A convenient synthesis of N-linked diglycose derivatives based on one-pot tandem Staudinger/aza-Wittig/reduction and biological evaluation

• Published in: Carbohydrate research 2013-05, Vol.372, p.15-22
• Main Authors: Zhang, Pingzhu, Li, Yinbo, Liu, Ming, Wang, Yanfei, Li, Cuicui, Ma, Donglai, Chen, Hua, Wang, Kerang, Li, Xiaoliu, Zhang, Jinchao
• Format: Article
• Language: English
• Subjects: Aldehydes - chemistry; alpha-amylase; alpha-Amylases - antagonists & inhibitors; alpha-glucosidase; Amines - chemistry; Anti-HIV Agents - chemistry; Anti-HIV Agents - pharmacology; antineoplastic agents; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antitumor; beta-glucosidase; bioactive properties; Carbohydrate Conformation; Chemistry Techniques, Synthetic; Disaccharidases - chemical synthesis; Disaccharidases - pharmacology; Drug Evaluation, Preclinical - methods; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - pharmacology; Glycosidase inhibition; Glycoside Hydrolase Inhibitors; HeLa Cells - drug effects; HIV Reverse Transcriptase - antagonists & inhibitors; Humans; N-linked diglycoses; One pot reaction; Staudinger/aza-Wittig/reduction; sugars
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2013.02.002

A series of novel N-linked diglycose derivatives were conveniently and directly synthesized based on the key step of one-pot tandem Staudinger/aza-Wittig/reduction reaction followed by deprotection. Some compounds exhibited good cytotoxicity to A-549. A series of novel N-linked diglycose derivatives 9 and 10 were conveniently and directly synthesized based on the key step of one-pot tandem Staudinger/aza-Wittig/reduction reaction from the azido sugar and sugar-derived aldehyde followed by deprotection. The biological activities against glycosidases (α-amylase, α-glucosidase, and β-glucosidase) and HIV-RT and antitumor activity of these compounds were preliminarily evaluated.