2-甲氧基-3-喹啉羧酸 | 70659-29-9

• 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
• 中文名称: 2-甲氧基-3-喹啉羧酸
• 英文名称: 2-methoxyquinoline-3-carboxylic acid
• CAS: 70659-29-9
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: SWFGCMGJIYVJFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲氧基-3-喹啉羧酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of Triketone–Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

  摘要：

  4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is one of the most important targets for herbicide discovery. In the search for new HPPD inhibitors with novel scaffolds, triketone-quinoline hybrids were designed and subsequently optimized on the basis of the structure -activity relationship (SAR) studies. Most of the synthesized compounds displayed potent inhibition of Arabidopsis thaliana HPPD (AtHPPD), and some of them exhibited broad-spectrum and promising herbicidal activity at the rate of 150 g ai/ha by postemergence application. Most promisingly, compound III-1, 3-hydroxy-2-(2-methoxy-7-(methylthio)quinoline-3-carbonyl)cyclohex-2-enone (K-i = 0.009 mu M, AtHPPD), had broader spectrum of weed control than mesotrione. Furthermore, compound III-1 was much safer to maize at the rate of 150 g ai/ha than mesotrione, demonstrating its great potential as herbicide for weed control in maize fields. Therefore, triketone-quinoline hybrids may serve as new lead structures for novel herbicide discovery.

  DOI：

  10.1021/acs.jafc.5b01530
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium methylate 作用下， 生成 2-甲氧基-3-喹啉羧酸
  参考文献：
  名称：

  Meyer,H., Monatshefte fur Chemie, 1907, vol. 28, p. 38

  摘要：

  DOI：

文献信息

• [EN] COMPOUNDS FOR USE IN THE TREATMENT OF KINETOPLASTID INFECTION<br/>[FR] COMPOSÉS UTILISÉS POUR TRAITER UNE INFECTION CINÉTOPLASTIDE
  申请人：IRBM SCIENCE PARK S P A

  公开号：WO2018115275A1

  公开（公告）日：2018-06-28

  The present invention relates to a class of novel heterocyclic compounds, to pharmaceutical compositions comprising the compounds and their use in the treatment of kinetoplastid infections.

  本发明涉及一类新颖的杂环化合物，以及包含这些化合物的药物组合物及其在治疗运动毛虫感染中的用途。
• Discovery of Highly Selective and Potent HDAC3 Inhibitors Based on a 2-Substituted Benzamide Zinc Binding Group
  作者：Jian Liu、Younong Yu、Joseph Kelly、Deyou Sha、Abdul-Basit Alhassan、Wensheng Yu、Milana M. Maletic、Joseph L. Duffy、Daniel J. Klein、M. Katharine Holloway、Steve Carroll、Bonnie J. Howell、Richard J. O. Barnard、Scott Wolkenberg、Joseph A. Kozlowski

  DOI：10.1021/acsmedchemlett.0c00462

  日期：2020.12.10

  selectivity of histone deacetylase inhibitors (HDACis) is greatly impacted by the zinc binding groups. In an effort to search for novel zinc binding groups, we applied a parallel medicinal chemistry (PMC) strategy to quickly synthesize substituted benzamide libraries. We discovered a series containing 2-substituted benzamides as the zinc binding group which afforded highly selective and potent HDAC3 inhibitors

