An efficient synthesis of novel pyrazole-based heterocycles as potential antitumor agents

dc.AffiliationOctober University for modern sciences and Arts (MSA)
dc.contributor.authorAbdallah M.A.
dc.contributor.authorGomha S.M.
dc.contributor.authorAbbas I.M.
dc.contributor.authorKazem M.S.H.
dc.contributor.authorAlterary S.S.
dc.contributor.authorMabkhot Y.N.
dc.contributor.otherDepartment of Chemistry
dc.contributor.otherFaculty of Science
dc.contributor.otherCairo University
dc.contributor.otherGiza
dc.contributor.other12613
dc.contributor.otherEgypt; Department of Chemistry
dc.contributor.otherFaculty of Dentistry
dc.contributor.otherOctober University for Modern Science & Arts
dc.contributor.otherGiza
dc.contributor.other12613
dc.contributor.otherEgypt; Department of Chemistry
dc.contributor.otherCollege of Science
dc.contributor.otherKing Saud University
dc.contributor.otherP.O. Box 2455
dc.contributor.otherRiyadh
dc.contributor.other11451
dc.contributor.otherSaudi Arabia
dc.date.accessioned2020-01-09T20:41:19Z
dc.date.available2020-01-09T20:41:19Z
dc.date.issued2017
dc.descriptionScopus
dc.description.abstractA new series of pyrazolylpyridines was prepared by reaction of ethyl-3-acetyl-1,5-diphenyl-1H-pyrazole-4-carboxylate with the appropriate aldehyde, malononitrile, or ethyl acetoacetate and an excess of ammonium acetate under reflux in acetic acid. Similarly, two novel bipyridine derivatives were prepared by the above reaction using terephthaldehyde in lieu of benzaldehyde derivatives. In addition, a series of 1,2,4-triazolo[4,3-a]pyrimidines was synthesized by a reaction of 6-(pyrazol-3-yl)pyrimidine-2-thione with a number of hydrazonoyl chlorides in dioxane and in the presence of triethylamine. The structure of the produced compounds was established by elemental analyses and spectral methods, and the mechanisms of their formation was discussed. Furthermore, the pyrazolyl-pyridine derivatives were tested as anticancer agents and the results obtained showed that some of them revealed high activity against human hepatocellular carcinoma (HEPG2) cell lines. � 2017 by the authors.en_US
dc.description.urihttps://www.scimagojr.com/journalsearch.php?q=21100829268&tip=sid&clean=0
dc.identifier.doihttps://doi.org/10.3390/app7080785
dc.identifier.doiPubMed ID :
dc.identifier.issn20763417
dc.identifier.otherhttps://doi.org/10.3390/app7080785
dc.identifier.otherPubMed ID :
dc.identifier.urihttps://t.ly/veeBY
dc.language.isoEnglishen_US
dc.publisherMDPI AGen_US
dc.relation.ispartofseriesApplied Sciences (Switzerland)
dc.relation.ispartofseries7
dc.subjectOctober University for Modern Sciences and Arts
dc.subjectجامعة أكتوبر للعلوم الحديثة والآداب
dc.subjectUniversity of Modern Sciences and Arts
dc.subjectMSA University
dc.subjectAntitumor activityen_US
dc.subjectMulticomponent reactionsen_US
dc.subjectPyrazolesen_US
dc.subjectPyrazolyl-pyridinesen_US
dc.subjectPyridinesen_US
dc.titleAn efficient synthesis of novel pyrazole-based heterocycles as potential antitumor agentsen_US
dc.typeArticleen_US
