Abstract
A new series of indole-based-sulfonamide derivatives (A1–A8) was synthesized by treating 5-fluoro-1H-indole-3-carbohydrazide with different aryl-sulfonyl chloride in the presence of pyridine. All synthesized derivatives (A1–A8) were characterized by different analytical methods. The electrochemical behavior of these compounds (A1–A8) was investigated in detail using cyclic voltammetry (CV) and square wave voltammetry (SWV) at the pencil graphite electrode (PGE). In the present study, the redox behavior of all derivatives varies due to the nature of substitutions in the indole sulfonamide moiety. Various fundamental electrochemical parameters, including the standard heterogeneous rate constants (ks), and the electroactive surface coverage (Г) were calculated from the obtained CVs. The obtained results shed light on the understanding of structure–activity relationships of this class of compounds.
Highlights
Indole ring exists in several naturally occurring alkaloids [1]
Synthesis of indole‐based‐sulfonamide derivatives The synthesis of indole-based-sulfonamide derivatives (A1–A8) began with the synthesis of 5-fluoro1H-indole-3-carbohydrazide (I) which was synthesized by heating under reflux methyl 5-fluoro-1H-indole3-carboxylate with mixture of hydrazine and methanol. 5-Fluoro-1H-indole-3-carbohydrazide (I) reacted with different aryl sulfonyl chloride in the presence of pyridine
The results indicated that, in acidic buffer solution the oxidation peak potential appeared at higher positive values and shifted to lower values with an increase in pH, which indicating that the electron transfer process is more in neutral and basic buffer solution
Summary
Indole ring exists in several naturally occurring alkaloids [1]. Indole derivatives were reported to have biological effects [2], anti-inflammatory [3], antitubercular [4], and antimicrobial [5] activities. Thio-indole based analogs act as antifungal [6], antimicrobial [7], antibacterial, analgesic [8, 9], anticonvulsant [10], antioxidant [11], antidepressant [12], antihypertensive [13], and antiviral agents [14]. Mainly at the C3 position, possess hydrophilic features like sulfonyl group, and is regarded as an appropriate pharmacophore equivalent for replacing active sites in drug design [15–17]. The redox properties of the indole sulfonamide may be very useful for their efficient uses.
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