Novel 1,2,4-oxadiazole/pyrrolidine hybrids as DNA gyrase and topoisomerase IV inhibitors with potential antibacterial activity

Frejat, Firas Obaid Arhema; Cao, Yaquan; Zhai, Hongjin; Abdel‐Aziz, Salah A.; Gomaa, Hesham A.M.; Youssif, Bahaa G.M.; Wu, Chunli

doi:10.1016/j.arabjc.2021.103538

Cited by 17 publications

(12 citation statements)

References 36 publications

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“…Compared to Ciprofloxacin (30 and 60 ng/mL, respectively), compound 87 exhibited excellent antibacterial activity against Gram-positive bacteria, with MIC values of 62 and 24 ng/mL against Escherichia coli and Staphylococcus aureus , respectively. Moreover, the cytotoxicity of compound 87 was very low 88 .…”

Section: Oxadiazolementioning

confidence: 97%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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Oxadiazole is a five-membered heterocyclic compound containing two nitrogen atoms and one oxygen atom. The 1,3,4-oxadiazole and 1,2,4-oxadiazole have favourable physical, chemical, and pharmacokinetic properties, which significantly increase their pharmacological activity via hydrogen bond interactions with biomacromolecules. In recent years, oxadiazole has been demonstrated to be the biologically active unit in a number of compounds. Oxadiazole derivatives exhibit antibacterial, anti-inflammatory, anti-tuberculous, anti-fungal, anti-diabetic and anticancer activities. In this paper, we report a series of compounds containing oxadiazole rings that have been published in the last three years only (2020–2022) as there was no report or their activities described in any article in 2019, which will be useful to scientists in research fields of organic synthesis, medicinal chemistry, and pharmacology.

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Section: Oxadiazolementioning

confidence: 97%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Antibiotic resistance has generated a significant and inability to meet medical requirements for the research and establishment of innovative forms of antibacterial medications (Al‐Wahaibi et al, 2021; Bassetti et al, 2013; Frejat, Cao, Zhai, et al, 2022; Sugden et al, 2016; Toner et al, 2015; Ventola, 2015). The majority of present chemotherapeutics have acquired resistance in bacterial strains (Chan et al, 2015; Gardete & Tomasz, 2014; Müller et al, 2017), necessitating the hunt for novel antibiotics capable of suppressing resistance mechanisms.…”

Section: Biological Actionsmentioning

confidence: 99%

A comprehensive review of recent advances in the biological activities of quinazolines

Gomaa

2022

Chem Biol Drug Des

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Quinazoline heterocycles are critical in the development of medications.Quinazoline derivatives have been intensively researched, providing a wide range of compounds with diverse biological roles. The quinazoline nucleus has garnered a lot of attention in medical chemistry in recent years. It was assumed to be a pharmacophore component in the development of physiologically interesting drugs. This review is an attempt to increase the potential of quinazoline by highlighting a wide range of advancements demonstrated by numerous derivatives of the quinazoline moiety, as well as focusing on diverse pharmacological actions of the quinazoline moiety. This review compiles recent studies on the quinazoline moiety described in the literature by researchers.

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“…On the other hand, many oxadiazole derivatives are known to possess a wide range of bioactivities such as antibacterial, [22] antitubercular, [23] anti‐inflammatory, [24] antitrypanosomal, [25] antioxidant, [26] anticonvulsant, [27] anticancer, [28] EGFR [29] and carbonic anhydrase [30] inhibitors.…”

Section: Introductionmentioning

confidence: 99%

“…Increasing interest towards the benzimidazole ring system has been observed as it is the basis for the development of many compounds with a diversity of biological activities such as antibacterial, [9] antimicrobial, [10] antifungal, [11] antioxidant, [12] anticancer, [13] anti-inflammatory, [14] antiprotozoal, [15] antiviral, [16] antidiabetic, [17] antihypertensive, [18] antimycobacterial, [19] antithrombin [20] and tubulin inhibitor. [21] On the other hand, many oxadiazole derivatives are known to possess a wide range of bioactivities such as antibacterial, [22] antitubercular, [23] anti-inflammatory, [24] antitrypanosomal, [25] antioxidant, [26] anticonvulsant, [27] anticancer, [28] EGFR [29] and carbonic anhydrase [30] inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, in Vitro and in Silico Studies of Benzimidazole‐Linked Oxadiazole Derivatives as Anti‐inflammatory Agents

et al. 2022

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In this study, 24 new benzimidazole‐oxadiazole hybrids were designed and synthesized as anti‐inflammatory agents. It was measured their stabilizing potentials against heat‐induced human erythrocyte membrane hemolysis for anti‐inflammatory activity. Compound 5 w bearing cyclohexyl as R2 group at the 2nd position of oxadiazole ring and 3,4‐dimethoxy phenyl at the 2nd position of benzimidazole showed the highest membrane stabilizing activity with IC50= 0.50 mM. Antioxidant activity screening of compounds synthesized by ABTS and DPPH radical scavenging assay methods was performed. Molecular docking studies of all compounds were performed against COX‐1 and COX‐2 with Glide XP. Moreover, to examine the protein‐ligand stability of the most active compound 5 w, molecular dynamics simulations of 100 ns duration were performed with COX‐1 and COX‐2 using Gromacs.

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Novel 1,2,4-oxadiazole/pyrrolidine hybrids as DNA gyrase and topoisomerase IV inhibitors with potential antibacterial activity

Cited by 17 publications

References 36 publications

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

A comprehensive review of recent advances in the biological activities of quinazolines

Design, Synthesis, in Vitro and in Silico Studies of Benzimidazole‐Linked Oxadiazole Derivatives as Anti‐inflammatory Agents

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