ethyl 6-(tert-butyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

• 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: ethyl 6-(tert-butyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
• 英文别名: ethyl 6-tert-butyl-4(1H)-quinolone-3-carboxylate；6-tert-Butyl-4-hydroxy-quinoline-3-carboxylic acid ethyl ester；ethyl 6-tert-butyl-4-oxo-1H-quinoline-3-carboxylate
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: XJTQOCCGSVWPFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 6-(tert-butyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 6-(tert-butyl)-N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 4-oxoquinoline-3-carboxamides derivatives as potent anti-fibrosis agents

  摘要：

  Thirty-one 4-oxoquinoline-3-carboxamides derivatives were synthesized and evaluated for their anti-fibrotic activities by the inhibition of TGF-beta 1-induced total collagen accumulation and anti-inflammatory activities by the inhibition of LPS-stimulated TNF-alpha production. Among them, three compounds (10a, 10l and 11g) exhibited potent inhibitory effects on both TGF-beta 1-induced total collagen accumulation and LPS-stimulated TNF-a production. Furthermore, oral administrations of 10l at a dose of 20 mg/kg/day for 4 weeks effectively alleviated lung inflammation and injury, and decreased lung collagen accumulation in bleomycin-induced pulmonary fibrosis model. Histopathological evaluation of lung tissue confirmed 10l as a potential, orally active agent for the treatment of pulmonary fibrosis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.071
• 作为产物：
  描述：

  以 二苯醚 为溶剂， 反应 1.5h， 生成 ethyl 6-(tert-butyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  4-HYDROXYQUINOLINE-3-CARBOXAMIDES AND HYDRAZIDES AS ANTIVIRAL AGENTS

  摘要：

  公开号：

  EP1042295B1

文献信息

• Chromanylurea compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor and uses thereof
  申请人：Gomtsyan Arthur

  公开号：US20060128689A1

  公开（公告）日：2006-06-15

  Compounds that are antagonists of the VR1 receptor, having formula (I) or a pharmaceutically acceptable salt, prodrug, or salt of a prodrug thereof, wherein A 1 , A 2 , A 3 , A 4 , R 7 , R 8 , R 9 , X, Y, Z, L, n, and m, are as defined herein, and are useful in disorders prevented or ameliorated by inhibiting the VR1 receptor.

  对VR1受体拮抗剂，其化学式为(I)或其药用可接受的盐、前药或前药的盐，其中A1、A2、A3、A4、R7、R8、R9、X、Y、Z、L、n和m的定义如本文所述，并且在通过抑制VR1受体预防或改善的疾病中具有用处。
• Conjugate Addition Routes to 2‐Alkyl‐2,3‐dihydroquinolin‐4(1 <i>H</i> )‐ones and 2‐Alkyl‐4‐hydroxy‐1,2‐dihydroquinoline‐3‐carboxylates
  作者：Alex Kingsbury、Steve Brough、Antonio Pedrina McCarthy、William Lewis、Simon Woodward

  DOI：10.1002/ejic.201901036

  日期：2020.3.27

  quinolin‐4(1H)‐ones to provide 2‐alkyl‐2,3‐dihydroquinolin‐4(1H)‐ones (14 examples, 54–99 % yield). Asymmetric versions require AlEt3 to Boc‐protected ethyl 6‐substituted 4(1H)‐quinolone‐3‐carboxylates (6‐R group = all halogens, n/i/t‐alkyls, CF3) and provide 61–91 % yield, 30–86 % ee; any halogen, Me, or CF3 provide the highest stereoselectivities (76–86 % ee). Additions of AlMe3 or Al(nC8H17)3 provide ≈ 45 and

  在CuBr · SMe2 / PPh3催化下（5/10 mol％）RMgCl（R = Me，Et，n Pr，CH = CH 2，n Bu，i Bu，n C 5 H 11，c C 6 H 11，Bn ，CH 2 Bn，n C 11 H 23）容易地（–78°C）对Cbz或Boc保护的喹啉-4（1 H）-酮进行1,4加成，从而提供2-烷基-2-3,2-二氢喹啉- 4（1 H）-1 （14例，产率54–99％）。非对称版本需要AlEt 3到Boc保护的乙基6取代的4（1 H）-喹诺酮-3-羧酸盐（6-R基团=所有卤素，n / i / t-烷基，CF 3），收率61-91％，ee 30-86％; 任何卤素，Me或CF 3均可提供最高的立体选择性（76–86％ee）。AlMe 3或Al（n C 8 H 17）3的添加在母体中的添加提供≈45和≈75％ee（6-R = H）。配体（S）‐（BINOL）P–N（CHPh
• 4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents
  申请人：Pharmacia & Upjohn Company

  公开号：US06093732A1

  公开（公告）日：2000-07-25

  The present invention provides 4-hydroxyquinoline-3-carboxamide and hydrazide compounds of formula I ##STR1## These compounds are useful to treat or prevent the herpesviral infections, particularly, human cytomegaloviral infection.

  本发明提供了式I的4-羟基喹啉-3-甲酰胺和肼化合物。这些化合物可用于治疗或预防疱疹病毒感染，特别是人类巨细胞病毒感染。
• CHROMANYLUREA COMPOUNDS THAT INHIBIT VANILLOID RECEPTOR SUBTYPE 1 (VR1) RECEPTOR AND USES THEREOF
  申请人：Gomtsyan Arthur

  公开号：US20110152250A1

  公开（公告）日：2011-06-23

  Compounds that are antagonists of the VR1 receptor, having formula (I) or a pharmaceutically acceptable salt, prodrug, or salt of a prodrug thereof, wherein A 1 , A 2 , A 3 , A 4 , R 7 , R 8 , R 9 , X, Y, Z, L, n, and m, are as defined herein, and are useful in disorders prevented or ameliorated by inhibiting the VR1 receptor.

  具有以下式子（I）或其药学上可接受的盐、前药或前药的盐的拮抗VR1受体的化合物，在其中A1、A2、A3、A4、R7、R8、R9、X、Y、Z、L、n和m如本文所定义，并且在抑制VR1受体有益于预防或改善疾病。
• US7812019B2
  申请人：——

  公开号：US7812019B2

  公开（公告）日：2010-10-12