dcterms.isReferencedByKam, D., Kim, K., Kim, H.-S., Liu, H.K., Studies on film formation on cathodes using pyrazole derivatives as electrolyte additives in the Li-ion battery (2009) Electrochem. Commun., 11, pp. 1657-1660; Keter, F.K., Darkwa, J., Perspective: The potential of pyrazole-based compounds in medicine Biometals, 2012 (25), pp. 9-21; Yutilov, Y.M., Smolyar, N.N., Minkina, L., Synthesis of 3-(3 -Aminobenzoylamido)-1-(2 ,4 ,6 -trichlorophenyl) pyrazol-5-one, an intermediate in the synthesis of the purple component of color photographic materials (2005) Russ. J. Appl. Chem., 78, pp. 278-280; Tingle, C.C., Rother, J.A., Dewhurst, C.F., Lauer, S., King, W.J., Fipronil: Environmental fate, ecotoxicology, and human health concerns (2003) Rev. Environ. Contam. Toxicol., 176, pp. 1-66; Metwally, M.A., Abdel-Galil, E., Metwally, A., Amer, F.A., New azodisperse dyes with thiazole, thiophene, pyridone and pyrazolone moiety for dyeing polyester fabrics (2012) Dyes Pigment., 92, pp. 902-908; Aly, H.M., El-Gazzar, M.G., Novel pyrazole derivatives as anticancer and radiosensitizing agents (2012) Arzneimittelforschung, 62, pp. 105-112; Puthiyapurayil, P., Poojary, B., Chikkanna, C., Buridipad, S.K., Design, synthesis and biological evaluation of a novel series of 1,3,4-oxadiazole bearing N-methyl-4-(trifluoromethyl) phenyl pyrazole moiety as cytotoxic agents (2012) Eur. J. Med. Chem., 53, pp. 203-210; Hassan, G.S., Kadry, H.H., Abou-Seri, S.M., Ali, M.M., Mahmoud, A.E., Synthesis and in vitro cytotoxic activity of novel pyrazolo[3,4-d]pyrimidines and related pyrazole hydrazones toward breast adenocarcinoma MCF-7 cell line (2011) Bioorg. Med. Chem., 19, pp. 6808-6817; El-Zahar, M.I., El-Karim, S.S.A., Haiba, M.E., Khedr, M.A., Synthesis, antitumor activity and molecular docking study of novel benzofuran-2-yl pyrazole pyrimidine derivatives (2011) Acta Pol. Pharm., 68, pp. 357-373; El-Gamal, M.I., Sim, T.B., Hong, J.H., Cho, J.-H., Yoo, K.H., Oh, C.-H., Synthesis of 1H-pyrazole-1-carboxamide derivatives and their antiproliferative activity against melanoma cell line (2011) Arch. Pharm., 344, p. 197; Sharshira, E.M., Hamada, N.M.M., Synthesis and antimicrobial evaluation of some pyrazole derivatives (2012) Molecules, 17, pp. 4962-4971; Ragavan, R.V., Vijayakumar, V., Kumari, N.S., Synthesis and antimicrobial activities of novel 1,5-diaryl pyrazoles (2010) Eur. J. Med. Chem., 45, pp. 1173-1180; Ouyang, G., Chen, Z., Cai, X.-J., Song, B.-A., Bhadury, P.S., Yang, S., Jin, L.-H., Zeng, S., Synthesis and antiviral activity of novel pyrazole derivatives containing oxime esters group (2008) Bioorg. Med. Chem., 16, pp. 9699-9707; Sanchez-Moreno, M., Gomez-Contreras, F., Navarro, P., Marin, C., Ramirez-Macias, I., Olmo, F., Sanz, A.M., Yunta, M.J., In vitro leishmanicidal activity of imidazole- or pyrazole-based benzo[g]phthalazine derivatives against Leishmania infantum and Leishmania braziliensis species (2012) J. Antimicrob. Chemoth., 67, pp. 387-397; El-Din, M.M.M., Senbel, A.M., Bistawroos, A.A., El-Mallah, A., El-Din, N.A.N., Bekhit, A.A., El Razik, H.A.A., A novel COX-2 inhibitor pyrazole derivative proven effective as an anti-inflammatory and analgesic drug (2011) Basic Clin. Pharmacol., 