SYNTHESIS OF NOVEL 3-AMINO-2-(1H)-THIOXO-4(3H)-QUINAZOLINONE DERIVATIVES. PART 3

被引:1
作者
Nawrocka, Wanda [1 ]
Wojcicka, Anna [1 ]
Nowicka, Anna [1 ]
机构
[1] Wroclaw Med Univ, Dept Drugs Technol, PL-50140 Wroclaw, Poland
关键词
Acylation; ammonolysis; 3-amino-2(1H)-thioxo-4(3H)-quinazolinone; 3-amino-2-ethoxy-carbo-nylmethylthio-4(3H)-quinazolinone derivatives; synthesis; 4(3H)-QUINAZOLINONE DERIVATIVES; 3-AMINO-2(1H)-THIOXO-4(3H)-QUINAZOLINONE; ACID;
D O I
10.1080/10426507.2011.582055
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of novel derivatives containing the quinazolinone-4 moiety is described. 3-Amino-2(1H)-tioxo-4(3H)-quinazolinone (1) forms a sodium salt 2, which was subjected to reaction with dicarboxylic acid chlorides such as chloroformyl ethyl formate and malonyl chloride, leading to the corresponding ester 3 and acid 4, respectively. 3-Amino-2-ethoxycarbonylmethylthio-4(3H)-quinazolinone (5) was acylated or ammonolyzed and products of various chemical structure were obtained. The chemical structures 3, 4, 6-12, and 14-18 were identified by the results of elemental analysis and their IR, H-1 NMR, and mass spectra.
引用
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页码:79 / 87
页数:9
相关论文
共 29 条
[1]  
Amin A. H., 1970, ARZNEIMIT TELFORSCH, V14, P218
[2]  
[Anonymous], 1996, MERCK INDEX ENCY CHE, p[903, 1019]
[3]   Novel quinazolinone derivatives as possible antitumor agents [J].
Barakat, Saber El-Sayed ;
Ghorab, Moustafa M. ;
Saker, Helmy M. ;
Rabo, Mahmoud M. Abd .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (01) :65-77
[4]  
Barker A. J., 1994, Brit. UK. Pat. Appl. Gr, Patent No. [2.271, 11.06, 2271]
[5]  
Huszcza E., 2007, [No title captured], Patent No. 382856
[6]  
JOHNE S, 1981, PHARMAZIE, V36, P583
[7]  
Klinowska-Torz J., 1994, ACTA POL PHARM, V51, P249
[8]   Some new 2,3,6-trisubstituted quinazolinones as potent anti-inflammatory, analgesic and COX-II inhibitors [J].
Kumar, A ;
Sharma, S ;
Bajaj, AK ;
Sharma, S ;
Panwar, H ;
Singh, T ;
Srivastava, VK .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (23) :5293-5299
[9]   The chemistry of recently isolated naturally occurring quinazolinone alkaloids [J].
Mhaske, Santosh B. ;
Argade, Narshinha P. .
TETRAHEDRON, 2006, 62 (42) :9787-9826
[10]  
Nawrocka W, 2002, Boll Chim Farm, V141, P84