Work

Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis

Year: 2023

Type: article

Abstract: The biological activity of compounds directly depends on the three-dimensional arrangement of affinity fragments since a high degree of pharmacophore compliance with the binding site is required. 3-Benzylidene oxindoles are privileged structures due to their wide spectrum of biological activity, synthetic availability, and ease of modification. In particular, both kinase inhibitors and kinase activators can be found among 3-benzylidene oxindoles. In this work, we studied model compounds obtained via oxindole condensation with aldehydes and alkylphenones. These condensation products can exist in the form of E- and Z-isomers and also undergo isomerization in solutions. The factors causing isomeric transformation of these compounds were established. Comparative kinetic studies to obtain quantitative characteristics of UV-driven isomerization were first performed. The results obtained indicate dramatic differences in two subclasses, which should be considered when developing biologically active molecules.

Source: International Journal of Molecular Sciences

DOI: 10.3390/ijms241411339

Authors: Daria Novikova, Tatyana Grigoreva, Vladislav Gurzhiy, Vyacheslav Tribulovich

Institutions: St. Petersburg State Technological Institute, St Petersburg University

Language: English

Topic: Heterocyclic Compound Synthesis and Bioactivity

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $2,780

Funders: Saint Petersburg State University, Russian Science Foundation