Imidazole derivatives as antiparasitic agents and use of molecular modeling to investigate the structure–activity relationship

Adeyemi, Oluyomi Stephen; Eseola, Abiodun Omokehinde; Plass, Winfried; Atolanı, Olubunmi; Sugi, Tatsuki; Han, Yongmei; Batiha, Gaber El Saber; Kato, Kentaro; Awakan, Oluwakemi Josephine; Olaolu, Tomilola D.; Nwonuma, Charles Obiora; Alejolowo, Omokolade Oluwaseyi; Owolabi, Akinyomade; Rotimi, Damilare; Kayode, Omowumi Titilola

doi:10.1007/s00436-020-06668-6

Cited by 31 publications

(20 citation statements)

References 31 publications

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“…The electron-donating or electron-withdrawing substituents on the phenyl moieties as well as the steric bulkiness due to the presence of aromatic rings may play a role in the differential activity towards the parasite, as well as towards the host cells. While electronic effects could be considered to play a role in the action of the tested compounds, the electron-donating or electron-withdrawing capacity of the aromatic substituents did not appear to dramatically alter anti- T. gondii activity [ 30 ].…”

Section: Resultsmentioning

confidence: 99%

Exploring the Antiparasitic Activity of Tris-1,3,4-Thiadiazoles against Toxoplasma gondii-Infected Mice

et al. 2022

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Nitrogen-containing atoms in their core structures have been exclusive building blocks in drug discovery and development. One of the most significant and well-known heterocycles is the 1,3,4-thidiazole nucleus, which is found in a wide range of natural products and therapeutic agents. In the present work, certain tris-1,3,4-thiadiazole derivatives (6, 7) were synthesized through a multi-step synthesis approach. All synthesized compounds were characterized using different spectroscopic tools. Previously, thiadiazole compounds as anti-Toxoplasma gondii agents have been conducted and reported in vitro. However, this is the first study to test the anti-Toxoplasma gondii activity of manufactured molecular hybrids thiadiazole in an infected mouse model with the acute RH strain of T. gondii. All the observed results demonstrated compound (7)’s powerful activity, with a considerable reduction in the parasite count reaching 82.6% in brain tissues, followed by liver and spleen tissues (65.35 and 64.81%, respectively). Inflammatory and anti-inflammatory cytokines assessments proved that Compound 7 possesses potent antiparasitic effect. Furthermore, docking tests against TgCDPK1 and ROP18 kinase (two major enzymes involved in parasite invasion and egression) demonstrated compound 7’s higher potency compared to compound 6 and megazol. According to the mentioned results, tris-1,3,4-thiadiazole derivatives under test can be employed as potent antiparasitic agents against the acute RH strain of T. gondii.

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Section: Resultsmentioning

confidence: 99%

Exploring the Antiparasitic Activity of Tris-1,3,4-Thiadiazoles against Toxoplasma gondii-Infected Mice

et al. 2022

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“…Among the five imidazole derivatives, compound M29 demonstrated an excellent selectivity against T. gondii versus the host cells. 39 …”

Section: Anti-microbial Properties Of Imidazole Derivativesmentioning

confidence: 99%

Imidazole as a Promising Medicinal Scaffold: Current Status and Future Direction

Alghamdi¹,

Suliman²,

Almutairi³

et al. 2021

DDDT

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Various imidazole-containing compounds have been tested for their medical usefulness in clinical trials for several disease conditions. The rapid expansion of imidazole-based medicinal chemistry suggests the promising and potential therapeutic values of imidazole-derived compounds for treating incurable diseases. Imidazole core scaffold contains three carbon atoms, and two nitrogen with electronic-rich characteristics that are responsible for readily binding with a variety of enzymes, proteins, and receptors compared to the other heterocyclic rings. Herein, we provide a thorough overview of the current research status of imidazole-based compounds with a wide variety of biological activities including anti-cancer, anti-microbial, anti-inflammatory and their potential mechanisms including topoisomerase IIR catalytic inhibition, focal adhesion kinase (FAK) inhibition, c-MYC G-quadruplex DNA stabilization, and aurora kinase inhibition. Additionally, a great interest was reported in the discovery of novel imidazole compounds with anti-microbial properties that break DNA double-strand helix and inhibit protein kinase. Moreover, anti-inflammatory mechanisms of imidazole derivatives include inhibition of COX-2 enzyme, inhibit neutrophils degranulation, and generation of reactive oxygen species. This systemic review helps to design and discover more potent and efficacious imidazole compounds based on the reported derivatives, their ADME profiles, and bioavailability scores that together aid to advance this class of compounds.

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“…[65][66][67][68][69][70][71] Indeed, imidazole derivatives are an important category of heterocyclic compounds demonstrating biological properties and medicinal applications, which can be prepared using appropriate substrates through MCR strategy. 32,67,68,[72][73][74][75][76][77][78][79][80][81][82][83][84] This bunch of 1,3-diazoles exhibits therapeutic behaviors such as antibiotics, 85,86 antifungals, 87,88 and antagonistic activity. 89 Imidazole compounds are used in some medicines, such as the new Alpidem, [90][91][92] Cimetidine, Etomidate, Ketoconazole, 93,94 antiviral Daclatasvir 95,96 and Nitroimidazole (Fig.…”

Section: Introductionmentioning

confidence: 99%

Pyromellitic diamide–diacid bridged mesoporous organosilica nanospheres with controllable morphologies: a novel PMO for the facile and expeditious synthesis of imidazole derivatives

Valiey

Dekamin

2022

Nanoscale Adv.

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Imidazole derivatives as antiparasitic agents and use of molecular modeling to investigate the structure–activity relationship

Cited by 31 publications

References 31 publications

Exploring the Antiparasitic Activity of Tris-1,3,4-Thiadiazoles against Toxoplasma gondii-Infected Mice

Exploring the Antiparasitic Activity of Tris-1,3,4-Thiadiazoles against Toxoplasma gondii-Infected Mice

Imidazole as a Promising Medicinal Scaffold: Current Status and Future Direction

Pyromellitic diamide–diacid bridged mesoporous organosilica nanospheres with controllable morphologies: a novel PMO for the facile and expeditious synthesis of imidazole derivatives

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