- Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-Methoxystypandrone and its analogues
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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-protease structure-activity relationships of these compounds have been described.
- Singh, Sheo B,Graham, Pia L,Reamer, Robert A,Cordingley, Michael G
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- Synthesis of 2-Methoxystypandrone: Comments on the Structure of Ventilaginone
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The structure of 2-methoxystypandrone a naphthoquinone isolated from Polygonum cuspidatum, Rhamnus fallax, and Ventilago calyculata is confirmed by synthesis as 6-acetyl-5-hydroxy-2-methoxy-7-methylnaphthalene-1,4-dione (1).The structure proposed for ventilaginone, an unusual naphthalene isolated from Ventilago maderaspatana, 8,9-dimethoxy-5-methylnaphtho-1,3-dioxin-4-yl methyl ketone (17), is shown by synthesis to be erroneous.Alternative structures are considered.
- Hughes, Andrew B.,Sargent, Melvyn V.
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p. 449 - 452
(2007/10/02)
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