Cytotoxic and Antifungal Activities of Diverse α-Naphthylamine Derivatives

dc.contributor.authorKouznetsov, Vladímir V.
dc.contributor.authorSortino, Maximiliano
dc.contributor.authorZacchino, Susana A.
dc.contributor.authorVargas Méndez, Leonor Y.
dc.contributor.authorGupta, Mahabir P.
dc.date.accessioned2020-02-03T11:51:22Z
dc.date.available2020-02-03T11:51:22Z
dc.date.issued2012-10-23
dc.description.abstractDiverse α-naphthylamine derivatives were easily prepared from corresponding aldimines derived from commercially available α-naphthaldehyde and anilines or isomeric pyridinecarboxyaldehydes and α-naphthylamine. The secondary amines obtained were tested as possible antifungal and cytotoxic agents. The diverse N-aryl-N-[1-(1-naphthyl)but-3-enyl]amines obtained were active (IC50 < 10 µg/mL) against breast (MCF-7), non-small cell lung (H-460), and central nervous system (SF-268) human cancer cell lines, while N-(pyridinylmethyl)- naphthalen-1-amines resulted in activity against (MIC 25–32 µg/mL) some human opportunistic pathogenic fungi including yeasts, hialohyphomycetes, and dermatophytes.spa
dc.description.domainhttp://unidadinvestigacion.usta.edu.cospa
dc.format.mimetypeapplication/pdf
dc.identifier.doihttps://doi.org/10.3797/scipharm.1209-03spa
dc.identifier.urihttp://hdl.handle.net/11634/21360
dc.publisher.branchCRAI-USTA Bogotáspa
dc.relation.referencesSeayad A, Ahmed M, Klein H, Jackstell R, Gross T, Beller M. Internal Olefins to Linear Amines. Science. 2002; 297: 1676–1678. http://dx.doi.org/10.1126/science.1074801spa
dc.relation.referencesKleemann A, Engel J. Pharmaceutical Substances, Thieme: New York, 1999.spa
dc.relation.referencesEvers A, Hessler G, Matter H, Klabunde T. Virtual Screening of Biogenic Amine-Binding G-Protein Coupled Receptors:  Comparative Evaluation of Protein- and Ligand-Based Virtual Screening Protocols. J Med Chem. 2005; 48: 5448–5465. http://dx.doi.org/10.1021/jm050090ospa
dc.relation.referencesSalvatore RN, Yoon CH, Jung KW. Synthesis of secondary amines. Tetrahedron. 2001; 57: 7785–7811. http://dx.doi.org/10.1016/S0040-4020(01)00722-0spa
dc.relation.referencesHenkel T, Brunne RM, Mueller H, Reichel F. Statistical Investigation into the Structural Complementarity of Natural Products and Synthetic Compounds. Angew Chem Int Ed. 1999; 38: 643–747. http://dx.doi.org/10.1002/(SICI)1521-3773(19990301)38:5<643::AID-ANIE643>3.0.CO;2-Gspa
dc.relation.referencesAbdel-Magid AF, Mehrman SJ. A Review on the Use of Sodium Triacetoxyborohydride in the Reductive Amination of Ketones and Aldehydes. Org Process Res Dev. 2006; 10: 971–1031. http://dx.doi.org/10.1021/op0601013spa
dc.relation.referencesMiller EC. Some Current Perspectives on Chemical Carcinogenesis in Humans and Experimental Animals: Presidential Address. Cancer Res. 1978; 38: 1479–1496. http://www.ncbi.nlm.nih.gov/pubmed/348302spa
dc.relation.referencesButler MA, Iwasaki M, Guengerich FP, Kadlubar FF. Human cytochrome P-450PA (P-450IA2), the phenacetin O-deet-hylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines. Proc Nat Acad Sci U S A. 1989; 86: 7696–7700. http://dx.doi.org/10.1073/pnas.86.20.7696spa
dc.relation.referencesHecht SS. Cigarette smoking: cancer risks, carcinogens, and mechanisms. Langenbecks Arch Surg. 2006; 391: 603–613. http://dx.doi.org/10.1007/s00423-006-0111-zspa
dc.relation.referencesTaboada MC, Rodriguez B, Millán R, Míguez I. Role of dietary L-arginine supplementation on serum parameters and intestinal enzyme activities in rats fed an excess-fat diet. Biomed Pharm. 2006; 60: 10–13. http://dx.doi.org/10.1016/j.biopha.2005.07.014spa
