412296-65-2

Upstream product

• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 100-63-0 phenylhydrazine 

Downstream Products

• 1423043-84-8 5-[3-(2-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-2H-tetrazole 
• 1431855-45-6 5-[3-(2-chlorophenyl)-1-phenyl-1H-pyrazol-4-ylmethylene]-2-(2,4-dimethoxyphenylamino)thiazol-4-one 
• 1401664-96-7 C₂₅H₁₈ClN₃O₃ 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 1,3-diaryl pyrazole derivatives as potential antibacterial and anti-inflammatory agents

Three series of 1,3-diaryl pyrazole derivatives bearing aminoguanidine or furan-2-carbohydrazide moieties have been synthesized, characterized and evaluated for antibacterial and anti-inflammatory activities. Most of the synthesized compounds showed potent inhibition of several Gram-positive bacterial strains (including multidrug-resistant clinical isolates) and Gram-negative bacterial strains with minimum inhibitory concentration values in the range of 1-64 μg/mL. Compounds 6g, 6l and 7l presented the most potent inhibitory activity against Gram-positive bacteria (e.g. Staphylococcus aureus 4220), Gram-negative bacteria (e.g. Escherichia coli 1924) and the fungus, Candida albicans 7535, with minimum inhibitory concentration values of 1 or 2 μg/mL. Compared with previous studies, these compounds exhibited a broad spectrum of inhibitory activity. Furthermore, compound 7l showed the greatest anti-inflammatory activity (93.59% inhibition, 30 min after intraperitoneal administration), which was more potent than the reference drugs ibuprofen and indomethacin.

Synthesis, Characterization, and Biological Evolution of New Pyrazole Derivatives of 4-(4-Aminophenyl)morpholin-3-one through Ugi Reaction

A new heterocyclic library was synthesized using multicomponent reactions (MCRs). A green strategy during which a set of molecules with an excellent diversity is generated with a minimum of synthetic effort, time, and by-products formation. This new series prepared using the Ugi MCRs in which aldehyde, amine, acid, and isocyanide reacts to make α-bisamide. During this work, we practice the Ugi reaction to synthesize an extremely functionalized heterocyclic library which was characterized and tested for biological evaluation. This innovative synthetic route involves for pyrazole derivatives of 4-(4-aminophenyl)morpholin-3-one by Ugi four component reaction and methanol as a solvent in good yield and high purity. All the produced compounds of library were characterized using 1H-NMR, IR, and mass spectroscopic methods.

New library of pyrazole–imidazo[1,2-α]pyridine molecular conjugates: Synthesis, antibacterial activity and molecular docking studies

A library of novel pyrazole–imidazo[1,2-α]pyridine scaffolds was designed and synthesized through a one-pot three-component tandem reaction. The structures of synthesized conjugates were confirmed by spectroscopic techniques (NMR, IR and HRMS). In vitro antibacterial evaluation of the twelve synthesized molecules (7a, 8a–k) against methicillin-resistant Staphylococcus aureus and normal strains of Escherichia coli, Salmonella typhimurium, Klebsiella pneumonia and Pseudomonas aeruginosa established 8b, 8d, 8e, 8h and 8i as potent antibacterial agents with superior minimum bactericidal concentration, compared with standard drug ciprofloxacin. Molecular docking studies of all active compounds into the binding site of glucosamine-6-phosphate synthase were further performed in order to have a comprehensive understanding of putative binding modes within the active sites of the receptor.

Microwave-assisted Vilsmeier-Haack synthesis of Pyrazole-4-carbaldehydes

The synthesis of 4-formylpyrazoles using Vilsmeier-Haack reagent is a common protocol in pyrazole chemistry. An efficient microwave-assisted synthesis of 4-formylpyrazoles by employing Vilsmeier-Haack reagent (OPC-VH) derived from phthaloyl dichloride/dimethylformamide has been described. This method offers the advantages of operational simplicity, avoiding the use of POCl3 as toxic reagents and reuse of the by-product in the preparation of phthaloyl dichloride.

