Discovery of New Ginsenol-like Compounds with High Antiviral Activity

A number of framework amides with a ginsenol backbone have been synthesized using the Ritter reaction. We named the acetamide as Ginsamide. A method was developed for the synthesis of the corresponding amine and thioacetamide. The new compounds revealed a high activity against H1N1 influenza, which was confirmed using an animal model. Biological experiments were performed to determine the mechanism of action of the new agents, a ginsamide-resistant strain of influenza virus was obtained, and the pathogenicity of the resistant strain and the control strain was studied. It was shown that the emergence of resistance to Ginsamide was accompanied by a reduction in the pathogenicity of the influenza virus.

Tropylium-Promoted Ritter Reactions

The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuable N-alkyl amide products. However, this reaction has not been frequently...

Ritter-type iodo(III)amidation of unactivated alkynes for the stereoselective synthesis of multisubstituted enamides

The Ritter reaction, Brønsted- or Lewis acid-mediated amidation of alkene or alcohol with nitrile via a carbocation, represents a classical method for the synthesis of tertiary amides. Although analogous reaction...

Effective approach to a synthesis of fluorine-containing 4-acylamino-4,5,6,7-tetrahydrobenzisoxazoles

On the example of synthesis of 4-acetylamino-3-fluoroalkyl(aryl)-4,5,6,7-tetrahydro-1,2-benzisoxazoles, the effective approach to a synthesis of novel 4-acylamino-4,5,6,7-tetrahydro-1,2-benzisoxazoles is proposed. 3-Fluoroalkyl(aryl)- 6,7-dihydro-1,2-benzisoxazol-4-ones were reduced by a sodium borohydride in isopropanol to obtain 3-fluoroalkyl(aryl)- 4,5,6,7-tetrahydro-1,2-benzisoxazol-4-ols that in the conditions of the Ritter reaction (acetonitrile, acetic acid, sulfuric acid) gave target 4-acylamino derivatives with 80–94 % yields.

Antiproliferative activities of tricyclic amides derived from β-caryophyllene via the Ritter reaction against MDA-MB-231 breast cancer cells

Tricyclic amides were successfully synthesised from β-caryophyllene via the Ritter reaction. Amides 3c and 6b inhibited proliferation of MDA-MB-231 cells. Compound 6b inhibited cell cycle progression and induced predominantly apoptotic cell death.