Chemistry of Trisdecacyclic Pyrazine Antineoplastics: The Cephalostatins and Ritterazines

被引：92

作者：

Lee, Seongmin ^{[2
]}

LaCour, Thomas G. ^{[1
]}

Fuchs, Philip L. ^{[1
]}

机构：

[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

[2] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

CHEMICAL REVIEWS | 2009年 / 109卷 / 06期

基金：

美国国家卫生研究院;

关键词：

HEXACYCLIC STEROID UNIT; ORNITHOGALUM-SAUNDERSIAE; CHOLESTANE GLYCOSIDES; SOLASODINE GLYCOSIDES; STRUCTURE ELUCIDATION; EFFICIENT SYNTHESIS; ANTICANCER ACTIVITY; NATURAL COMPOUND; SYN-ELIMINATION; CANCER-CELLS;

D O I：

10.1021/cr800365m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A significant review on the chemistry of trisdecacyclic pyrazine antineoplastics is reported. The Pettit team worked to isolate the caphalostatins from hemochordate worm 'Cephalodiscus gilchristi' to find natural products of medicinal significance, while the Fusetani team isolated the ritterazines from the tunicate 'Ritterella tokioka'. The cephalostatins and ritterazines, a family of 45 trisdecacyclic bissteroidal pyrazines, showed excellent cytotoxicity against human tumors. It was also found that all cephalostatins possess two highly oxygenated steroidal spiroketal units linked by a central pyrazine ring. Fusetani's group also conducted the structure determination of 26 ritterazines from extracts of the tunicate Ritterella tokioka. The National Cancer Institute tested and declared cephalostatins as the most powerful anticancer agents.

引用

页码：2275 / 2314

页数：40

共 111 条

[1]

Atta-ur-Rahman, 1999, ALKALOIDS, V52, P233

[2] Diterpenoid and steroidal alkaloids [J].

AttaurRahman ;

Choudhary, MI .

NATURAL PRODUCT REPORTS, 1997, 14 (02) :191-203

[3] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[4]

Bäsler S, 2000, HELV CHIM ACTA, V83, P1854, DOI 10.1002/1522-2675(20000809)83:8<1854::AID-HLCA1854>3.0.CO

[5]

2-4

[6] CURADERM - REPLY [J].

BEARDMORE, GL ;

HART, V ;

WILSON, P ;

FRANCIS, D .

MEDICAL JOURNAL OF AUSTRALIA, 1989, 150 (06) :350-351

[7] Design, synthesis and evaluation of a novel series of spiroketals based on the structure of the antibacterial gyrase inhibitor novobiocin [J].

Bell, W ;

Block, MH ;

Cook, C ;

Grant, JA ;

Timms, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (18) :2789-2801

[8] A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins [J].

Betancor, C ;

Freire, R ;

Pérez-Martín, I ;

Prangé, T ;

Suárez, E .

ORGANIC LETTERS, 2002, 4 (08) :1295-1297

[9] SYNTHESIS OF A C-14,C-15 DIHYDRO DERIVATIVE OF THE SOUTH HEXACYCLIC STEROID UNIT OF CEPHALOSTATIN-1 .2. SPIROKETAL SYNTHESIS AND STEREOCHEMICAL ASSIGNMENT BY NMR-SPECTROSCOPY [J].

BHANDARU, S ;

FUCHS, PL .

TETRAHEDRON LETTERS, 1995, 36 (46) :8351-8354

[10] DUNAIMYCINS, A NEW COMPLEX OF SPIROKETAL 24-MEMBERED MACROLIDES WITH IMMUNOSUPPRESSIVE ACTIVITY .3. IMMUNOSUPPRESSIVE ACTIVITIES OF DUNAIMYCINS [J].

BURRES, NS ;

PREMACHANDRAN, U ;

FRIGO, A ;

SWANSON, SJ ;

MOLLISON, KW ;

FEY, TA ;

KRAUSE, RA ;

THOMAS, VA ;

LANE, B ;

MILLER, LN ;

MCALPINE, JB .

JOURNAL OF ANTIBIOTICS, 1991, 44 (12) :1331-1341

← 1 2 3 4 5 6 7 8 9 10 →