Synthesis and Biological Evaluation of Antitumor-Active Arglabin Derivatives

被引:28
作者
Csuk, Rene [1 ]
Heinold, Anke [1 ]
Siewert, Bianka [1 ]
Schwarz, Stefan [1 ]
Barthel, Alexander [1 ]
Kluge, Ralph [1 ]
Stroehl, Dieter [1 ]
机构
[1] Univ Halle Wittenberg, Bereich Organ Chem, D-06120 Halle, Saale, Germany
关键词
Arglabin; Arborescin; Antitumor activity; Guaianolides; SCHISTOSOMICIDAL SESQUITERPENE LACTONE; ESTAFIATIN; 1,10-EPIARBORESCIN; STEREOCHEMISTRY; ASSIGNMENT; ARBORESCIN; PRODUCTS;
D O I
10.1002/ardp.201100065
中图分类号
R914 [药物化学];
学科分类号
100705 [微生物与生化药学];
摘要
Arglabin derivatives varied at the endo- or exo-cyclic double bond were synthesized and studied in a colorimetric sulforhodamine B assay for their cytotoxicity. Variations on the endocyclic double bond led to compounds of reduced cytotoxicity whereas derivatives from the reaction of the alpha-methylene-gamma-butyrolactone moiety led to compounds of similar or only slightly reduced cytotoxicity but different, cell line-dependent selectivity. In addition, arglabin is an excellent starting material for the synthesis of the guaianolide arborescin.
引用
收藏
页码:215 / 222
页数:8
相关论文
共 40 条
[1]
Abil'daeva A. Zh., 2004, Eksperimental'naya i Klinicheskaya Farmakologiya, V67, P37
[2]
Adekenov, 1998, Pharmaceutical compositions containing arglabin and arglabin derivatives, Patent No. [9848789A1, 9848789]
[3]
Adekenov S. M., 2008, [No title captured], Patent No. [WO2008035958A1, 2008035958]
[4]
Adekenov S.M., 1999, WO Patent, Patent No. 9964003
[5]
ADEKENOV SM, 1982, KHIM PRIR SOEDIN+, P655
[6]
ADEKENOV SM, 1991, KHIM PRIR SOEDIN+, P33
[7]
ALONSOPERARNAU D, 1994, AN QUIM, V90, P473
[9]
SYNTHESES OF ARBORESCIN, 1,10-EPIARBORESCIN, AND (11S)-GUAIA-3,10(14)-DIENO-13,6-ALPHA-LACTONE, THE KEY INTERMEDIATE IN GREENE AND CRABBES ESTAFIATIN SYNTHESIS, AND THE STEREOCHEMICAL ASSIGNMENT OF ARBORESCIN [J].
ANDO, M ;
AKAHANE, A ;
YAMAOKA, H ;
TAKASE, K .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3909-3916
[10]
STUDIES ON THE SYNTHESIS OF SESQUITERPENE LACTONES .16. THE SYNTHESES OF 11-BETA,13-DIHYDROKAUNIOLIDE, ESTAFIATIN, ISODEHYDROCOSTUSLACTONE, 2-OXODESOXYLIGUSTRIN, ARBORESCIN, 1,10-EPIARBORESCIN, 11-BETA,13-DIHYDROLUDARTIN, 8-DEOXY-11-BETA,13-DIHYDRORUPICOLIN-B, 8-DEOXYRUPICOLIN-B, 3,4-EPILUDARTIN, LUDARTIN, KAUNIOLIDE, DEHYDROLEUCODIN, AND LEUCODIN [J].
ANDO, M ;
IBAYASHI, K ;
MINAMI, N ;
YOSHIMURA, H ;
NAKAMURA, T ;
ISOGAI, K .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (04) :433-445