Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure–activity relationships of 2-methoxystypandrone and its analogues

…, PL Graham, RA Reamer, MG Cordingley

Index: Singh, Sheo B; Graham, Pia L; Reamer, Robert A; Cordingley, Michael G Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 24 p. 3143 - 3146

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Citation Number: 32

Abstract

2-Methoxystypandrone, a naphthoquinone, was isolated from a Chinese herb Polygonum cuspidatum by bioassay guided fractionation using HRV 3C-protease assay. It showed an IC50 value of 4.6 μM and is moderately selective. A new 10-step, total synthesis of 2- methoxystypandrone was accomplished in 45% overall yield using a Diels–Alder approach. Several analogues of this compound were prepared. Isolation, synthesis and HRV 3C- ...