PREPARATION OF alpha-ACETYLOXY-N-CYCLOHEXYLAMIDES VIA PASSERINI REACTION USING DIMETHYLCARBONATE AS ECO-FRIENDLY SOLVENT

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dc.citation.issue1
dc.citation.volume41
dc.contributor.authorOliveira, Barbara R.[UNIFESP]
dc.contributor.authorSilva, Carla C. [UNIFESP]
dc.contributor.authorCalado, Juliana C. P. [UNIFESP]
dc.contributor.authorBatista, Wagner L. [UNIFESP]
dc.contributor.authorSiqueira, Fernanda A. [UNIFESP]
dc.contributor.authorLongo, Luiz S., Jr. [UNIFESP]
dc.coverageSao Paulo
dc.date.accessioned2020-07-02T18:52:04Z
dc.date.available2020-07-02T18:52:04Z
dc.date.issued2018
dc.description.abstractA series of alpha-acetyloxy-N-cyclohexylamides was efficiently obtained via Passerini reaction of cyclohexyl isocyanide, acetic acid, and different aromatic and aliphatic aldehydes using refluxing dichloromethane or dimethylcarbonate (DMC). Reactions performed with DMC led to desired products in moderate to good yields, corroborating this solvent as a eco-friendly alternative to the chlorinated solvents commonly used in this transformation. The alpha-acetyloxy-N-cyclohexylamides thus obtained were tested against Escherichia coli, Bacillus cereus, Pseudomonas aeruginosa, and Staphylococcus aureus, as well as promastigote forms of L.(L.) amazonensis. The alpha-(Acetyloxy)-N-cyclohexyl- pentanamide showed low antibacterial activity against Gram-positive (S. aureus and B. cereus) and Gram negative (E. coli and P. aeruginosa) bacteria (MIC = 8,3-16,5 mmol L-1), while alpha-(acetyloxy)-N-cyclohexyl-4-bromo-benzeneacetamide showed leishmanicidal activitity (IC50 = 0,099 mmol L-1).en
dc.description.affiliationUniv Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Dept Ciencias Farmaceut, Campus Diadema,Rua Sao Nicolau 210, BR-09913030 Diadema, SP, Brazil
dc.description.affiliationUniv Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Dept Quim, Campus Diadema,Rua Sao Nicolau 210, BR-09913030 Diadema, SP, Brazil
dc.description.affiliationUnifespUniv Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Dept Ciencias Farmaceut, Campus Diadema,Rua Sao Nicolau 210, BR-09913030 Diadema, SP, Brazil
dc.description.affiliationUnifespUniv Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Dept Quim, Campus Diadema,Rua Sao Nicolau 210, BR-09913030 Diadema, SP, Brazil
dc.description.sourceWeb of Science
dc.format.extent92-99
dc.identifierhttps://dx.doi.org/10.21577/0100-4042.20170140
dc.identifier.citationQuimica Nova. Sao Paulo, v. 41, n. 1, p. 92-99, 2018.
dc.identifier.doi10.21577/0100-4042.20170140
dc.identifier.fileWOS000425722500013.pdf
dc.identifier.issn0100-4042
dc.identifier.urihttps://repositorio.unifesp.br/handle/11600/53857
dc.identifier.wosWOS:000425722500013
dc.language.isopor
dc.publisherSoc Brasileira Quimica
dc.relation.ispartofQuimica Nova
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectacetyloxy-N-cyclohexylamidesen
dc.subjectPasserini reactionen
dc.subjectdimethylcarbonateen
dc.subjectgreen chemistryen
dc.subjectantibacterial activityen
dc.subjectleishmanicidal activityen
dc.titlePREPARATION OF alpha-ACETYLOXY-N-CYCLOHEXYLAMIDES VIA PASSERINI REACTION USING DIMETHYLCARBONATE AS ECO-FRIENDLY SOLVENTen
dc.typeinfo:eu-repo/semantics/article
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