  组蛋白去乙酰化酶抑制剂 (HDACis) 的选择性受锌结合基团的影响很大。为了寻找新的锌结合基团，我们应用平行药物化学 (PMC) 策略快速合成取代的苯甲酰胺文库。我们发现了一系列含有 2-取代苯甲酰胺作为锌结合基团的系列，它们提供了高度选择性和有效的 HDAC3 抑制剂，例如具有 2-甲硫基苯甲酰胺的化合物16。化合物16抑制 HDAC3 的 IC 50为 30 nM，并且比所有其他 HDAC 同种型具有 >300 倍的前所未有的选择性。有趣的是，2-甲硫的微妙的变化，以在一个2-羟基苯甲酰胺20保留 HDAC3 效力，但失去了对 HDAC 1 和 2 的所有选择性。这种选择性的显着差异是由 HDACis 16和20与 HDAC2 结合的 X 射线晶体结构合理化的，揭示了对催化锌离子的不同结合模式。这一系列 HDAC3 选择性抑制剂用作工具化合物，用于研究在 Jurkat 2C4 细胞模型中为
• Cannizzaro reaction of 2-chloro-3-formylquinolines and its synthetic utility for 2-acetylfuro[2,3-b]quinolines: The alkaloid analogues
  作者：DEVADOSS KARTHIK KUMAR、RAJAKANDHAN SHANKAR、SUBRAMANIAM PARAMESWARAN RAJENDRAN

  DOI：10.1007/s12039-012-0297-2

  日期：2012.9

  Cannizzaro reaction of 2-chloro-3-formylquinolines was investigated under two different conditions. Under both conditions, redox and methoxylation proceeded simultaneously and gave 2-methoxy-3-formylquinolines, 2-methoxyquinolin-3-yl-methanols and 2-methoxyquinoline-3-carboxylic acids. The synthesized 2-methoxy-3-formylquinolines were then condensed with acetone in the presence of sulphuric acid to give 4-(2-methoxy-quinolin-3-yl)-but-3-en-2-ones which in turn were bromocyclized and dehydrobrominated to get 2-acetylfuro[2,3-b]quinolines.

  在两种不同条件下研究了 2-氯-3-甲酰基喹啉的 Cannizzaro 反应。在这两种条件下，氧化还原和甲氧基化反应同时进行，生成了 2-甲氧基-3-甲酰基喹啉、2-甲氧基喹啉-3-基甲醇和 2-甲氧基喹啉-3-羧酸。合成的 2-甲氧基-3-甲酰基喹啉随后在硫酸存在下与丙酮缩合，得到 4-（2-甲氧基-喹啉-3-基）-丁-3-烯-2-酮，再将其溴化和脱氢溴化，得到 2-乙酰基呋喃并[2,3-b]喹啉。
• [EN] COMPOUNDS FOR USE IN THE TREATMENT OF DISORDERS THAT ARE AMELIORATED BY INHIBITION OF HDAC<br/>[FR] COMPOSÉS POUR L'UTILISATION DANS LE TRAITEMENT DE TROUBLES QUI SONT AMÉLIORÉS PAR L'INHIBITION DE HDAC
  申请人：IRBM SCIENCE PARK S P A

  公开号：WO2014023754A1

  公开（公告）日：2014-02-13

  The present invention relates to compounds of formula (I) and (IV), and pharmaceutically acceptable salts, tautomers, stereoisomers thereof, which are inhibitors of histone deacetylase (HDAC). The compounds of the present invention are for usein the treatment of disorders that are ameliorated by inhibition of HDACsuch ascancer and hemoglobinopathieslike β-thalassemia or sickle cell anemia.

  本发明涉及式(I)和(IV)的化合物，以及其药用盐、互变异构体、立体异构体，它们是组蛋白去乙酰化酶（HDAC）的抑制剂。本发明的化合物用于治疗通过抑制HDAC得到改善的疾病，如癌症和血红蛋白病，如β-地中海贫血或镰状细胞贫血。
• [EN] INHIBITORS OF NF-KB<br/>[FR] INHIBITEURS DU FACTEUR NF-KB
  申请人：PROFECTUS BIOSCIENCES INC

  公开号：WO2010111460A1

  公开（公告）日：2010-09-30

  The invention relates to compounds of formulae (1) and (2), and pharmaceutically acceptable salts thereof for the treatment of cancer, inflammation, auto-immune diseases, diabetes and diabetic complications, infection, cardiovascular disease and ischemia-reperfusion injuries.

  该发明涉及式（1）和式（2）的化合物，以及其药学上可接受的盐，用于治疗癌症、炎症、自身免疫性疾病、糖尿病和糖尿病并发症、感染、心血管疾病和缺血再灌注损伤。