Synthesis and therapeutic potential of imidazole containing compounds

Abstract

Imidazole is a five-membered heterocyclic moiety that possesses three carbon, two nitrogen, four hydrogen atoms, and two double bonds. It is also known as 1, 3-diazole. It contains two nitrogen atoms, in which one nitrogen bear a hydrogen atom, and the other is called pyrrole type nitrogen. The imidazole name was reported by Arthur Rudolf Hantzsch (1857–1935) in 1887. 1, 3-diazole is an amphoteric in nature i.e. it shows both acidic and basic properties. It is a white or colorless solid that is highly soluble in water and other polar solvents. Due to the presence of a positive charge on either of two nitrogen atom, it shows two equivalent tautomeric forms. Imidazole was first named glyoxaline because the first synthesis has been made by glyoxal and ammonia. It is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. The derivatives of 1, 3-diazole show different biological activities such as antibacterial, antimycobacterial, anti-inflammatory, antitumor, antidiabetic, anti-allergic, antipyretic, antiviral, antioxidant, anti-amoebic, antihelmintic, antifungal and ulcerogenic activities, etc. as reported in the literature. There are different examples of commercially available drugs in the market which contains 1, 3-diazole ring such as clemizole (antihistaminic agent), etonitazene (analgesic), enviroxime (antiviral), astemizole (antihistaminic agent), omeprazole, pantoprazole (antiulcer), thiabendazole (antihelmintic), nocodazole (antinematodal), metronidazole, nitroso-imidazole (bactericidal), megazol (trypanocidal), azathioprine (anti rheumatoid arthritis), dacarbazine (Hodgkin's disease), tinidazole, ornidazole (antiprotozoal and antibacterial), etc. This present review summarized some pharmacological activities and various kinds of synthetic routes for imidazole and their derived products.

Tuning Anti-Biofilm Activity of Manganese(II) Complexes: Linking Biological Effectiveness of Heteroaromatic Complexes of Alcohol, Aldehyde, Ketone, and Carboxylic Acid with Structural Effects and Redox Activity

“…A large number of heteroaromatic compounds containing pyridine or imidazole core are associated with diverse pharmacological properties such as antimicrobial, anticonvulsant, antiviral, antifungal, etc. [25][26][27][28]60]. The tuning of the activity of the imidazole and pyridine derivatives consisted of placing appropriate functional groups in the mentioned cores.…”

“…According to the reports, functional groups containing oxygen and sulfur donors have a potential role in fighting cancer cells and bacteria [22,23]. Additionally, imidazole and pyridine are well-known pharmacists whose derivatives are currently used against various diseases [24][25][26][27][28]. In our research, we employed the N,O-donor ligands, in which imidazole and pyridine were substituted by -OH, -CHO, and -COOH functional groups.…”

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

“…Purine ring systems may also be preformed and modified at electrophilic sites in the process of analog preparation. Imidazole-containing heterocycles are also known as privileged scaffolds due to their wide range of biological activities, prompting the publication of comprehensive review articles detailing such activities [ 15 , 28 , 29 ]. In 2017, Ali et al summarized the potential of imidazoles as anticancer agents [ 6 ].…”

TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions

“…[4][5][6] The diverse therapeutic properties of these heterocycles include anti-inammatory, antiproliferative, antimicrobial, anticancer, antihypertensive and inhibition of p38 MAP-kinase, angiotensin II receptor blockers and cytotoxicity. [7][8][9][10][11][12][13] Imidazole-based compounds have also been used as important precursors in synthesizing pharmaceuticals and natural products like alkaloids. 5,9,[13][14][15] Some representative examples of biologically active multisubstituted imidazole drugs are shown in Fig.…”