Synthesis of New Oxindoles and Determination of Their Antibacterial Properties

Abstract

A versatile method for the synthesis of new oxindoles was developed by the reaction between substituted isatins and 5-aminopyrazoles. The reaction was carried out at room temperature in ethanol using p-toluenesulfonic acid as the catalyst. The products were obtained with acceptable to excellent yields (44–96%). Structures of the new compounds were unambiguously established by spectroscopic and analytical techniques. The antibacterial activity was determined by microdilution assays. Compounds 3b, 3e, and 3g showed antistaphylococcal activity, particularly compound 3e displayed a potent activity against the vancomycin intermediate Staphylococcus aureus (VISA). Compounds 3i, 3j, and 3o inhibited Neisseria gonorrhoeae growth.

Unprecedented, catalyst‐free, and rapid one‐pot, three‐component green synthesis of substituted 3‐hydroxy‐2‐oxindoles in water

“…Furthermore, pyrazole heterocycle is pharmaceutically important that has been explored as a potential chemotherapeutic agent in medicinal chemistry [15][16][17][18][19][20][21][22][23]. Recently, Pablo et al reported that 3-(4-Pyrazolyl)oxindoles obtained by reaction of 5-aminopyrazoles with isatins possess potent antibacterial properties [24]. Figure 1 shows the selective representative examples of compounds containing bioactive 3-hydroxy-2-oxindoles and pyrazole.…”

Design, synthesis and molecular modeling study of substituted indoline-2-ones and spiro[indole-heterocycles] with potential activity against Gram-positive bacteria

“…The scaffold possesses diverse biological activities including anti-inflammatory (1), anticonvulsant (2), antidepressant (3), antiallergic (4), antitubercular (5), antidiabetic (6), antiviral (7) and antimicrobial activity (8)(9)(10)(11). Oxindole and other related ring systems also exhibit several biological activities (12)(13)(14)(15). Thiosemicarbazone derivatives of indoline-2,3-dione show appreciable antifungal, antibacterial and antiviral activities in vivo and in vitro (16).…”

Reação de fenton em formamida: síntese rápida de oxindóis e isoquinolina-1,3-dionas via adição/ciclização radicalar tandem

“…As substituições nas diferentes posições como C-3, NH e hidrogênios do anel aromático por diversos grupos funcionais, levam a atividades biológicas diversificadas. [54][55][56][57][58][59][60][61][62] Alguns exemplos de oxindóis que exibem atividades biológicas interessantes são representados na Figura 3. O Nintedanib (xlviii) é um inibidor da tirosina quinase de múltiplos receptores.…”

“…60 Por outro lado, o composto (lii) foi avaliado quanto à atividade antibacteriana contra Staphylococcus aureus, mostrando-se um candidato com atividade antiestafilocócica promissora. 61 Ainda, o oxindol (liii) exibiu excelente atividade antitubercular in vitro contra a cepa H37Rv de Mycobacterium tuberculosis. 62…”