Improved synthesis of isogranulatimide, a G2 checkpoint inhibitor. Syntheses of didemnimide C, isodidemnimide A, neodidemnimide A, 17-methylgranulatimide, and isogranulatimides A-C

被引:58
作者
Piers, E
Britton, R
Andersen, RJ
机构
[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
[2] Univ British Columbia, Dept Earth & Ocean Sci, Vancouver, BC V6T 1Z1, Canada
关键词
D O I
10.1021/jo9914723
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise, improved synthesis of isogranulatimide (6), a naturally occurring substance with G2 checkpoint inhibition activity, is described. Also reported are the syntheses of didemnimide C (18), isodidemnimide A (24), neodidemnimide A (36), 17-methylgranulatimide (9), and isogranulatimides A (10), B (11), and C (12). Compounds 9-12, congeners of isogranulatimide (6), are now available for biological evaluation.
引用
收藏
页码:530 / 535
页数:6
相关论文
共 35 条
[1]   2-AMINOPURINE OVERRIDES MULTIPLE CELL-CYCLE CHECKPOINTS IN BHK CELLS [J].
ANDREASSEN, PR ;
MARGOLIS, RL .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (06) :2272-2276
[2]   Granulatimide and isogranulatimide, aromatic alkaloids with G2 checkpoint inhibition activity isolated from the Brazilian ascidian Didemnum granulatum:: Structure elucidation and synthesis [J].
Berlinck, RGS ;
Britton, R ;
Piers, E ;
Lim, L ;
Roberge, M ;
da Rocha, RM ;
Andersen, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9850-9856
[3]   CATALYTIC TRANSFER HYDROGENATION [J].
BRIEGER, G ;
NESTRICK, TJ .
CHEMICAL REVIEWS, 1974, 74 (05) :567-580
[4]  
Bunch RT, 1996, CLIN CANCER RES, V2, P791
[5]   ACTION OF CAFFEINE ON X-IRRADIATED HELA-CELLS .3. ENHANCEMENT OF X-RAY-INDUCED KILLING DURING G2 ARREST [J].
BUSSE, PM ;
BOSE, SK ;
JONES, RW ;
TOLMACH, LJ .
RADIATION RESEARCH, 1978, 76 (02) :292-307
[6]   2,5-DILITHIATION OF N-PROTECTED IMIDAZOLES - SYNTHESES OF 2,5-DISUBSTITUTED DERIVATIVES OF 1-METHOXYMETHYL-IMIDAZOLE, 1-TRIPHENYLMETHYL-IMIDAZOLE, AND 1-(N,N-DIMETHYLSULPHONAMIDO)-IMIDAZOLE [J].
CHADWICK, DJ ;
NGOCHINDO, RI .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03) :481-486
[7]   CAFFEINE OVERCOMES A RESTRICTION POINT ASSOCIATED WITH DNA-REPLICATION, BUT DOES NOT ACCELERATE MITOSIS [J].
DOWNES, CS ;
MUSK, SRR ;
WATSON, JV ;
JOHNSON, RT .
JOURNAL OF CELL BIOLOGY, 1990, 110 (06) :1855-1859
[8]  
EILS S, 1998, SYNTHESIS-STUTTGART, P275
[9]  
FAN SJ, 1995, CANCER RES, V55, P1649
[10]   A new one step synthesis of maleimides by condensation of glyoxylate esters with acetamides [J].
Faul, MM ;
Winneroski, LL ;
Krumrich, CA .
TETRAHEDRON LETTERS, 1999, 40 (06) :1109-1112