Issue 43, 2023

Hydrogen-bond-assisted topochemical synthesis of a multivalent zwitterionic tetramer via concomitant cross- and homo [2+2] photocycloadditions. Theoretical antiviral activity against SARS-CoV-2

Abstract

Compound [(3-H2PA)(HCh)]·2H2O (1) represents a novel example of an ionic co-crystal that undergoes regioselectively a triple photoreaction to form a rare multivalent tetramolecular zwitterion (2) with a pentacyclic ladderane-like core in high yield. Molecular docking and molecular dynamics show that this molecule can bind well to the interface between the spike protein of SARS-CoV-2 and the cell surface receptor ACE2 with which it forms a complex to facilitate infection. At the same time, it could theoretically decrease viral replication.

Graphical abstract: Hydrogen-bond-assisted topochemical synthesis of a multivalent zwitterionic tetramer via concomitant cross- and homo [2+2] photocycloadditions. Theoretical antiviral activity against SARS-CoV-2

Supplementary files

Article information

Article type
Paper
Submitted
29 Aug 2023
Accepted
28 Sep 2023
First published
29 Sep 2023

New J. Chem., 2023,47, 19925-19932

Hydrogen-bond-assisted topochemical synthesis of a multivalent zwitterionic tetramer via concomitant cross- and homo [2+2] photocycloadditions. Theoretical antiviral activity against SARS-CoV-2

A. Escalona, F. W. Heinemann, A. Briceño, Y. J. Alvarado, J. L. Paz, C. Lossada, L. González-Paz, R. Toro and J. A. Henao, New J. Chem., 2023, 47, 19925 DOI: 10.1039/D3NJ04041K

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