Synthesis, Characterization, and Antibacterial Activity of New Isatin Derivatives

Abstract

1H-indol-2,3-dione (isatin) class of biologically active compounds have analgesic, anti-microbial, anti-inflammatory, anti-tubercular, anti-proliferative properties, and is also useful for the treatment of SARS-CoV. Schiff bases containing isatin moiety are known to have broad spectrum of biological activities like anti-viral, anti-tubercular, anti-fungal, and anti-bacterial. In this work, several Schiff base derivatives have been synthesized using two methods (synthetic and microwave) by reacting isatin with o -phenylenediamine. The synthesized compounds were structurally characterized and their in-vivo antimicrobial activity was tested against Gram-negative and Gram-positive bacteria using the inhibition zone method. Several newly synthesized isatin derivatives were found effective as antimicrobial agents and showed good potency (compounds 3c , 3d , 6a , 6b , 6d ). Compound 3c displayed higher antimicrobial activity than standard drug (Amoxicillin) against Staphylococcus aureus at higher concentration (16 μg/mL) and against Escherichia coli at lower concentration (1 μg/mL).

5-chloro-3-(2-(2,4-dinitrophenyl) hydrazono)indolin-2-one: synthesis, characterization, biochemical and computational screening against SARS-CoV-2

“…Synthesis of isatin derivatives have gained attention in recent years due to their biological potential as anticancer (Abadi et al 2006 ; Vine et al 2007 ; Ashraf et al 2006; Han et al 2014 ; Singh et al 2012 ; Solomon et al 2009 ; Uddin et al 2007 ; Vine et al 2009 ), antimalarial (Kumar et al 2014 ; Raj et al 2014 ), antiviral (Abbas et al 2013 ; Zhang et al 2014 ; Sin et al 2009 ), and antimicrobial agents (Kumar et al 2010 ; Nandakumar et al 2010 ). For example, it has been reported that halogenation at C-5 produces compounds with increased antimicrobial activity (Gurkok et al 2008 ; Nathani et al 2011 ; Nain et al 2023 ; Patel et al 2006 ). The in silico evaluation of some isatin-hydrazone derivatives has also been reported and shown to exhibit diverse properties, including potential interactions with topoisomerase, dihydrofolate reductase, and Chikungunya virus envelope and protease proteins, among others (Bittencourt et al 2016 ; Mishra et al 2016 ; Velasques et al 2017 ).…”

5-chloro-3-(2-(2,4-dinitrophenyl) hydrazono)indolin-2-one: synthesis, characterization, and biochemical and computational screening against SARS-CoV-2

“…Isatin derivatives, mostly those substituted at C-3 such as isatin-3-hydrazones, are generally employed as ligands for transition metal complexes (El-Sawi et al Nandakumar et al 2010). For example, it has been reported that halogenation at C-5 produces compounds with more antimicrobial activity (Gurkok et al 2008;Nathani et al 2011;Nain et al 2023; Patel et al 2016). The in silico evaluation of some isatin-hydrazone derivatives has also been reported and shown to exhibit diverse properties, including potential interactions with topoisomerase, dihydrofolate reductase, and Chikungunya virus envelope and protease proteins, among others (Bittencourt et al 2016;Mishra et al 2016; Velasques et al 2017).…”