405271-32-1Relevant academic research and scientific papers
Synthesis and structure-activity relationships of thioflavone derivatives as specific inhibitors of the ERK-MAP kinase signaling pathway
Kataoka, Tadashi,Watanabe, Shin-Ichi,Mori, Eiji,Kadomoto, Ryoji,Tanimura, Susumu,Kohno, Michiaki
, p. 2397 - 2407 (2007/10/03)
Condensation of nitrobenzaldehydes 3 and α-[o-(p-methoxybenzylthio) benzoyl] sulfoxide 4 gave α-sulfinyl enones 5. Treatment of 5 with formic acid caused cyclization followed by debenzylation to afford 3-(methylsulfinyl) thioflavanones 6. Double-bond formation with elimination of methanesulfenic acid was performed by refluxing 6 in benzene, and, finally, the nitro group of 2-phenyl-4H-1-benzothiopyran-4-one (thioflavones) 7 was reduced with tin in tetrafluoroboric acid. Various 2′-aminothioflavones 8 thus prepared were evaluated for their inhibitory effects on the ERK-MAP kinase pathway. In a cell-based assay, 2-(2′-amino-3 ′-methoxyphenyl)-4H-1-benzothiopyran-4-one (8b) showed a more potent inhibitory effect than the corresponding oxygen compound (PD98059, 1) on the Raf-induced activation of the ERK-MAP kinase pathway as well as cell proliferation. Furthermore, compound 8b selectively and potently inhibited the proliferation of tumor cells in which the ERK-MAP kinase pathway is constitutively activated.
A new synthesis of 4H-1-benzothiopyran-4-ones using (trimethylsilyl)methylenetriphenylphosphorane
Kumar, Pradeep,Bodas, Mandar S
, p. 9755 - 9758 (2007/10/03)
The reaction of silyl ester of S-acyl(aroyl) thiosalicylic acids 3 with (trimethylsilyl)methylenetriphenylphosphorane 4 in step wise fashion leads to the acylphosphoranes 7, which subsequently undergo intramolecular Wittig cyclization on the thiolester carbonyl to afford the 4H-1-benzothiopyran-4-ones 8 in good to excellent yields.
