一些新型5-(2-取代-1,3-噻唑-5-基)-2-羟基苯甲酰胺及其2-烷氧基衍生物作为潜在抗真菌剂的合成
Synthesis of some new 5-(2-substituted-1,3-thiazol-5-yl)-2-hydroxy benzamides and their 2-alkoxy derivatives as possible antifungal agents.
作者信息
Narayana B, Vijaya Raj K K, Ashalatha B V, Kumari N Suchetha, Sarojini B K
机构信息
Department of Post-Graduate Studies and Research in Chemistry, Mangalore University, Mangalagangotri 574199, India.
出版信息
Eur J Med Chem. 2004 Oct;39(10):867-72. doi: 10.1016/j.ejmech.2004.06.003.
The 2-hydroxy-5-(1,3-thiazol-5-yl) benzamide (4a), 5-(2-amino-1, 3-thiazol-5-yl)-2-hydroxy benzamide (4b), 2-hydroxy-5-(2-alkyl-1,3-Thiazol-5-yl) benzamide (4c and 4d), 5-(2-[(N-substituted aryl)amino]-1,3-thiazol-5-yl)2-hydroxy benzamides (6a-j) were prepared by reacting 5-(bromoacetyl) salicylamide (2) with thiourea, thioformamide, thioalkylamide (3c-d) and substituted thioureas (5a-j) in absolute ethanol. These compounds were converted to 5-(2-substituted-1,3-thiazol-5-yl)-2-alkoxybenzamides and 5-(2-N-(substituted aryl)-1,3-thiazol-5-yl)-2-alkoxy benzamides (8a-g) by reacting with n-alkylbromides (7a-b) in presence of a base. The newly synthesized compounds were characterized by IR, (1)H-NMR and mass spectral data. Compounds were also screened for their antifungal activity.
通过使5-(溴乙酰基)水杨酰胺(2)与硫脲、硫代甲酰胺、硫代烷基酰胺(3c - d)以及取代硫脲(5a - j)在无水乙醇中反应，制备了2 - 羟基 - 5 - (1,3 - 噻唑 - 5 - 基)苯甲酰胺(4a)、5 - (2 - 氨基 - 1,3 - 噻唑 - 5 - 基)-2 - 羟基苯甲酰胺(4b)、2 - 羟基 - 5 - (2 - 烷基 - 1,3 - 噻唑 - 5 - 基)苯甲酰胺(4c和4d)、5 - (2 - [(N - 取代芳基)氨基]-1,3 - 噻唑 - 5 - 基)2 - 羟基苯甲酰胺(6a - j)。在碱的存在下，通过使这些化合物与正烷基溴(7a - b)反应，将它们转化为5 - (2 - 取代 - 1,3 - 噻唑 - 5 - 基)-2 - 烷氧基苯甲酰胺和5 - (2 - N - (取代芳基)-1,3 - 噻唑 - 毛基)-2 - 烷氧基苯甲酰胺(8a - g)。通过红外光谱、¹H - 核磁共振光谱和质谱数据对新合成的化合物进行了表征。还对这些化合物的抗真菌活性进行了筛选。
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