169944-36-9Relevant articles and documents
Synthesis of isoflavones by tandem demethylation and ring-opening/cyclization of methoxybenzoylbenzofurans
Kunyane, Phaladi,Sonopo, Molahlehi S.,Selepe, Mamoalosi A.
supporting information, p. 3074 - 3082 (2019/11/19)
The unexpected conversion of benzoylbenzofurans into isoflavones through an intramolecular cascade that involves deprotection and ring-opening/cyclization is described. This was discovered in an investigation of the possible transformation of benzoylbenzofurans into coumaronochromones. This route affords isoflavones in two major steps from acetophenones and benzoquinones. The transformation was validated by synthesizing differently substituted isoflavone derivatives and further applied to a concise synthesis of a potential anticancer lead compound, glaziovianin A (1).
Amberlyst-15 in PEG-400: Green synthesis of 3-benzoyl-5-hydroxy benzofuran and naphtho[1,2-b]furan derivatives at room temperature
Bathula, Surendra Bose,Khagga, Mukkanti,Venkatasubramanian, Hariharakrishnan
, p. 353 - 360 (2017/07/26)
Background: Oxygen heterocycles exhibit diverse biological and pharmacological activities. In particular, benzofurans are available in a wide number of natural products and have drawn considerable attention over the last few years due to their profound physiological and biological properties. The aim of this paper describes a green methodology to synthesize this potent molecule with high selectivity by using ionic resin in PEG at room temperature. Methods: The methodology is very simple and easily accessible at room temperature. It uses low catalyst loadings and is recycled subsequently. In addition, detailed experimental procedure for the selected compounds including the spectral data are provided. Results: Among the various ionic resins attempted, Amberlyst-15 in PEG-400 was the choice of selection for the synthesis of 3-benzoyl-5-hydroxy benzofuran and naphtho[1,2-b]furan derivatives at room temperature in an environmentally friendly method. This catalyst system resulted in excellent yields in short reaction times and high selectivity. Conclusion: We have developed a green highly efficient and environmentally friendly protocol for the facile synthesis of 3-benzoyl-5-hydroxy benzofuran and naphtho[1,2-b]furan derivatives at room temperature in high yields (>90-95%) using nontoxic and inexpensive ion exchange resin Amberlyst-15. The notable advantages of the catalyst approach enables the reactions with high selectivity, short reactions time and excellent yields without generating any waste and was reused.
Identification of benzofuran-3-yl(phenyl)methanones as novel SIRT1 inhibitors: Binding mode, inhibitory mechanism and biological action
Wu, Jiahui,Li, Yi,Chen, Kaixian,Jiang, Hualiang,Xu, Ming-Hua,Liu, Dongxiang
, p. 441 - 450 (2013/03/29)
SIRT1 is a NAD+-dependent deacetylase. Here we described new SIRT1 inhibitors with the scaffold of benzofuran-3-yl(phenyl)methanone. The inhibitors were predicted to bind in C-pocket of SIRT1, forming hydrophobic interactions with Phe273, Phe312 and Ile347. Introducing hydroxyl to meta position of phenyl may form H-bond with Asn346. Indeed, (2,5-dihydroxyphenyl)(5- hydroxy-1-benzofuran-3-yl)methanone (16), an analogue with hydroxyls at ortho and meta positions, showed greater inhibition. The binding mode was validated by structural modifications and kinetic studies. Since C-pocket is the site where the nicotinamide moiety of NAD+ binds and the hydrolysis takes place, binding of 16 in C-pocket would block the transformation of NAD+ to productive conformation and hence inhibit the deacetylase activity. Consistently, 16 inhibited SIRT1 through up-regulating p53 acetylation on cellular level.
