BIOMAT Database Logo BIOMAT Database Logo

Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2. 2009

George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Department of Chemistry and Biochemistry, Cancer Research Institute, Arizona State University, PO Box 871604, Tempe, Arizona 85287-1604, USA. bpettit@asu.edu

A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.

UI MeSH Term Description Entries
D007783 Lactones Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure. Large cyclic lactones of over a dozen atoms are MACROLIDES. Lactone
D010647 Phenyl Ethers Ethers that are linked to a benzene ring structure. Diphenyl Oxide,Diphenyl Oxides,Diphenyl Ethers,Ethers, Diphenyl,Ethers, Phenyl,Oxide, Diphenyl,Oxides, Diphenyl
D011355 Prodrugs A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. Drug Precursor,Drug Precursors,Pro-Drug,Prodrug,Pro-Drugs,Precursor, Drug,Precursors, Drug,Pro Drug,Pro Drugs
D004354 Drug Screening Assays, Antitumor Methods of investigating the effectiveness of anticancer cytotoxic drugs and biologic inhibitors. These include in vitro cell-kill models and cytostatic dye exclusion tests as well as in vivo measurement of tumor growth parameters in laboratory animals. Anticancer Drug Sensitivity Tests,Antitumor Drug Screens,Cancer Drug Tests,Drug Screening Tests, Tumor-Specific,Dye Exclusion Assays, Antitumor,Anti-Cancer Drug Screens,Antitumor Drug Screening Assays,Tumor-Specific Drug Screening Tests,Anti Cancer Drug Screens,Anti-Cancer Drug Screen,Antitumor Drug Screen,Cancer Drug Test,Drug Screen, Anti-Cancer,Drug Screen, Antitumor,Drug Screening Tests, Tumor Specific,Drug Screens, Anti-Cancer,Drug Screens, Antitumor,Drug Test, Cancer,Drug Tests, Cancer,Screen, Anti-Cancer Drug,Screen, Antitumor Drug,Screens, Anti-Cancer Drug,Screens, Antitumor Drug,Test, Cancer Drug,Tests, Cancer Drug,Tumor Specific Drug Screening Tests
D000972 Antineoplastic Agents, Phytogenic Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. Antineoplastics, Botanical,Antineoplastics, Phytogenic,Agents, Phytogenic Antineoplastic,Botanical Antineoplastics,Phytogenic Antineoplastic Agents,Phytogenic Antineoplastics
D001632 Bibenzyls Compounds that include 1,2-diphenylethane in their structure. Bisbenzyls
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D018360 Crystallography, X-Ray The study of crystal structure using X-RAY DIFFRACTION techniques. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) X-Ray Crystallography,Crystallography, X Ray,Crystallography, Xray,X Ray Crystallography,Xray Crystallography,Crystallographies, X Ray,X Ray Crystallographies

Related Publications

George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Antineoplastic agents 460. Synthesis of combretastatin A-2 prodrugs.
January 2001, Anti-cancer drug design,
George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Antineoplastic agents 322. synthesis of combretastatin A-4 prodrugs.
June 1995, Anti-cancer drug design,
George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Antineoplastic agents 463. Synthesis of combretastatin A-3 diphosphate prodrugs.
December 2000, Anti-cancer drug design,
George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Synthesis of potential antineoplastic agents. XIV. Some 2-substituted 2,3-dihydro-1h-perimidines.
July 1966, Journal of medicinal chemistry,
George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Antineoplastic agents. 379. Synthesis of phenstatin phosphate.
May 1998, Journal of medicinal chemistry,
George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Antineoplastic agents 393. Synthesis of the trans-isomer of combretastatin A-4 prodrug.
December 1998, Anti-cancer drug design,
George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Synthesis of novel spin-labelled combretastatin A-4 derivatives as potential antineoplastic agents.
January 2012, Natural product research,
George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Synthesis and mechanistic studies of novel spin-labeled combretastatin derivatives as potential antineoplastic agents.
March 2013, Bioorganic & medicinal chemistry,
George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Antineoplastic agents 429. Syntheses of the combretastatin A-1 and combretastatin B-1 prodrugs.
June 2000, Anti-cancer drug design,
George R Pettit, and Peter D Quistorf, and Jeremy A Fry, and Delbert L Herald, and Ernest Hamel, and Jean-Charles Chapuis
Antineoplastic agents. 548. Synthesis of iodo- and diiodocombstatin phosphate prodrugs.
March 2012, Journal of natural products,
Copied contents to your clipboard!