Synthesis of novel antitumor agent 1-methoxy-5,10-dioxo-5,10-dihydro-1H-benzo-[g]isochromene carboxylic acid (3-dimethylylaminopropyl)amide with a dual role Pd(II) catalyst

被引:91
作者
Mondal, S [1 ]
Nogami, T [1 ]
Asao, N [1 ]
Yamamoto, Y [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/jo035016x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and simple method for the synthesis of 1-methoxy-5,10-dioxo-5,10-dihydro-1H-benzo[g]isochromene-3-carboxylic acid (3-(dimethylamino)propyl)amide 4c was developed. The key step involves the easy formation of 1,3-disubstituted cyclic alkenyl ether, an important framework of isochromene natural products, with a dual role Pd-(II) catalyst.
引用
收藏
页码:9496 / 9498
页数:3
相关论文
共 32 条
[1]   Vitamin K-active derivatives of 2-methyl-1,4-naphthohydroquinone [J].
Ansbacher, S ;
Fernholz, E ;
Dolliver, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :155-158
[2]   Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: Synthesis of cyclic alkenyl ethers from acetylenic aldehydes [J].
Asao, N ;
Nogami, T ;
Takahashi, K ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :764-765
[3]  
ATTARDO G, 1998, Patent No. 148251
[4]   ADRIAMYCIN - NEW ANTICANCER DRUG WITH SIGNIFICANT CLINICAL ACTIVITY [J].
BLUM, RH ;
CARTER, SK .
ANNALS OF INTERNAL MEDICINE, 1974, 80 (02) :249-259
[5]   Synthetic strategies towards pyranonaphthoquinone antibiotics [J].
Brimble, MA ;
Nairn, MR ;
Prabaharan, H .
TETRAHEDRON, 2000, 56 (14) :1937-1992
[6]  
GIANNI L, 1983, REV BIOCHEM TOXICOL, P1
[7]   Isochromenes and their quinones through cyclisations with bisacetonitriledichloropalladium(II) [J].
Giles, RGF ;
Green, IR ;
Taylor, CP .
TETRAHEDRON LETTERS, 1999, 40 (26) :4871-4872
[8]   PREPARATION OF CARBOXYLIC AMIDES FROM ALDEHYDES BY OXIDATION [J].
GILMAN, NW .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (14) :733-&
[9]   ANTITUMOR AGENTS .89. PSYCHORUBRIN, A NEW CYTOTOXIC NAPHTHOQUINONE FROM PSYCHOTRIA RUBRA AND ITS STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
HAYASHI, T ;
SMITH, FT ;
LEE, KH .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) :2005-2008
[10]   ADRIAMYCIN AND THE HEART [J].
HENDERSON, IC ;
FREI, E .
NEW ENGLAND JOURNAL OF MEDICINE, 1979, 300 (06) :310-312