Uses of cyanoacetylhydrazine in heterocyclic synthesis: Novel synthesis of pyrazole derivatives with anti-tumor activities

dc.AffiliationOctober University for modern sciences and Arts (MSA)
dc.contributor.authorMohareb R.M.
dc.contributor.authorEl-Sayed N.N.E.
dc.contributor.authorAbdelaziz M.A.
dc.contributor.otherDepartrment of Chemistry
dc.contributor.otherFaculty of Science
dc.contributor.otherCairo University
dc.contributor.otherGiza 12613
dc.contributor.otherEgypt; Department of Organic Chemistry
dc.contributor.otherFaculty of Pharmacy
dc.contributor.otherOctober University for Modern Sciences and Arts (MSA)
dc.contributor.otherEl-Wahaat Road
dc.contributor.otherOctober City
dc.contributor.otherGiza 12411
dc.contributor.otherEgypt; National Organization for Drug Control and Research
dc.contributor.otherP.O. Box 29
dc.contributor.otherCairo 11421
dc.contributor.otherEgypt; College of Science
dc.contributor.otherDepartment of Chemistry
dc.contributor.otherKing Saud University
dc.contributor.otherRiyadh 11932
dc.contributor.otherSaudi Arabia; Preparatory Year Department
dc.contributor.otherAL-Ghad International Colleges for Health Sciences
dc.contributor.otherTabuk Male
dc.contributor.otherTabuk 41321
dc.contributor.otherSaudi Arabia; Basic Science Department
dc.contributor.otherModern Academy for Engineering and Technology in Maadi
dc.contributor.otherMaadi 11431
dc.contributor.otherCairo
dc.contributor.otherEgypt
dc.date.accessioned2020-01-25T19:58:27Z
dc.date.available2020-01-25T19:58:27Z
dc.date.issued2012
dc.descriptionScopus
dc.description.abstractThe reaction of cyanoacetylhydrazine with chloroacetyl chloride gave N?-(2-chloroacetyl)-2-cyanoacetohydrazide. The latter underwent cyclization to afford 1-(5 amino-3-hydroxy-1H-pyrazol-1-yl)-2-chloroethanone, which underwent nucleophilic substitution to give 3-(5-amino-3-hydroxy-1H- pyrazol-1-yl)-3-oxopropanenitrile. The latter two compounds were used as key synthons to synthesize new thiophene, pyran, thiazole and some fused heterocyclic derivatives. The antitumor activity of the newly synthesized compounds was evaluated against three human tumor cells lines, namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) and some of these compounds were found to exhibit much higher inhibitory effects towards the three tumor cell lines than the Gram positive control doxorubicin. � 2012 by the authors.en_US
dc.identifier.doihttps://doi.org/10.3390/molecules17078449
dc.identifier.doiPubMedID22790561
dc.identifier.issn14203049
dc.identifier.otherhttps://doi.org/10.3390/molecules17078449
dc.identifier.otherPubMedID22790561
dc.identifier.urihttps://t.ly/P5WGM
dc.language.isoEnglishen_US
dc.relation.ispartofseriesMolecules
dc.relation.ispartofseries17
dc.subjectAntitumoren_US
dc.subjectPyrazoleen_US
dc.subjectThiazoleen_US
dc.subjectThiopheneen_US
dc.subjectantineoplastic agenten_US
dc.subjectheterocyclic compounden_US
dc.subjecthydrazine derivativeen_US
dc.subjectpyrazoleen_US
dc.subjectpyrazole derivativeen_US
dc.subjectarticleen_US
dc.subjectchemistryen_US
dc.subjectdrug screeningen_US
dc.subjecthumanen_US
dc.subjectstructure activity relationen_US
dc.subjectsynthesisen_US
dc.subjecttumor cell lineen_US
dc.subjectAntineoplastic Agentsen_US
dc.subjectCell Line, Tumoren_US
dc.subjectDrug Screening Assays, Antitumoren_US
dc.subjectHeterocyclic Compoundsen_US
dc.subjectHumansen_US
dc.subjectHydrazinesen_US
dc.subjectPyrazolesen_US
