Synthesis and In vitro Study of Cytotoxic Activity of New Tetrazole-Containing 2,4-Diamino-1,3,5-triazine Derivatives

Russian Journal of General Chemistry - New tetrazole-containing derivatives of 2,4-diamino-1,3,5-triazine were synthesized. The cytotoxic activity of the obtained compounds against Huh-7 and HeLa...     

Kinetics of azidation of isomeric benzenedicarbonitriles

Rate constants and activation parameters of two-step azidation of isomeric dicyanobenzenes with dimethylammonium azide in DMF at 70–100°C were determined. Tetrazole rings are formed from cyano groups in dicyanobenzenes in a stepwise mode following the 1,3-dipolar cycloaddition pattern. The rate of azidation of isomeric dicyanobenzenes is considerably higher than the rate of subsequent azidation of intermediate cyanophenyltetrazolides. The azidation rate constant decrease in going from m-dicyanobenzene to its para and ortho isomers.     

Synthesis,Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine 2 and 3-N-phthalyl 22 amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC₅₀ 21 μM) and 42 (IC₅₀ 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC_50′s 67 and 107 μM) and -2 (IC_50′s 86 and 68 μM correspondingly) serotypes.     

Kinetics and mechanism of 5-vinyltetrazole alkylation

Alkylation of NH-unsubstituted 5-vinyltetrazole with methyl iodide in the presence of triethylamine in acetonitrile solution led to the formation of isomeric 1- and 2-methyl-5-vinyltetrazoles in 1:1 ratio. The reaction rate constants were measured at 25–55°C. According to the thermodynamic parameters of the reaction [ΔH ^≠ 66 kJ mol^?1, ΔS^≠-74 (mol K)^?1, 298 K] the limiting stage of the reaction consists in the electrophilic attack of methyl iodide on an H-complex of the heterocycle with triethylamine.     

Synthesis and antiviral activity of nonannulated tetrazolylpyrimidines

Chemistry of Heterocyclic Compounds - Nonannulated tetrazolylpyrimidines in the structure of which the heterocyclic fragments are separated by hydrazinocarbonylmethyl, methylpyrazolyl groups or a...     

Vinyltetrazoles: I. Synthesis of NH-unsubstituted 5-vinyltetrazole

The NH-unsubstituted 5-vinyltetrazole was obtained in 55% yield by exhaustive methylation of 5-(β-dimethylaminoethyl)tetrazole with dimethyl sulfate at the terminal dimethylamino group with the subsequent elimination of a proton from the α-CH₂ group and Hofmann β-cleavage of the intermediate 5-(β-trimethylammoniumethyl)tetrazolide methyl sulfate. The microwave irradiation was shown to reduce 5-fold the time of the synthesis of the initial substrate, 5-(β-dimethylaminoethyl)tetrazole.     

Kinetics and mechanism of 1-phenyl-5-methyltetrazole nitration in HNO3–H2SO4 system

Russian Journal of Organic Chemistry - At nitration of 1-phenyl-5-methyltetrazole with nitric acid in aqueous solutions of sulfuric acid of 84–96% concentration a mixture forms of...