2256-22-6

Usage

Class

Pyrazole

Ring structure

Pyrazole

Chlorophenyl groups

Two (4-chlorophenyl)

Phenyl group

One (1-phenyl)

Double bond

Between the carbon atoms in the 3rd and 4th positions of the pyrazole ring

Applications

Pharmaceutical and research (building block in synthesis of complex molecules, ligand in coordination chemistry)

Biological activities

Potential for further study in medicinal or agricultural chemistry

Upstream product

• 18278-29-0 (1E,4E)-1,5-bis(4-chlorophenyl)-1,4-pentadiene-3-one 
• 100-63-0 phenylhydrazine 
• 104-88-1 4-chlorobenzaldehyde 
• 18278-29-0 1,5-bis(4-chlorophenyl)-1,4-pentadien-3-one 

Downstream Products

• 53103-82-5 5-(4-chlorophenyl)-3-[(E)-2-(4-chlorophenyl)ethenyl]-1-phenyl-1H-pyrazole 

Relevant academic research and scientific papers

Some 1,3,5-trisubstituted pyrazoline derivatives targeting breast cancer: Design, synthesis, cytotoxic activity, EGFR inhibition and molecular docking

Different 1,3,5-trisubstituted pyrazoline derivatives 2a-c, 3-c, 4a-f, 6a-c, 7a-f and 8a-d were prepared via condensation reaction of the appropriate chalcone 1a-c or 5a-c with various hydrazine derivatives. All compounds were screened for their cytotoxicity against breast MCF-7 cancer cell line and the normal fibroblasts WI-38. Thirteen compounds 2a, 3a, 3c, 4a-d, 6c, 7d, 7e, 8b, 8d and 8f revealed promising cytotoxicity against MCF-7 compared to the reference standard staurosporine and they were safe to the normal fibroblasts WI-38. In addition, compounds 3c, 6c, 7d, 8b and 8d elicited higher cytotoxicity than erlotinib and exhibited promising EGFR inhibitory activity at submicromolar level comparable to that of erlotinib except for compound 8b that may exert its cytotoxicity via another mechanism besides EGFR inhibition. Molecular docking of 3c, 6c, 7d, 8b and 8d in the active site of EGFR confirmed the obtained results.

Cellulose sulfonic acid as a green, efficient, and reusable catalyst for Nazarov cyclization of unactivated dienones and pyrazoline synthesis

A high yielding, eco-friendly and simple procedure for the synthesis of five membered carbo- and heterocycles through cellulose sulfonic acid (CSA) mediated electrocyclization processes has been developed. Cellulose sulfonic acid (CSA) not only was able to induce the cyclization of "unactivated" dienones generating cyclopentenoids; it was also able to trigger the cyclization of α,β-unsaturated hydrazones giving rise to pyrazolines in excellent yields under green reaction conditions. The ease of catalyst recovery and reusability, short reaction time, simple experimental and work-up procedure; compared to the conventional methods, makes this protocol practical, environmentally friendly and economically desirable. The cellulose-SO3H (CSA) was characterized by FT-IR spectroscopy, powder X-ray diffraction (XRD) and Scanning Electron Microscopy (SEM) analyses, and catalyst stability was judged by thermogravimetry/differential thermal analysis (TG/DTA). The catalyst can be recycled several times without significant loss of catalytic activity.

Synthesis of 1,5-diaryl-3-arylethenyl-2-pyrazolines under ultrasound irradiation

Synthesis of 1,5-diaryl-3-arylethenyl-2-pyrazolines via the reaction of 1,5-diaryl-1,4-pentadien-3-one and phenyl hydrazine in glacial acetic acid was carried out in 32-80 % yields under ultrasound irradiation. This procedure has the advantages of mild conditions, short reaction time and high yield.

Oxidative addition of N-aminophthalimide to alkenyl-4,5-dihydropyrazoles and alkenylpyrazoles. Synthesis of aziridinylpyrazoles

Oxidation of N-aminophthalimide with lead tetraacetate in the presence of 1,5-diaryl-3-[(E)-2-arylethenyl]-1H-pyrazoles, as well as of 1,3-diphenyl-5-[(E)-2-phenylethenyl]-1H-pyrazole, gives adducts at the exocyclic C=C bond, the corresponding phthalimidoaziridinylpyrazoles. From 1,5-diphenyl-3-[(1E,3E)-4-phenyl-1,3-butadienyl]-1H-pyrazole, only product of addition at both exocyclic C=C bonds was obtained. In the reaction with 1-phenyl-3-[(1E,3E)-4-phenyl-1,3-butadienyl]-5-[(E)-2-phenylethenyl] -1H-pyrazole, the adduct at the styryl C=C bond was isolated. Analogous 4,5-dihydropyrazoles, 1,5-diphenyl-3-[(1E,3E)-4-phenyl-1,3-butadienyl]-4,5- dihydro-1H-pyrazole and 1-phenyl-3-[(1E,3E)-4-phenyl-1,3-butadienyl]-5-[(E)-2- phenylethenyl]-4,5-dihydro-1H-pyrazole, turned out to be inert in oxidative addition of N-aminophthalimide.

ACTIVATED Ba(OH)2 AS CATALYST IN ORGANIC SYNTHESIS

Several barium hydroxide catalysts have been prepared.Of these, the one called C-200 has been shown to be the most active.It has been used in several organic reactions: aldol and Claisen-Schmidt condensations, ester hydrolysis, esterification of acid chlorides, Williamson's ether synthesis, benzil-benzilic acid rearrangement and the synthesis of Δ2-pyrazolines.