108, pp. 263-273; Raffa, D., Migliara, O., Maggio, B., Plescia, F., Cascioferro, S., Cusimano, M.G., Tringali, G., Plescia, F., Pyrazolobenzotriazinone derivatives as COX inhibitors: Synthesis, biological activity, and molecularmodeling studies (2010) Arch. Pharm. Chem. Life Sci., 10, pp. 631-638; Tomazetti, J., Avila, D.S., Ferreira, A.P., Martins, J.S., Souza, F.R., Royer, C., Baker yeast-induced fever in young rats: Characterization and validation of an animal model for antipyretics screening (2005) J. Neurosci. Methods, 147, pp. 29-35; Dekhane, D.V., Pawar, S.S., Gupta, S., Shingare, M.S., Patil, C.R., Thore, S.N., Synthesis and anti-inflammatory activity of some new 4,5-dihydro-1,5-diaryl-1H-pyrazole-3-substituted-heteroazole derivatives (2011) Bioorg. Med. Chem. Lett., 21, pp. 6527-6532; Agrawal, R., Jain, P., Dikshit, S.N., Apixaban: A new player in the anticoagulant class (2012) Curr. Drug Targets, 13, pp. 863-875; Backhouse, K., Sarac, I., Shojaee-Moradie, F., Stolinski, M., Robertson, M.D., Frost, G.S., Bell, J.D., Russell-Jones, D., Fatty acid flux and oxidation are increased by rimonabant in obese women (2012) Metabolis, 61, pp. 1220-1223; Ranu, B.C., Jana, R., Sowmiah, S., An improved procedure for the three-component synthesis of highly substituted pyridines using ionic liquid (2007) J. Org. Chem., 72, pp. 3152-3154; Abbas, I.M., Gomha, S.M., Elaasser, M.M., Bauomi, M.A., Synthesis and biological evaluation of new pyridines containing imidazole moiety as antimicrobial and anticancer agents (2015) Turk. J. Chem., 39, pp. 334-346; Xu, W.C., Zhou, Q., Ashendel, C.L., Chang, C.T., Chang, C.J., Novel protein kinase C inhibitors: Synthesis and PKC inhibition of ?-substituted polythiophene derivatives (1999) Bioorg. Med. Chem. Lett., 9, pp. 2279-2282; Zhao, L.X., Moon, Y.S., Basnet, A., Kim, E.K., Jahng, Y., Park, J.G., Jeong, T.C., Lee, C.O., The discovery and synthesis of novel adenosine receptor (A2A) antagonists (2004) Bioorg. Med. Chem. Lett., 14, pp. 1333-1336; Zhao, L.X., Sherchan, J., Park, J.K., Jahng, Y., Jeong, B.S., Jeong, T.C., Lee, C.S., Lee, E.S., Synthesis, cytotoxicity and structure-activity relationship study of terpyridines (2006) Arch. Pharm. Res., 29, pp. 1091-1095; Son, J.K., Zhao, L.X., Basnet, A., Thapa, P., Karki, R., Na, Y., Jahng, Y., Lee, C.S., Synthesis of 2,6-diaryl-substituted pyridines and their antitumor activities (2008) Eur. J. Med. Chem., 43, pp. 675-682; Thapa, P., Karki, R., Choi, H.Y., Choi, J.H., Yun, M., Jeong, B.S., Jung, M.J., Cho, W.J., Synthesis of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure�activity relationship (2010) Bioorg. Med. Chem., 18, pp. 2245-2254; Jeong, B.S., Choi, H.Y., Thapa, P., Karki, R., Lee, E., Nam, J.M., Na, Y., Lee, E.S., Synthesis, Topoisomerase I and II Inhibitory activity, cytotoxicity, and structure-activity relationship study of rigid analogues of 2,4,6-trisubstituted pyridine containing 5,6-dihydrobenzo[h]quinoline moiety (2011) Bull. Korean Chem. Soc., 32, pp. 303-306; Eryazici, I., Moorefield, C.N., Newkome, G.R., Square-Planar Pd(II), Pt(II), and Au(III) Terpyridine Complexes: Their Syntheses, Physical