A novel series of esters  and hydrazones  was synthesized from 1-phenyl-2-(4-aryl-1,3,4,5-tetrahydropyrido[2,3-b][1,4]diazepin- 2-ylidene) ethanones. Subsequent treatment of 1-phenyl- 2-(4-phenyl- 1,3,4,5-tetrahydropyrido[2,3-b][1,4]diazepin-2-ylidene) -ethanone, with p-chlorobenzaldehyde furnished azine p-chlo- robenzylidenohydrazone 1-phenyl-2-(4-phenyl-1,3,4,5- tetrahydro- pyrido[2,3-b][1,4]diazepin-2-ylidene)ethanone. Long- standing heating of 4–(p-chlorophenylene)-2-(2-oxo-2-phenylethylidene)-1,2,3,4- tetrahydropyrido[2,3-b][1.4]diazepine-5-carboxylic acid ethyl ester with hydrazine hydrate afforded 3-[1-(p-chlorophenylene)- 2-(5-phenyl- 1H-pyrazol-3-yl)-ethyl]-1,3- dihydroimida-zo[4,5-]- pyridin-2-one , the product of thermoisomerisation of hydrazide. The structures of the compounds were identified by the results of elemental analysis and their IR, 1H NMR and MS spectra. Additionally, the structure of 3-[1-(p-chlorophenylene)-2-(5-phenyl-1H- pyrazol-3-yl)-ethyl]-1,3-dihydroimidazo[4,5-b]pyridin-2-one was confirmed by X-ray diffraction method.
The selected compounds were examined for their antiproliferative activity in in vitro screening assay. The following human cancer lines were used: HL-60 (leukemia), HCV-29T (urinary bladder), SW 707 (rectal), HepG2 (liver) and MES-SA (uterine).
One among tested compounds, 3-[1-(p-chlorophenyle- ne)-2-(5-phenyl-1H-pyrazol-3-yl)-ethyl]-1,3-dihydroimidazo[4,5-b]pyridin-2-one exhibited significant antiproliferative activity against the cells of all cell lines applied. It seems that the activity of compound can be attributed to the presence of pyridine, imidazole and pyrazole rings in the molecule. 4-(p-Chlorophenylene)- 2-(oxo-2-phenylethylidene)-1,2,3,4-tetrahydropyrido[2,3-b][1,4]- di- azepine-5-carboxylic acid propyl ester and  4-(p-chloro- phenylene)-2-(oxo-2-phenylethy-lidene)-1,2,3,4-tetrahydropyrido[2,3-b][1,4]diazepine-5-carboxylic acid  isobutyl ester were active only against two cancer cell lines, namely HL-60 leukemia and HCV-29T urinary bladder cancer. 4–(p-Chlorophenylene)-2-(2-oxo- 2-pheny- lethylidene)-1,2,3,4-tetrahydro-pyrido[2,3-b][1.4]diazepine-5-carbo- xylic acid ethyl ester  revealed activity exclusively against HL-60 leukemia cells.

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1. Synthesis of new 2-aminobenzimidazole derivatives. Reaction of 2-arylideneaminobenzimidazole with selected nitriles containing active methylene group.
2. PRIMARY CYTOTOXICITY EVALUATION OF NEW HETEROCYCLIC SYSTEMS WITH PYRIDODIAZEPINE.
3. SYNTHESIS AND ANTIPROLIFERATIVE ACTIVITY IN VITRO OF NEW 2-AMINOBENZIMIDAZOLE DERIVATIVES. PART 3. REACTIONS OF 2-ARYLIDENE- AMINOBENZIMIDAZOLE WITH SELECTED 1,3-DIKETONES.