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Stereoselective Synthesis of Spirooxindole Derivatives Using One-Pot Multicomponent Cycloaddition Reaction and Evaluation of Their Antiproliferative Efficacy

2020-10-16Artigo científico Acesso aberto
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dc.contributor.authorGhosh, Rajat
dc.contributor.authorVítor, Jorge M. B.
dc.contributor.authorMendes, Maria Eduarda
dc.contributor.authorPaulo, Alexandra
dc.contributor.authorAcharya, Pratap Chandra
dc.date.accessioned2023-08-14T17:09:37Z
dc.date.available2023-08-14T17:09:37Z
dc.date.issued2020-10-16
dc.date.updated2022-10-19T21:39:24Z
dc.description.abstractA highly stereoselective, one-pot, multicomponent method has been developed to synthesize pyrrolizidine- and N-methyl pyrrolidine-substituted spirooxindole derivatives. The [3 + 2] cycloaddition reaction involves the reaction between the dipole azomethine ylides, generated in situ from the reaction between isatin and secondary amino acids such as L-proline or sarcosine, and α,β-unsaturated carbonyl compounds as the dipolarophile. The reaction condition was optimized to achieve excellent regio- and stereoselectivity. Products were obtained in good yield using ethanol as a solvent at the reflux temperature. The newly synthesized spirooxindole derivatives were evaluated for their antiproliferative efficacy against National Cancer Institute (NCI)-60 cancer cell lines and DNA G-quadruplex (G4) interaction capacity. Compound 14b produced selective cytotoxicity against leukemia, renal, colon, and prostate cancer cell lines at a 10 μM concentration. The G4 interaction studies further suggested that these spirooxindole derivatives were devoid of any activity as DNA G4 ligands.pt_PT
dc.description.sponsorshipThis research work was supported by grants from the Council of Scientific & Industrial Research (CSIR), New Delhi [CSIR Extramural Research Grant No. 02(0329)/17/EMR], and the European Molecular Biology Organization (EMBO), Heidelberg [EMBO STF No. 7702], sanctioned to the principal investigator P.C.A. A.P. acknowledges FCT (Portugal) for financial support through project grant PTDC/QUI-QOR/29664/2017 and FCT and COMPETE Program (SAICTPAC/0019/2015). J.B.V. research was financed by New England Biolabs, Inc. The authors express their gratitude to National Cancer Institute (NCI), Bethesda, for carrying out the in vitro cytotoxicity assay, Dr. Rakesh Yadav, Department of Pharmacy, Banasthali Vidyapith, Rajasthan, for providing the NMR spectra, and Dr. Nitesh Sahu for the HPLC and ESI-MS data.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationGhosh R, Vitor JB, Mendes E, Paulo A, Acharya PC. Stereoselective synthesis of spirooxindole derivatives using one-pot multicomponent cycloaddition reaction and evaluation of their antiproliferative efficacy. ACS Omega [Internet]. 27 de outubro de 2020;5(42):27332–43. Disponível em: https://pubs.acs.org/doi/10.1021/acsomega.0c03675pt_PT
dc.identifier.doi10.1021/acsomega.0c03675pt_PT
dc.identifier.slugcv-prod-2054205
dc.identifier.urihttp://hdl.handle.net/10451/58873
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherACS Publishingpt_PT
dc.relationPRECISION ONCOLOGY BY INNOVATIVE THERAPIES AND TECHNOLOGIES
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acsomega.0c03675pt_PT
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/pt_PT
dc.titleStereoselective Synthesis of Spirooxindole Derivatives Using One-Pot Multicomponent Cycloaddition Reaction and Evaluation of Their Antiproliferative Efficacypt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardNumberPTDC/QUI-QOR/29664/2017
oaire.awardNumberSAICTPAC/0019/2015
oaire.awardTitlePRECISION ONCOLOGY BY INNOVATIVE THERAPIES AND TECHNOLOGIES
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FQUI-QOR%2F29664%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/9471 - RIDTI/SAICTPAC%2F0019%2F2015/PT
oaire.citation.endPage27343pt_PT
oaire.citation.issue42pt_PT
oaire.citation.startPage27332pt_PT
oaire.citation.titleACS Omegapt_PT
oaire.citation.volume5pt_PT
oaire.fundingStream3599-PPCDT
oaire.fundingStream9471 - RIDTI
person.familyNameVítor
person.familyNameMendes
person.familyNamePaulo
person.familyNameAcharya
person.givenNameJorge
person.givenNameMaria Eduarda
person.givenNameAlexandra
person.givenNameDr. Pratap Chandra
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person.identifier.orcid0000-0002-5432-8787
person.identifier.ridM-3279-2013
person.identifier.ridE-1398-2015
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person.identifier.scopus-author-id7801493621
person.identifier.scopus-author-id7103403420
person.identifier.scopus-author-id7003821508
person.identifier.scopus-author-id55013744900
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.cv.cienciaidFF19-99F4-3964 | Jorge Manuel Barreto Vítor
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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