Synthesis of Bioactive Natural Polymethoxyflavones and Their Vinyl Ether Derivatives

被引:9
作者
Cai Shuang-lian [1 ]
Liu Shuang [1 ]
Liu Li [1 ]
Wang Qiu-an [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China
关键词
Flavonoid; Polymethoxyflavone; Prenylation; Farnesylation; INHIBITION; FLAVONES; CITRUS; NOBILETIN;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
Bioactive natural polymethoxyflavones 1-6 and their vinyl ether derivatives 7-15 were synthesized by bromination, aromatic nucleophilic substitution, methylation, benzyl protection, Friedel-Crafts acetylation, aldol condensation, cyclization, DDQ dehydrogenation, regioselective demethylation, debenzylation and O-prenylation or O-farnesylation with resorcinol and appropriate substituted benzaldehydes as starting materials. Among them, compounds 7-15 are new compounds. Natural products 2-4 were firstly total synthesized. The syntheses of compounds 1, 5 and 6 were efficiently improved by the new synthetic routes. The structures of all synthetic compounds were confirmed by NMR, IR spectra and MS.
引用
收藏
页码:631 / 636
页数:6
相关论文
共 21 条
[1]
Interactive effects of polymethoxy flavones from Citrus on cell growth inhibition in human neuroblastoma SH-SY5Y cells [J].
Akao, Yukihiro ;
Itoh, Tomohiro ;
Ohguchi, Kenji ;
Iinuma, Munekazu ;
Nozawa, Yoshinori .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (06) :2803-2810
[2]
4′-Demethylnobiletin, a Bioactive Metabolite of Nobiletin Enhancing PKA/ERK/CREB Signaling, Rescues Learning Impairment Associated with NMDA Receptor Antagonism via Stimulation of the ERK Cascade [J].
Al Rahim, Md ;
Nakajima, Akira ;
Saigusa, Daisuke ;
Tetsu, Naomi ;
Maruyama, Yuji ;
Shibuya, Masatoshi ;
Yamakoshi, Hiroyuki ;
Tomioka, Yoshihisa ;
Iwabuchi, Yoshiharu ;
Ohizumi, Yasushi ;
Yamakuni, Tohru .
BIOCHEMISTRY, 2009, 48 (32) :7713-7721
[3]
Biotransformation of polymethoxylated flavonoids:: Access to their 4′-O-demethylated metabolites [J].
Buisson, Didier ;
Quintin, Jerome ;
Lewin, Guy .
JOURNAL OF NATURAL PRODUCTS, 2007, 70 (06) :1035-1038
[4]
Synthesis, biochemical, and cellular evaluation of farnesyl monophosphate prodrugs as farnesyltransferase inhibitors [J].
Clark, Michelle K. ;
Scott, Sarah A. ;
Wojtkowiak, Jonathan ;
Chirco, Rosemarie ;
Mathieu, Patricia ;
Reiners, John J., Jr. ;
Mattingly, Raymond R. ;
Borch, Richard F. ;
Gibbs, Richard A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (14) :3274-3282
[5]
Prenyloxyphenylpropanoids as novel lead compounds for the selective inhibition of geranylgeranyl transferase I [J].
Epifano, Francesco ;
Curini, Massimo ;
Genovese, Salvatore ;
Blaskovich, Michelle ;
Hamilton, Andrew ;
Sebti, Said M. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (09) :2639-2642
[6]
Inhibitory effects of polymethoxy flavones isolated from Citrus reticulate on degranulation in rat basophilic leukemia RBL-2H3:: Enhanced inhibition by their combination [J].
Itoh, Tomohiro ;
Ohguchi, Kenji ;
Iinuma, Munekazu ;
Nozawa, Yoshinori ;
Akao, Yukihiro .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (16) :7592-7598
[7]
Jacob R, 1968, PHYTOCHEMISTRY, V7, P169
[8]
Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent [J].
Jahaniani, F ;
Ebrahimi, SA ;
Rahbar-Roshandel, N ;
Mahmoudian, M .
PHYTOCHEMISTRY, 2005, 66 (13) :1581-1592
[9]
Identification of nobiletin, a polymethoxyflavonoid, as an enhancer of adiponectin secretion [J].
Kunimasa, Kazuhiro ;
Kuranuki, Sachi ;
Matsuura, Nobuyasu ;
Iwasaki, Nozomi ;
Ikeda, Megumi ;
Ito, Akira ;
Sashida, Yutaka ;
Mimaki, Yoshihiro ;
Yano, Masamichi ;
Sato, Mayumi ;
Igarashi, Yasuhiro ;
Oikawa, Tsutomu .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (07) :2062-2064
[10]
Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines [J].
Li, Shiming ;
Pan, Min-Hsiung ;
Lai, Ching-Shu ;
Lo, Chih-Yu ;
Dushenkov, Slavik ;
Ho, Chi-Tang .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (10) :3381-3389