Ecofriendly one-pot synthesis and antiviral evaluation of novel pyrazolyl pyrazolines of medicinal interest

Abstract

Abstract:Ethyl 3-acetyl-1,5-diphenyl-1 H -pyrazole-4-carboxylate reacts with a variety of arylaldehydes by grinding method in the presence of a catalytic amount of sodium hydroxide at ambient temperature to give the respective chalcones. The latter compounds react also by grinding method with nitrogen nucleophiles such as hydrazine hydrate, phenylhydrazine, and thiosemicarbazide to afford the corresponding pyrazol-3-yl pyrazolines. A series of 6-pyrazolylpyrimidine-2-thione derivatives were prepared by reaction of the above chalcones with thiourea by grinding method in the presence of a catalytic amount of sodium hydroxide at room temperature. In addition, 7-pyrazolylpyridopyrimidine-3-thione was prepared by reaction of chalcone with 6-aminothiouracil. All the newly synthesized compounds were characterized on the basis of elemental analysis and spectral data (IR, 1 H and 13 C NMR, mass). Moreover, some of the products were evaluated for their antiviral activity against the herpes virus at different concentrations. The results obtained indicated that compounds 4a, 4b, 4f, 5a, 5b, and 5c have promising activity.

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

“…According to recent papers on N ‐aryl pyrazolines, the introduction of the aryl group at the N ‐1 position of the dihydropyrazole ring leads to biological activity improvement. [ 33,45–48 ] However, chlorophenyl derivatives may enhance potency and binding efficiency compared to their unsubstituted phenyl derivatives. [ 2,49,50 ] In addition, these derivatives show an improvement in metabolic stability and pharmacokinetic profile, as recently demonstrated by Eggert et al, [ 49 ] who identified that the 3,4‐dichloro derivative (IC 50 = 0.08 μM) is more active than the corresponding 4‐chloro (IC 50 = 0.8 μM) and unsubstituted phenyl derivatives (IC 50 > 20 μM) against SMYD2 for the treatment of cancer.…”

Synthesis and antitumor activity of some nitrogen heterocycles bearing pyrimidine moiety

“…[55,67,68] Revealed the cytotoxicity of pyrimidine derivatives as potential anticancer agents against the two cell lines MCF7 and HePG2. So, the in vitro antiproliferative activity of the newly Pyrimidine derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) were assessed against human liver (HepG2) and breast (MCF7) cancer cell lines in addition to the normal fibroblast (WI-38) and compared to the activity of doxorubicin. The results were expressed as growth inhibitory concentration (IC50) values, which represent the compound concentrations required to produce a 50% inhibition of cell growth after 72 hours of incubation, compared with the untreated controls (Table 1), Figure 4.…”

An Efficient Synthesis of Novel Pyrazole-Based Heterocycles as Potential Antitumor Agents

“…The cytotoxicity of the synthesized pyridines 4a,b,e and 6a,b,e was evaluated against the human liver carcinoma cell line (HepG2-1) using doxorubicin as a reference drug (IC50 value of doxorubicin On the other hand, chalcone 10, prepared by the reaction of 1 with benzaldehyde in ethanol containing catalytic amounts of NaOH [54], was used for preparation of 6-(pyrazol-3-yl) pyrimidine-2-thione derivative 11 via its reaction with thiourea in ethanol containing a catalytic amount of sodium hydroxide [54]. Reaction of the latter compound 11 with a number of hydrazonoyl chlorides 12a-h [55] in dioxane in the presence of triethylamine afforded the respective products 15a-h through the non-isolated intermediates 13 and 14 (Scheme 5).…”