947-95-5Relevant articles and documents
Synthesis and biological evaluation of novel triazole substituted pyrazolyl-methylenehydrazinyl-5-arylidene thiazolidinone derivatives as antibacterial and cytotoxic agents
Pogaku, Vinay,Eslavath, Ravi Kumar,Dayakar,Singh, Surya S.,Basavoju, Srinivas
, p. 6079 - 6098 (2017)
Novel triazole substituted pyrazolyl-methylenehydrazinyl-5-arylidene thiazolidinone derivatives 6a–n and 7a–l were synthesized and characterized by Fourier transform infrared, 1H and 13C nuclear magnetic resonance, mass spectrometry and elemental (CHN) analysis. The in vitro antibacterial (6a–n and 7a–l) and cytotoxic (6a–n) activities were evaluated for these compounds. The results revealed that the compounds 6b, 6i, 6k, 7b, 7h displayed good antibacterial activity. The compounds 6c (IC50?=?5.4?μM), 6l (IC50?=?6.3?μM) and 6f (IC50?=?9.85?μM) were effective for inhibition of human breast cancer cell line MCF-7. Similarly, the compounds 6b (IC50?=?8.7?μM) and 6c (IC50?=?9.06?μM) were shown to have effective inhibition on human cervical cancer cell line Hela.
Modification, Biological Evaluation and SAR Studies of Novel 1H-Pyrazol Derivatives Containing N,N′-Disubstituted Urea Moiety as Potential Anti-melanoma Agents
Ruan, Ban-Feng,Lin, Meng-Xue,Shao, Qin,Wang, Tian-Hong,Zhang, Qing,Dong, Yu-Lu,Bu, Chao-Nan,Xu, Hua-Jian,Zhou, Ben-Guo,Li, Qing-Shan
, (2018)
Malignant melanomas are amongst the most aggressive cancers. BRAF Inhibitors have exhibited therapeutic effects against BRAF-mutant melanoma. In continuation of our earlier studies on anti-melanoma agents based on 1H-pyrazole skeleton, two sets of novel compounds that include 1H-pyrazole-4-amines FA1 – FA13 and corresponding urea derivatives FN1 – FN13 have been synthesized and evaluated for their BRAFV 600E inhibitory and antiproliferation activities. Compound FN10 displayed the most potent biological activity against BRAFV 600E (IC50 = 0.066 μm) and the A375 human melanoma cell line (GI50 = 0.81 μm), which was comparable to the positive control vemurafenib, and more potent than our previously reported 1H-pyrazole-3-amines and their urea derivatives. The results of SAR studies and molecular docking can guide further optimization and may help to improve potency of these pyrazole-based anti-melanoma agents.
Bipyrazole-based palladium(II) complexes as DNA intercalator and artificial metallonuclease
Thakor, Khyati P.,Lunagariya, Miral V.,Bhatt, Bhupesh S.,Patel, Mohan N.
, p. 233 - 245 (2019)
Abstract: Substituted 3′-methyl-1′,2-diphenyl-3,4-dihydro-1′H,2H-3,4′-bipyrazole and their square planar palladium(II) complexes of type [Pd(4n)Cl2], where 4n = bipyrazole-based ligands, have been synthesized. The compounds have been characterized by various techniques like elemental analysis, mass, absorption, IR, 1H NMR and 13C NMR spectroscopy. The complexes have been further analyzed by thermogravimetric analysis (TGA), conductance measurement and energy-dispersive X-ray spectroscopy (EDX). Interaction between compounds and herring sperm DNA has been studied by absorption titration, viscosity measurement, ethidium bromide displacement titration, and molecular docking study. The binding strength between compounds and DNA has been checked in terms of Kb, Ksv, and Kf values; while spontaneity of interaction has been checked by evaluating thermodynamic parameters like Gibb’s free energy, enthalpy change (?H°) and entropy change (?S°). The plasmid cleavage efficacy of complexes has been evaluated by gel electrophoresis technique. The minimum inhibitory concentration of compounds has been evaluated against pathogens such as Staphylococcus aureus, Escherichia coli, B. subtilis, S. marcescens and Pseudomonas aeruginosa. The in vivo and in vitro cytotoxic activity has been performed using cell viability assay and brine shrimp lethality bioassay. Graphical abstract: [Figure not available: see fulltext.].
Evolution of 1, 3, 5-trisubstituted bipyrazole scaffold based platinum(II) complexes as a biological active agent
Lunagariya, Miral V.,Patel, Mohan N.,Pursuwani, Bharat H.,Thakor, Khyati P.
, p. 455 - 483 (2018)
Square planar mononuclear platinum(II) complexes having general formula [Pt(Ln)Cl2], (where, Ln = L1–4) were synthesized with neutral bidentate heterocyclic 1,3,5-trisubstituted bipyrazole based ligands. The syn
Microwave assisted one-pot synthetic route to imidazo[1,2-: A] pyrimidine derivatives of imidazo/triazole clubbed pyrazole and their pharmacological screening
Prasad, Pratibha,Kalola, Anirudhdha G.,Patel, Manish P.
