Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl) carbonylamino] alkanoates and methyl 2-[2-(4,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-ypcarbonyl-amino)alkanamido] alkanoate

被引：0
作者：
Fathalla, Walid [1 ]
Pazdera, Pavel [2 ]
机构：
[1] Port Said Univ, Phys & Math Engn Dept, Fac Engn, Port Said, Egypt
[2] Masaryk Univ, Ctr Syntheses Sustainable Condit & Their Manageme, Fac Sci, Brno, Czech Republic
来源：
ARKIVOC | 2017年
关键词：
Amino acid esters; DCC coupling method; azide coupling method; direct amino acid condensation; anisotropy; intramolecular hydrogen bond interactions; linomide; MULTIPLE-SCLEROSIS; DERIVATIVES; QUINOLINE; LINOMIDE;
D O I：
10.3998/ark.5550190.p009.946
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates 7a-f has been developed by the direct condensation of ethyl [4-hydroxy-2-oxo-1-phenyl-1,2-dihydro-3-quinoline] carboxylate 4 with amino acid ester hydrochloride in the presence of triethylamine. The quinoline amino acid esters 7a-f were the key intermediate for the preparation of a series of methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino)alkanamido] alkanoate 10-13(a-f) via azide coupling method with amino acid ester. [GRAPHICS]
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收藏
页码：158 / 173
页数：16
相关论文
共 20 条
  • [1] Synthesis of novel 4-substituted-7-trifluoromethylquinoline derivatives with nitric oxide releasing properties and their evaluation as analgesic and anti-inflammatory agents
    Abadi, AH
    Hegazy, GH
    El-Zaher, AA
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (20) : 5759 - 5765
  • [2] Synthesis and antimalarial evaluation of novel pyridine quinoline hybrids
    Acharya, Badri Narayan
    Thavaselvam, D.
    Kaushik, Mahabir Parshad
    [J]. MEDICINAL CHEMISTRY RESEARCH, 2008, 17 (08) : 487 - 494
  • [3] Allen CFH, 1939, ORG SYNTH, V19, P6
  • [4] Linomide reduces the rate of active lesions in relapsing-remitting multiple sclerosis
    Andersen, O
    Lycke, J
    Tollesson, PO
    Svenningsson, A
    Runmarker, B
    Linde, AS
    Astrom, M
    Gjorstrup, P
    Ekholm, S
    [J]. NEUROLOGY, 1996, 47 (04) : 895 - 900
  • [5] Studies on disease-modifying antirheumatic drugs: Synthesis of novel quinoline and quinazoline derivatives and their anti-inflammatory effect
    Baba, A
    Kawamura, N
    Makino, H
    Ohta, Y
    Taketomi, S
    Sohda, T
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (26) : 5176 - 5182
  • [6] CHEMISTRY OF 2H-3,1-BENZOXAZINE-2,4(1H)DIONE (ISATOIC ANHYDRIDE) .7. REACTIONS WITH ANIONS OF ACTIVE METHYLENES TO FORM QUINOLINES
    COPPOLA, GM
    HARDTMANN, GE
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (08) : 1605 - 1610
  • [7] Emami S., 2010, Iranian Journal of Pharmaceutical Research, P123, DOI [10.22037/IJPR.2010.628, DOI 10.22037/IJPR.2010.628, 10.22037/ijpr.2010.628]
  • [8] Gootz TD, 1998, QUINOLONES, 2ND EDITION, P29
  • [9] Novel Tacrine-8-Hydroxyquinoline Hybrids as Multifunctional Agents for the Treatment of Alzheimer's Disease, with Neuroprotective, Cholinergic, Antioxidant, and Copper-Complexing Properties
    Isabel Fernandez-Bachiller, Maria
    Perez, Concepcion
    Gonzalez-Munoz, Gema C.
    Conde, Santiago
    Lopez, Manuela G.
    Villarroya, Mercedes
    Garcia, Antonio G.
    Isabel Rodriguez-Franco, Maria
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (13) : 4927 - 4937
  • [10] Jones G., 2008, CHEM HETEROCYCLIC 1, V32
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