Synthesis of new series of quinoxaline based MAO-inhibitors and docking studies

被引：45

作者：

Khattab, Sherine N. ^{[1
]}

Hassan, Seham Y. ^{[1
]}

Bekhit, Adnan A. ^{[2
]}

El Massry, Abdel Moneim ^{[1
]}

Langer, Vratislav ^{[3
]}

Amer, Adel ^{[1
]}

机构：

[1] Univ Alexandria, Fac Sci, Dept Chem, Alexandria, Egypt

[2] Univ Alexandria, Fac Pharm, Dept Pharmaceut Chem, Alexandria 21521, Egypt

[3] Chalmers Univ, Dept Chem & Biol Engn, SE-41296 Gothenburg, Sweden

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2010年 / 45卷 / 10期

关键词：

Quinoxalines; 1,2,4]Tnazolo[4,3-a]quinoxalines; Oxidation; Oxidative cyclization; Monoamine oxidase inhibitors; MONOAMINE-OXIDASE; AMINO-ACIDS; DERIVATIVES;

D O I：

10.1016/j.ejmech.2010.07.008

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of 2-benzy1-3-(2-arylidenehydrazinyl)quinoxalines 3, 4-benzyl-1-aryl-(1,2,4]triazolo[4,3-a]quinoxalines 4 and phenyl(1-aryl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)methanones 5 analogues were synthesized and investigated for their monoamine oxidase (MAO) inhibitory property. The inhibition profile was found to be competitive for compounds 3k, 3m, 5f and 5n with MAO-A selectivity Observation of the docked positions of these compounds revealed interactions with many residues previously reported to have an effect on the inhibition of the enzyme. The structural features of the new compounds have been determined from the microanalytical, IR, (1)H, (13)C NMR spectral studies and X-ray crystalography. (C) 2010 Elsevier Masson SAS. All rights reserved

引用

页码：4479 / 4489

页数：11

共 20 条

[1]

Amer A., 1997, 16 INT C HET CHEM PO

[2] MONOAMINE-OXIDASE INHIBITORS AND THE CHEESE EFFECT [J].

ANDERSON, MC ;

HASAN, F ;

MCCRODDEN, JM ;

TIPTON, KF .

NEUROCHEMICAL RESEARCH, 1993, 18 (11) :1145-1149

[3]

[Anonymous], Molecular Operating Environment (MOE)

[4]

BASFORD RE, 1967, METHOD ENZYMOL, V10, P96

[5] Design and synthesis of some substituted 1H-pyrazolyl-oxazolidines or 1H-pyrazolyl-thiazolidines as anti-inflammatory-antimicrobial agents [J].

Bekhit, AA ;

Fahmy, HTY .

ARCHIV DER PHARMAZIE, 2003, 336 (02) :111-118

[6]

BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3

[7] A versatile synthetic route to chiral quinoxaline derivatives from amino acids precursors [J].

El-Faham A. ;

El Massry A.M. ;

Amer A. ;

Gohar Y.M. .

Letters in Peptide Science, 2002, 9 (1) :49-54

[8] Synthesis of 3-benzyl-2-substituted quinoxalines as novel monoamine oxidase A inhibitors [J].

Hassan, SY ;

Khattab, SN ;

Bekhit, AA ;

Amer, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (06) :1753-1756

[9] Interactions of nitrogen-containing xenobiotics with monoamine oxidase (MAO) isozymes A and B: SAR studies on MAO substrates and inhibitors [J].

Kalgutkar, AS ;

Dalvie, DK ;

Castagnoli, N ;

Taylor, TJ .

CHEMICAL RESEARCH IN TOXICOLOGY, 2001, 14 (09) :1139-1162

[10]

Keleci N. G., 2009, BIOORGAN MED CHEM, V17, P675

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