Novel O-methyl goniofufurone and 7-epi-goniofufurone derivatives: synthesis, in vitro cytotoxicity and SAR analysis

Abstract

Novel goniofufurone (1) and 7-epi-goniofufurone (2) derivatives bearing a methoxy group at the C-5 and/or C-7 positions were prepared and their in vitro antitumour activity against some human tumour cell lines was evaluated.

Divergent synthesis and antitumour activity of novel conformationally constrained (−)-muricatacin analogues

“…Starting compound 2 was prepared from D-glucose in two synthetic steps as previously reported by us. 23 Methyl derivative 2 was treated with periodic acid in dry ethyl acetate and the crude aldehyde 3 was obtained. Compound 3 reacted with stabilized ylide, Ph3P=CHCO2Me, in anhydrous MeOH and gave the expected Zolefin 4 (69 %) as the major product of Wittig olefination.…”

Synthesis of anti-proliferative [3.3.0]furofuranone derivatives by lactonization and functionalization of C-glycosyl compounds

“…[37][38][39] Conformationally constrained goniofufurone mimics with 1,3-dioxane heterocyclic ring embedded in 5,7-positions were designed and evaluated [40,41] and a series of conformationally restricted analogs with halogen, azido or benzyloxy groups at the C-7 position were recently described. [42] Mimics bearing a methoxy group at C-5 and C-7 positions [43] and C-7-alkyloxymethyl groups (C6-C13) were recently investigated. [44] Related to Crassalactones B and C, Popsavin et al also designed and evaluated structural features through a 3D-QSAR model for various styryl lactones and the crucial effect of the cinnamic acid ester moiety at C-7 was highlighted.…”