1400930-55-3Relevant academic research and scientific papers
Unified syntheses of gramniphenols F and G, cicerfuran, morunigrol C and its derivative
Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
, p. 1183 - 1186 (2016)
The first syntheses of natural benzofurans, gramniphenols F and G, morunigrol C and its 3′,5′-di-O-methyl analogue along with the synthesis of cicerfuran are achieved by a unified synthetic sequence using 7-hydroxycoumarin, 5-bromoresorcinol, 2,4-dihydroxybenzaldehyde, and sesamol as building blocks. Ramirez gem-dibromoolefination, Miyaura borylation, Suzuki coupling have been successfully exploited in the synthesis. Additionally, their anti-inflammatory effects were also investigated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages. The compounds exhibited significant inhibition of iNOS mediated nitric oxide (NO) production with no cytotoxicity at 10 μM concentration and IC50 values are found in the range from 9.1 to 25.2 μM.
Synthetic methods for Gramniphenols F and G, Cicerfuran, Morunigrol C and its Derivative
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Paragraph 0029; 0030, (2017/07/11)
The present invention relates to a method for preparing natural benzofurans including gramniphenol F, gramniphenol G, morunigrol C and 3andprime;,5andprime;-di-O-methyl analogues thereof and cicerfuran by using 2,4-dihydroxybenzaldehyde, 5-bromoresorcinol and sesamol. In the method according to the present invention, region-selective prenylation, Ramirez gem-dibromo olefination, Miyaura borylation and Suzuki coupling are used. In addition, the compounds were determined for anti-inflammatory effects through a test for production of nitrogen oxide in liposaccharide-induced RAW-264.7 macrophages. All of the compounds show weak to medium (16-42%) inhibitory activities, are not toxic and have an IC_50 value of 9.1 to 25.2 andmu;M.COPYRIGHT KIPO 2017
Positional chemoselectivity in the Zn(II)-mediated removal of phenol protecting groups
Fleury, Lauren M.,Gianino, Joseph B.,Ashfeld, Brandon L.
supporting information, p. 5376 - 5379 (2012/10/30)
A protocol was developed for the chemoselective ortho-deprotection of polyphenolic substrates using readily available ZnIIX2 salts. This procedure provides exceptional positional selectivity for the deprotection of phenols that reside adjacent to directing carbonyl functionality in the presence of similar protecting groups at the meta and para positions. Good to excellent yields of the desired free phenols were obtained (≤96%), and a wide assortment of protecting groups was readily removed under the reaction conditions.
