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

2001; Elsevier BV; Volume: 11; Issue: 24 Linguagem: Inglês

10.1016/s0960-894x(01)00648-5

1464-3405

Sheo B. Singh, Pia Graham, Robert A. Reamer, Michael G. Cordingley,

Phytochemistry and Biological Activities

2-Methoxystypandrone, a naphthoquinone, was isolated from a Chinese herb Polygonum cuspidatum by bioassay guided fractionation using HRV 3C-protease assay. It showed an IC(50) value of 4.6 microM 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-protease structure-activity relationships of these compounds have been described.