77635-38-2

Upstream product

• 5340-12-5 1,2-bis(1-(3-nitrophenyl)ethylidene)hydrazine 
• 100-63-0 phenylhydrazine 
• 121-89-1 3-Nitroacetophenone 
• 59-88-1 phenylhydrazine hydrochloride 
• 100-19-6 (4-nitrophenyl)ethanone 

Downstream Products

• 121-89-1 3-Nitroacetophenone 
• 333327-63-2 3?( 3?nitrophenyl)-1?phenyl?1H?pyrazole?4?carbaldehyde 
• 1393711-74-4 1,4-dihydro-2,6-dimethyl-4-(3-(3-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)pyridine-3,5-dicarbonitrile 
• 6127-50-0 2-(3-nitrophenyl)-1H-indole 

Relevant academic research and scientific papers

Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors

The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.

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.

Copper catalyzed cyanomethylation reaction of 4-thiazolidinone

An effective copper catalyzed Cross Dehydrogenative Coupling (CDC) reaction of 4-thiazolidinones with acetonitrile has been developed. The described strategy undergoes radical pathway by employing copper, oxidant and easily available acetonitrile as a cya

Synthesis and Pharmacological Screening of Difluorophenyl Pyrazole Chalcone Conjugates as Antifungal, Anti-Inflammatory, and Antioxidant Agents

Abstract: A new series of difluoro phenyl pyrazole chalcone was prepared by utilizing PEG 400 as a catalyst and investigated for their antifungal, anti-inflammatory, and antioxidant activity. The compounds 3-[3-(4-bromo-phenyl)-1-phenyl-1H-pyrazol-4-yl]-1-(2,4-difluloro-phenyl)-propenone (IVc), 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVd), 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVe), and 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-propenone (IVg) exhibited promising antifungal activity at MIC of 25 and 50 μg/mL against selected human pathogenic fungi. Synthesized compounds 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVe), 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVd), 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-propenone (IVg) and 1-(2,4-difluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVa) showed good anti-inflammatory activities comparable to the standard drug diclofenac sodium. Compounds 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVe), 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVd) and 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-propenone (IVg) showed good hydrogen peroxide scavenging potential as compared to the butylated hydroxyl toluene. The conjugates 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVe), 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-propenone (IVg), and 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVd) found more potent than standard ascorbic acid in DPPH radical scavenging assay as well as ferrous reducing power assay. The conjugates showed good interactions with the target protein in docking study.

Synthesis and biological evaluation of pyrazole linked benzothiazole-β-naphthol derivatives as topoisomerase I inhibitors with DNA binding ability

A series of new pyrazole linked benzothiazole-β-naphthol derivatives were designed and synthesized using a simple, efficient and ecofriendly route under catalyst-free conditions in good to excellent yields. These derivatives were evaluated for their cytotoxicity on selected human cancer cell lines. Among those, the derivatives 4j, 4k and 4l exhibited considerable cytotoxicity with IC50 values ranging between 4.63 and 5.54 μM against human cervical cancer cells (HeLa). Structure activity relationship was elucidated by varying different substituents on benzothiazoles and pyrazoles. Further, flow cytometric analysis revealed that these derivatives induced cell cycle arrest in G2/M phase and spectroscopic studies such as UV–visible, fluorescence and circular dichroism studies showed that these derivatives exhibited good DNA binding affinity. Additionally, these derivatives can effectively inhibit the topoisomerase I activity. Viscosity studies and molecular docking studies demonstrated that the derivatives bind with the minor groove of the DNA.

Synthesis and antioxidant evaluation of dihydropyrimidinone integrated pyrazoles

A series of novel ethyl 6-[2-(3-aryl-1-phenyl-1H-pyrazol-4-yl)vinyl]-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylates (9a-9d) has been synthesized by adopting a multistep synthetic strategy. The structure of the targets was confirmed on the basis of physical and spectral techniques. The synthetically achieved targets were evaluated for their antioxidant activity by in-vitro DPPH free radical scavenging assay. Of the chemical entities screened, most of them exhibit good to better radical scavenging profile and among those, the nitro substituent bearing molecule 9c displayed the highest activity (82%) with IC50 value 621.6 μM. Further, as a representative molecule, compound 9a has been subjected to density functional theory calculations employing B3LYP method with 6311(++G) basis set to optimize its structure.

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.

Design, synthesis and cytotoxicity evaluation of pyrazolyl pyrazoline and pyrazolyl aminopyrimidine derivatives as potential anticancer agents

In an attempt to find bio-active heterocyclic analogues, a series of novel 1-(5-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-3-(pyridin-3-yl)-4,5-dihydropyrazol-1-yl)ethanones 5a–i and 4-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-6-(pyridine-3-yl)pyrimidin-2-amines 6a–i were designed, synthesized, and evaluated for their in vitro cytotoxicity against a panel of human cancer cell lines namely, HeLa (human cervix), NCI-H460 (human lung), PC-3 (human prostate), and NIH-3T3 (mouse embryo fibroblasts) cell lines. Most of these compounds exhibited moderate to good cytotoxicity against the tested cancer cell lines and weak toxicity against normal cell line. Analogs 5f, 5g, 5i, 6b–g showed significant cytotoxicity as compared to the standard drug etoposide. The compound 6g exhibited superior activity with IC50 value of 5.47 ± 0.44 μM against Hela cancer cell line.

Palladium-catalyzed [5+2] oxidative annulation of N-Arylhydrazones with alkynes through C–H activation to synthesize Benzo[d][1,2]diazepines

An efficient and novel method using palladium catalyst for the synthesis of benzo[d][1,2]diazepines by [5 + 2] annulation of N-arylhydrazones with alkynes has been developed. This methodology undergoes through eight membered palladacycle serving as a back

Synthesis, Characterization, Molecular Docking Studies and Anticancer Activity of Schiff Bases Derived from 3-(Substituted phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde and 2-Aminophenol

Abstract: A series of new Schiff bases were synthesized by microwave assisted reactions of substituted 1-phenyl-1H-pyrazole-4-carbaldehyde and 2-aminophenol in ethanol and characterized by elemental analysis and spectroscopic (IR, 1H NMR and MS) data. The crystal structures of four compounds were studied using single-crystal XRD data. Molecular docking studies of all synthesized compounds were performed into the binding site of a protein 3GCW to gain comprehensive understanding into possible binding modes. These compounds were also screened for anticancer activity against the liver (HEP-G2) cell line using the sulphorhodamine-B assay method. Adriamycin i.e. doxorubicin was used as reference standard. One of the compounds shows anticancer activity close to the famous anticancer agent doxorubicin, which was used as control in this study. It is observed that all molecules show activity close to the standard in high concentrations only. Graphical Abstract: Present study describes the anticancer activity and crystal structure study of Schiff bases of substituted pyrazole-4-carbaldehyde with 2-aminophenol. Docking study of all compounds against human hepatoma cell line, HEP-G2 correlates with in vitro activity. [Figure not available: see fulltext.].