Properties, Supramolecular Constructs, and Biomedical Activities (2008) Chem. Rev., 108, pp. 1834-1895; Patel, K.K., Plummer, E.A., Darwish, M., Rodger, A., Hannon, M.J., Aryl substituted ruthenium bis-terpyridine complexes: Intercalation and groove binding with DNA (2002) J. Inorg. Biochem., 91, pp. 220-229; Weber, L., The application of multi-component reactions in drug discovery (2002) Curr. Med. Chem., 9, pp. 2085-2093; Hulme, C., Gore, V., Multi-component reactions: Emerging chemistry in drug discovery from xylocain to crixivan (2003) Curr. Med. Chem., 10, pp. 51-80; Nair, V., Rajesh, C., Vinod, A.U., Bindu, S., Sreekanth, A.R., Mathen, J.S., Balagopal, L., Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes (2003) Acc. Chem. Res., 36, pp. 899-907; Andrade, C.K.Z., Barreto, A.S., Silva, W.A., Microwave assisted solvent-, support- and catalyst-free synthesis of enaminones (2008) Ark. Arch. Org. Chem., 12, pp. 226-232; Bortolini, O., D'Agostino, M., De Nino, A., Maiuolo, L., Nardi, M., Sindona, G., Solvent-free, microwave assisted 1,3-cycloaddition of nitrones with vinyl nucleobases for the synthesis of N,O-nucleosides (2008) Tetrahedron, 64, pp. 8078-8081; Ganesan, S., Muthuraaman, B., Madhavan, J., Mathew, V., Maruthamuthu, P., Suthanthiraraj, S.A., The use of 2,6-bis (N-pyrazolyl) pyridine as an efficient dopant in conjugation with poly(ethylene oxide) for nanocrystalline dye-sensitized solar cells (2008) Electrochim. Acta, 53, pp. 7903-7907; Manikandan, P., Padmakumar, K., Justin Thomas, K.R., Varghese, B., Onodera, H., Manoharan, P.T., Lattice-Dictated Conformers in Bis(pyrazolyl)pyridine-Based Iron(II) Complexes: M�ssbauer, NMR, and Magnetic Studies (2001) Inorg. Chem., 40, pp. 6930-6939; Jameson, D.L., Goldsby, K.A., 2,6-bis(N-pyrazolyl)pyridines: The convenient synthesis of a family of planar tridentate N3 ligands that are terpyridine analogs (1990) J. Org. Chem., 55, pp. 4992-4994; Zoppellaro, G., Enkelmann, V., Geies, A., Baumgarten, M., A Multifunctional High-Spin Biradical Pyrazolylbipyridine-bisnitronylnitroxide (2004) Org. Lett., 6, pp. 4929-4932; Prakash, O., Hussain, K., Kumar, R., Wadhwa, D., Sharma, C., Aneja, K.R., Synthesis and antimicrobial evaluation of new1,4-dihydro-4-pyrazolylpyridines and 4-Pyrazolylpyridines (2011) Org. Med. Chem. Lett., 1, pp. 1-7; Motaung, M.P., Ajibade, P.A., Ru(II) and Co(II) Complexes of bis(pyrazolyl)pyridine and pyridine-2,6-dicarboxylic Acid: Synthesis, Photo Physical Studies and Evaluation of Solar Cell Conversion Efficiencies (2015) Int. J. Electrochem. Sci., 10, pp. 8087-8096; Zoppellaro, G., Geies, G., Enkelmann, V., Baumgarten, M., 2,6-Bis(pyrazolyl)pyridine Functionalised with Two Nitronylnitroxide and Iminonitroxide Radicals (2004) Eur. J. Org. Chem., 2004, pp. 2367-2374; Gomha, S.M., Salah, T.A., Abdelhamid, A.O., Synthesis, characterization and pharmacological evaluation of some novel thiadiazoles and thiazoles incorporating pyrazole moiety as potent anticancer agents (2015) Monatsh. Chem., 146, pp. 149-158; Gomha, S.M., Abdel-aziz, H.M., Synthesis and antitumor activity of 1,3,4-thiadiazole derivatives bearing