106009-19-2Relevant academic research and scientific papers
Microwave-assisted synthesis and antimicrobial activity of novel spiro 1,3,4-thiadiazolines from isatin derivatives
da Costa, Daniel Pereira,de Castro, Aleff Cruz,da Silva, Girlyanderson Araújo,Lima-Junior, Claudio Gabriel,de Andrade Júnior, Francisco Patricio,de Oliveira Lima, Edeltrudes,Vaz, Boniek Gontijo,da Silva, Lidya Cardoso
, p. 766 - 776 (2021)
This work describes the synthesis of spiro 1,3,4-thiadiazolines from isatin-β-thiosemicarbazone acetylation, using microwave irradiation as a source of heating the reaction medium. N-substituted isatin derivatives were used as substrates to obtain thiosemicarbazones by adding thiosemicarbazide to the isatin ketone carbonyl. The final synthetic step was the reaction of thiosemicarbazones with acetic anhydride under microwave irradiation to get the spiro compounds. Reaction times ranged from 6 to 18 minutes resulting in yields of up to 90%. Biological assays have shown promising antibacterial and antifungal activity, especially spiro thiadiazolines derived from allylated isatins. All the proposed molecules proved to be potential drug candidates based on the results of the in silico investigation, with satisfactory drug-likeness and drug-score, respecting Lipinski's rule. The use of the microwave reactor was efficient for the synthesis of thiosemicarbazones and spiro compounds, resulting in a significant reduction in reaction times with conventional heating. Taking into account the threat of antimicrobial resistance, this work presents a series of bioactive molecules that are easily obtained via microwave reaction.
Synthesis, anti-proliferative activity, theoretical and 1H NMR experimental studies of Morita–Baylis–Hillman adducts from isatin derivatives
Alencar-Filho, Edilson B.,Araújo, Edigenia C. C.,Brito, Vinicius B. M.,Lima-Júnior, Claudio G.,Martins, Felipe T.,Milit?o, Gardenia C. G.,Oliveira, Boaz G.,Santos, Gilmar F.,Silva, Fábio P. L.,Silva, Thiago D. S.,Souza, Júlia L. C.,Vasconcellos, Mário L. A. A.
, p. 265 - 281 (2020)
Abstract: Quaternary or spirocyclic 3-substituted-3-hydroxy-2-oxindole is considered a privileged scaffold. In other words, it is a molecular core present on several compounds with a wide spectrum of biological activities. Among its precursors, activated ketones (isatin nucleus) can be used as interesting starting points to Morita–Baylis–Hillman adducts derivatives, a class of compounds with good cytotoxic potential. In this paper, we present the synthesis, anti-proliferative activity against lung cancer cell line and a theoretical conformational study of 21 of Morita–Baylis–Hillman adducts from isatin derivatives, by DFT quantum chemical calculations, followed by a SAR and QSAR analysis. Besides, an efficient synthetic protocol and good biological activity profile were highlighted interesting observations about 1H NMR experimental spectra, molecular modeling results and crystallographic data available. Graphical abstract: [Figure not available: see fulltext.]
SYNTHESIS OF SUBSTITUTED THIENOTHIAZOLES AND INDOLOTHIAZOLES
Pinkin, L. D.,Dzyubenko, V. G.,Abramenko, P. I.,Shpileva, I. P.
, p. 345 - 352 (2007/10/02)
Alkylene-, halo-, and aryl-substituted 2-methylthienothiazoles were obtained by the action of phosphorus pentasulfide on the corresponding 2-acetylamino-3-bromo- or 2-acetylamino-3-hydroxythiophenes in an organic solvent with heating. 2-Oximes of halo- and methyl-substituted isatins were converted by reduction and acetylation into 2-hydroxy-3-acetylaminoindoles, from which 2-methylindolo-thiazoles were obtained by the action of phosphorous pentasulfide with heating in xylene.
