Advances in Synthesis, Derivatization and Bioactivity of Isatin: A Review

Abstract

Background: Isatin (IST) is a crucial pharmacologically active compound, chemically known as indole-1H-2,3- dione. Development of different IST based analogues acquired significant awareness because of its pronounced therapeutic importance such as analgesic, anticancer, anti-inflammatory, antitubercular, antimicrobial, antifungal, antiviral (effective against SARS coronavirus 3C protease) and many other activities, and represent an important class of heterocyclic compounds that can be used as a precursor for the synthesis of many useful drugs. Objective: Previously many articles were reported on IST synthesis and their different pharmacological activities but herein, we mentioned 59 different synthesis schemes of several IST derivatives/hybrids derived from the substitution of the nitrogen, aromatic ring, the second and third position of IST along with most potent molecule among each of synthesized libraries with their structural activity relationship (SAR). Using these standardized approaches several biological important compounds were developed like sunitinib, nintedanib, indirubin, etc and several studies have been carried out in nowadays to develop newer compounds having fewer side effects and also overcome the problem of resistance. Conclusion: This report critically reviews the different strategies for the designs and synthesis of several IST based compounds having different biological activities with SAR which can favour further investigation and modification for the development of new and more potent entities.

Isatis indigotica: from (ethno) botany, biochemistry to synthetic biology

“…Isatin (indole-1 H -2,3-dione) is obtained from Isatis plants after the oxidation of indigo is complete (Chauhan et al, 2020 ). Indirubin may be produced as a byproduct of isatin production.…”

“…Isatin is also an endogenous component of mammalian tissues and body fluids, where it has a variety of activities such as anti-viral, anti-corrosive, and transthyretin fibrillogenesis inhibitory activity (Abbas et al, 2013 ; Gonzalez et al, 2009 ; Zhang et al, 2014 ). The metabolic route by which isatin is produced is not clear, although it may result from the synthesis pathway of tryptophan to indole in bacteria followed by oxidation in the liver in humans (Chauhan et al, 2020 ).…”

A Review on Isatin and Its Derivatives: Synthesis, Reactions and Applications

“…Attack at C-2 may also occur if the system contains electron-withdrawing groups in the benzene ring or at the nitrogen (Fig. 1) [25][26][27]. Baeyer suggested in 1882 that isatin has two tautomeric forms, lactam (1) and lactim (2), in which a proton transfer occurs between the nitrogen atom and the oxygen present at the second carbon.…”

Evaluation of Antimicrobial and Antioxidant Activity of Newly Synthesized NMannich Bases from Methyl Salicylate

“…The latest developments of isatin dimers as pharmacologically relevant scaffolds and the structure-activity connection have established the direction for the creation and development of isatin dimers that have better efficiency and reduced toxicity (Zhang et al, 2020). Many approaches that may be used in the design and synthesis of several IST-based compounds with a variety of biological activities with SAR, which can favour future exploration and modification for the creation of new and more powerful entities (Chauhan et al, 2021). An agar diffusion cup-plate approach was used in order to examine each of the synthetic chemicals for their potential to inhibit the growth of bacteria and fungi.…”