1256160-12-9

Upstream product

• 1608504-27-3 C₅₂H₈₆F₂O₈Si₅ 
• 2596-50-1 (-)-epigallocathechin gallate 
• 76903-88-3 3,4-difluorobenzoyl chloride 
• 455-86-7 3,4-Difluorobenzoic acid 
• 1394226-60-8 (2R,3R)-5,7-bis(benzyloxy)-2-[3',4',5'-tris(benzyloxy)phenyl]chroman-3-yl 3,4-difluorobenzoate 

Relevant academic research and scientific papers

Towards the discovery of drug-like epigallocatechin gallate analogs as Hsp90 inhibitors

(-)-Epigallocatechin gallate (EGCG) is the major flavonoid of green tea and has been widely explored for a range of biological activities including anti-infective, anti-inflammatory, anti-cancer, and neuroprotection. Existing structure-activity data for EGCG has been largely limited to exploration of simple ethers and hydroxyl deletion. EGCG has poor drug-like properties because of multiple phenolic hydroxyl moieties and a metabolically labile ester. This work reports a substantial expansion of structure-activity understanding by exploring a range of semi-synthetic and synthetic derivatives with ester replacements and variously substituted aromatic and alicyclic groups containing more drug-like substituents. Structure-activity relationships for these molecules were obtained for Hsp90 inhibition. The results indicate that amide and sulfonamide linkers are suitable ester replacements. Hydroxylated aromatic rings and the cis-stereochemistry in EGCG are not essential for Hsp90 inhibition. Selected analogs in this series are more potent than EGCG in a luciferase refolding assay for Hsp90 activity.

Semisynthesis of fluoro-substituted benzoates of Epi-gallocatechin

In the present study, four fluoro-substituted benzoates of epi-gallocatechin (EGC) were prepared through a semisynthetic strategy, and the yield of benzylation of epi-gallocatechin gallate (-)-EGCG was improved by using freshly purified (-)-EGCG as starting material and a mild base of K 2CO3. All structures of new compounds were characterized by 1H NMR, 13C NMR, high-resolution mass spectrometry, and optical rotation.