, p. 12666 - 12676 (2018)
An efficient synthesis of imidazo[1,2-a]pyrimidine derivatives of pyrazole in excellent yield over a short reaction time based on a microwave-assisted, one-pot three-component condensation reaction of pyrazole aldehyde clubbed with imidazole 4 and triazole 5 nuclei, (substituted-phenyl/hetero-aryl)ethanones 6(a-g), and 2-amino benzimidazole 7 in the presence of the strong base KOH is described. All the compounds were screened for their preliminary in vitro antimicrobial, antituberculosis and antimalarial activities against a panel of pathogenic strains. The majority of the compounds exhibited excellent inhibitory action against S. typhi, S. pneumoniae, B. subtilis, and C. tetani. Some of the compounds showed good antifungal activity and moderate antituberculosis activity as compared to first line drugs. Two of the compounds 8b and 9b exhibited excellent antimalarial activity against P. falciparum strains.
Design, synthesis, antibacterial evaluation and molecular docking studies of novel pyrazole/1,2,4-oxadiazole conjugate ester derivatives
Depa, Navaneetha,Erothu, Harikrishna
, p. 1087 - 1098 (2021/02/26)
The development of new antimicrobial drugs is most needed due to rapid growth in global antimicrobial resistance. Thus, in this context, a series of novel pyrazole/1,2,4-oxadiazole conjugate ester derivatives (7a–j) was synthesized. All the derivatives we
Design and synthesis of pyrazolone-based compounds as potent blockers of SARS-CoV-2 viral entry into the host cells
Karpoormath, Rajshekhar,Kehinde, Idowu,Kushwaha, Babita,Kushwaha, Narva Deshwar,Mahlalela, Mavela Cleopus,Obakachi, Vincent A.,Shinde, Suraj Raosaheb
, (2021/06/16)
SARS-CoV-2 are enveloped positive-stranded RNA viruses that replicate in the cytoplasm. It relies on the fusion of their envelope with the host cell membrane to deliver their nucleocapsid into the host cell. The spike glycoprotein (S) mediates virus entry into cells via the human Angiotensin-converting enzyme 2 (hACE2) protein located on many cell types and tissues' outer surface. This study, therefore, aimed to design and synthesize novel pyrazolone-based compounds as potential inhibitors that would interrupt the interaction between the viral spike protein and the host cell receptor to prevent SARS-CoV 2 entrance into the cell. A series of pyrazolone compounds as potential SARS-CoV-2 inhibitors were designed and synthesized. Employing computational techniques, the inhibitory potentials of the designed compounds against both spike protein and hACE2 were evaluated. Results of the binding free energy from the in-silico analysis, showed that three compounds (7i, 7k and 8f) and six compounds (7b, 7h, 7k, 8d, 8g, and 8h) showed higher and better binding high affinity to SARS-CoV-2 Sgp and hACE-2, respectively compared to the standard drugs cefoperazone (CFZ) and MLN-4760. Furthermore, the outcome of the structural analysis of the two proteins upon binding of the inhibitors showed that the two proteins (SARS-CoV-2 Sgp and hACE-2) were stable, and the structural integrity of the proteins was not compromised. This study suggests pyrazolone-based compounds might be potent blockers of the viral entry into the host cells.
Synthesis of Selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and Their C-H Activation
Choi, In-Hui,Jalani, Hitesh B.,Jeong, Jin-Hyun
supporting information, p. 321 - 325 (2020/12/01)
We disclose the synthesis of selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and their aryl derivatives for the first time by using selenopyran ring formation via an in situ-generated selenide that reacts directly with α-halo-β-ynone-bearing substituted pyrazole
A novel synthetic method of organoselenum compounds
-
Paragraph 0122-0126; 0127-0132, (2021/09/07)
The present application can synthesize a selenopyrano pyrazolone derivative, one of an organic selenium compound, in a simple and excellent yield. Provided is a synthesis method of an organic selenium compound which is eco-friendly at low temperature and
Design, synthesis, and biological evaluation of novel benzimidazole derivatives as sphingosine kinase 1 inhibitor
Khairat, Sarah H. M.,Omar, Mohamed A.,Ragab, Fatma A. F.,Roy, Sonam,Turab Naqvi, Ahmad A.,Abdelsamie, Ahmed S.,Hirsch, Anna K. H.,Galal, Shadia A.,Hassan, Md. Imtaiyaz,El Diwani, Hoda I.
, (2021/06/17)
Sphingosine kinase 1 (SphK1) has emerged as an attractive drug target for different diseases. Recently, discovered SphK1 inhibitors have been recommended in cancer therapeutics; however, selectivity and potency are great challenges. In this study, a novel series of benzimidazoles was synthesized and evaluated as SphK1 inhibitors. Our design strategy is twofold: It aimed first to study the effect of replacing the 5-position of the benzimidazole ring with a polar carboxylic acid group on the SphK1-inhibitory activity and cytotoxicity. Our second aim was to optimize the structures of the benzimidazoles through the elongation of the chain. The enzyme inhibition potentials against all the synthesized compounds toward SphK1 were evaluated, and the results revealed that most of the studied compounds inhibited SphK1 effectively. The binding affinity of the benzimidazole derivatives toward SphK1 was measured by fluorescence binding and molecular docking. Compounds 33, 37, 39, 41, 42, 43, and 45 showed an appreciable binding affinity. Therefore, the SphK1-inhibitory potentials of compounds 33, 37, 39, 41, 42, 43, and 45 were studied and IC50 values were determined, to reveal high potency. The study showed that these compounds inhibited SphK1 with effective IC50 values. Among the studied compounds, compound 41 was the most effective one with the lowest IC50 value and a high cytotoxicity on a wide spectrum of cell lines. Molecular docking revealed that most of these compounds fit well into the ATP-binding site of SphK1 and form hydrogen bond interactions with catalytically important residues. Overall, the findings suggest the therapeutic potential of benzimidazoles in the clinical management of SphK1-associated diseases.
