Mostrar el registro sencillo del ítem
Design, characterization and quantum chemical computations of a novel series of pyrazoles derivatives with potential anti-proinflammatory response
dc.contributor.author | Burboa-Schettino, Pia | |
dc.contributor.other | Bustos, Carlos | |
dc.contributor.other | Molins, Elies | |
dc.contributor.other | Figueroa, Xavier F | |
dc.contributor.other | Llanquinao, Jesus | |
dc.contributor.other | Zarate, Ximena | |
dc.contributor.other | Vallejos, Gabriel | |
dc.contributor.other | Diaz-Uribe, Carlos | |
dc.contributor.other | Vallejo, William | |
dc.contributor.other | Schott, Eduardo | |
dc.date.accessioned | 2022-11-15T21:01:54Z | |
dc.date.available | 2022-11-15T21:01:54Z | |
dc.date.issued | 2020-06-24 | |
dc.date.submitted | 2020-03-21 | |
dc.identifier.uri | https://hdl.handle.net/20.500.12834/924 | |
dc.description.abstract | The synthesis and characterization of the full family of 11 pyrazoles were performed by means of UV–Vis, FTIR, 1 H NMR, 13C NMR, two-dimensional NMR experiments and DFT simulations. As pyrazoles are known for showing diverse biological actions, they were also tested in the NCI-60 cancer cell line panel, showing moderate to good activity against different cell lines. Furthermore, the anti-proinflammatory activity test of a set of pyrazoles of the form (E)-4-((4-bro mophenyl)diazenyl)-3,5-dimethyl-1-R-phenyl-1H-pyrazole was performed, this is based on the study of the blockage of the increase in intracellular [Ca2+] observed in response to plateletactivating factor (PAF) treatment of four pyrazoles (i.e. 6, 8, 9 and 10), which successfully displayed [Ca2+] channel inhibition. Therefore, the obtained intracellular [Ca2+] signal results indicate that the pyrazole family characterized in this study, in particular compounds 6 and 10, are potent blockers of the PAF-initiated Ca2+ signaling that mediates the hyperpermeability typically observed during the development of inflammation. | spa |
dc.format.mimetype | application/pdf | spa |
dc.language.iso | eng | spa |
dc.rights.uri | http://creativecommons.org/licenses/by-nc/4.0/ | * |
dc.source | Arabian Journal of Chemistry | spa |
dc.title | Design, characterization and quantum chemical computations of a novel series of pyrazoles derivatives with potential anti-proinflammatory response | spa |
dcterms.bibliographicCitation | Abunada, N.M., Hassaneen, H.M., Abu Samaha, A.S.M., Miqdad, O. A., 2009. Synthesis and antimicrobial evaluation of some new pyrazole, pyrazoline and chromeno[3,4-c]pyrazole derivatives. J. Braz. Chem. Soc. 20, 975–987. https://doi.org/10.1590/S0103- 50532009000500024. | spa |
dcterms.bibliographicCitation | Aggarwal, V.K., de Vicente, J., Bonnert, R.V., 2003. A novel one-pot method for the preparation of pyrazoles by 1,3-dipolar cycloadditions of diazo compounds generated in situ. J. Org. Chem. 68, 5381–5383. https://doi.org/10.1021/jo0268409. | spa |
dcterms.bibliographicCitation | B’Bhatt, H., Sharma, S., 2017. Synthesis and antimicrobial activity of pyrazole nucleus containing 2-thioxothiazolidin-4-one derivatives. Arab. J. Chem. 10, S1590–S1596. https://doi.org/10.1016/j. arabjc.2013.05.029. | spa |
