BiocatalyticProduction of Chiral Benzotriazoles Employing Conventional Heating and Microwave Radiation

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dc.citation.issue3
dc.citation.volume4
dc.contributor.authorMeirelles, Matheus A.
dc.contributor.authorJeller, Alex H.
dc.contributor.authorFerreira, Irlon M.
dc.contributor.authorRaminelli, Cristiano [UNIFESP]
dc.contributor.authorFaria, Raquel S.
dc.contributor.authorSilveira-Lacerda, Elisangela de Paula
dc.contributor.authorPorto, Andre L. M.
dc.coverageSharjah
dc.date.accessioned2020-07-17T14:03:31Z
dc.date.available2020-07-17T14:03:31Z
dc.date.issued2017
dc.description.abstractBackground: This paper describes the synthesis of chiral 1,2,3-benzotriazoles by the enzymatic kinetic resolution of beta-azidoalcohols using lipase from Candida antarctica B followed by a [3+ 2] cycloaddition reaction involving benzyne formation from 2-(trimethylsilyl) phenyl triflate and CsF under conventional heating and microwave radiation. (+/-)-1,2,3-Benzotriazoles were tested in vitro to evaluate their cytotoxic effects on S180 tumor cells using the colorimetric MTT assay. They showed IC50 values comparable to the IC50 value of cisplatin. Methods: Synthesis of azidoalcohols and 1,2,3-benzotriazoles were carried out under microwave radiation and conventional heating. Enzymatic kinetic resolution of (+/-)-azidoalcohols were obtained by Candida antarctica B in orbital shaker. Enzymatic reactions were analyzed using Shimadzu LC-10AD HPLC equipment with UV detector (190-254 nm) and Chiralcel OD-H chiral column (0.46 cm +/- 25 cmen
dc.description.abstract5 +/- m). Results: Preparation of (+/-)-azidoalcohols was used the corresponding epoxides and NaN3 in water at 90 degrees C. When the reactions were performed under microwave heating, the compounds were obtained in higher yields (80 and 85%, respectively) and shorter reaction times (10 and 90 min, respectively) versus conventional heating. The (+/-)-1,2,3-benzotriazoles were produced by the [3+ 2] cycloaddition reaction between (+/-)-azidoalcohols and 2-(trimethylsilyl) phenyl triflate in the presence of CsF using acetonitrile as solvent at 70 degrees C under conventional heating or microwave radiation. CAL-B was employed in kinetic resolution of (+/-)-azidoalcohols yielding enantioenriched products. cytotoxic effects on S180 tumor cells using the colorimetric MTT assay. Conclusion: Chiral 1,2,3-benzotriazoles were synthesized from enzymatic kinetic resolution of (+/-)azidoalcohols using Candida antarctica B followed by a [3+ 2] cycloaddition reaction involving the benzyne formation from 2-(trimethylsilyl) phenyl triflate and CsF under conventional heating and microwave radiation. The chiral 1,2,3-benzotriazoles were obtained after 15 min under microwave radiation with 55-56% yields. The (+/-)-1,2,3-benzotriazoles were tested in vitro to evaluate their cytotoxic effects on S180 tumor cell line using the colorimetric MTT assay and showed IC50 values comparable to the IC50 value of cisplatin.en
dc.description.affiliationUniv Sao Paulo, Inst Quim Sao Carlos, Lab Quim Organ & Biocatalise, Av Joao Dagnone,Ed Quim Ambiental, BR-13563120 Sao Carlos, SP, Brazil
dc.description.affiliationUniv Estadual Mato Grosso do Sul, Coordenacao Quim, Rod Dourados Itahum,Km 12, BR-79804970 Dourados, MS, Brazil
dc.description.affiliationUniv Fed Amapa, Colegiado Quim, Grp Biocatalise & Biotransformacao Quim Organ, Rod JK,KM 02, BR-68902280 Macapa, Amapa, Brazil
dc.description.affiliationUniv Fed Sao Paulo, Dept Ciencias Exatas & Terra, Rua Prof Artur Riedel 275, BR-09972270 Diadema, SP, Brazil
dc.description.affiliationUniv Fed Goias, Inst Ciencias Biol, Lab Genet Mol & Citogenet, Rua R-2a,Campus Samambaia, BR-74690900 Goiania, Go, Brazil
dc.description.affiliationUnifespUniv Fed Sao Paulo, Dept Ciencias Exatas & Terra, Rua Prof Artur Riedel 275, BR-09972270 Diadema, SP, Brazil
dc.description.provenanceMade available in DSpace on 2020-07-17T14:03:31Z (GMT). No. of bitstreams: 0 Previous issue date: 2017en
dc.description.sourceWeb of Science
dc.description.sponsorshipConselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)
dc.description.sponsorshipFundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)
dc.description.sponsorshipFAPESP
dc.description.sponsorshipIDFAPESP: 2012/18605-3
dc.description.sponsorshipIDFAPESP: 2012/22841-4
dc.format.extent191-198
dc.identifierhttp://dx.doi.org/10.2174/2213335603666161101152243
dc.identifier.citationCurrent Microwave Chemistry. Sharjah, v. 4, n. 3, p. 191-198, 2017.
dc.identifier.doi10.2174/2213335603666161101152243
dc.identifier.issn2213-3356
dc.identifier.urihttps://repositorio.unifesp.br/handle/11600/55469
dc.identifier.wosWOS:000410862700003
dc.language.isoeng
dc.publisherBentham Science Publ Ltd
dc.relation.ispartofCurrent Microwave Chemistry
dc.rightsAcesso restrito
dc.subject1,2,3-benzotriazolesen
dc.subjectbiocatalysisen
dc.subjectCAL-Ben
dc.subjectmicrowave radiationen
dc.subjectbeta-azidoalcoholsen
dc.titleBiocatalyticProduction of Chiral Benzotriazoles Employing Conventional Heating and Microwave Radiationen
dc.typeArtigo
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