176168-90-4Relevant academic research and scientific papers
Synthesis and comparative structure-activity study of carbohydrate-based phenolic compounds as α-glucosidase inhibitors and antioxidants
MacHida, Shota,Mukai, Saki,Kono, Rina,Funato, Megumi,Saito, Hiroaki,Uchiyama, Taketo
, (2019/12/04)
Twenty-one natural and unnatural phenolic compounds containing a carbohydrate moiety were synthesized and their structure-activity relationship (SAR) was evaluated for α-glucosidase inhibition and antioxidative activity. Varying the position of the galloyl unit on the 1,5-anhydro -D-glucitol (1,5-AG) core resulted in changes in the α-glucosidase inhibitory activity and notably, particularly strong activity was demonstrated when the galloyl unit was present at the C-2 position. Furthermore, increasing the number of the galloyl units significantly affected the α-glucosidase inhibition, and 2,3,4,6-tetra-galloyl-1,5-AG (54) and 2,3,4,6-tetra-galloyl-d-glucopyranose (61) exhibited excellent activities, which were more than 13-fold higher than the α-glucosidase inhibitory activity of acertannin (37). Moreover, a comparative structure-activity study suggested that a hemiacetal hydroxyl functionality in the carbohydrate core and a biaryl bond of the 4,6-O-hexahydroxydiphenoyl (HHDP) group, which are components of ellagitannins including tellimagrandin I, are not necessary for the α-glucosidase inhibitory activity. Lastly, the antioxidant activity increased proportionally with the number of galloyl units.
A mild and efficient method for the selective cleavage of primary p-methoxybenzyl protecting group of saccharides by Co2(CO)8-Me2PhSiH-CO system
Qian, Peng-Zhan,Yao, Wang,Huang, Lu-Bai,Meng, Xiang-Bao,Li, Zhong-Jun
supporting information, p. 5238 - 5241 (2015/08/19)
A mild and efficient method to selectively cleave p-methoxybenzyl (PMB) ether with a catalytic amount of Co2(CO)8, hydrosilane and CO (1 atm) is presented. The cleavage reaction shows regioselectivity to primary O-PMB of a variety of
Two-directional olefinic-ester ring-closing metathesis using reduced ti alkylidenes. A rapid entry into polycyclic ether skeletons
Zhang, Yuan,Rainier, Jon D.
supporting information; experimental part, p. 237 - 239 (2009/06/28)
The use of a reduced titanium ethylidene reagent in an efficient two-directional approach to polycyclic ether skeletons is described.
Synthesis of a ring-oxygenated variant of the 2-carboxy-6- hydroxyoctahydroindole core of aeruginosin 298-A from glucose
Nie, Xiaoping,Wang, Guijun
, p. 8687 - 8692 (2007/10/03)
The design and synthesis of a new core structure, a ring-oxygenated variant of 2-carboxy-6-hydroxyoctahydroindole (Choi) from D-glucose, is reported. Choi, a rigid bicyclic unnatural amino acid, is the core structure of about 15 aeruginosins natural compounds. These compounds are thrombin, trypsin, and factor VIIa inhibitors and Choi is important for their biological activity. The ring-oxygenated variant of 2-carboxy-6-hydroxyoctahydroindole can potentially be used as a surrogate of Choi in the design and synthesis of aeruginosin-based thrombin inhibitors. & 2005 American Chemical Society.
Synthetic studies on sialoglycoconjugates 81: Synthesis of positional isomers of sialyl lewis X epitope containing 1-deoxy-D-glucose in place of n-acetylglucosamine, and their inhibitory activity to selectin-mediated adhesion
Yoshida, Masahiro,Suzuki, Takako,Ishida, Hideharu,Kiso, Makoto,Hasegawa, Akira
, p. 147 - 162 (2007/10/03)
Three sialyl-LeX epitope analogs, which carry fucose and α-sialyl-(2→3)-galactose residues at O-2 and O-3, O-3 and O-2, and O-4 and O-6 positions of 1-deoxy-D-glucose backbone, respectively, have been synthesized. Glycosylation of 1,5-anhydro-4