dcterms.bibliographicCitation | Baraldi, P.G., Beria, I., Cozzi, P., Bianchi, N., Gambari, R., Romagnoli, R., 2003. Synthesis and growth inhibition activity of alpha-bromoacrylic heterocyclic and benzoheterocyclic derivatives of distamycin A modified on the amidino moiety. Bioorg. Med. Chem. 11, 965–975. | spa |
dcterms.bibliographicCitation | Bardakos, V., Sucrow, W., Fehlauer, A., 1975. Enhydrazine, 10. Einige aliphatische Enhydrazone. Chem. Ber. 108, 2161–2170. https://doi. org/10.1002/cber.19751080702. | spa |
dcterms.bibliographicCitation | Barrett, A.G.M., 1991. Heterosubstituted nitroalkenes in synthesis. Chem. Soc. Rev. 20, 95. https://doi.org/10.1039/cs9912000095 | spa |
dcterms.bibliographicCitation | Barrett, A.G.M., Graboski, G.G., 1986. Conjugated Nitroalkenes: Versatile Intermediates in Organic Synthesis. Chem. Rev. 86, 751– 762. https://doi.org/10.1021/cr00075a002. | spa |
dcterms.bibliographicCitation | Bertolasi, V., Pretto, L., Ferretti, V., Gilli, P., Gilli, G., 2006. Interplay between steric and electronic factors in determining the strength of intramolecular N-H O resonance-assisted hydrogen bonds in benaminones. Acta Crystallogr. Sect. B Struct. Sci. 62, 1112–1120. https://doi.org/10.1107/S0108768106036421. | spa |
dcterms.bibliographicCitation | Bezenc¸on, O., Remenˇ, L., Richard, S., Roch, C., Kessler, M., Ertel, E. A., Moon, R., Mawet, J., Pfeifer, T., Capeleto, B., 2017. Discovery and evaluation of Cav3.2-selective T-type calcium channel blockers. Bioorganic Med. Chem. Lett. 27, 5326–5331. https://doi.org/ 10.1016/j.bmcl.2017.09.062 | spa |
dcterms.bibliographicCitation | Bishop, B., Brands, K., Gibb, A., Kennedy, D., 2003. Regioselective Synthesis of 1,3,5-Substituted Pyrazoles from Acetylenic Ketones and Hydrazines. Synthesis (Stuttg). 2004, 43–52. https://doi.org/ 10.1055/s-2003-44376. | spa |
dcterms.bibliographicCitation | Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G.L., De Caro, L., Giacovazzo, C., Polidori, G., Spagna, R., 2005. SIR2004: an improved tool for crystal structure determination and refinement. J. Appl. Crystallogr. 38, 381–388. https://doi.org/ 10.1107/S002188980403225X. | spa |
dcterms.bibliographicCitation | Bustos, C., Pe´rez-Cerda, M., Alvarez-Thon, L., Barrales-Salcedo, E., Garland, M.T., 2012. (E)-3,5-Dimethyl-1-p-tolyl-4-(p-tolyldiazenyl)-1H-pyrazole. Acta Crystallogr. Sect. E Struct. Reports Online 68, o353–o354. https://doi.org/10.1107/S1600536812000360 | spa |
dcterms.bibliographicCitation | Bustos, C., Sa´nchez, C., Schott, E., Alvarez-Thon, L., Fuentealba, M., 2007. 3,5-Dimethyl-1-(4-nitro-phen-yl)-4-[(E)-(2,3,4,5,6-penta-fluoro-phen-yl) diazen-yl]-1H-pyrazole. Acta Crystallogr. Sect. E Struct. Reports Online 63, o1138–o1139. https://doi.org/10.1107/ S160053680605464X | spa |
dcterms.bibliographicCitation | Bustos, C., Schott, E., Rı´os, M., Sa´nchez, C., Ca´rcamo, J.-G., 2009. Facile Synthesis Of Isoxazoles And Pyrazoles From Β-Diketohydrazones. J. Chil. Chem. Soc. 54, 267–268. | spa |
