Acylhydrazones and Their Biological Activity: A Review

Abstract

Due to the structure of acylhydrazones both by the pharmacophore –CO–NH–N= group and by the different substituents present in the molecules of compounds of this class, various pharmacological activities were reported, including antitumor, antimicrobial, antiviral, antiparasitic, anti-inflammatory, immunomodulatory, antiedematous, antiglaucomatous, antidiabetic, antioxidant, and actions on the central nervous system and on the cardiovascular system. This fragment is found in the structure of several drugs used in the therapy of some diseases that are at the top of public health problems, like microbial infections and cardiovascular diseases. Moreover, the acylhydrazone moiety is present in the structure of some compounds with possible applications in the treatment of other different pathologies, such as schizophrenia, Parkinson’s disease, Alzheimer’s disease, and Huntington’s disease. Considering these aspects, we consider that a study of the literature data regarding the structural and biological properties of these compounds is useful.

Synthesis, Biological Investigation, and Molecular Docking of Novel Benzimidazole‐Hydrazone Hybrids as Potential Anticancer Agent Candidates

“…It has been reported in the literature that imine compounds are found in polar solvents such as dimethyl‐d6 sulfoxide in high proportion as E geometric isomer, while the proportion of Z geometric isomer increases in solvents of low polarity and in cases where intramolecular hydrogen bond formation is possible [33,34] . In the NMR spectra of such compounds, some signals appear as double sets [35–37] . When the 13 C NMR spectra were analyzed, it was observed that E/Z isomer was formed in compound 4 f and their ratio was E/Z =5/3 and E isomer was formed more because it is thermodynamically more stable.…”

“…[33,34] In the NMR spectra of such compounds, some signals appear as double sets. [35][36][37] When the 13 C NMR spectra were analyzed, it was observed that E/Z isomer was formed in compound 4 f and their ratio was E/ Z = 5/3 and E isomer was formed more because it is thermodynamically more stable.…”

Synthesis of Arylsulfonyl Hydrazone Derivatives: Antioxidant Activity, Acetylcholinesterase Inhibition Properties, and Molecular Docking Study

“…Substituted benzene sulfonic acid derivatives, particularly benzene-sulfonyl hydrazones, have attracted more attention during the past decades because of their numerous potential uses in medicinal chemistry. [1][2] The pharmacological properties of benzene sulfonyl hydrazones, such as enzymatic modulation, [3][4] analgesia, [5] and antifungal [6] and antibacterial potential [7][8][9][10][11][12] are mainly well recognized. Besides that, it also contains a broad spectrum of bioactivity such as anticancer 1-3, [13][14][15][16][17][18][19][20][21] antidepressant properties [22][23] and activity against Alzheimer's disease [24][25][26] (Figure 1).…”

“…Substituted benzene sulfonic acid derivatives, particularly benzene‐sulfonyl hydrazones, have attracted more attention during the past decades because of their numerous potential uses in medicinal chemistry [1–2] . The pharmacological properties of benzene sulfonyl hydrazones, such as enzymatic modulation, [3–4] analgesia, [5] and antifungal [6] and antibacterial potential [7–12] are mainly well recognized.…”

The design, synthesis, and biological activity assay of malononitrile oxime ether compounds as effective fungicides

“…Acylhydrazones as reactive groups include both amide and imine structures and therefore can act as both hydrogen bond donors and acceptors. 12 Acylhydrazones have a strong coordination ability and a variety of coordination modes that allow flexibility in the orientation of the acylhydrazone structure in space, 13 so they can easily form stable hydrogen bonds or other interactions with biological targets, increasing the affinity for the receptor and thus affecting its biological activity. 14 The commercially available fungicide benquinox (Fig.…”