Abstract
Inspired by the significant α-glucosidase inhibitory activities of (+)- and (−)-pericosine E, we herein designed and synthesized 16 analogs of these marine natural products bearing a methoxy group instead of a chlorine atom at C6. Four of these compounds exhibited moderate α-glucosidase inhibitory activities, which were weaker than those of the corresponding chlorine-containing species. The four compounds could be prepared by coupling reactions utilizing the (−)-pericosine B moiety. An additional in silico docking simulation suggested that the reason of reduced activity of the C6-methoxylated analogs might be an absence of hydrogen bonding between a methoxy group with the surrounding amino acid residues in the active site in α-glucosidase.
Highlights
Pericosines A–C and E (1–4) are marine natural products produced by the fungus Periconia byssoidesOUPS-N133 derived from sea hare Aplysia kurodai (Figure 1) [1]
Syntheses of Pericosine E Analogs Methoxy-Substituted at C6
The corresponding enantiomers were synthesized by similar methods to afford sixteen C6-methoxylated pericosine E analogs
Summary
Pericosines A–C and E (1–4) are marine natural products produced by the fungus Periconia byssoides. The unique carbasugar structures of these species and the significant antitumor activity of pericosine A have drawn increased attention to pericosines A–C (1–3) as synthetic targets and inspired numerous synthetic studies [2,3,4,5,6,7,8,9]. In the course of our continuing studies on the total synthesis of marine natural products, we realized the first total syntheses of both enantiomers of 4 and its six stereoisomers, further elucidating their selective α-glucosidase inhibitory activities. (1–4)with with synthetic synthetic 5 and the above, we aimed to design and synthesize pericosine E analogs bearing a
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