dc.subjectStructure-Activity Relationshipen_US
dc.titleUses of cyanoacetylhydrazine in heterocyclic synthesis: Novel synthesis of pyrazole derivatives with anti-tumor activitiesen_US
dc.typeArticleen_US
dcterms.isReferencedByLiu, X.-H., Cui, P., Song, B.-A., Bhadury, P.S., Zhu, H.-L., Wang, S.-F., Synthesis, structure and antibacterial activity of novel 1-(5-substituted-3-substituted-4,5-dihydropyrazol-1-yl)ethanone oxime ester derivatives (2008) Bioorganic and Medicinal Chemistry, 16 (7), pp. 4075-4082. , DOI 10.1016/j.bmc.2008.01.035, PII S0968089608000503; 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) Bioorgan. Med. Chem., 16, pp. 9699-9707; Abdel-Hafez, E.M.N., Rahma, G.E.A.A., Aziz, M.A., Radwan, M.F., Farag, H.H., Design synthesis and biological investigation of certain pyrazole-3-carboxylic acid derivatives as novel carriers for nitric oxide (2009) Bioorgan. Med. Chem., 17, pp. 3829-3837; Park, H.-J., Lee, K., Park, S.-J., Ahn, B., Lee, J.-C., Cho, H., Lee, K.-I., Identification of antitumor activity of pyrazole oxime ethers (2005) Bioorganic and Medicinal Chemistry Letters, 15 (13), pp. 3307-3312. , DOI 10.1016/j.bmcl.2005.03.082, PII S0960894X05004051; Ouyang, G., Cai, X.J., Chen, Z., Song, B.A., Bhadury, P.S., Yang, S., Jin, L.H., Zeng, S., Synthesis and antiviral activities of pyrazole derivatives containing an oxime moiety (2008) J. Agric. Food Chem., 56, pp. 101601-102607; Dai, H., Li, Y.Q., Du, D., Qin, X., Zhang, X., Yu, H.B., Fang, J.X., Synthesis and biological activities of novel pyrazole oxime derivatives containing a 2-chloro-5-thiazolyl moiety (2008) Food Chem., 56, pp. 10805-10810; Riyadh, S.M., Farghaly, T.A., Abdallah, M.A., Abdalla, M.M., El-Aziz, M.R.A., New pyrazoles incorporating pyrazolylpyrazole moiety: Synthesis, anti-HCV and antitumor activity (2010) Eur. J. Med. Chem., 45, pp. 1042-1050; Anzaldi, M., MacCio, C., Mazzei, M., Bertolotto, M., Ottonello, L., Dallegri, F., Balbi, A., Antiproliferative and proapoptotic activities of a new class of pyrazole derivatives in HL-60 cells (2009) Chem. Biodivers., 6, pp. 1674-1684; El-Shafei, A., Fadda, A.A., Khalil, A.M., Ameen, T.A.E., Badria, F.A., Synthesis antitumor evaluation, molecular modeling and quantitative structure-activity relationship (QSAR) of some novel arylazopyrazolodiazine and triazine analogs (2009) Bioorgan. Med. Chem., 17, pp. 5096-5105; Huang, K.H., Veal, J.M., Fadden, P.R., Rice, J.W., Eaves, J., Strachan, J.P., Barabasz, A.F., Ma, W., Discovery of Novel 2-Aminobenzamide Inhibitors of Heat Shock Protein 90 as Potent, Selective and Orally Active Antitumor Agents (2009) J. Med. Chem., 52, pp. 4288-4305; Chandanshive, J.Z., Bonini, B.F., Tiznado, W., Escobar, C.A., Caballero, J., Femoni, C., Fochi, M., Franchini, M.C., 1, 3-Dipolar Cycloaddition of Nitrile Imines with Cyclic ?-?-Unsaturated Ketones: A Regiochemical Route to Ring-Fused Pyrazoles (2011) Eur. J. Org. Chem., pp. 4806-4811; Chandanshive, J.Z., Bonini, B.F., Gentili, D., Fochi, M., Bernardi, L., Franchini, M.C., Regiocontrolled synthesis of ring-fused thieno[2, 3-c]pyrazoles through 1, 3-dipolar cycloaddition of nitrile imines with sulfur-based acetylenes (2010) Eur. J. Org. Chem., 33, pp. 6440-6447; Bondock, S., Fadaly, W., Metwally, M.A., Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety (2010) Eur. J. Med. Chem., 45, pp. 3692-3701; Mohareb, R.M., Samir, E.M., The Reaction of cyanoacetylhydrazine with chloroacetone: Synthesis of 1, 2, 4-triazine, 1, 3, 4-oxadiazine and their fused derivatives with antitumor activities (2012) Open J. Med. Chem., 2, pp. 1-9; Mohareb, R.M., Ibrahim, R.A., Moustafa, H.E., Hydrazide-hydrazones in the synthesis of 1, 3, 4-oxadiazine, 1, 2, 4-triazine and pyrazole derivatives with anti-tumor activities (2010) Open Org. Chem. J., 4, pp. 8-14; Mohareb, R.M., Schatz, J., Anti-tumor and anti-leishmanial evaluations of 1, 3, 4-oxadiazine, pyran derivatives derived from cross-coupling reactions of ?