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About: Pyrazole is a(n) research topic. Over the lifetime, 12131 publication(s) have been published within this topic receiving 151905 citation(s). The topic is also known as: 1,2-Diazole & Hpz.
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Journal ArticleDOI
Abstract: Herein we reported the utility of one-pot multicomponent based [3+2] cycloaddition reaction transformation to prepare a new two hybrids of spirooxindoles engrafted with pyrazole skeleton. Upon treatment of the electron-deficient olefins based pyrazole motif with in situ the generated azomethine ylides (AY) of sarcosine with the 6-chloro-isatin afforded spiroadducts. To enlighten the regio- and diastereo-selectivity of these spiroheterocycles, single crystal X-ray diffraction analysis was presented. Using Hirshfeld calculations, many short distance contacts such as O…H, Cl…H, N…H, H…C, C…C and Cl…S have a great impact on the molecular packing and the crystal stability of 8a and 8b. The latter showed some Cl…Cl inter halogen interactions (Cl1…Cl3; 3.358 A). In addition, DFT calculations were used to compute the electronic properties as well as the 1H- and 13C-NMR spectra of the studied systems. Both compounds are polar where 8b (3.995 Debye) has higher dipole moment than 8a (3.414 Debye). The NMR chemical shifts were calculated and found in excellent correlations between the calculated and experimental data were obtained (R2 = 0.94–0.98).

1 citations

Journal ArticleDOI
Abstract: Cancer is still incurable and it is considered as a main health problem worldwide. The identification of novel compounds with high toxicity and low side effects is one of the biggest challenges among interested researchers. In this study, a rapid and simple strategy for synthesis of spiro[indolo[2,1-b]quinazoline-pyrano[2,3-c]pyrazole] derivatives via sequential four-component reaction of isatoic anhydride, isatin, malononitrile, and 3-methyl-pyrazolones in CH2Cl2 at room temperature is described. This procedure has short reaction time and mild reaction conditions. Simple purification and no chromatographic process, are the other notable advantages of this protocol which make it attractive. To evaluate the anticancer activity of our synthetic compounds, pancreatic cancer cell (Panc1), cancer cell of breast (MDA-MB-231), colon cancer cell (HT-29), and normal human adult dermal fibroblast (HDF) were firstly cultured and by using MTT assay, the possible toxicity of related compounds was analyzed. Our results suggested that no compounds have 50% growth inhibitory concentration (IC50) values lower than etoposide (as a reference drug) against all cancer cell lines and among nine synthetic compounds, only 4a compound was effective against Panc1 pancreatic cancer cells.

Journal ArticleDOI
TL;DR: In vitro studies showed that compounds 3e and 3f were the most effective showing high potential AChE inhibitory activities with respective IC50 values, and in silico predictions of toxicity analysis indicated that these compounds should have good oral bioavailability.
Abstract: A new set of hybrid derivatives bearing pyrazole and coumarin scaffold 3a-f was synthesized and confirmed by different spectroscopic techniques (1H NMR, 13C NMR, FT-IR) and mass spectrometry. This study aimed to evaluate the inhibitory activity of new derivatives against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) using Galanthamine as standard drugs. In vitro studies showed that compounds 3e and 3f were the most effective showing high potential AChE inhibitory activities with respective IC50 values of 4.41±0.53 and 5.04±0.96 µg/ml. Compounds 3a and 3b were found to be the best butyrylcholinesterase inhibitor with an IC50 value comparable to that of the standard drugs. All the newly synthesized derivatives 3a–f are evaluated for their antioxidant activity and showed good activity. Molecular docking study was also carried to get insights into binding interactions of synthesized compounds to act as AChE and BChE inhibitors. The docking study of compound 3e with AChE enzyme showed that PAS are occupied by the ligand. In silico predictions of toxicity analysis indicated that these compounds should have good oral bioavailability.

Journal ArticleDOI
Abstract: We have described solvent-free preparation of new pyrano[2,3-c]-pyrazole-5-carbonitriles (1-10) from the reaction of 1,3-diketo ester, aryl hydrazine, aromatic aldehyde, and malononitrile catalyzed by Zinc triflate (which was recycled and reused up to five times) under microwave irradiation (MWI) at 80–120 °C. An augmented yield with shorter reaction times is the added advantage of the present work. All synthesized molecules were screened for anti-malarial, anti-microbial, anti-tuberculosis, and anti-cancer activities. Most of the tested compounds exhibited prominent anti-bacterial and anti-malarial activity, and some analogs showed anti-cancer activity.

Journal ArticleDOI
Abstract: One-pot multicomponent reaction of ethyl 3-oxobutanoate or ethyl 3-oxo-3-phenylpropanoate, hydrazine hydrate, malononitrile, various aldehydes in ethanolic piperidine solution under Microwave irradiation gave 6-amino-4-aryl/hetaryl-3-methyl/pheny-1,4-dihydropyran[2,3-c]pyrazole-5-carbonitriles. The structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR, 13C NMR-APT, MS data and elemental analysis. Furthermore, the cytotoxic activity properties were evaluated against the human cancer cell lines PC-3, SKOV-3, HeLa and A549 in comparison to the positive controls Vinblastine and Doxorubicin, employing the viability assay. The obtained results confirmed that some of the tested molecules revealed strong and selective cytotoxic activities against the four cancer cell lines. Herein, frontier molecular orbitals (FMO), electron affinity (EA), ionization potential (IP) and molecular electrostatic potential (MEP) was carried out to understand the active sites and biological active nature of pyrano[2,3-c]pyrazole synthesized compounds. A systematic study was performed then frontier molecular orbitals energies, active sites and molecular descriptors were compared with reference drug. The molecular docking was accomplished onto thymidylate synthase (TS) protein. The compounds with highest efficiency exhibited promising binding interactions and binding affinities into active site.

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