Labanauskas L, Kalcas V, Udrenaite E, Gaidelis P, Brukstus A, Dauksas V
Faculty of Chemistry, Vilnius University, Vilnius, Lithuania.
Pharmazie. 2001 Aug;56(8):617-9.
New 1-acylderivatives of 5-alkylthio-3-(3,4-dimethoxyphenyl)-4H-1,2,4-triazole (5c-f, 6d-f) were synthesized by the acylation of 5-alkylthio-3-(3,4-dimethoxyphenyl)-4H-1,2,4-triazoles (3, 4) with acyl chlorides. The compounds 3, 4 were obtained by the alkylation of 3-(3,4-dimethoxyphenyl)-1H-1,2,4-triazole-5-thiol (2) sodium salt with alkyl iodides. Compound 2 and 2-amino-5-(3,4-dimethoxyphenyl)-1,3,4-thiadiazole (8) were prepared by the treatment of 3,4-dimethoxybenzoylthiosemicarbazide (1) with sodium hydroxide or acetyl chloride (and then sodium hydroxide), respectively. Related 2-acylamino-5-(3,4-dimethoxyphenyl)-1,3,4-thiadiazoles (7c, e, f) were synthesized by the acylation of compound 8 with acyl chlorides. 3-(3,4-Dimethoxyphenyl)-4-phenyl-4,5-dihydro-1H-1,2,4-triazole-5-thione (9) was N-acylated with acyl chlorides or S-methylated with iodomethane to give 1-acyl-3-(3,4-dimethoxyphenyl)-4-phenyl-4,5-dihydro-1H- 1,2,4-triazole-5-thiones (10a, b) or 3-(3,4-dimethoxyphenyl)-5-methylthio-4-phenyl-4H-1,2,4-triazole (11) respectively. The synthesized compounds 6d, 7a, c, 10a, b, 11 exhibit anti-inflammatory activity.
通过5-烷基硫基-3-(3,4-二甲氧基苯基)-4H-1,2,4-三唑(3,4)与酰氯的酰化反应合成了新型的5-烷基硫基-3-(3,4-二甲氧基苯基)-4H-1,2,4-三唑的1-酰基衍生物(5c-f,6d-f)。化合物3,4是通过3-(3,4-二甲氧基苯基)-1H-1,2,4-三唑-5-硫醇(2)钠盐与烷基碘的烷基化反应得到的。化合物2和2-氨基-5-(3,4-二甲氧基苯基)-1,3,4-噻二唑(8)分别通过用氢氧化钠或乙酰氯(然后用氢氧化钠)处理3,4-二甲氧基苯甲酰硫代氨基脲(1)制备。相关的2-酰氨基-5-(3,4-二甲氧基苯基)-1,3,4-噻二唑(7c,e,f)通过化合物8与酰氯的酰化反应合成。3-(3,4-二甲氧基苯基)-4-苯基-4,5-二氢-1H-1,2,4-三唑-5-硫酮(9)用酰氯进行N-酰化或用碘甲烷进行S-甲基化，分别得到1-酰基-3-(3,4-二甲氧基苯基)-4-苯基-4,5-二氢-1H-1,2,4-三唑-5-硫酮(10a,b)或3-(3,4-二甲氧基苯基)-5-甲硫基-4-苯基-4H-1,2,4-三唑(11)。合成的化合物6d、7a、c、10a、b、11具有抗炎活性。