dcterms.bibliographicCitation | Card, G.L., Blasdel, L., England, B.P., Zhang, C., Suzuki, Y., Gillette, S., Fong, D., Ibrahim, P.N., Artis, D.R., Bollag, G., Milburn, M. V., Kim, S.-H., Schlessinger, J., Zhang, K.Y.J., 2005. A family of phosphodiesterase inhibitors discovered by cocrystallography and scaffold-based drug design. Nat. Biotechnol. 23, 201–207. https:// doi.org/10.1038/nbt1059. | spa |
dcterms.bibliographicCitation | Cossi, M., Scalmani, G., Rega, N., Barone, V., 2002. New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution. J. Chem. Phys. 117, 43. https://doi.org/10.1063/1.1480445. | spa |
dcterms.bibliographicCitation | Dago, C.D., Le Maux, P., Roisnel, T., Brigaudeau, C., Bekro, Y.A., Mignen, O., Bazureau, J.P., 2018. Preliminary structure-activity relationship (SAR) of a novel series of pyrazole SKF-96365 analogues as potential store-operated calcium entry (SOCE) inhibitors. Int. J. Mol. Sci. 19. https://doi.org/10.3390/ ijms19030856 | spa |
dcterms.bibliographicCitation | Deng, X., Mani, N.S., 2006. Reaction of N-monosubstituted hydrazones with nitroolefins: a novel regioselective pyrazole synthesis. Org. Lett. 8, 3505–3508. https://doi.org/10.1021/ol061226v | spa |
dcterms.bibliographicCitation | Denmark, S.E., Baiazitov, R.Y., Nguyen, S.T., 2001. Tandem double intramolecular [4 + 2]/[3 + 2] cycloadditions of nitroalkenes. Org. Lett. 3, 2907–2910. https://doi.org/10.1021/ol016385n | spa |
dcterms.bibliographicCitation | Elguero, J., 1996. In: Comprehensive Heterocyclic Chemistry II. Elsevier, pp. 1–75. https://doi.org/10.1016/B978-008096518- 5.00059-9 | spa |
dcterms.bibliographicCitation | Elguero, J., 1984. In: Comprehensive Heterocyclic Chemistry. Elsevier, pp. 167–303. https://doi.org/10.1016/B978-008096519-2.00072-2. | spa |
dcterms.bibliographicCitation | Elguero, J., Guerrero, A., Go´mez de la Torre, F., De la Hoz, A., Jalo´n, F.A., Manzano, B.R., Rodrı´guez, A., 2001. New complexes with pyrazole-containing ligands and different metallic centres. Comparative study of their fluxional behaviour involving M-N bond rupture. New J. Chem. 25, 1050–1060. https://doi.org/10.1039/ b102318g | spa |
dcterms.bibliographicCitation | Escario, J.A., Igea, A.M., Contreras, M., Martinez-Fernandez, A.R., Claramunt, R., Lopez, C., 1988. Antiparasitic activity of nine pyrazole derivatives against Trichomonas vaginalis, Entamoeba invadens and Plsmodium berghei. Ann. Trop. Med. Parasitol. 82, 257–262. https://doi.org/10.1080/00034983.1988.11812241 | spa |
dcterms.bibliographicCitation | Farrugia, L.J., 1999. WinGX suite for small-molecule single-crystal crystallography. J. Appl. Crystallogr. 32, 837–838. https://doi.org/ 10.1107/S0021889899006020. | spa |
dcterms.bibliographicCitation | Foti, F., Grassi, G., Risitano, F., 1999. First synthesis of a bromonitrilimine. Direct formation of 3- bromopyrazole derivatives. Tetrahedron Lett. 40, 2605–2606. https://doi.org/10.1016/S0040- 4039(99)00227-0 | spa |
dcterms.bibliographicCitation | Gaete, P.S., Lillo, M.A., Ardiles, N.M., Pe´rez, F.R., Figueroa, X.F., 2012. Ca 2+-activated K + channels of small and intermediate conductance control eNOS activation through NAD(P)H oxidase. Free Radic. Biol. Med. 52, 860–870. https://doi.org/10.1016/j. freeradbiomed.2011.11.036. | spa |
