Antiviral Activity of (1,9a)-1-[(1,2,3-Triazol-1-yl)methyl]octahydro-1-quinolizines from the Alkaloid Lupinine.

Influenza is a disease of significant morbidity and mortality. The number of anti-influenza drugs is small; many of them stimulate the appearance of resistant strains. This article presents the results of assessing the antiviral activity of 1,2,3-triazole-containing derivatives of alkaloid lupinine for their ability to suppress the reproduction of orthomyxoviruses (influenza viruses: A/Vladivostok/2/09 (H1N1) and A/Almaty/8/98 (H3N2)).

Synthesis of 2-azirine-2,2-dicarboxylic acids and their derivatives.

Methods for the preparation of 3-aryl-2-azirine-2,2-dicarboxylic acids and their amides, esters, and azides by FeCl-catalyzed isomerization of 3-aryl-5-chloroisoxazole-4-carbonyl chlorides into 3-aryl-2-azirine-2,2-dicarbonyl dichlorides followed by their reaction with nucleophiles are reported. Two approaches to the preparation of 3-aryl-5-chloroisoxazole-4-carbonyl chlorides have been developed.

Antioxidant Effects of Tryptanthrin Oxime.

We studied the radical-binding and antioxidant activities of the alkaloid tryptanthrin (TR) and its new synthetic derivative tryptanthrin oxime (TR-Ox), as well as the cytoprotective activity of TR-Ox under conditions of oxidative stress. The antiradical activity of TR-Ox was revealed in the test of binding with stable chromogen radical 2,2-diphenyl-1-picrylhydrazyl and in the superoxide radical generation test (riboflavin photoreduction reaction with detection by NBT reduction). TR-Ox was inferior to ionol and dihydroquercetin by the antiradical activity.

DBU-Promoted Cyclizations of Cyclopentyl-Substituted Oxazapolyenes to Cyclopentapyridones and Hydroxypyrroles: Experimental and DFT Study.

1,1-Di(alkoxycarbonyl)-4-cyclopentyl-2-azabuta-1,3-dienes react with DBU to form two types of heterocyclic products: 1-cyclopenta[]pyrid-1-ones and 3-hydroxy-1-pyrroles. These previously unobserved transformations proceed through the formation of 1-azapentadienyl anion which undergoes 1,6-shift of the alkoxycarbonyl group to the cyclopentyl moiety followed by 1,6-cyclization to form the cyclopentapyridone (path ) and 1,5-cyclization accompanied by 1,3-shift of the methoxy group followed by dialkyl carbonate elimination to afford the hydroxypyrrole (path ). The mechanisms of the reactions were studied using DFT calculations.