Synthesis of pyranicin and its inhibitory action with bovine heart mitochondrial complex I

被引:24
作者
Hattori, Yasunao [1 ,2 ,3 ]
Furuhata, Shin-ichi [2 ]
Okajima, Motonori [2 ]
Konno, Hiroyuki [2 ,4 ]
Abe, Masato [2 ,5 ]
Miyoshi, Hideto [2 ,5 ]
Goto, Tetsuhisa [1 ,2 ]
Makabe, Hidefumi [1 ,2 ]
机构
[1] Shinshu Univ, Interdisciplinary Grad Sch Sci & Technol, Nagano 3994598, Japan
[2] Shinshu Univ, Grad Sch Agr, Integrated Dept, Nagano 3994598, Japan
[3] Shinshu Univ, Satellite Venture Business Lab, Nagano 3994598, Japan
[4] Kyoto Prefectural Univ Med, Grad Sch Med Sci, Dept Chem, Kyoto 602, Japan
[5] Kyoto Univ, Div Appl Life Sci, Grad Sch Agr, Kyoto 6068501, Japan
关键词
D O I
10.1021/ol702902w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total synthesis of pyranicin was achieved using Cl2Pd(CH3CN)(2)-catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of this compound for mitochondrial NADH-ubiquinone oxidoreductase (complex I) was slightly poorer than that of ordinary mono-THF acetogenins such as cis-solamin.
引用
收藏
页码:717 / 720
页数:4
相关论文
共 28 条
[1]   Dynamic function of the alkyl spacer of acetogenins in their inhibitory action with mitochondrial complex I (NADH-ubiquinone oxidoreductase) [J].
Abe, M ;
Murai, M ;
Ichimaru, N ;
Kenmochi, A ;
Yoshida, T ;
Kubo, A ;
Kimura, Y ;
Moroda, A ;
Makabe, H ;
Nishioka, T ;
Miyoshi, H .
BIOCHEMISTRY, 2005, 44 (45) :14898-14906
[2]   Annonaceous acetogenins: Recent progress [J].
Alali, FQ ;
Liu, XX ;
McLaughlin, JL .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540
[3]   Unusual bioactive annonaceous acetogenins from Goniothalamus giganteus [J].
Alali, FQ ;
Rogers, L ;
Zhang, Y ;
McLaughlin, JL .
TETRAHEDRON, 1998, 54 (22) :5833-5844
[4]   Total synthesis of jimenezin via an intramolecular allylboration [J].
Bandur, Nina G. ;
Brueckner, David ;
Hoffmann, Reinhard W. ;
Koert, Ulrich .
ORGANIC LETTERS, 2006, 8 (17) :3829-3831
[5]  
BECKER H, 1996, ANGEW CHEM, V108, P447
[6]   Acetogenins from Annonaceae:: recent progress in isolation, synthesis and mechanisms of action [J].
Bermejo, A ;
Figadère, B ;
Zafra-Polo, MC ;
Barrachina, I ;
Estornell, E ;
Cortes, D .
NATURAL PRODUCT REPORTS, 2005, 22 (02) :269-303
[7]   Total synthesis of (-)-mucocin [J].
Crimmins, Michael T. ;
Zhang, Yan ;
Diaz, Frank A. .
ORGANIC LETTERS, 2006, 8 (11) :2369-2372
[8]   Molecular simplification in bioactive molecules:: Formal synthesis of (+)-muconin [J].
Crisóstomo, FRP ;
Carrillo, R ;
León, LG ;
Martín, T ;
Padrón, JM ;
Martín, VS .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06) :2339-2345
[9]   Enantioselective total synthesis of the potent antitumor agent (-)-mucocin using a temporary silicon-tethered ring-closing metathesis cross-coupling reaction [J].
Evans, PA ;
Cui, J ;
Gharpure, SJ ;
Polosukhin, A ;
Zhang, HR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (48) :14702-14703
[10]   Total synthesis of 34-hydroxyasimicin and its photoactive derivative for affinity labeling of the mitochondrial complex I [J].
Han, HN ;
Sinha, MK ;
D'Souza, LJ ;
Keinan, E ;
Sinha, SC .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (09) :2149-2158