dc.relation.referencesWilson ZMP, Bowman RE, Smith HJ, Nicholls PJ, Hewlins MJE. Potential Protein Kinase C Inhibitors. 8,9,10,11α:-Tetrahydro-7αH-7,11-methano-12,12- dimethylcycloocta[de]naphthyl-9-amines. J Pharm Pharmacol. 1996; 48: 160–171. http://dx.doi.org/10.1111/j.2042-7158.1996.tb07116.xspa
dc.relation.referencesKovacic P, Somanathan R. Novel, unifying mechanism for aromatic primary-amines (therapeutics, carcinogens and toxins): electron transfer, reactive oxygen species, oxidative stress and metabolites. Med Chem Commun. 2011; 2: 106–112. http://dx.doi.org/10.1039/c0md00233jspa
dc.relation.referencesUrbina JMG, Cortés JC, Palma A, López SN, Zacchino SA, Enriz DR, Ribas JC, Kouznetsov V. Inhibitors of the Fungal Cell Wall. Synthesis of 4-Aryl-4-N-arylamine-1-butenes and Related Compounds with Inhibitory Activities on β(1±3) Glucan and Chitin Synthases. Bioorg Med Chem. 2000; 8: 691–698. http://dx.doi.org/10.1016/S0968-0896(00)00003-1spa
dc.relation.referencesVargas MLY, Castelli MV, Kouznetsov VV, Urbina GJM, López SN, Sortino M, Enriz RD, Ribas JC, Zacchino SA. In Vitro Antifungal Activity of New Series of Homoallylamines and Related Compounds with Inhibitory Properties of the Synthesis of Fungal Cell Wall Polymers. Bioorg Med Chem. 2003; 11: 1531–1550. http://dx.doi.org/10.1016/S0968-0896(02)00605-3spa
dc.relation.referencesKouznetsov VV, Rivero Castro J, Ochoa Puentes C, Stashenko EE, René Martínez J, Ochoa C, Montoro Pereira D, Nogal Ruiz JJ, Fernández Portillo C, Muelas Serrano S, Gómez Barrio A, Bahsas A, Amaro-Luis J. Synthesis and Antiparasitic Properties of New 4-N-Benzylamino-4-Hetarylbut-1-enes. Arch Pharm. 2005; 338: 32–37. http://dx.doi.org/10.1002/ardp.200400909spa
dc.relation.referencesSuvire DF, Sortino M, Kouznetsov VV, Vargas MLY, Zacchino SA, Mora Cruz U, Enriz RD. Structure–activity relationship study of homoallylamines and related derivatives acting as antifungal agents. Bioorg Med Chem. 2006; 14: 1851–1862. http://dx.doi.org/10.1016/j.bmc.2005.10.036spa
dc.relation.referencesKouznetsov VV, Astudillo Saavedra L, Vargas Méndez LY, Cazar Ramírez ME. Synthesis of some secondary amine derivatives bearing a heteroaryl fragment. J Chil Chem Soc. 2004; 49: 197–203. http://dx.doi.org/10.4067/S0717-97072004000400010spa
dc.relation.referencesKouznetsov V, Rodríguez W, Stashenko E, Ochoa C, Vega C, Rolón M, Montero Pereira D, Escario JA, Gómez Barrio A. Transformation of schiff bases derived from alpha-naphthaldehyde. Synthesis, spectral data and biological activity of new-3-aryl-2-(α-naphthyl)-4-thiazolidinones and N-aryl-N-[1-(α-naphthyl)but-3- enyl]amines. J Heterocycl Chem. 2004; 41: 995–999. http://dx.doi.org/10.1002/jhet.5570410624spa
dc.relation.referencesFuglseth E, Otterholt E, Høgmoen H, Sundby E, Charnock C, Hoff BH. Chiral derivatives of Butenafine and Terbinafine: synthesis and antifungal activity. Tetrahedron. 2009; 65: 9807–9813. http://dx.doi.org/10.1016/j.tet.2009.09.067spa
dc.relation.referencesMonks A, Scudiero DA, Johnson GS, Pauli KD, Sausville EA. Mini-review. The NCI anti-cancer drug screen: a smart screen to identify effectors of novel targets. Anticancer Drug Des. 1997; 12: 533–541. http://www.ncbi.nlm.nih.gov/pubmed/9365500spa
dc.rightsAtribución-NoComercial-CompartirIgual 2.5 Colombia
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/2.5/co/
dc.subject.keywordα-Naphthylaminesspa
dc.subject.keywordAntifungal propertiesspa
dc.subject.keywordCytotoxic agentsspa
dc.titleCytotoxic and Antifungal Activities of Diverse α-Naphthylamine Derivativesspa
dc.type.categoryGeneración de Nuevo Conocimiento: Artículos publicados en revistas especializadas - Electrónicosspa

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