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• 106-49-0 p-toluidine 
• 545-06-2 trichloroacetonitrile 

Relevant academic research and scientific papers

Design, synthesis, and pharmacological evaluation of novel 1,2,4-triazol-3-amine derivatives as potential agonists of GABAA subtype receptors with anticonvulsant and hypnotic effects

In the current study, a series of novel 1,2,4-triazol-3-amine derivatives were designed, synthesized, and biologically evaluated in vivo for their anticonvulsant and hypnotic effects in the pentylenetetrazole (PTZ)-induced seizures, maximal electroshock (MES)-induced seizures, and pentobarbital-induced sleeping tests. Furthermore, the possible side effects of the most potent compounds on the memory, motor coordination, and muscle strength were evaluated in passive avoidance, rotarod, and grip strength tests, respectively. The designed compounds with the main benzodiazepine pharmacophores including aromatic ring and proton accepting group completely mimiced the structure of zolpidem as an α1-selective agonist of GABAA receptor. Compounds 5c (ED50 ≈ 52.5 mg/kg) and 5 g (ED50 ≈ 16.5 mg/kg) in the PTZ test were the most potent compounds among the designed compounds. In the MES test, the observed ED50s for compounds 5c and 5 g were reduced to around 11.8 mg/kg and 10.5 mg/kg, respectively. The considerable hypnotic effect in a dose-dependent manner was observed following the administration of newly synthesized compounds. In all experiments administration of flumazenil as an antagonist of benzodiazepines receptor fully antagonized observed effects which indicated the involvement of GABAA receptors. Since there was no negative effect on memory, motor coordination, and muscle strength following the administration of compounds 5c and 5g as the most potent compounds, it could be concluded that the novel compounds most likely act through α1-containing GABAA receptors and possess no affinity for α5-containing receptors. The newly designed compounds could be considered as leading compounds in synthesizing novel GABAA receptor agonists with minimum side effects.

A new route for the synthesis of functionalized benzo[d]imidazo[5,1-b]thiazol-1-amine derivatives from benzothiazole, trichloroacetamidines and terminal alkynes

A novel class of substituted benzo[d]imidazo[5,1-b]thiazol-1-amine derivatives was synthesized utilizing a one-pot Cu-catalyzed cycloaddition of benzothiazole, trichloroacetonitrile, various amines and terminal alkynes in acetonitrile at room temperature. The speed of this simple four-component reaction along with mild conditions, high yields, readily available starting materials, the ease of work-up without using pollutant precious metals–catalysts, and column chromatography are important features of the presented procedure.

Design, synthesis and anti-diabetic activity of novel 1, 2, 3-triazole-5-carboximidamide derivatives as dipeptidyl peptidase-4 inhibitors

The inhibitors of the enzyme dipeptidyl peptidase type 4 (DPP-4), as a potent stimulator of insulin secretion and an inhibitor of glucagon secretion from the pancreas, have been considered as promising agents for the treatment of type 2 diabetes mellitus. In this study, a novel series of 1, 2, 3-triazole-5-carboximidamide derivatives were designed, synthesized, and inhibitory activity evaluated against the DPP-4 enzyme. All of the compounds represented inhibitory activity, and among them, compounds 6a, 6b, and 6c showed desirable inhibitory activity of DPP-4 with IC50 values of 14.75 nM, 6.75 nM, and 6.57 nM, respectively. Compound 6a with a dose of 10 mg/kg showed glucose tolerance enhancement during OGTT in NMRI mice. Moreover, chronic treatment of Wistar rats for 14 days with compound 6a showed a significant decrease in blood glucose levels of diabetic rats, which was similar to sitagliptin as a standard.

Synthesis of functionalized benzothiadiazine 1,1-dioxide derivatives via intramolecular C–H activation reactions of trichloroacetamidine and benzenesulfonyl chloride

The synthesis of functionalized benzothiadiazine 1,1-dioxide derivatives was achieved through a novel three-component intramolecular C–H activation reaction of trichloroacetonitrile, benzenesulfonyl chloride, and various primary amines. This reaction was performed in the presence of catalytic copper(I) and L-proline as the ligand in tetrahydrofuran at room temperature.