Synthesis And Biological Activities Of 3-aliphatic Group-1,2,4-triazole Mannich Bases

Fifty-six new types of target products were first designed and synthesized by Mannich reaction from 3-aliphatic group-4-amino-5-sulfhydryl-1,2,4-triazoles,substituted aryl and morpholine(or piperazine)and other active groups.There are 14 intermediate Schiff bases and 42 final product Mannich bases.The target molecules were characterized and bioassay tested.First,two aliphatic acids(n-hexyl and n-lauric acid)were used as raw materials and reacted with thiocarbohydrazide respectively in the absence of a solvent to afford 3-aliphatic group-4-amino-5-sulfhydryl-1,2,4-triazoles(PT and UT).Then seven aromatic aldehydes were reacted with the above two kinds of 3-aliphatic group-4-amino-5-sulfhydryl-1,2,4-triazoles with concentrated sulfuric acid as catalyst,the 14 kinds of aliphatic aromatic triazole Schiff bases(PTS 1-7 and UTS 1-7)were synthesized for the first time.By N-Mannich reaction,14 kinds of Schiff bases were first successfully converted to 42 kinds of aliphatic Mannich products(PTM 1-21 and UTM 1-21),and their structures were characterized by Infrared spectrum,11 NMR and 13C NMR,etc.Second,the plant growth regulating activities of the target molecules were evaluated.Cytokinin activity was measured by cucumber rooting test.In test concentration,all compounds showed good promotive effect,and most of the results were in A-level,showing good cytokinin activity,wherein PTM 9 showed the most obvious effect of promoting with the rate of up to 92.5%.The auxin activity of the compounds was evaluated by means of wheat sheath test.In the test concentrations,the effect of auxin activity is medium with general level of B or C.As a result,the target compounds might be used as plant growth regulating reagents.Third,the herbicidal activity of the target molecules were also tested and the results show that,their herbicidal activity was excellent in the test concentration,except for PTM 14.The inhibition rates were all more than 42.5%,and PTM 8 had the highest rate of inhibitory,up to 97.7%.Almost all target molecules might be used as herbicidal reagents.Fourth,the inhibitory activity of the target molecules against Cdc25B was screened,and the results showed the inhibition rates of 16 kinds of compounds were above 50%,the highest inhibitory rate was(98.86 ± 0.00)?g/mL,The results of a further IC50 values test showed that 9 compounds PTM 8,PTM 19,PTM 20,UTM 1,UTM 10,UTM 13,UTM 14,UTM 19 and UTM 20 exhibited better inhibitory activity than the positive reference sodium orthovanadate[(1.86 ± 0.24)?g/mL],their IC50 values were 0.69± 0.11,0.16± 0.01,0.52±0.12,1.79± 0.28,1.29 ± 0.11,1.06± 0.10,1.23 ± 0.34,0.23± 0.01,0.62± 0.30 ?g/mL.Analyzing the structure of the compounds,it was found that when methoxy,fluoro,chloro,pyridine,furan and ferrocenyl groups were in the molecular structure,the compound could behave high inhibitory activity.Among the high active molecules,the number of long chain aliphatic compounds was more than the number of short chain aliphatic compounds,this indicated that such kind structural molecules could be used as potential Cdc25B inhibitors for cancer treatment.