Synthesis and evaluation of 6-(dibromomethyl)-5-nitropyrimidines as potential antitumor agents

Journal of Medicinal Chemistry

Volumn 40, Issue 5, 1997, Pages 766-770

  Thompson, M Daniel ^a   Cupps, Thomas L ^a   Wise, Dean S ^a   Wotring, Linda L ^a   Townsend, Leroy B ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

6 (DIBROMOMETHYL) 2 METHOXY 4 MORPHOLINO 5 NITROPYRIMIDINE; 6 (DIBROMOMETHYL) 5 NITROPYRIMIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER GROWTH; CANCER INHIBITION; CELL PROLIFERATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; MOUSE; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL DIVISION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR STRUCTURE; NEOPLASMS, EXPERIMENTAL; PURINE NUCLEOSIDES; PYRIMIDINES; RIBONUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0031042105     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9605546     Document Type: Article

References (11)

1. Cupps, T. L.; Wise, D. S.; Townsend, L. B. Synthetic Strategies Toward the Synthesis of 2,4-Dimethoxypyrrolo[3,2-d]pyrimidine. J. Org. Chem. 1983, 48, 1060-1064.
2. Cupps, T. L.; Wise, D. S.; Townsend, L. B. A Novel Three-Step Synthesis of a Pyrrolo[3,2-d]pyrimidine C-Nucleoside. J. Org. Chem. 1986, 51, 1058-1064.
3. Backer, H. J.; Grevenstuk, A. B. Quelques Sulfanilamidopyrimidines Substituées. Recl. Trav. Chim. Pays-Bas 1945, 64, 115-121.
4. Bacon, R. G. R.; Hamilton, S. D. Metal Ions and Complexes in Organic Reactions. Part XVIII. Structural Variations in the Production of Polycyclic Heterocyclic Systems by Iron(II)-Promoted Cyclizations of Nitro-substituted Precursors. J. Chem. Soc., Perkin Trans. I 1974, 1970-1975.
5. Kerfanto, M. Preparation of Aldehydes by the Action of Morpholine on gem-Dihalogeno Compounds. Angew. Chem., Int. Ed. Engl. 1962, 1, 459.
6. Renau, T. E.; Lee, J. S.; Kim, H.; Young, C. G.; Wotring, L. L.; Townsend, L. B.; Drach, J. C. Relationship Between Cytotoxicity and Conversion of Thiosangivamycin Analogs to Toyocamycin Analogs in Cell Culture Medium. Biochem. Pharmacol. 1994, 48, 801-807.
7. (a) Sladek, N. E. Potentiation of the Cytotoxic Action of Melphalan and "Activated" Cyclophosphamide Against Cultured Tumor Cells by Centrophenoxine. J. Pharmacol. Exp. Ther. 1977, 200, 17-24.
8. (b) Pratt, W. B.; Ruddon, R. W.; Ensminger, W. D.; Maybaum, J. The Anticancer Drugs. 2nd ed.; Oxford University Press: New York, 1994; pp 108-154.
9. Data kindly provided by the Developmental Therapeutics Program, Division of Cancer Treatment, National Cancer Institute, NIH. T/C% = life span of treated mice/life span of control tumor-bearing mice x 100.
10. Wotring, L. L.; Townsend, L. B. Study of Cytotoxicity and Metabolism of 4-Amino-3-Carboxamido-1-(β-D-ribofuranosyl)-pyrazolo[3,4-d]pyrimidine Using Inhibitors of Adenosine Kinase and Adenosine Deaminase. Cancer Res. 1979, 39, 3018-3023.
11. Kawasaki, A. M.; Wotring, L. L.; Townsend, L. B. Synthesis and Cytotoxicity Studies of 8-Amino-6-methyl-2-β-D-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene (7-Aza-TCN) and the Corresponding 2′-Deoxy- and Arabinonucleoside Analogues. J. Med. Chem. 1990, 33, 3170-3176.