Synthesis and antiviral evaluation of 6'-acylamido-6'-deoxy-α-D-mannoglycerolipids.
Eight new aminomannoglycerolipids (2a-h) with linear, branched, or aromatic acyl chains were synthesized and evaluated for their anti-influenza A virus (IAV) activity. By comparing six mannosyl donors with different protecting and leaving groups, the critical glycosylation reaction employed mannosyl trichloroacetimidate with 2-O-benzoyl protecting group as the donor to give the glycoside with absolute α-anomeric selectivity. The bioactivity results showed that the branched compound 2g could effectively inhibit IAV multiplication in MDCK cells with IC50 69.9μM.
Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China.
Jun
J
Zhang
Yihua
Y
Sun
Wei
W
Wang
Xiaoshuang
X
Zhang
Chunxia
C
Li
Huashi
H
Guan
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002236:Carbohydrate Conformation; D002477:Cells; D004285:Dogs; D004305:Dose-Response Relationship, Drug; D006017:Glycolipids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D009980:Influenza A virus / Q000187:drug effects*; D061985:Madin Darby Canine Kidney Cells / Q000187:drug effects / Q000821:virology; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D006017:Glycolipids
Aminoglycoglycerolipid; Glycosylation; Influenza A virus; α-Anomeric selectivity