-bromo-6H-1, 3, 4- oxadiazine derivatives (2011) Bioorgan. Med. Chem., 19, pp. 2707-2713; Khalil, A.M., Berghot, M.A., Gouda, M.A., Synthesis and antibacterial activity of some new thiazole and thiophene derivatives (2009) Eur. J. Med. Chem., 44, pp. 4434-4440; McKibben, B.P., Cartwright, C.H., Castelhano, A.L., Practical synthesis of tetrasubstituted thiophenes for use in compound libraries (1999) Tetrahedron Letters, 40 (30), pp. 5471-5474. , DOI 10.1016/S0040-4039(99)01108-9, PII S0040403999011089; Balamurugan, K., Perumal, S., Sunil, A., Reddy, A.S.K., Yogeeswari, P., Sriram, D.A., Facile domino protocol for the regioselective synthesis and discovery of novel 2-amino-5-arylthieno [2, 3-b] thiophene as antimycobacterial agents (2009) Tetrahedron Lett., 50, pp. 6191-6195; Ye, D., Zhang, Y., Wang, F., Zheng, M., Zhang, X., Luo, X., Shen, X., Liu, H., Novel thiophene derivatives as PTP1B inhibitors with selectivity and cellular activity (2010) Bioorgan. Med. Chem., 18, pp. 1773-1782; Mansour, S.A., Mahmoud, S.B., Saleh, I.A., Mostafa, M.G., Ant-breast cancer activity of some novel 1, 2-dihydropyridine, thiophene and thiazole derivatives (2011) Eur. J. Med. Chem., 46, pp. 137-141; Scrowston, R.M., Recent advances in the chemistry of benzo [b]-thiophene (1981) Adv. Heterocycl. Chem., 29, pp. 171-249; Parida, K.M., Rath, D., Amine functionalized MCM-41: An active and reusable catalyst for Knoevenagel condensation reaction (2009) J. Mol. Catal. A: Chem., 310, pp. 93-100; Jain, D., Mishra, M., Rani, A., Synthesis and characterization of novel aminopropylated fly ash catalyst and its beneficial application in base catalyzed Knoevenagel condensation reaction (2012) Fuel Process. Technol., 95, pp. 119-126; Tisseh, Z.N., Dabiri, M., Nobahar, M., Khavasi, H.R., Bazgir, A., Catalyst-free aqueous and highly diastereoselective synthesis of new 5-substituted 1H-tetrazoles via a muti-component domino Knoevenagel condensation/1, 3- dipolar cycloaddition reaction (2012) Tetrahedron, 68, pp. 1769-1773; Atamanyuk, D.V., Ostapiuk, Y.V., Kryshchyshyn, A.P., A new domino-Knoevenagel-hetero- Diels-Alder reaction (2008) Tetrahedron Lett., 49, pp. 4648-4651; Cateni, F., Zilic, J., Zacchigna, M., Bonivento, P., Frausin, F., Scarcia, V., Synthesis and biological properties of new ?-methylene- butyrolactones and ?, ?-unsaturated ?-butyrolactones (2006) Eur. J. Med. Chem., 41, pp. 192-200; Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J.T., Boyd, M.R., New colorimetric cytotoxicity assay for anticancer-drug screening (1990) Journal of the National Cancer Institute, 82 (13), pp. 1107-1112; Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paul, K., Vistica, D., Hose, C., Vaigro-Wolff, A., Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines (1991) J. Natl. Cancer Inst., 83, pp. 757-766
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:
molecules-17-08449.pdf
Size:
226.86 KB
Format:
Adobe Portable Document Format
Description: