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Related Experiment Video

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Curation of Computational Chemical Libraries Demonstrated with Alpha-Amino Acids

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Expanding Complex Morpholines Using Systematic Chemical Diversity.

Sunny Ann Tang¹, Afton Fults², Shelton R Boyd¹

¹Verna and Marrs McLean Department of Biochemistry and Molecular Pharmacology, Baylor College of Medicine, One Baylor Plaza, Houston, Texas 77030, United States.

Organic Letters

|March 20, 2024

Summary

This summary is machine-generated.

Researchers synthesized 24 diverse methyl-substituted morpholine derivatives using systematic chemical diversity. These novel compounds offer new possibilities for drug discovery and medicinal chemistry applications.

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Area of Science:

Organic Chemistry
Medicinal Chemistry
Drug Discovery

Background:

The morpholine heterocycle is a key structural motif in numerous bioactive compounds and FDA-approved drugs.
The synthesis of complex, C-functionalized morpholine derivatives is an underexplored area in organic chemistry.

Purpose of the Study:

To expand the chemical diversity of morpholine scaffolds through regiochemical and stereochemical variation.
To synthesize a collection of methyl-substituted morpholine acetic acid esters.

Main Methods:

Employed systematic chemical diversity (SCD) principles.
Utilized enantiomerically pure amino acids and amino alcohols as starting materials.
Generated 24 distinct substituted morpholine compounds.

Main Results:

Successfully synthesized 24 diverse C-substituted morpholines.
Achieved systematic variation in both regiochemistry and stereochemistry (relative and absolute).
Produced methyl-substituted morpholine acetic acid esters.

Conclusions:

The synthesized morpholine derivatives are valuable for fragment screening.
These compounds can serve as versatile building blocks in medicinal chemistry and library synthesis.
This work expands the accessible chemical space of morpholine scaffolds.