Disruption of Crystal Packing in Thieno[2,3-b]pyridines Improves Anti-Proliferative Activity

doi:10.3390/molecules27030836

Paper

Disruption of Crystal Packing in Thieno[2,3-b]pyridines Improves Anti-Proliferative Activity

Published Jan 27, 2022 · Natalie A. Haverkate, E. Leung, L. Pilkington

Molecules

Q1 SJR score

2

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0

Influential Citations

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Abstract

3-Amino-2-arylcarboxamido-thieno[2,3-b]pyridines have been shown to have anti-proliferative activity, but are also known to have poor solubility. This has been previously proposed to be due to their extensive planarity, which allows for intermolecular stacking and crystal packing. We herein report the synthesis of fifteen novel thieno[2,3-b]pyridines that have incorporated bulky, but easily cleavable, ester and carbonate functional groups in an effort to decrease crystal packing. The addition of these ‘prodrug-like’ moieties into the thieno[2,3-b]pyridine resulted in compounds with increased activity against HCT-116 colon cancer cells and the triple-negative breast cancer cell line MDA-MB-231.

Study Snapshot

Adding bulky, easily cleavable, ester and carbonate functional groups to thieno[2,3-b]pyridines improves their anti-proliferative activity against colon cancer cells and triple-negative breast cancer cells.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Disruption of Crystal Packing in Thieno[2,3-b]pyridines Improves Anti-Proliferative Activity

References

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Citations

2-Thiopyridone-based stilbazoles: synthesis, photo-physical properties and sensing of Hg(II) and Cd(II) ions

Stilbazoles with improved photophysical properties and high selectivity for mercury (Hg(II)) and cadmium (Cd(II)) detection in aqueous media have been developed for environmental monitoring and biological sensing.

Synthesis and Anti-Proliferative Activity of 5-Benzoyl and 5-Benzylhydroxy Derivatives of 3-Amino-2-Arylcarboxamido-Thieno[2-3-b]Pyridines

Novel thieno[2-3-b]pyridine analogues with shorter benzoyl or secondary benzyl alcohol tethers maintain potent anti-proliferative activity against cancer cells, offering a more concise synthesis route.