Efficient synthesis of a new compound family, 9-aryl-5H-imidazo [2,1-d][1,2,5]triazepin-6(7H)-ones

被引:11
作者
Foldesi, Tamas [1 ]
Dancso, Andras [1 ]
Simig, Gyula [1 ]
Volk, Balazs [1 ]
Milen, Matyas [1 ]
机构
[1] Egis Pharmaceut Plc, Directorate Drug Subst Dev, POB 100, H-1475 Budapest, Hungary
关键词
Nitrogen heterocycles; Selectivity; Ring closure; Benzodiazepines; Isosteres; AMPA RECEPTOR ANTAGONISTS; ANTICONVULSANT ACTIVITY;
D O I
10.1016/j.tet.2016.07.029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Representatives of a new compound family, 9-aryl-5H-imidazo[2,1-d][1,2,5]triazepin-6(7H)-ones have been synthesized. As structural analogues of biologically active 1-aryl-2,3-benzodiazepine-4-ones, these compounds are potential drug candidates in the diseases of the central nervous system. An efficient five step synthesis starting from imidazole is described here for the preparation of the target compounds. Shorter routes have also been studied, however, these attempts failed. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5427 / 5432
页数:6
相关论文
共 25 条
[1]  
Andrasi F, 1995, US Pat, Patent No. [US 5459137, 5459137]
[2]  
BASTIAANSEN LAM, 1978, SYNTHESIS-STUTTGART, P675
[3]   1-aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: Novel AMPA receptor antagonists [J].
Chimirri, A ;
DeSarro, G ;
DeSarro, A ;
Gitto, R ;
Grasso, S ;
Quartarone, S ;
Zappala, M ;
Giusti, P ;
Libri, V ;
Constanti, A ;
Chapman, AG .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (08) :1258-1269
[4]   7,8-methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists [J].
De Sarro, A ;
De Sarro, G ;
Gitto, R ;
Grasso, S ;
Micale, N ;
Quartarone, S ;
Zappala, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (08) :971-976
[5]   A novel synthesis of imidazo[2,1-d][1,2,4]triazine and imidazo[2,1-d][1,2,5]triazepine derivatives via ketene-N,N-acetal [J].
ElSaghier, AMM ;
Maihub, AA ;
AlShirayda, HA .
SYNTHETIC COMMUNICATIONS, 1997, 27 (14) :2433-2444
[6]  
Foye W.O.L.T.L.W.D.A., 2013, Foye's principles of medicinal chemistry
[7]   Synthesis and anticonvulsant activity of novel and potent 1-aryl-7,8-methylenedioxy-1,2,3,5-tetrahydro-4H-2,3-benzodiazepin-4-ones [J].
Grasso, S ;
De Sarro, G ;
De Sarro, A ;
Micale, N ;
Polimeni, S ;
Zappalà, M ;
Puia, G ;
Baraldi, M ;
De Micheli, C .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (04) :463-466
[8]   Synthesis and anticonvulsant activity of novel and potent 2,3-benzodiazepine AMPA/kainate receptor antagonists [J].
Grasso, S ;
De Sarro, G ;
De Sarro, A ;
Micale, N ;
Zappalà, M ;
Puia, G ;
Baraldi, M ;
De Micheli, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) :4414-4421
[9]   A NOVEL SPECIFIC BINDING-SITE FOR HOMOPHTHALAZINES IN THE RAT-BRAIN [J].
HORVATH, EJ ;
HUDAK, J ;
PALKOVITS, M ;
LENKEI, Z ;
FEKETE, MIK ;
ARANYI, P .
EUROPEAN JOURNAL OF PHARMACOLOGY, 1993, 236 (01) :151-153
[10]  
HORVATH K, 1989, ARZNEIMITTELFORSCH, V39-2, P894