dcterms.bibliographicCitation | Grigg, R., Dowling, M., Jordan, M.W., Sridharan, V., 1987. X=YZH Systems as potential 1,3-dipoles : Part 13. Prototropic generation of azomethine imines from hydrazones. Tetrahedron 43, 5873–5886. | spa |
dcterms.bibliographicCitation | Hay, P.J., Wadt, W.R., 1985. Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals. J. Chem. Phys. 82, 299. https://doi.org/ 10.1063/1.448975. | spa |
dcterms.bibliographicCitation | Huisgen, R., Huisgen, R., 1963. 1,3-Dipolar Cycloadditions. Past and Future. Angew. Chemie Int. Ed. English 2, 565–598. https://doi. org/10.1002/anie.196305651 | spa |
dcterms.bibliographicCitation | Jiang, Y., Wen, K., Zhou, X., Schwegler-Berry, D., Castranova, V., He, P., 2008. Three-dimensional localization and quantification of PAF-induced gap formation in intact venular microvessels. Am. J. Physiol. Circ. Physiol. 295, H898–H906. https://doi.org/10.1152/ ajpheart.00309.2008. | spa |
dcterms.bibliographicCitation | Jung, M.E., Trifunovich, I.D., 1992. Efficient synthesis of 20 ,30 - dideoxynucleosides and 20 ,30 -dideoxy C-nucleosides from D-glucosamine. Tetrahedron Lett. 33, 2921–2924. https://doi.org/ 10.1016/S0040-4039(00)79561-X. | spa |
dcterms.bibliographicCitation | Kumar, J.S.D., Prabhakaran, J., Arango, V., Parsey, R.V., Underwood, M.D., Simpson, N.R., Kassir, S.A., Majo, V.J., Van Heertum, R.L., Mann, J.J., 2004. Synthesis of [O-methyl-11C]1- (2-chlorophenyl)-5-(4- methoxyphenyl)-4-methyl-1H-pyrazole-3- carboxylic acid piperidin-1-ylamide: A potential PET ligand for CB1 receptors. Bioorganic Med. Chem. Lett. 14, 2393–2396. https://doi.org/10.1016/j.bmcl.2004.03.034. | spa |
dcterms.bibliographicCitation | Kumar, R., Arora, J., Ruhil, S., Phougat, N., Chhillar, A.K., Prasad, A.K., 2014. Synthesis and Antimicrobial Studies of Pyrimidine Pyrazole Heterocycles. Adv. Chem. 2014, 1–12. https://doi.org/ 10.1155/2014/329681. | spa |
dcterms.bibliographicCitation | Le Fevre, G., Hamelin, J., 1980. Addition de phe´nylhydrazones aux ole´pines en milieu neutre. Tetrahedron 36, 887–891. https://doi.org/ 10.1016/0040-4020(80)80039-1. | spa |
dcterms.bibliographicCitation | Lillo, M.A., Gaete, P.S., Puebla, M., Ardiles, N.M., Poblete, I., Becerra, A., Simon, F., Figueroa, X.F., 2018. Critical contribution of Na+-Ca2+ exchanger to the Ca2+-mediated vasodilation activated in endothelial cells of resistance arteries. FASEB J. 32, 2137–2147. https://doi.org/10.1096/fj.201700365RR | spa |
dcterms.bibliographicCitation | M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A.R., J.R. Cheeseman, T.A. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A., Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B.S., A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L., Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J.D., J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A.P., n.d. Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT, EUA | spa |
dcterms.bibliographicCitation | Makino, K., Kim, H.S., Kurasawa, Y., 1998. Synthesis of Pyrazoles. J. Heterocycl. Chem. 35, 489–497. | spa |
dcterms.bibliographicCitation | Mancera, M., Rodriguez, E., Roff, I., Galbis, J.A., 1988. Stereoselective Syntheses of Nitropyrazolines by 1,3-Dipolar Cycloaddition of Diazoalkanes to Sugar Nitro Olefins. J. Org. Chem. 53, 5648–5651. | spa |
