Synthesis and antitumor activity of novel pyrazolylenaminone and bis(pyrazolyl)ketones via hydrazonoyl halides

Abstract

3‐Acetyl‐4‐benzoyl‐1,5‐diphenylpyrazole reacts with DMF‐DMA to give the novel enaminone 2. The reaction of the latter with various hydrazonoyl halides afforded regioselectively the respective substituted (3‐pyrazolyl)(4‐pyrazolyl)ketones 4 in good over all yield. The preliminary screening for the antitumor activity of the synthesized compounds 2 and 4a, 4b, 4c, 4d, 4e, 4f, 4g against human breast cancer cell line (MCF‐7) revealed that both compounds 2 and 4b have high‐antitumor activity. SAR is discussed. J. Heterocyclic Chem., 46, 548 (2009).

Synthesis, Reactions and Antitumour Screening of new Enaminones

“…3 Condensation of each of the pyrazoles 5a-e with N,N-dimethylformamidedimethylacetal (DMF-DMA) yielded the respective enaminones 6a-e in 75-85% yield (Scheme 1). The structures of the enaminones 6a-e were confirmed by their spectra (MS, IR and 1 H NMR (see Experimental).…”

“…Recently, we reported that heterocyclic enaminones of types 1 and 2 (Scheme 1) each exhibited an unexpected activity against the human breast cancer cell line MCF-7. [1][2][3] Also, several reports indicate that cyclic enaminones of type 3a-d (Scheme 1) proved to exhibit anticonvulsant properties and represent a new exciting series of compounds with efficacy in reducing seizures and hence are of great potential for the treatment of epilepsy. [4][5][6][7][8][9][10][11] In the light of these findings and in continuation of our recent work on the utility of enaminones for synthesis of hetaryl-pyrazoles, 1,2 it was thought interesting to synthesise new substituted enaminones 6 (Scheme 2) and explore their antitumor activity to shed some light upon structure activity relationships (SAR) and to study their reactions with some nitrogen and carbon nucleophiles.…”

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

“…In this synthesis strategy, nitrile imine derivatives ( 278 ) were firstly synthesized from hydrazonoyl halides compounds ( 277 ). Then, the bispyrazole compounds ( 282 ) were obtained by the regioselective 1,3‐dipolar cyclo addition reaction [65] . (Scheme 38).…”

Microwave‐Assisted Synthesis of Novel Bis(thiazoles) Incorporating Piperazine Moiety

“…Thiazole derivatives demonstrate significant biological properties such antifungal (abafungin), antimicrobial (sulfazole), anti‐inflammatory, anticancer, anticonvulsant, anti‐HIV, antihypertensive, anti‐gout (febuxostat), and antidiabetic activities (Figure ) . In addition, bis‐heterocyclic compounds as well as hybrid molecules, whose pharmacophores are integrated into a single molecule, were reported to display various biological activities, especially as fungicidal, antibacterial, tuberculostatic, anthelmintic, and antiamoebic . Because of the significant bioactivity and wide range of application of piperazine and thiazole derivatives as well as bis‐heterocyclic compounds, several publications reported concerning the synthesis of these derivatives .…”