10591-75-0

Upstream product

• 99-90-1 para-bromoacetophenone 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 6127-49-7 2-(4-bromophenyl)indole 
• 99466-25-8 3-(4-bromophenyl)-5-phenacyl-1-phenylpyrazole 
• 112382-62-4 4-[5-(4-Bromo-phenyl)-2-phenyl-2H-pyrazol-3-yl]-phenol 
• 36640-41-2 3-(4-bromophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 112382-72-6 2-[5-(4-Bromo-phenyl)-2-phenyl-2H-pyrazol-3-yl]-phenol 
• 99-90-1 para-bromoacetophenone 
• 108446-73-7 (E)-3-[3-(4-Bromo-phenyl)-1-phenyl-1H-pyrazol-4-yl]-acrylic acid 
• 108446-80-6 3-(4-bromophenyl)-1-phenylpyrazole-4-propionic acid 
• 108446-68-0 2-[3-(4-Bromo-phenyl)-1-phenyl-1H-pyrazol-4-ylmethylene]-malonic acid 
• 108446-86-2 2-[3-(4-Bromo-phenyl)-1-phenyl-1H-pyrazol-4-ylmethylene]-malonic acid diethyl ester 
• 1118429-24-5 1-phenyl-3-(4-chlorophenyl)-1H-pyrazole-4-carboxaldehyde semicarbazone 
• 849801-80-5 3-(4-Bromophenyl)-5-chloro-1-phenyl-1H-pyrazolo-4-carbaldehyde 
• 1013120-87-0 2-[3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl]-1,3-benzothiazole 
• 1263379-81-2 2-[3-(4-bromo-phenyl)-1-phenyl-1H-pyrazol-4-yl]benzothiazoline 

Relevant academic research and scientific papers

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.

One-pot Synthesis of 3-phenyl-4-pyrazolylmethylene-isoxazol-(5H)-ones Catalyzed by Sodium Benzoate in Aqueous Media under the Influence of Ultrasound Waves: A Green Chemistry Approach

A series of 4-pyrazolylmethylene-3-phenylisoxazol-5(4H)-ones have been prepared from Knoevenagel condensation of pyrazole-4-carbaxaldehyde with isoxazolone precursors or via one-pot three-component cyclocondensation of pyrazole-4-carbaxaldehyde with β-ketoesters and hydroxylamine hydrochloride in the presence of sodium benzoate in water under the influence of ultrasonic waves. The merits of this method are efficient, clean, green, easy work-up, high yields, and shorter reaction time, and the catalyst could be recycled easily without affecting the catalytic activity.

Synthesis and biological evaluation of 1,3,4-trisubstituted pyrazole analogues as anti-mycobacterial agents

A series of 1,3,4-trisubstituted pyrazole derivatives (3a–f), (4a–r), (5a–f) and (6a–f) have been synthesized and evaluated for their Mycobacterium tuberculosis (MTB) (H37Rv) inhibitory activity. The structures of newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral analysis. Among the thirty six compounds screened for in vitro anti-mycobacterial activity against MTB, three compounds 3b, 3e and 3f demonstrated significant growth inhibitory activity with minimum inhibitory concentration of 0.78 μg/ml. The selected compounds were further tested for cytotoxic activity against normal human dermal fibroblast cell lines using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide (MTT) assay and exhibited no significant cytotoxicity. Molecular docking simulation studies were carried out in order to better understand the hypothetical binding interaction to the MTB NADH-dependent enoyl–acyl carrier protein reductase.

In vitro studies of potent aldose reductase inhibitors: Synthesis, characterization, biological evaluation and docking analysis of rhodanine-3-hippuric acid derivatives

Inhibitors of aldose reductase are rate-limiting enzymes and could play a key role to prevent the complications of diabetes. In our attempt to develop novel inhibitors of aldose reductase, the derivatives of rhodanine-3-hippuric acid-pyrazole hybrid were synthesized and characterised by spectral data. The biological studies reveal that all the compounds show an excellent activity against ALR2 with IC50 values ranging from 0.04 to 1.36 μM. Among these the synthesised compounds 6a-m, 6g and 6e showed specific inhibitory activity with IC50 values of 0.04 and 0.06 μM respectively against ALR2 and found to be more potent than epalrestat (IC50 = 0.87 μM), the only aldose reductase inhibitor currently used in the therapy. Molecular docking analysis using the AR-NADP+ complex as a receptor was performed with all the synthesized compounds. All the compounds exhibit a well-defined binding mode within the AR active site, similarly to previous described AR inhibitors, with the anion head group bound to the catalytic center, blocking thus its activity. By forming hydrogen bonds with Tyr48 and His110 of the protein from ALR2 (PDB ID: 2FZD), the compounds 6g and 6e interrupt the proton donation mechanism, which is necessary for the catalytic activity of ALR2.