dcterms.bibliographicCitation | Menozzi, G., Mosti, L., Fossa, P., Mattioli, F., Ghia, M., 1997. xDialkylaminoalkyl ethers of phenyl-(5-substituted 1-phenyl-1Hpyrazol-4-yl)methanols with analgesic and anti-inflammatory activity. J. Heterocycl. Chem. 34, 963–968. | spa |
dcterms.bibliographicCitation | Miller, R.D., Reiser, O., 1993. The synthesis of Electron DonorAcceptor Substituted Pyrazoles. J. Heterocycl. Chem. 30, 755–763. | spa |
dcterms.bibliographicCitation | Nakano, Y., Hamaguchi, M., Nagai, T., 1989. A synthetic route to bicyclic pyrazolenines via 3-chloropyrazolines and the ring opening of pyrazolenines to diazoalkenes. J. Org. Chem. 54, 5912–5919. | spa |
dcterms.bibliographicCitation | Norris, T., Colon-Cruz, R., Ripin, D.H.B., 2005. New hydroxypyrazoline intermediates, subtle regio-selectivity and relative reaction rate variations observed during acid catalyzed and neutral pyrazole cyclization. Org. Biomol. Chem. 3, 1844–1849. https://doi. org/10.1039/b500413f. | spa |
dcterms.bibliographicCitation | Osella, D., Milone, L., Nervi, C., Ravera, M., 1995. Electronic interactions in organometallic dimers. An electrochemical approach. J. Organomet. Chem. 488, 1–7. | spa |
dcterms.bibliographicCitation | Padwa, A., 2009. 1,3-Dipolar cycloaddition chemistry. Volumes 1 and 2. Edited by Albert Padwa. John Wiley and Sons. New York, 1984. Volume 1: XIII + 817 pages. Volume 2: XIII + 704 pages. ISBN 0-471-08364-X (set). $295.00 for the two-volume set. J. Heterocycl. Chem. 23, 1899–1899. https://doi.org/10.1002/jhet.5570230658. | spa |
dcterms.bibliographicCitation | Parham, W.E., Bleasdale, J.L., 1951. The Condensation of Diazo Compounds with Nitroo¨lefins. II. 3-Bromo- and 3-Nitropyrazoles. J. Am. Chem. Soc. 73, 4664–4666. https://doi.org/10.1021/ja01154a051. | spa |
dcterms.bibliographicCitation | Parham, W.E., Braxton, H.G., O’Connor, P.R., 1961. Reaction of Diazo Compounds with Nitroolefins. VI. The Reaction of Diphenyldiazomethane with 1-Nitropropene. J. Org. Chem. 26, 1805–1807. https://doi.org/10.1021/jo01065a027. | spa |
dcterms.bibliographicCitation | Penning, T.D., Talley, J.J., Bertenshaw, S.R., Carter, J.S., Collins, P. W., Docter, S., Graneto, M.J., Lee, L.F., Malecha, J.W., Miyashiro, J.M., Rogers, R.S., Rogier, D.J., Yu, S.S., Anderson, G.D., Burton, E.G., Cogburn, J.N., Gregory, S.A., Koboldt, C.M., Perkins, W.E., Seibert, K., Veenhuizen, A.W., Zhang, Y.Y., Isakson, P.C., 1997. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl] benze nesulfonamide (SC-58635, celecoxib). J. Med. Chem. 40, 1347–1365. https://doi.org/10.1021/jm960803q. | spa |
dcterms.bibliographicCitation | Rassolov, V.A., Ratner, M.A., Pople, J.A., Redfern, P.C., Curtiss, L. A., 2001. 6–31G* basis set for third-row atoms. J. Comput. Chem. 22, 976–984. https://doi.org/10.1002/jcc.1058.abs. | spa |
dcterms.bibliographicCitation | Sammelson, R.E., Caboni, P., Durkin, K.A., Casida, J.E., 2004. GABA receptor antagonists and insecticides: common structural features of 4-alkyl-1-phenylpyrazoles and 4-alkyl-1-phenyltrioxabicyclooctanes. Bioorg. Med. Chem. 12, 3345–3355. https://doi.org/ 10.1016/j.bmc.2004.03.069 | spa |
