放。这些结果表明，化合物2e表现出优异的杀真菌活性，可能是对抗植物真菌病害的潜在杀真菌候选物。

表征谱图