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

Compound [(3-H 2 PA)(HCh)]·2H 2 O ( 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 s...

Full description

Saved in:
Bibliographic Details
Published in:New journal of chemistry 2023-11, Vol.47 (43), p.19925-19932
Main Authors: Escalona, Ana, Heinemann, Frank W, Briceño, Alexander, Alvarado, Ysaias J, Paz, José Luis, Lossada, Carla, González-Paz, Lenin, Toro, Robert, Henao, José Antonio
Format: Article
Language:
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Compound [(3-H 2 PA)(HCh)]·2H 2 O ( 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. A multivalent zwitterionic tetramer with a pentacyclic ladderane-like core is obtained by a triple topochemical photoreaction, assisted by hydrogen bonding interactions.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj04041k