Synthesis and antileukemic activities of furanyl, pyranyl, and ribosyl derivatives of 4-(3,3-dimethyl-1-triazeno)imidazole-5-carboxamide and 3-(3,3-dimethyl-1-triazeno)pyrazole-4-carboxamide. 1979

R A Earl, and L B Townsend

From the reaction of silylated 4-(3,3-dimethyl-1-triazeno)imidazole-5-carboxamide (DTIC, 5) and 3-(3,3-dimethyl-1-triazeno)pyrazole-4-carboxamide (DTPC, 9) with 2-chlorotetrahydrofuran, we have isolated in both cases a single tetrahydrofuran-2-yl derivative. However, when silylated DTPC was reacted with 2-chlorotetrahydropyran, two tetrahydropyran-2-yl compounds were obtained, and these were shown to be positional isomers on the basis of 1H NMR and UV data. These furanyl and pyranyl derivatives were tested for antileukemic activity (L-1210, in vivo) and the results were compared with the results obtained for the corresponding ribosyl derivatives of DTIC and DTPC.

UI MeSH Term Description Entries
D007939 Leukemia L1210 An experimental LYMPHOCYTIC LEUKEMIA of mice. Leukemia L 1210,L 1210, Leukemia,L1210, Leukemia
D011714 Pyrans Pyran
D011720 Pyrazoles Azoles of two nitrogens at the 1,2 positions, next to each other, in contrast with IMIDAZOLES in which they are at the 1,3 positions.
D003606 Dacarbazine An antineoplastic agent. It has significant activity against melanomas. (from Martindale, The Extra Pharmacopoeia, 31st ed, p564) DTIC,5-(3,3-Dimethyl-1-triazeno)imidazole-4-carboxamide,Biocarbazine,DIC,DTIC-Dome,Decarbazine,Deticene,Dimethyl Imidazole Carboxamide,Dimethyl Triazeno Imidazole Carboxamide,ICDT,NSC-45388,Carboxamide, Dimethyl Imidazole,DTIC Dome,DTICDome,Imidazole Carboxamide, Dimethyl,NSC 45388,NSC45388
D005663 Furans Compounds with a 5-membered ring of four carbons and an oxygen. They are aromatic heterocycles. The reduced form is tetrahydrofuran. Tetrahydrofurans
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D012266 Ribose A pentose active in biological systems usually in its D-form. D-Ribose,D Ribose
D014226 Triazenes Compounds with three contiguous nitrogen atoms in linear format, H2N-N Diazoamino Compounds,Compounds, Diazoamino

Related Publications

R A Earl, and L B Townsend
May 1969, Journal of medicinal chemistry,
R A Earl, and L B Townsend
December 1971, Journal of medicinal chemistry,
R A Earl, and L B Townsend
November 1971, The Journal of pharmacology and experimental therapeutics,
R A Earl, and L B Townsend
October 1972, Cancer chemotherapy reports,
Copied contents to your clipboard!