Topological control of supramolecular crystal structures of phenylene bis-monothiooxamate derivatives and in vitro anticancer activity

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dc.creatorTamyris Teixeira da Cunha
dc.creatorWillian Xerxes Coelho Oliveira
dc.creatorIvana Marques Marzano
dc.creatorCarlos Basílio Pinheiro
dc.creatorElene Cristina Pereira Maia
dc.creatorCynthia Lopes Martins Pereira
dc.date.accessioned2023-02-01T17:55:11Z
dc.date.accessioned2025-09-09T00:02:21Z
dc.date.available2023-02-01T17:55:11Z
dc.date.issued2017
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.identifier.doihttps://doi.org/10.1016/j.molstruc.2017.08.051
dc.identifier.issn1872-8014
dc.identifier.urihttps://hdl.handle.net/1843/49387
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of Molecular Structure
dc.rightsAcesso Restrito
dc.subjectQuímica supramolecular
dc.subjectCristalografia
dc.subjectCristalografia de raio X
dc.subjectEstrutura molecular
dc.subjectSíntese orgânica
dc.subjectCompostos organossulfurados
dc.subjectTestes químicos e reagentes
dc.subjectAgentes antineoplasicos
dc.subjectLeucemia
dc.subject.otherThiooxamate
dc.subject.otherSynthesis
dc.subject.otherLawesson's reagent
dc.subject.otherSupramolecular chemistry
dc.subject.otherX-ray crystallography
dc.titleTopological control of supramolecular crystal structures of phenylene bis-monothiooxamate derivatives and in vitro anticancer activity
dc.typeArtigo de periódico
local.citation.epage811
local.citation.spage803
local.citation.volume1149
local.description.resumoThis paper describes the synthesis, physical characterization, X-ray crystal structures and antitumoral activity against human carcionogenic cells of three new diethyl ester acid derivatives of phenylene bis-monothiooxamate compounds, namely Et2H2opbta (1), Et2H2mpbta (2) and Et2H2ppbta (3) [opbta = N,N′-1,2-phenylenebis(2-thiooxamate), mbpta = N,N′-1,3-phenylenebis(2-thiooxamate) and ppbta = N,N′-1,4-phenylenebis(2-thiooxamate)]. Compounds 1–3 were obtained under mild conditions by reaction of the corresponding N,N′-phenylenebis(oxamate) analogues and Lawesson's reagent resulting in the formation of C==S bonds at the carbonyl amide functions. Crystal structures of 1–3 consist of 1D supramolecular assemblies of centrosymmetric H2Et2ppbta (3) or noncentrosymmetric chiral H2Et2opbta (1) and H2Et2mpbta (2) molecules with opposite helical chirality (M and P enantiomers) resulting from intermolecular N - H⋯O (1 and 3) or N-H⋯S (2) hydrogen bonds between the amide hydrogen atoms and the carbonyl ester oxygen or thionyl amide sulfur atoms from the thiooxamate moieties respectively, together with weak S⋯S bonds between the thionyl amide sulfur atoms (1). The cytotoxicity of H2Et2xpbta [x = o (1), m (2) and p (3)] against chronic myelogenous leukemia cells was evaluated and the bioactivity follows the order 1 >> 2 > 3, compound 1 being six and ten times more active than 2 and 3, respectively.
local.identifier.orcidhttps://orcid.org/0000-0002-3224-2624
local.identifier.orcidhttps://orcid.org/0000-0003-0722-5352
local.identifier.orcidhttps://orcid.org/0000-0001-6152-7146
local.identifier.orcidhttps://orcid.org/0000-0002-8674-1779
local.identifier.orcidhttps://orcid.org/0000-0003-2699-6232
local.identifier.orcidhttps://orcid.org/0000-0002-3799-8092
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE FÍSICA
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.sciencedirect.com/science/article/pii/S0022286017311183

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