81534-38-5

Upstream product

• 2485-62-3 L-Cysteine methyl ester 
• 58690-20-3 trapain 
• 1486-47-1 3,4,5-tris(benzyloxy)benzoyl chloride 

Downstream Products

• 96691-90-6 2,3-di-O-galloyl-D-⁴C₁-glucopyranose 

Relevant academic research and scientific papers

The synthesis and antitumor activity of twelve galloyl glucosides

Twelve galloyl glucosides 1-12, showing diverse substitution patterns with two or three galloyl groups, were synthesized using commercially available, low-cost D-glucose and gallic acid as starting materials. Among them, three compounds, methyl 3,6-di-O-galloyl-?±-D-glucopyranoside (9), ethyl 2,3-di-O-galloyl-?±-D-glucopyranoside (11) and ethyl 2,3-di-O-galloyl-?2-D-glucopyranoside (12), are new compounds and other six, 1,6-di-O-galloyl-?2-D-glucopyranose (1), 1,4,6-tri-O-galloyl-?2-D-glucopyranose (2), 1,2-di-O-galloyl-?2-D-glucopyranose (3), 1,3-di-O-galloyl-?2-D-glucopyranose (4), 1,2,3-tri- O-galloyl-?±-D-glucopyranose (6) and methyl 3,4,6-tri-O-galloyl-?±-D-glucopyranoside (10), were synthesized for the first time in the present study. In in vitro MTT assay, 1-12 inhibited human cancer K562, HL-60 and HeLa cells with inhibition rates ranging from 64.2% to 92.9% at 100 ??g/mL, and their IC50 values were determined to be varied in 17.2-124.7 ??M on the tested three human cancer cell lines. In addition, compounds 1-12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at 100 ??g/mL in the in vitro MTT assay, and in vivo antitumor activity of 1 and 2 was also detected in murine sarcoma S180 tumor-bearing Kunming mice using taxol as positive control.

REACTION OF DEHYDROELLAGITANNINS WITH L-CYSTEINE METHYL ESTER

Reaction of dehydroellagitannins (e.g. 1) with L-cysteine methyl ester (5) at room temperature yielded the condensation products (e.g. 3 and 4), together with a partial hydrolysate (e.g. 2), while heating the mixture at 80 deg C afforded 4 and the hydrolysate (2) in fairly good yields.In addition, reduction of a dehydrohexahydroxydiphenoyl ester group to a hexahydroxy-diphenoyl group with thiols is also described.