Topological control of supramolecular crystal structures of phenylene bis-monothiooxamate derivatives and in vitro anticancer activity
Carregando...
Data
Título da Revista
ISSN da Revista
Título de Volume
Editor
Universidade Federal de Minas Gerais
Descrição
Tipo
Artigo de periódico
Título alternativo
Primeiro orientador
Membros da banca
Resumo
This 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.
Abstract
Assunto
Química supramolecular, Cristalografia, Cristalografia de raio X, Estrutura molecular, Síntese orgânica, Compostos organossulfurados, Testes químicos e reagentes, Agentes antineoplasicos, Leucemia
Palavras-chave
Thiooxamate, Synthesis, Lawesson's reagent, Supramolecular chemistry, X-ray crystallography
Citação
Curso
Endereço externo
https://www.sciencedirect.com/science/article/pii/S0022286017311183