14964-98-8Relevant academic research and scientific papers
Concise synthesis and cellular evaluation of 3′-formyl-4′,6′-dihydroxy-2′-methoxy-5′-methylchalcone (FMC) and its analogues
Zhuo, Xiang,En-Zhen, Li,Hai, Liang,Hong-Ju, Guo,Ning, Shi,Xue-Hui, Zhang,Qi-Fang, Qian,Jiu-Hong, Wu
, p. 3139 - 3147 (2014)
3′-Formyl-4′,6′-dihydroxy-2′-methoxy-5′-methylchalcone (FMC) was a natural product isolated from Cleistocalyx operculatus. A four-step synthetic strategy toward FMC and its four analogues (1b-1e) was first developed. All compounds were synthesized from commercially available 2,4,6-trihydroxyacetophenone; formylation at 3′ position under Vilsmeier-Haack conditions was followed by the introduction of a methyl group at 5′ position. The key step of selective methylation at 2′ position was achieved by trimethylsilyldiazomethane (TMSCHN2). Then substituted aromatic aldehydes were condensed through Claisen-Schmidt reaction in the presence of potassium hydroxide. All structures were confirmed by 1H NMR, 13C NMR, and high-resolution mass spectra. FMC and analogues were screened for their antiproliferative activity.
Isolation, Synthesis, and Antisepsis Effects of a C-Methylcoumarinochromone Isolated from Abronia nana Cell Culture
Lee, Wonhwa,Lee, Doohyun,Lee, Yuri,Lee, Taeho,Song, Kyung-Sik,Yang, Eun-Ju,Bae, Jong-Sup
, p. 1173 - 1182 (2018/05/31)
Only a few isoflavones have been isolated from plants of the genus Abronia. The biological properties of compounds isolated from Abronia species have not been well established, and their antisepsis effects have not been reported yet. In the present study, a new C-methylcoumarinochromone, was isolated from Abronia nana suspension cultures. Its structure was deduced as 9,11-dihydroxy-10-methylcoumarinochromone (boeravinone Y, 1) by spectroscopic data analysis and verified by chemical synthesis. The potential inhibitory effects of 1 against high mobility group box 1 (HMGB1)-mediated septic responses were investigated. Results showed that 1 effectively inhibited lipopolysaccharide-induced release of HMGB1 and suppressed HMGB1-mediated septic responses, in terms of reduction of hyperpermeability, leukocyte adhesion and migration, and cell adhesion molecule expression. In addition, 1 increased the phagocytic activity of macrophages and exhibited bacterial clearance effects in the peritoneal fluid and blood of mice with cecal ligation and puncture-induced sepsis. Collectively, these results suggested that 1 might have potential therapeutic activity against various severe vascular inflammatory diseases via inhibition of the HMGB1 signaling pathway.
Anti-AIDS agents 68. The first total synthesis of a unique potent anti-HIV chalcone from genus Desmos
Nakagawa-Goto, Kyoko,Lee, Kuo-Hsiung
, p. 8263 - 8266 (2007/10/03)
The first total synthesis of a unique highly functionalized and potent anti-HIV chalcone 1, isolated from genus Desmos, was achieved from commercially available 2,4,6-trihydroxytoluene (3) or 2,4,6-trihydroxybenzaldehyde (2) in five (from 3) or six steps (from 2).
Synthesis of aurentiacin
Hossain, M. Amzad
, p. 324 - 326 (2007/10/03)
Aurentiacin 7 has been isolated from Pityrogramma triangularis var. pallida and synthesised from phloroacetophenone 1 in several steps. All the new products have been characterised on the basis of spectral data and micro analysis.
A C-Methylbiflavone from Cephalotaxus harringtonia K. Koch
Agil, Mohammad,Rahman, Wasiur,Hasaka, Noriko,Okigawa, Masayoshi,Kawano, Nobusuke
, p. 1389 - 1392 (2007/10/02)
6-C-Methyl-7-O-methylamentoflavone (1) isolated from the leaves of Cephalotaxus harringtonia K.Koch (Cephalotaxaceae) has been identified on the basis of the spectral data of its hexamethyl ether (1a) and its penta-acetate (1b).The location of the C-methyl group was first deduced from 1H n.m.r. studies with a lanthanide shift reagent and confirmed by a synthesis of the hexamethyl ether (1a).
