Synthesis of 2,8-disubstituted imidazo[1,5-a]pyrimidines with potent antitumor activity

Journal of Medicinal Chemistry

Volumn 42, Issue 9, 1999, Pages 1661-1666

  Matsumoto, Hiroatsu ^a   Ikeda, Kazuyoshi ^b   Nagata, Nobuyuki ^a   Takayanagi, Hiroaki ^c   Mizuno, Yoshihisa ^a   Tanaka, Motohiro ^d   Sasaki, Takuma ^d  

^a Minophagen Pharmaceutical Co   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c KITASATO UNIVERSITY   (Japan)

^d KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDROIMIDAZO[1,5 A]PYRIMIDINE DERIVATIVE; 8 THIOCARBAMOYL 1,2 DIHYDROIMIDAZO[1,5 A]PYRIMIDIN 2(1H) THIONE; 8 THIOCARBAMOYL 1,2,3,4 TETRAHYDROIMIDAZO[1,5 A]PYRIMIDIN 2(1H) THIONE; ANTINEOPLASTIC AGENT; FLUOROURACIL; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA CELL; MOUSE; NONHUMAN; SQUAMOUS CELL CARCINOMA; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL DIVISION; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; IMIDAZOLES; INHIBITORY CONCENTRATION 50; MICE; MODELS, MOLECULAR; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0033529011     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980731y     Document Type: Article

References (7)

1. Kaneko, T.; Hara, S.; Matsumoto, H.; Takeuchi, T.; Mori, T.; Ikeda, K.; Mizuno, Y. A series of novel acyclic nucleosides. IV. Synthesis of N1-sulfur analogues of acyclovir, directed toward improved antiviral activities. Chem. Pharm. Bull. 1991, 39, 871-875.
2. Hara, S.; Kaneko, T.; Matsumoto, H.; Nishino, T.; Takeuchi, T.; Mori, T.; Ikeda, K.; Mizuno, Y. Synthesis of 6-sulfur analogues of oxanosine and closely related derivatives thereof. Nucleosides Nucleotides 1992, 11, 571-582.
3. The cytotoxicity of these compounds was determined by a published method: Carmichael, J.; DeGraff, W. G.; Grazdar, A. F.; Minna, J. D.; Mitchell, J. B. Assessment of chemosensitivity testing. Cancer Res. 1987, 47, 936-942.
4. Ochiai, E.; Shibata, S. Polarization of aromatic heterocycles (IV). Polarization of imidazole ring systems. J. Pharm. Soc. Jpn. 1939, 59, 185-195.
5. Novison, T.; O'Brien, D. E.; Robins, R. K. The synthesis of certain 8-cyano-2,4-disubstituted imidazo[1,5-a]pyrimidines. J. Heterocycl. Chem. 1974, 11, 873-878.
6. Chern, J.-W.; Lee, C.-C.; Liaw, Y.-C.; Wang, A. H.-J. Heterocyclic compounds I. Reaction of o-amino-carboxyamide with β-diketones: Synthesis of imidazo[1,5-a]pyrimidine and pyrazolo[1,5-a]pyrimidine derivatives. Heterocycles 1992, 34, 1133-1145.
7. Al-Shaar, A. M. H.; Chambers, R. K.; Gilmour, D. W.; Lythgoe, D. J.; McClenaghan, I.; Ramsdem, C. A. The synthesis of heterocyeles via addition-elimination reactions of 4- and 5-aminoimidazoles. J. Chem. Soc., Perkin Trans. I 1992, 2789-2811.