Synthesis, structural reassignment, and biological activity of type B MAO inhibitors based on the 5H-indeno[1,2-c]pyridazin-5-one core

被引：34

作者：

Frederick, Raphael

Dumont, Willy

Ooms, Frederic

Aschenbach, Lindsey

van der Schyf, Cornelis J.

Castagnoli, Neal

Wouters, Johan

Krief, Alain ^{[1
]}

机构：

[1] Fac Univ Notre Dame Paix, Lab Chim Organ Synth, COS, B-5000 Namur, Belgium

[2] Fac Univ Notre Dame Paix, Drug Design & Discovery Ctr, Lab Chim Biol Struct, B-5000 Namur, Belgium

[3] Fac Univ Notre Dame Paix, Drug Design & Discovery Ctr, Dept Pharm, B-5000 Namur, Belgium

[4] Virginia Tech, Dept Chem, Blacksburg, VA 24061 USA

[5] Texas Tech Univ, Hlth Sci Ctr, Dept Pharmaceut Sci, Amarillo, TX 79106 USA

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2006年 / 49卷 / 12期

关键词：

D O I：

10.1021/jm051091j

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis and enzyme inhibitor properties of reversible type B monoamine oxidase inhibitors are described. These compounds belong to the 5H-indeno[ 1,2-c] pyridazine family and possess a hydrophobic benzyloxy or 4,4,4-trifluorobutoxy side chain which, in contrast to a previous assignment, has been unambiguously located at C( 8) of the heterocyclic moiety. Investigation of the regioisomeric structures establishes that substitution of the 5H-indeno[ 1,2-c] pyridazin-5-one core at C( 7) vs C( 8) dramatically influences the MAO-inhibiting properties of these compounds.

引用

收藏

页码：3743 / 3747

页数：5

相关论文

共 50 条

[41] Synthesis and biological activity of new imidazo [1,2-c]pyrimidin-5(6H)-one, imidazo [2,1-b]purin-4(5H)-one and imidazo [2,1-i]purine as antioxidant and antibacterial agents [J].

Boukhallout, Fath Eddine ;

Dehamchia, Mohamed ;

Bayou, Samir ;

Adaika, Chaima ;

Mohammed, Abdelhafeez M. A. ;

Regainia, Zine .

INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 34 (03) :421-430

[42] CYCLIZATION REACTIONS OF 1,2-BIS(2-CYANOPHENYL)PROPIONITRILES .2. SYNTHESIS OF 5-AMINO-4,7-DIMETHOXY-11H-INDENO[1,2-C]ISOQUINOLIN-11-ONE [J].

ANDO, K ;

TOKOROYA.T ;

KUBOTA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1974, 47 (04) :1014-1017

[43] Design, synthesis and biological evaluation of novel selective thiol-based histone deacetylase(HDAC) VI inhibitors bearing indeno[1,2-c]pyrazole or benzoindazole scaffold [J].

Qihao Xu ;

Shujia Yu ;

Yijun Cai ;

Jinyu Yang ;

Linxiang Zhao ;

Dan Liu .

Chemical Research in Chinese Universities, 2018, 34 :75-83

[44] Synthesis and biological evaluation of benzo[4,5]imidazo[1,2-c] pyrimidine and benzo[4,5]imidazo[1,2-a]pyrazine derivatives as anaplastic lymphoma kinase inhibitors [J].

Tardy, Sebastien ;

Orsato, Alexandre ;

Mologni, Luca ;

Bisson, William H. ;

Donadoni, Carla ;

Gambacorti-Passerini, Carlo ;

Scapozza, Leonardo ;

Gueyrard, David ;

Goekjian, Peter G. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (04) :1303-1312

[45] Imidazo[1,2-c]pyrimidin-5(6H)-one inhibitors of CDK2: Synthesis, kinase inhibition and co-crystal structure [J].

Jansa, Josef ;

Jorda, Radek ;

Skerlova, Jana ;

Pachl, Petr ;

Perina, Miroslav ;

Reznickova, Eva ;

Heger, Tomas ;

Gucky, Tomas ;

Rezacova, Pavlina ;

Lycka, Antonin ;

Krystof, Vladimir .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2021, 216

[46] Design, Synthesis, and Biological Activity of Novel Octahydro-1H-pyrrolo[3,2-c]pyridine Derivatives as C-C Chemokine Receptor Type 5 (CCR5) Antagonists [J].

Wang, Yujie ;

Halambage, Upul ;

Zeng, Chengchu ;

Hu, Liming .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (09) :2385-2391

[47] p-TSA-catalyzed one-pot synthesis and docking studies of some 5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives as anticonvulsant agents [J].

Ahmed, Kamaal ;

Dubey, Balkrishna ;

Nadeem, Sayyed ;

Shrivastava, Birendra ;

Sharma, Pankaj .

CHINESE CHEMICAL LETTERS, 2016, 27 (05) :721-725

[48] p-TSA-catalyzed one-pot synthesis and docking studies of some 5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives as anticonvulsant agents [J].

Kamaal Ahmed ;

Balkrishna Dubey ;

Sayyed Nadeem ;

Birendra Shrivastava ;

Pankaj Sharma .

Chinese Chemical Letters, 2016, 27 (05) :721-725

[49] SYNTHESIS OF PYRROLO[1,2-C]IMIDAZOL-5-ONE, PYRROLO[1,2-A]IMIDAZOL-5-ONE AND PYRROLO[1,2-B]PYRAZOL-6-ONE (3 ISOMERIC AZAPYRROLIZINONES), BY PYROLYSIS OF MELDRUMS ACID-DERIVATIVES [J].

MCNAB, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (03) :653-656

[50] CARDIOTONIC AGENTS .4. SYNTHESIS AND BIOLOGICAL EVALUATION OF N-SUBSTITUTED 2,4,4A,5-TETRAHYDRO-3H-INDENO[1,2-C]PYRIDAZIN-3-ONES - RIGID STRUCTURES DERIVED FROM CI-930 AND ANALOGS [J].

SIRCAR, I ;

DUELL, BL ;

CAIN, MH ;

BURKE, SE ;

BRISTOL, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2142-2148

← 1 2 3 4 5 →