Highly efficient one-pot synthesis of α-aminophosphonates using nanoporous AlSBA-15 catalyst in a three-component system

Nanoporous AlSBA-15 catalysts with different nSi/nAl ratios (41, 129, and 210) were synthesized using a hydrothermal method. These catalysts were characterized by XRD, N2 sorption, TPD-NH3, FT-IR, SEM and TEM. XRD analyses of AlSBA-15 catalysts confirmed the presence of well-ordered crystalline structure with p6mm symmetry. The specific surface area and specific pore volume of the AlSBA-15 catalysts are in the range of 480 to 757?m2/g and 0.65 to 0.95?cm3/g, respectively. The catalytic performance of nanoporous AlSBA-15 catalysts are used as an outstanding catalytic system for one-pot synthesis of α-aminophosphonates via Kabachnik-Fields reaction in a three-component system using amines (primary/secondary), carbonyl compounds (aldehydes/ketones) and diethyl phosphite. The major advantages of the present contributions are excellent yields, short reaction time, simple experimental technique, high chemo-selectivity, catalyst recyclability, easy work-up procedure and green approach. Three-component synthesis of α-aminophosphonates follows first imine formation from amine and aldehyde/ketone followed by phosphate addition. The experimental findings suggest that the nanoporous AlSBA-15 catalysts can be recycled and reused up to six cycles without any loss in the catalytic performance.

Microwave-assisted synthesis and biological evaluation of pyrazole-4-carbonitriles as antimicrobial agents

An efficient microwave-assisted method of synthesis of pyrazole-4-carbonitriles has been developed. Condensation of pyrazole-4-carbaldehydes with hydroxylamine hydrochloride followed by reaction of the resulting oximes with the Vilsmeier-Haack reagent pre-formed from phthaloyl dichloride and dimethylformamide under microwave irradiation afforded the corresponding pyrazole-4-carbonitriles in 73percent to 91percent yield. The operational simplicity, avoidance of toxic reagents such as POCl3, shorter reaction time, higher yield compared to the classical version, easy work up, and the use of the by-product in the regeneration of phthaloyl dichloride are the advantages of this methodology. All the target compounds were tested for antimicrobial activity against Gram-positive bacteria Bacillus cereus and Staphylococcus aureus; Gram-negative bacteria Escherichia coli and Yersinia enterocolitica, and the fungal species Candida albicans.

Pyrazolylphenanthroimidazole heterocycles: Synthesis, biological and molecular docking studies

The synthesis of a series of novel pyrazolylphenanthroimidazoles 6a-6j has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques. Among them, the molecules possessing para-bromo (6d), para-methyl (6f) and para-nitro (6j) phenyl substituents on the pyrazole scaffold displayed similar anti-inflammatory activity and the one with no substituents on the aryl unit (6a) exhibited the highest anti-inflammatory profile. While investigating the DPPH radical scavenging activity, the synthesized chemical entity with a para-methoxyphenyl group attached at the pyrazole structural motif (6i) revealed the highest activity when compared to the other synthesized molecules. Furthermore, the evaluation of cytotoxic activity of the synthesized molecule (6a) exerted significant activity against both the pancreatic cell lines such as AsPC1 and SW1990. Besides, while performing the molecular docking studies of 6a with B-cell lymphoma 2, an appreciable binding affinity (-9.04 kcal mol-1) has been observed. The results of the present examination imply that these chemical entities could be used as efficient intermediates for the construction of biopertinent molecules. This journal is

Discovery of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups as potential PTP1B inhibitors

Two series of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, IIIv was found to have the best in vitro inhibition activity against PTP1B (IC50 = 0.67 ± 0.09 μM) and the best selectivity (9-fold) between PTP1B and T-cell protein tyrosine phosphatase (TCPTP). Molecular docking studies demonstrated that compounds IIIm, IIIv and IVg could occupy simultaneously at both the catalytic site and the adjacent pTyr binding site. These results provide novel lead compounds for the design of inhibitors of PTP1B as well as other PTPs.

Synthesis of novel pyrazolyl tetrazoles as selective COX-2 inhibitors

A series of novel pyrazolyl tetrazoles were synthesized by introducing tetrazole moiety at the fourth position of 1,3-substituted pyrazole nucleus. Synthesis was carried out by cyclization of different pyrazolonitriles using sodium azide in the presence of triethylammonium chloride as phase transfer catalyst. The structures of the synthesized compounds were confirmed on the basis of physical and spectral data. Among the synthesized compounds, 4b and 4e displayed significant anti-inflammatory activity with no observable ulcerogenic effect when compared with diclofenac sodium. Furthermore, compounds 4b and 4e were found to have COX-2 selectivity with a ratio of 0.44 and 0.48, respectively.

Synthesis of novel 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties as potential antibacterial agents

In the present study, a series of 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties were synthesized and their antimicrobial activities were tested against various Gram-positive and Gram-negative bacteria. 1,3-diaryl-4-formylpyrazoles were synthesized as key intermediates following a Vilsmeier-Haack strategy. Several compounds with an MIC of 2 μg/mL, exhibited stronger antibacterial activity against the methicillin-resistant Staphylococcus aureus (MRSA) than the controls. None of the compounds showed any activity against Gram-negative bacteria.