coumarine ring (2015) Heterocycles, 91, pp. 583-592; Dawood, K.M., Gomha, S.M., Synthesis and anti-cancer activity of 1,3,4-thiadiazole and 1,3-thiazole derivatives having 1,3,4-oxadiazole moiety (2015) J. Heterocycl. Chem., 52, pp. 1400-1405; Abbas, I.M., Gomha, S.M., Elneairy, M.A.A., Elaasser, M.M., Mabrouk, B.K.A., Antimicrobial and anticancer evaluation of novel synthetic tetracyclic system through Dimroth rearrangement (2015) J. Serb. Chem. Soc., 80, pp. 1251-1264; Gomha, S.M., Abbas, I.M., Elneairy, M.A.A., Elaasser, M.M., Mabrouk, B.K.A., Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones (2015) Turk. J. Chem., 39, pp. 510-531; Gomha, S.M., Zaki, Y.H., Abdelhamid, A.O., Utility of 3-acetyl-6-bromo-2H-chromen-2-one for synthesis of new heterocycles as potential anticancer agents (2015) Molecules, 20, pp. 21826-21839; Gomha, S.M., Riyadh, S.M., Mahmmoud, E.A., Elaasser, M.M., Chitosan-grafted-poly(4-vinylpyridine) as a novel copolymer basic catalyst for synthesis of arylazothiazoles and 1,3,4-thiadiazoles under microwave irradiation (2015) Chem. Heterocycl. Comp., 51, pp. 1030-1038; Gomha, S.M., Salah, T.A., Hassaneen, H.M.E., Abdel-aziz, H., Khedr, M.A., Synthesis, characterization and molecular docking of novel bioactive thiazolyl-thiazole derivatives as promising cytotoxic antitumor drug (2016) Molecules, 21 (3); Gomha, S.M., Badrey, M.G., Edrees, M.M., Heterocyclization of a bis-thiosemicarbazone of 2,5-diacetyl-3,4-disubstituted-thieno[2,3-b]thiophene bis-thiosemicarbazones leading to bis-thiazoles and bis-1,3,4-thiadiazoles as anti-breast cancer agents (2016) J. Chem. Res., 40, pp. 120-125; Gomha, S.M., Abdallah, M.A., Mourad, M.A., Elaasser, M.M., Application of Mannich and Michael reactions in synthesis of pyridopyrimido[2,1-b][1,3,5]thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones and their biological activity (2016) Heterocycles, (92), pp. 688-699; Ibrahim, M.K., El-Ghandour, A.H.H., Abou-hadeed, K., Abdelhafiz, I.S. Utility of hydzidoyl chlorides: Synthesis of new pyrazoles, pyrazolo[3,4-d]pyridazines, pyrazolo[4,5-b]pyridines and pyrazolo[4,5-d] pyrimidine derivatives (1992) J. Ind. Chem. Soc., 69, pp. 378-380; Gomha, S.M., Abdalla, M.A., Abdelaziz, M., Serag, N., Eco-friendly one-pot synthesis and antiviral evaluation of pyrazolyl chalcones and pyrazolines of medicinal interest (2016) Turk. J. Chem., 40, pp. 484-498; Shawali, A.S., Gomha, S.M., A new entry for short and regioselective synthesis of [1,2,4]triazolo[4,3-b][1,2,4]-triazin-7(1H)-one (2000) Adv. Synth. Catal., (342), pp. 599-604; Gomha, S.M., Riyadh, S.M., Abbas, I.M., Bauomi, M.A., Synthetic utility of ethylidenethiosemicarbazide: Synthesis and and anti-cancer activity of 1,3-thiazines and thiazoles with imidazole moiety (2012) Heterocycles, 87, pp. 341-356
dcterms.sourceScopus

Files

Original bundle

Now showing 1 - 2 of 2
Loading...
Thumbnail Image
Name:
avatar_scholar_256.png
Size:
6.31 KB
Format:
Portable Network Graphics
Description:
Loading...
Thumbnail Image
Name:
An_Efficient_Synthesis_of_Novel_Pyrazole-Based_Het.pdf
Size:
1.37 MB
Format:
Adobe Portable Document Format
Description: