The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity

Abstract

Reaction of 4-oxo-4-(3,4-dichlorophenyl)-2-butenoic acid (1) with antipyrin (2) gave the corresponding butanoic acid 3. Reaction of 3 with hydrazines gave the pyridazinone derivatives 5a,b. Compounds 5a,b were used to prepare the corresponding dithio derivatives. Reaction of 5a with POCl3 unexpectedly gave the chloropyridazine derivative 7, which is used to prepare the corresponding thio derivative. The hitherto unknown reactions of this chloro derivative with 2-amino-3-carbethoxy-4,5-dimethylthiophene and 2-amino-3-carbethoxy tetrahydrobenzothiophene have now been described. The behaviour of the chloro derivative toward hydrazine hydrate, sodium azide and anthranilic acid was also studied. Some of the new compounds showed antimicrobial and antifungal activities.

An Efficient Synthesis and Reactions of Novel Indol-ylpyridazinone Derivatives with Expected Biological Activity

“…Reaction of 1 with indole in dry benzene gave 4-anthracen-9-yl-2-(1H-indol-3-yl)-4-oxo-butyric acid (2). Cyclocondensation of 2 with hydrazine hydrate, phenyl hydrazine, semicarbazide and thiosemicarbazide in dry benzene [28][29][30][31] gave 6-anthracen-9-yl-4-(1H-indol-3-yl)-4,5-dihydro-2H-pyridazin-3-one, 6-anthracen-9-yl-4-(1H-indol-3-yl)-2-phenyl-4,5-dihydro-2H-pyridazin-3-one, 3-anthracen-9-yl-5-(1H-indol-3-yl)-6-oxo-5,6-dihydro-4H-pyridazine-1-carboxylic acid amide and 3-anthracen-9-yl-5-(1H-indol-3-yl)-6-oxo-5,6-dihydro-4H-pyridazine-1-carbothioic acid amides 3a-d, respectively (Scheme 1). Physical properties, mass spectral data and elemental analyses for the synthesized compounds 1-3d are given in Table 1.…”

Synthesis, structure and cytotoxic activity of mixed-valent Cu(I)/Cu(II) salt containing a pyrazolone derivative as ligand

“…They have analgesic, antipyretic, antiinflammatory, antibacterial, antitumor activity [1][2][3][4][5][6][7][8][9]. The chemistry of pyrazolone derivatives has been expanded with the synthesis of their metal complexes, studies intended to explain their biological activity which might be based on their capacity to form complexes with some oligoelements.…”

Synthetic Routes to Selected Heterocycles Containing Antipyrine Moiety

“…Addition of 1 to ( E )‐4‐aryl‐oxobut‐4‐enoic acid 12 affords the carboxylic acid derivatives 13 that react with hydrazine at room temperature to give the acylic compound 14 . Carrying out the same reaction in refluxing butanol yields compound 15 (Scheme ).…”