5-Methylquinoline-2,4-diol

• 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: 5-Methylquinoline-2,4-diol
• 英文别名: 4-hydroxy-5-methyl-1H-quinolin-2-one
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: NACCMJCNDXXODO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Methylquinoline-2,4-diol 在 三氯氧磷 作用下， 生成 2,4-二氯-5-甲基喹啉
  参考文献：
  名称：

  5-氨基吡唑并喹诺酮的简便合成

  摘要：

  在三乙胺催化下，4-肼基喹啉-2-酮衍生物与2-(1-乙氧基取代烯)丙二腈在乙醇中一起回流，得到5-氨基-3-取代-1-(取代-2-氧代) -1,2-二氢喹啉-4-基)-1H-吡唑-4-甲腈。使用1 H NMR、13 C NMR 谱以及 HRMS阐明了产物的结构。二维核磁共振波谱也用于区分指定的结构与其他可能的环系统和区域异构体。讨论了目标化合物形成的合理机制。 图形概要

  DOI：

  10.1007/s00706-023-03112-0
• 作为产物：
  描述：

  (2-methyl-6-nitro-benzoyl)-malonic acid diethyl ester 在 磷化氢 、 氢碘酸 作用下， 生成 5-Methylquinoline-2,4-diol
  参考文献：
  名称：

  Gabriel; Thieme, Chemische Berichte, 1919, vol. 52, p. 1083

  摘要：

  DOI：

文献信息

• Inhibitors of macrophage migration inhibitory factor and methods for identifying the same
  申请人：——

  公开号：US20030195194A1

  公开（公告）日：2003-10-16

  Inhibitors of MIF are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: 1 including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R 1 , R 2 , R 3 , R 4 , X, Y and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

  提供了MIF的抑制剂，对治疗各种疾病具有实用性，包括与MIF活性相关的病理条件的治疗。MIF的抑制剂具有以下结构：包括立体异构体、前药和其药用盐，其中n、R1、R2、R3、R4、X、Y和Z如本文所定义。还提供了含有MIF抑制剂的组合物，与药用载体结合，以及使用方法。
• INHIBITORS OF MACROPHASE MIGRATION INHIBITORY FACTOR AND METHODS FOR IDENTIFYING THE SAME
  申请人：Gaeta C.A. Federico

  公开号：US20060094727A1

  公开（公告）日：2006-05-04

  Inhibitors of MIF are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R 1 , R 2 , R 3 , R 4 , X, Y and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

  提供了MIF抑制剂，其在治疗各种疾病方面具有用途，包括治疗与MIF活性相关的病理状况。MIF抑制剂具有以下结构：包括立体异构体，前药和其药学上可接受的盐，其中n，R1，R2，R3，R4，X，Y和Z如本文所定义。还提供了含有MIF抑制剂和药学上可接受的载体的组合物，以及使用它们的方法。
• INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR AND METHODS FOR IDENTIFYING THE SAME
  申请人：Gaeta C.A. Federico

  公开号：US20060194793A1

  公开（公告）日：2006-08-31

  Inhibitors of MIF are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R 1 , R 2 , R 3 , R 4 , X, Y and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

  提供了MIF抑制剂，具有治疗各种疾病的功效，包括治疗与MIF活性相关的病理条件。MIF抑制剂具有以下结构：包括立体异构体，前药和其药学上可接受的盐，其中n，R1，R2，R3，R4，X，Y和Z的定义如本文所述。同时还提供了含有MIF抑制剂和药学上可接受的载体的组合物，以及使用它们的方法。
• Inhibitors of macrophage migration inhibitory factor and methods for indentifying the same
  申请人：Gaeta C.A. Federice

  公开号：US20060235023A1

  公开（公告）日：2006-10-19

  Inhibitors of MIF are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R 1 , R 2 , R 3 , R 4 , X, Y and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

  提供了MIF的抑制剂，可用于治疗多种疾病，包括与MIF活性相关的病理条件的治疗。MIF的抑制剂具有以下结构：包括立体异构体、前药和其药学上可接受的盐，其中n、R1、R2、R3、R4、X、Y和Z的定义如本文所述。还提供了含有MIF抑制剂与药学上可接受的载体组合的组合物，以及使用它们的方法。
• Novel Pyrazoloquinolin-2-ones: Design, synthesis, docking studies, and biological evaluation as antiproliferative EGFR-TK inhibitors
  作者：Mohammed A.I. Elbastawesy、Ashraf A. Aly、Mohamed Ramadan、Yaseen A.M.M. Elshaier、Bahaa G.M. Youssif、Alan B. Brown、Gamal El-Din A Abuo-Rahma

  DOI：10.1016/j.bioorg.2019.103045

  日期：2019.9

  Two new series of diethyl 2-[2-(substituted-2-oxo-1,2-dihydroquinolin-4-yl)hydrazono]-succinates 6a-g and 1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazoles 7a-f have been designed and synthesized. The structures of the synthesized compounds were proved by IR, mass, NMR (2D) spectra and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, seven compounds were further examined against the most sensitive cell lines, leukemia CCRFCEM, and MOLT-4. 5-Amino-1-(6-bromo-2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazole-3,4-dicarbonitrile (7f) was the most active product, with IC50= 1.35 uM and 2.42 uM against MOLT-4 and CCRF-CEM, respectively. Also, it showed a remarkable inhibitory activity compared to erlotinib on the EGFR TK with IC50 = 247.14 nM and 208.42 nM, respectively. Cell cycle analysis of MOLT-4 cells treated with 7f showed cell cycle arrest at G2/M phase (supported by Caspases, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking study indicated that both the pyrazole moiety and the quinolin-2-one ring showed good fitting into EGFR (PDB code: 1M17). In order to interpret SAR of the designed compounds, and provide a basis for further optimization, molecular docking of the synthesized compounds to known EGFR inhibitors was performed. The study illustrated the effect of several factors on the compounds' activity.