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Vinyl sulfones.

Jessica H Wong¹, Marilyn M Olmstead, James C Fettinger

¹Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, USA.

Acta Crystallographica. Section C, Crystal Structure Communications

|March 7, 2008

Summary

This summary is machine-generated.

This study describes novel vinyl sulfone compounds as phosphate mimics for potential enzyme inhibition in cancer and HIV therapy. These structures show promise as therapeutic agents, with most exhibiting favorable properties for drug development.

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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Published on: January 3, 2018

Area of Science:

Organic Chemistry
Medicinal Chemistry
Crystallography

Background:

Phosphate isosteres are crucial in developing enzyme inhibitors for various diseases.
Vinyl sulfones offer a unique structural motif for mimicking phosphate groups.
Understanding the structural and electronic properties of these mimics is key for therapeutic applications.

Purpose of the Study:

To synthesize and characterize novel neutral vinyl sulfone compounds.
To evaluate their potential as phosphate isosteres for enzyme inhibition.
To investigate the structural features that enable phosphate mimicry.

Main Methods:

Synthesis of four neutral vinyl sulfone compounds, including phosphonate derivatives.
X-ray crystallography to determine the precise three-dimensional structures.
Comparative analysis of structural parameters (bond distances, angles) with phosphate backbones.

Main Results:

Successful synthesis of diisopropyl (2-phenylethenylsulfonylmethyl)phosphonate, diisopropyl {[2-(7-methoxy-1,3-benzodioxol-5-yl)ethenylsulfonyl]methylsulfonylmethyl}phosphonate, bis(trans-2-phenylethenyl) sulfone, and bis(trans-2-phenylethenylsulfonyl)methane.
Crystallographic data revealed that the sulfone group effectively mimics phosphate geometry.
The vinyl group influences S-C bond distances, contributing to the mimicry.

Conclusions:

The synthesized vinyl sulfones serve as effective phosphate isosteres.
These compounds hold potential for enzyme inhibition in cancer and HIV therapy.
The study provides valuable structural insights into designing novel therapeutic agents.