Abstract
Objective: The objective of the present work deals with the synthesis, characterization and evaluation of antimicrobial and antioxidant activity of N-phenylpropyl-3-substituted indoline-2-one derivatives.Methods: A series of new 3-hydroxy-3-(2-oxoethyl)-1-(3-phenylpropyl) indolin-2-one derivatives 3(a-l) and 3-(2-oxoethylidene)-1-(3-phenylpropyl) indolin-2-one derivatives 4(a-l) were synthesized by knoevenagel condensation of N-phenylpropyl–5-substituted indole-2,3-diones with various acetophenones analogues. The chemical structures of synthesized compounds were confirmed by IR, 1HNMR and Mass spectroscopic and elemental data. These compounds were also screened for their in vitro antimicrobial and antioxidant activities.Results: Novel compounds 3-hydroxy-3-(2-oxoethyl)-1-(3-phenylpropyl) indolin-2-one derivatives 3(a-l) and 3-(2-oxoethylidene)-1-(3-phenylpropyl) indolin-2-one derivatives 4(a-l) were synthesised and characterized using spectral and analytical data. The results of antibacterial and antifungal and antioxidant activities showed that some of the synthesized compounds exhibited promising results.Conclusion: All the newly synthesized compounds were screened for antimicrobial activity by cup plate method and antioxidant activity by the DPPH method using Ciprofloxacin and Amphotericin B as standards against gram positive and gram negative bacteria and fungi respectively.
Highlights
Infectious diseases are the main cause of mortality in the world and rapid increase of antimicrobial resistance among pathogenic strains is becoming a serious public health problem because microbes replicate very rapidly and get mutated which help the microbes to survive in the presence of an antimicrobial drug, these will quickly become predominant throughout the microbial population
Owing to increased microbial resistance, and various disorders caused by free radicals, and to develop more potent small molecules with enhanced antimicrobial and antioxidant properties, a series of N-phenylpropyl-3-substituted indoline-2-ones are synthesized by Knovenegal condensation
Indole-1H-2, 3-dione or Indoline-2, 3-dione commonly known as Isatin is a well-known natural product found in plants of genus Isatis and in couropita guianancis aubl [11]
Summary
Infectious diseases are the main cause of mortality in the world and rapid increase of antimicrobial resistance among pathogenic strains (bacterial and fungal) is becoming a serious public health problem because microbes replicate very rapidly and get mutated which help the microbes to survive in the presence of an antimicrobial drug, these will quickly become predominant throughout the microbial population.Free radicals play important roles in many physiological and pathological conditions [1]. Owing to increased microbial resistance, and various disorders caused by free radicals, and to develop more potent small molecules with enhanced antimicrobial and antioxidant properties, a series of N-phenylpropyl-3-substituted indoline-2-ones are synthesized by Knovenegal condensation. The biological and pharmacological properties of isatin and its derivatives have led to extensive use of these compounds as key intermediate in organic synthesis [13]. It is a core constituent of many alkaloids [14], drugs [15], as well as dyes [16]. The literature survey reveals that various derivatives of isatin possess diverse activities such as antibacterial [17], antifungal [18], antiviral [19], HIV [20], antimycobacterial [21], anticancer [22], anti-inflammatory [23], anticonvulsant activities [24] and acts as a potent antagonist on atrial natriuretic peptide receptors in vitro [25]
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