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Synthesis, Characterization, and Antifungal Activity of Some New Thieno[2,3-b]pyridines Incorporating Quinazoline or Benzimidazole Moiety
Russian Journal of Bioorganic Chemistry ( IF 1 ) Pub Date : 2021-08-21 , DOI: 10.1134/s1068162021040117
O. F. Ibrahim 1 , E. A. Bakhite 1 , S. A. M. Metwally 1 , Y. A. El-Ossaily 1, 2 , H. H. M. Abdu-Allah 3 , E. A. Al-Taifi 4 , M. Kandel 5, 6
Affiliation  

Abstract

Reaction of 4,6-dimethyl-3-cyanopyridine-2(1H)-thione (IIIa) or 4,5,6-trisubstituted-3-cyanopyridine-2(1H)-thiones (IIIbd) with 2-chloromethylquinazoline-4(3H)-one (IVa) furnished the corresponding 3-amino-2-(4-oxo-3,4-dihydroquinazolin-2-yl)thieno[2,3-b]pyridines (VIad). Reaction of aminothieno-pyridines (VIa, b, d) were reacted with triethyl orthoformate, acetic anhydride or nitrous acid to furnish pyridothienopyrimidoquinazolines (VIIIa, b, d), (IXa, b, d) or pyridothienotriazinoquinazolines (Xa, b, d). The new compound, 3-cyano-5-acetyl-6-methyl-4-styrylpyridine-2(1H)-thione (IIIe) was synthesized and reacted with 2-chloromethyl-1H-benzimadazole to give 5-acetyl-3-amino-2-(1H-benzimidazol-2-yl)-6-methyl-4-styryl-thieno[2,3-b]pyridine (XII) which was used as a key intermediate for synthesizing pyridothienopyrimidobenzimidazoles (XIII, XIV). All newly synthesized compounds were characterized on the basis of their elemental and spectral analyses. Also, most of the synthesized compounds were screened in vitro for their antifungal activity.



中文翻译:

一些含有喹唑啉或苯并咪唑部分的新型噻吩并[2,3-b]吡啶的合成、表征和抗真菌活性

摘要

的反应4,6-二甲基-3-氰基吡啶-2(1 H ^) -硫酮(IIIa受体)或4,5,6-三取代-3-氰基吡啶-2(1 H ^)-thiones(IIIb族- d)与2-氯甲基喹唑啉-4(3 H )-one ( IVa)提供相应的 3-amino-2-(4-oxo-3,4-dihydroquinazolin-2-yl)thieno[2,3- b ]pyridines ( VIad ) . 氨基噻吩并吡啶(VIabd)与原甲酸三乙酯、乙酸酐或亚硝酸反应得到吡啶并噻吩并嘧啶并喹唑啉(VIIIabd )、( IXabd ) 或吡啶并噻嗪并喹唑啉 ( Xabd )。合成了新化合物3-氰基-5-乙酰基-6-甲基-4-苯乙烯基吡啶-2( 1H )-硫酮( IIIe),并与2-氯甲基-1H-苯并咪唑反应生成5-乙酰基-3 -amino-2-(1 H -benzimidazol-2-yl)-6-methyl-4-styryl-thieno[2,3- b ]pyridine ( XII ) 是合成吡啶并嘧啶并苯并咪唑( XIII , XIV ) 的关键中间体)。所有新合成的化合物都根据其元素和光谱分析进行了表征。此外,大多数合成的化合物都经过体外抗真菌活性筛选。

更新日期:2021-08-21
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