title: N-Arylmethylaminoquercitols, a new series of effective antidiabetic agents having α-glucosidase inhibition and antioxidant activity.
abstract: A new series of N-arylalkylaminoquercitols were synthesized by reductive amination of aminoquercitol bisacetonide 5 and a variety of aryl aldehydes. The targeted N-substituted aminoquercitols having phenolic moiety (7a-7c) displayed significantly enhanced α-glucosidase inhibition, which is 26-32 times more potent than that of the unmodified aminoquercitol 6. In addition, compounds 7a-7c also retained antioxidant activity with relatively more pronounced potency than their original phenolics. This recent finding suggests an approach to develop effective antidiabetic agents by incorporating antioxidative moiety into aminocyclitol core structure.
authors.affiliation: Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Wisuttaya
authors.initials: W
authors.lastname: Worawalai
authors.affiliation: Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Sumrit
authors.initials: S
authors.lastname: Wacharasindhu
authors.affiliation: Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand. Electronic address: preecha.p@chula.ac.th.
authors.forename: Preecha
authors.initials: P
authors.lastname: Phuwapraisirisan
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D007004:Hypoglycemic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D011485:Protein Binding; D013329:Structure-Activity Relationship; D000520:alpha-Glucosidases / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000447:Aldehydes; D000975:Antioxidants; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents; D007294:Inositol; D000520:alpha-Glucosidases; C046273:5-deoxyinositol
keywords: Aminocyclitol; Diabetes; Glucosidase; Quercitol; Reductive amination