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Synthesis of New 2-Aminobenzimidazole Derivatives. Part 4. Reactions of 2-Arylideneaminobenzimidazole with Selected -Ketoesters

Nawrocka W. P., Kowalska M. W., Sztuba B., Dryś A., Wietrzyk J., Filip B.

Polish Journal of Chemistry

2007

Vol. 81, nr 10

1753-1753

Schiff bases 2–6 obtained from 2-aminobenzimidazole 1 with p-(N,N-diethylamino)-, p-chloro-, p-bromo-, 2,4-dimethoxy-, and 3,4-dimethoxybenzaldehyde were subjected to the reaction with 1,3-ketoester: methyl-, ethyl-, benzyl-, and t-butylacetoacetate to form derivatives of pyrimido[1,2-a]benzimidazole 7–23. 1H NMR spectra recorded for the compounds 20–23 in DMSO solution indicate the presence of two conformational forms. Compounds 2, 7–23 were examined for their antiproliferative activity in vitro against the cells of human lung cancer cell lines A549.

Synthesis and Antiproliferative Activity in vitro of 1-Phenyl-2-(4-aryl-1,3,4,5-tetrahydropyrido[2,3-b] [1,4]diazepin-2-ylidene)ethanone. Part I.

Liszkiewicz H., Kowalska M. W., Głowiak T., Wietrzyk J., Opolski A.

Polish Journal of Chemistry

2002

Vol. 76 / nr 11

1607-1617

Reaction of 2,3-diaminopyridine with equimolar amount of benzoylacetone in ethanol solution in the presence of catalytic amounts of acetic acid allowed to obtain 3-(2- amino-pyridin-3-ylamino)-1-phenyl-2-buten-1-one (4) instead of 2-methyl-4-phenyl- 3H-pyrido[2,3-b][1,5]diazepine (3) reported in the literature. Treatment of compound 4 with appropriate aromatic aldehydes: benzaldehyde and substituted benzaldehyde (4- methoxy-, 3,4-dimethoxy-, 3,4,5-trimethoxy-, 3-metyl-4-methoxy-, 3-hydroxy-, 4- diethyloamino-) in methanol solution in the presence of equimolar amount of potassium hydroxide gave 1-phenyl-2-(aryl-1,3,4,5-tetrahydropyrido[2,3-b][1,4]-diazepin-2- ylidene)-ethanones (7-13). Structures of compounds 4 and 7 were determined on a single crystal. Compounds 4 and 7-13 were examined for their antiproliferative activity in vitro against the cells of 7 human cancer cell lines, using SRB orMTTtechnique. Two out of all tested compounds revealed cytotoxic activity in vitro.