Design, synthesis, cytotoxicity, HuTopoIIα inhibitory activity and molecular docking studies of pyrazole derivatives as potential anticancer agents

In an attempt to find potential anticancer agents, a series of novel ethyl 4-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-2-oxo-6-(pyridin-3-yl)cyclohex-3-enecarboxylates 5a-i and 5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-3-(pyridin-3-yl)-4,5-dihydropyrazole-1-carbothioamides 6a-i were designed, synthesized and evaluated for their topoisomerase IIα inhibitory activity and in vitro cytotoxicity against a panel of cancerous cell lines (MCF-7, NCI-H460, HeLa) and a normal cell line (HEK-293T). Molecular docking studies of all the synthesized compounds into the binding site of topoisomerase IIα protein (PDB ID: 1ZXM) were performed to gain a comprehensive understanding into plausible binding modes. These compounds were also screened for in silico drug-likeliness properties on the basis of the absorption, distribution, metabolism and excretion (ADME) prediction. Among all the synthesized compounds, analogue 5d showed superior cytotoxicity with an IC50 value of 7.01?±?0.60?μM for HeLa, 8.55?±?0.35?μM for NCI-H460 and 14.31?±?0.90 for MCF-7 cancer cell lines. Further, compound 5d showed 70.82% inhibition of topoisomerase IIα at a concentration of 100?μM with maximum docking score of ?8.24. Results of ADME prediction revealed that most of these compounds showed in silico drug-likeliness properties within the ideal range.

Synthesis of novel pyrazole-thiadiazole hybrid as potential potent and selective cyclooxygenase-2 (COX-2) inhibitors

A series of 1,3,4-trisubstituted pyrazole derivatives (3a-f), (4a-f), and (5a-f) have been synthesized and evaluated for their cyclooxygenase (COX-1 and COX-2) inhibitory activity. The structures of newly synthesized compounds were characterized by IR, 1H NMR, and mass spectral analysis. All of the compounds showed good inhibition of COX-2 with IC50 of 1.33-17.5 μM. Among these derivatives, compound (5c) was the most potent and selective COX-2 inhibitor (IC50 = 1.33 μM), with a significant selectivity index (SI >60). Molecular docking studies were carried out in order to predict the hypothetical binding mode of these compounds to the COX-2 isoenzyme. The result of present study suggests that pyrazole-thiadiazole hybrid could be an interesting approach for the design of new selective COX-2 inhibitory agents.

Imidazole-pyrazole hybrids: Synthesis, characterization and in-vitro bioevaluation against α-glucosidase enzyme with molecular docking studies

Herein, substituted imidazole-pyrazole hybrids (2a-2n) were prepared via a multi component reaction employing pyrazole-4-carbaldehydes (1a-1d), ammonium acetate, benzil and arylamines as reactants. All the new compounds were characterized through their spectral and elemental analyses. Further these compounds were tested against α-glucosidase enzyme. The compounds 2k, 2l and 2n possessed good inhibition potencies, however, compounds 2f (IC50 value: 25.19 ± 0.004 μM) and 2m (IC50 value: 33.62 ± 0.03 μM) were the most effective compounds of the series. Furthermore, molecular docking helped to understand the binding interactions of 2f and 2m with the understudy yeast's α-glucosidase enzyme.

Probing the high potency of pyrazolyl pyrimidinetriones and thioxopyrimidinediones as selective and efficient non-nucleotide inhibitors of recombinant human ectonucleotidases

With the aim to discover novel, efficient and selective inhibitors of human alkaline phosphatase and nucleotide pyrophosphatase enzymes, two new series of pyrazolyl pyrimidinetriones (PPTs) (6a–g) and thioxopyrimidinediones (PTPs) (6h–n) were synthesized in good chemical yields using Knoevenagel condensation reaction between pyrazole carbaldehydes (4a–g) and pharmacologically active N-alkylated pyrimidinetrione (5a) and thioxopyrimidinedione (5b). The inhibition potential of the synthesized hybrid compounds was evaluated against human alkaline phosphatase (h-TNAP and h-IAP) and ectonucleotidase (h-NPP1 and h-NPP3) enzymes. Most of the tested analogs were highly potent with a variable degree of inhibition depending on the functionalized hybrid structure. The detailed structure-activity relationship (SAR) of PPT and PTP derivatives suggested that the compound with unsubstituted phenyl ring from PPT series led to selective and potent inhibition (6a; IC50 = 0.33 ± 0.02 μM) of h-TNAP, whereas compound 6c selectively inhibited h-IAP isozyme with IC50 value of 0.86 ± 0.04 μM. Similarly, compounds 6b and 6h were identified as the lead scaffolds against h-NPP1 and h-NPP3, respectively. The probable binding modes for the most potent inhibitors were elucidated through molecular docking analysis. Structure-activity relationships, mechanism of action, cytotoxic effects and druglikeness properties are also discussed.

Aqueous phase synthesis, crystal structure and biological study of isoxazole extensions of pyrazole-4-carbaldehyde derivatives

A series of novel isoxazol derivatives was synthesized by green route in aqueous phase at room temperature by the reaction of 3-methyl-4H-isoxazol-5-one with 3-(substituted phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde by one-pot Knoevenagel condensation method using sodium benzoate as a catalyst. Compounds were characterized on the basis of IR, 1H NMR, mass spectroscopy and melting point determination. Crystal structures of five compounds were determined by X-ray diffraction. The compounds formed were screened for antibacterial and antifungal activity. Some compounds showed activity close to ampicillin against E. coli, S. aureus, and S. pyogenus. Two compounds showed antifungal activity against C. albicans close to standard greseofulvin.

Design, synthesis and in vitro antitumor evaluation of novel pyrazole-benzimidazole derivatives

A series of novel pyrazole-benzimidazole derivatives (6–42) have been designed, synthesized and evaluated for their in vitro antiproliferative activity against the HCT116, MCF-7 and Huh-7 cell lines. Among them, compounds 17, 26 and 35 showed significant