Abstract
Various literature sources have documented sydnones as important molecules with exclusive chemical properties and a wide spectrum of bioactivities. Sydnone can be defined as a five-membered pseudo-aromatic heterocyclic molecule. Classically, 1,2,3-oxadiazole forms the main skeleton of sydnone. The molecule has delocalized balanced positive and negative charges. The five annular atoms share the positive charge and the enolate-like exocyclic oxygen atom bears the negative charge. The hydrogen atom at the position C4 was proved to have acidic and nucleophilic functionalities making the sydnone ring reactive towards electrophilic reagents. These unique chemical features enable sydnones to interact with biomolecules resulting in important therapeutic effects like anticancer, antidiabetic, antimicrobial, antioxidant and anti-inflammatory. Consequently, we aim from the current article to review the available chemical and pharmacological information on sydnone and its derivatives.
Highlights
Sydnones are the most studied compounds amongst the mesoionic family due to their interesting structures, chemical properties, synthetic utility and biological activities
1,2,3-oxadiazolium bearing a carbonyl function has recently been the major representative of sydnones because FTIR spectroscopy showed a carbonyl stretch frequency attached to C5 of the ring like in 4-acetyl-3-tolylsydnone which exhibited a strong band at 1783 cm-1 [3]
The present review demonstrates the important chemical and biological data on sydnones starting from their early discovery in 1935 until today
Summary
Sydnones are the most studied compounds amongst the mesoionic family due to their interesting structures, chemical properties, synthetic utility and biological activities. The sydnone ring can be prepared from the cyclization of N-nitroso amino acids with acetic anhydride [5]. Sydnone was prepared by Earl and his colleague by the cyclodehydration effect of acetic anhydride on the N-nitroso derivatives of amino acids.
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