dcterms.bibliographicCitation | Sheldrick, G.M., 1990. Phase annealing in SHELX-90: direct methods for larger structures. Acta Crystallogr. Sect. A 46, 467–473. https:// doi.org/10.1107/S0108767390000277 | spa |
dcterms.bibliographicCitation | Shoemaker, R.H., 2006. The NCI60 human tumour cell line anticancer drug screen. Nature Reviews Cancer., 813–823 https://doi.org/ 10.1038/nrc1951 | spa |
dcterms.bibliographicCitation | Sikorski, A., Trzybin´ski, D., 2013. Networks of intermolecular interactions involving nitro groups in the crystals of three polymorphs of 9-aminoacridinium 2,4-dinitrobenzoate 2,4-dinitrobenzoic acid. J. Mol. Struct. 1049, 90–98. https://doi.org/ 10.1016/j.molstruc.2013.06.031 | spa |
dcterms.bibliographicCitation | Surendra Kumar, R., Arif, I.A., Ahamed, A., Idhayadhulla, A., 2016. Anti-inflammatory and antimicrobial activities of novel pyrazole analogues. Saudi J. Biol. Sci. 23, 614–620. https://doi.org/10.1016/j. sjbs.2015.07.005 | spa |
dcterms.bibliographicCitation | Terrett, N.K., Bell, A.S., Brown, D., Ellis, P., 1996. Sildenafil (Viagra), a potent and selective inhibitor of Type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction. Bioorg. Med. Chem. 6, 1819–1824. | spa |
dcterms.bibliographicCitation | Tiruppathi, C., Minshall, R.D., Paria, B.C., Vogel, S.M., Malik, A.B., 2002. Role of Ca2+ signaling in the regulation of endothelial permeability. Vascul. Pharmacol. 39, 173–185. https://doi.org/ 10.1016/S1537-1891(03)00007-7 | spa |
dcterms.bibliographicCitation | Wustrow, D.J., Capiris, T., Rubin, R., Knobelsdorf, J.A., Akunne, H., Davis, M.D., Mackenzie, R., Pugsley, T.A., Zoski, K.T., Heffner, T.G., Wise, L.D., 1998. Pyrazolo[1,5-a]pyrimidine CRF-1 receptor antagonists. Bioorg. Med. Chem. Lett. 8, 2067–2070. | spa |
dcterms.bibliographicCitation | Yanai, T., Tew, D.P., Handy, N.C., 2004. A new hybrid exchangecorrelation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem. Phys. Lett. 393, 51–57. https://doi.org/ 10.1016/j.cplett.2004.06.011. | spa |
dcterms.bibliographicCitation | Yao, H.C., 1964. Azohydrazone Conversion. II. The Coupling of Diazonium Ion with b-Diketones. J. Am. Chem. Soc. 29, 2959– 2963. | spa |
datacite.rights | http://purl.org/coar/access_right/c_abf2 | spa |
oaire.resourcetype | http://purl.org/coar/resource_type/c_6501 | spa |
oaire.version | http://purl.org/coar/version/c_970fb48d4fbd8a85 | spa |
dc.audience | Público general | spa |
dc.identifier.doi | 10.1016/j.arabjc.2020.05.042 | |
dc.identifier.instname | Universidad del Atlántico | spa |
dc.identifier.reponame | Repositorio Universidad del Atlántico | spa |
dc.rights.cc | Attribution-NonCommercial 4.0 International | * |
dc.subject.keywords | Anti-proinflammatory; Platelet-activating factor; Pyrazoles; | spa |
dc.type.driver | info:eu-repo/semantics/article | spa |
dc.type.hasVersion | info:eu-repo/semantics/publishedVersion | spa |
dc.type.spa | Artículo | spa |
dc.publisher.place | Barranquilla | spa |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | spa |
dc.publisher.discipline | Química | spa |
dc.publisher.sede | Sede Norte | spa |