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7-氟-4-氯-喹啉的合成 被引量:2

Synthesis of 7-fluoro 4-chloro-quinoline
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摘要 以间氟苯胺与乙氧基亚甲基丙二酸二乙酯(Diethyl ethoxymethylenemalonate,EMME)为起始原料,经缩合得2-[(3-氟-苯氨基)-亚甲基]-丙二酸二乙酯(化合物3),化合物3高温环合得7-氟-4-氧代喹啉-3-羧酸乙酯(化合物4),化合物4再经水解、脱羧、氯化3步反应,合成目标化合物7-氟-4-氯-喹啉(化合物7),总收率51.63%(以间氟苯胺计).目标化合物结构以IR、ESI-MS和1H-NMR确证. Abstract: 7-fluoro-4-chloro-quinoline was prepared from m-fluoroaniline and Diethyl ethoxymethylene- malonate (EMME) by the condensation, thermal cyclization, hydrolysis, decarboxylation, chlotination reac- tion with the yield of 51.63 %. The structure was confirmed by IR, ESI-MS and ^1H-NMR.
出处 《沈阳化工大学学报》 CAS 2014年第4期319-321,共3页 Journal of Shenyang University of Chemical Technology
基金 辽宁省教育厅科学研究一般项目(L2013171)
关键词 7-氟-4-氯-喹啉 间氟苯胺 Could-Jacobs反应 7-fluoro 4-chloro-quinoline m-fluoroaniline Could-Jacobs reaction
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参考文献10

  • 1刘靖,王林,杨晓明.多靶点蛋白酪氨酸激酶抑制剂的研究进展[J].国际药学研究杂志,2009,36(3):161-171. 被引量:22
  • 2Wissner A, Brawner Floyd M B, Rabindran S K, et al. Syntheses and EGFR and HER-2 Kinase Inhibito- ry Activities of 4-anilinoquinoline-3-carbonitri|es: Analogues of Three Important 4-anilinoquinazolines Currently Undergoing Clinical Evaluation as Thera- peutic Antitumor Agents [ J ]. Bioorg Med ChemLett. ,2002,12 ( 20 ) :2893 - 2897.
  • 3Erlichman C, Hidalgo M, Boni J P, et al. Phase I Study of EKB-569, an Irreversible Inhibitor of the Epidermal Growth Factor Receptor in Patients with Advanced Solid Tumors [ J ]. J Clin Oncol, 2006,24 (15) :2252 -2260.
  • 4Cao X, You Q D, Li Z Y, et al. Design and synthesis of 7-alkoxy-4-heteroaryl a mino-3-quinolinecarboni- triles as Dual Inhibitors of c-Src Kinase and Nitric Oxide Synthase [ J ]. Bioorg Med Chem, 2008, 16 ( 11 ) :5890 - 5898.
  • 5Pawar V G, Sos M L, Rode H B, et al. Synthesis and Biological Evaluation of 4-anilinoquinolines as Pro- tein Inhibitors Epidermal Growth Factor Receptor[J]. J. Med. Chem,2010,53 (7) :2892 -2901.
  • 6Snyder H R, Freier H E, Kovacic P, et al. Synthesis of 4-Hydroxyquinolines. V II1. Some Halogen Con- taining 4-a minoquinoline Derivatives [ J ]. J. Am. Chem. Soc. ,1947,69(2) :371 -374.
  • 7Atldns R J, Breen G F, Crawford L P, et al. Synthet- ic Routes to Quinoline Derivatives:Novel Syntheses of 3-Butyryl-8-methoxy-4-[ (2-methylphenyl) a mi- no ] quinoline and 3-Butyryl-8- ( 2-hydroxyethoxy ) - 4- [ (2-methylphenyl) a mino ] quinoline [ J ]. Org. Process Res. Dev. , 1997,1 (3) : 185 - 197.
  • 8曾令国,李勤耕,徐启贵,田睿.抗疟药中间体4,7-二氯喹啉的工艺研究[J].中南药学,2006,4(1):28-29. 被引量:7
  • 9刘宝,尤启冬,李志裕.3-氰基-7-喹啉酰胺衍生物的合成和生物活性研究[J].药学学报,2009,44(8):879-884. 被引量:7
  • 10张淑兰,祝丽君,刘文东,张立夏,饶志,温建,宫平.4-(甲基苯胺基)-3-氰基喹啉类衍生物的合成及抗肿瘤活性[J].中国药物化学杂志,2010,20(4):269-274. 被引量:7

二级参考文献62

  • 1Jimeno A,Hidalgo M.Multitargeted therapy:can promiscuity be praised in an era of political correctness?[J].Crit Rev Oncol Hematol,2006,59(2):150-158.
  • 2De Jonge MJ,Verweij J.Multiple targeted tyrosine kinase inhibition in the clinic:all for one or one for all?[J].Eur J Cancer,2006,42(10):1351-1356.
  • 3Keith CT,Borisy AA,Stockwell BR.Multicomponent therapeutics for networked systems[J].Nat Rev Drug Discov,2005,4(1):71-78.
  • 4Arora A,Scholar EM.Role of tyrosine kinase inhibitors in cancer therapy[J].J Pharmacol Exp Ther,2005,315(3):971-979.
  • 5Blume-Jensen P,Hunter T.Oncogenic kinase signalling[J].Nature,2001,411(6835):355-365.
  • 6Konecny GE,Pegram MD,Venkatesan N,et al.Activity of the dual kinase inhibitor lapatinib (GW572016) against HER-2-overexpressing and trastuzumab-treated breast cancer cells[J].Cancer Res,2006,66(3):1630-1639.
  • 7Burris HA,Hurwitz HI,Dees EC,et al.Phase Ⅰ safety,pharmacokinetics,and clinical activity study of lapatinib (GW572016),a reversible dual inhibitor of epidermal growth factor receptor tyrosine kinases,in heavily pretreated patients with metastatic carcinomas[J].J Clin Oncol,2005,23(23):5305-5313.
  • 8Hanrahan EO,Heymach JV.Vascular endothelial growth factor receptor tyrosine kinase inhibitors vandetanib (ZD6474) and AZD2171 in lung cancer[J].Clin Cancer Res,2007,13(15):4617-4622.
  • 9Arnold AM,Seymour L,Smylie M,et al.Phase Ⅱ study of vandetanib or placebo in small-cell lung cancer patients after complete or partial response to induction chemotherapy with or without radiation therapy:National Cancer Institute of Canada Clinical Trials Group Study BR.20[J].J Clin Oncol,2007,25(27):4278-4284.
  • 10Eskens FA,Mom CH,Planting AS,et al.A phase Ⅰ dose escalation study of BIBW 2992,an irreversible dual inhibitor of epidermal growth factor receptor 1 (EGFR) and 2 (HER2) tyrosine kinase in a 2-week on,2-week off schedule in patients with advanced solid tumours[J].Br J Cancer,2008,98(1):80-85.

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