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(3S,4R)-Bengamide E(2) was synthesized starting from D-glucono-δ-lactone(3) and the key deoxygenation step from 13 to 15 was achieved by the application of NaBH_3CN and ZnI_2.Compared with natural bengamide E(1),the synthetic compound(35,4R)-bengamide E(2) was inactive against the cell growth of HUVEC and cancer cells.These data represent the significance of the stereochemistry at C-3 and C-4 of bengamides for structural recognition and binding with the target(s).
(3S, 4R) -Bengamide E (2) was synthesized starting from D-glucono-δ-lactone (3) and the key deoxygenation step from 13 to 15 was achieved by the application of NaBH_3CN and ZnI_2.Compared with natural bengamide E ( 1), the synthetic compound (35,4R) -bengamide E (2) was inactive against the cell growth of HUVEC and cancer cells. The data represents the significance of the stereochemistry at C-3 and C-4 of bengamides for structural recognition and binding with the target (s).