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Review of cytotoxic cephalostatins and ritterazines: isolation and synthesis.
- Source :
-
Journal of natural products [J Nat Prod] 2008 Mar; Vol. 71 (3), pp. 487-91. Date of Electronic Publication: 2008 Jan 15. - Publication Year :
- 2008
-
Abstract
- The cephalostatins and ritterazines comprise a family of structurally related natural products reported by Professors G. R. Pettit and N. Fusetani from 1988 -1998. Isolated from the invertebrate marine chordates Cephalodiscus gilchristi and Ritterella tokioka, the cephalostatins and ritterazines exhibit potent cytotoxicity toward the murine P388 lymphocytic leukemia cell line. In fact, cephalostatin 1 ( 1, ED 50 0.1-0.001 pM) proved to be one of the most powerful cancer cell growth inhibitors ever tested by the U.S. National Cancer Institute. The ritterazines and cephalostatins share many common structural features in which two highly oxygenated steroidal units with side chains forming either 5/5 or 5/6 spiroketals are fused via a pyrazine core. Professor P. L. Fuchs and colleagues reported the total syntheses of 1, cephalostatins 7 ( 7), and 12 ( 12), ritterazines K ( 30) and M ( 32), and cytotoxic analogues. The synthesis of 1, described in 1998, required 65 synthetic operations to complete.
- Subjects :
- Animals
Chordata, Nonvertebrate chemistry
Molecular Structure
Urochordata chemistry
Antineoplastic Agents chemical synthesis
Antineoplastic Agents chemistry
Antineoplastic Agents isolation & purification
Antineoplastic Agents pharmacology
Biological Products chemical synthesis
Biological Products chemistry
Biological Products isolation & purification
Biological Products pharmacology
Phenazines chemical synthesis
Phenazines chemistry
Phenazines isolation & purification
Phenazines pharmacology
Spiro Compounds chemical synthesis
Spiro Compounds chemistry
Spiro Compounds isolation & purification
Spiro Compounds pharmacology
Steroids chemical synthesis
Steroids chemistry
Steroids isolation & purification
Steroids pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 0163-3864
- Volume :
- 71
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 18197599
- Full Text :
- https://doi.org/10.1021/np070536z