Abstract
The present study reveals the robust and facile methodology for the synthesis of massively selective dispiro-3-phenylpyrrolothiazole hybrids via one-pot 1,3-dipolar cycloaddition reaction by environmentally supported solvents and to evaluate their biological activities. The quaternary ammonium salt eutectic mixture, acetylcholine iodide-ethylene glycol (ACI/EG) medium brings an efficient environment for the synthesis of dispiropyrrolothiazole with excellent yield in shorter reaction time than imidazolium ionic liquids. The eutectic mixture was recovered and reused without any significant drop in their catalytic activity. Among the eight synthesized compounds 4a–h, halogen derivatives are exhibiting significant antimicrobial activities against selected uropathogens pathogens. Interestingly, chloro and bromo derivatives exhibits the minimum inhibitory concentration (MIC) of 12.5 μg/ml and 6.25 μg/ml towards Escherichia coli, Klebsiella pneumonia, and Staphylococcus aureus respectively. In addition, the IC50 values of DPPH radicals with synthesized compounds are interesting, particularly compounds 4a, 4d and 4e shows lower than the control BHA indicating their potent scavenging ability of free radicals.
Highlights
Adult women become frequent victims than men at a ratio of 8:1 for urinary tract infection (UTI) because of their anatomical differences
Chemistry Cyclization of l-cysteine with benzaldehyde in water medium undergoes a smooth reaction yielding an analogue of proteinogenic amino acid, 2-phenyl-1,3-thiazolidine-4-carboxylic acid (1) at room temperature [30] which is used to generate in situ azomethine ylide with ninhydrin (2)
The required inexpensive quaternary ammonium salt eutectic mixture, acetylcholine iodide-ethylene glycol (ACI/EG) was prepared in good yield by mixing acetylcholine iodide and ethylene glycol at a 1: 9 molar ratio and the mixture was heated at 70 °C [35]
Summary
Adult women become frequent victims than men at a ratio of 8:1 for urinary tract infection (UTI) because of their anatomical differences. There is a need to develop a highly potent and efficient antimicrobial drug for the treatment of infectious diseases which is suitable to treat patients. Structurally rigid spiro heterocyclic analogues showed highly pronounced pharmacological properties and exist in many naturally occurring alkaloids [7]. Thiazolidine ring systems play an important role in organic synthesis antimicrobial substances such as penicillins, cephalosporins, narcodicins, thienamicyn and other compounds that have physiological activities have been prepared from thiazolidine [8]. It is noted that spiropyrrolothiazole analogues are interesting because of their wide range of biological activities such as anti-cancer [9], anti-diabetic [10], antibiotic [11], anti-inflammatory [12], hepatoprotective [13], anti-convulsant [14], anti-leukemic agents [15], Alzheimer disease [16], and good in anti-mycobacterial [17]. Indane-1,3-dione, indolin-2-one, and pyrrolothiazole ring with spiro junction will be a novel compound with efficient antimicrobial activities against UTI Synthesis and antimicrobial screening of a series of structurally complexed molecules with the above mentioned molecular units viz. indane-1,3-dione, indolin-2-one, and pyrrolothiazole ring with spiro junction will be a novel compound with efficient antimicrobial activities against UTI
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