Synthesis of 5-hydroxy- and 5-sulfanyl-substituted [1,2,3]triazolo[4,5-e][1,4]diazepines

被引:3
作者
Kemskiy, Sergiy V. [1 ]
Syrota, Natalia A. [2 ]
Bol'but, Andriy V. [1 ,3 ]
Dorokhov, Viktor I. [1 ]
Vovk, Mykhaylo V. [1 ]
机构
[1] Natl Acad Sci Ukraine, Inst Organ Chem, 5 Murmanska St, UA-02094 Kiev, Ukraine
[2] Natl Univ Kyiv Mohyla Acad, 2 Hryhoriya Skovorody St, UA-04655 Kiev, Ukraine
[3] Enamine Ltd, 78 Chervonotkatska St, UA-02094 Kiev, Ukraine
关键词
5-amino-N-(2,2-dimethoxyethyl)-1H-1,2,3-triazole-4-carboxamides; 1,2,3] triazolo[4,5-e][1,4] diazepines; intramolecular cyclization; thiofunctionalization; GUANASE; AZEPINOMYCIN; INHIBITORS; ANALOGS; ANESTHESIA;
D O I
10.1007/s10593-018-2350-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-Amino-N-(2,2-dimethoxyethyl)-1H-1,2,3-triazole-4-carboxamides in formic acid were subjected to intramolecular cyclization to 5-hydroxy[1,2,3] triazolo[4,5-e][1,4] diazepines, which were converted by treatment with S-nucleophiles to 5-thio-functionalized derivatives.
引用
收藏
页码:789 / 795
页数:7
相关论文
共 24 条
[1]   ANALOGS OF AZEPINOMYCIN - INHIBITORS OF GUANASE [J].
BHAN, A ;
HOSMANE, RS .
NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (3-5) :455-458
[2]   NOVEL INHIBITORS OF GUANASE [J].
BHAN, A ;
HOSMANE, RS .
TETRAHEDRON LETTERS, 1994, 35 (37) :6831-6834
[3]   Synthesis of new Di-, Tetra-, and hexahydropyrazolo[3,4-e][1,4]diazepine derivatives [J].
Bol'but, A. V. ;
Kemskii, S. V. ;
Vovk, M. V. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (07) :991-1002
[4]  
Cattet MRL, 1999, J ZOO WILDLIFE MED, V30, P354
[5]   A novel transition state analog inhibitor of guanase based on azepinomycin ring structure: Synthesis and biochemical assessment of enzyme inhibition [J].
Chakraborty, Saibal ;
Shah, Niti H. ;
Fishbein, James C. ;
Hosmane, Ramachandra S. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (02) :756-759
[6]   Crystallization and preliminary crystallographic analysis of Bacillus subtilis guanine deaminase [J].
Chang, YJ ;
Huang, CH ;
Hu, CY ;
Liaw, SH .
ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY, 2004, 60 :1152-1154
[7]   IMIDAZODIAZEPINEDIONES - A NEW CLASS OF ADENOSINE RECEPTOR ANTAGONISTS [J].
DALY, JW ;
HIDE, I ;
BRIDSON, PK .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) :2818-2821
[8]   PYRAZOLODIAZEPINES .2. 4-ARYL-1,3-DIALKYL-6,8-DIHYDROPYRAZOLO[3,4-E][1,4]DIAZEPIN-7(1H)-ONES AS ANTI-ANXIETY AND ANTICONVULSANT AGENTS [J].
DEWALD, HA ;
LOBBESTAEL, S ;
BUTLER, DE .
JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (12) :1562-1569
[9]   WHICH DEPRESSIONS RESPOND TO PLACEBO [J].
FAIRCHILD, CJ ;
RUSH, AJ ;
VASAVADA, N ;
GILES, DE ;
KHATAMI, M .
PSYCHIATRY RESEARCH, 1986, 18 (03) :217-226
[10]  
Henriksson K., WO Patent, Patent No. 2007040435