2,4‐Disubstituted Phenylhydrazonopyrazolone and Isoxazolone Derivatives as Antibacterial Agents: Synthesis, Preliminary Biological Evaluation and Docking Studies

Oraby, Ahmed K.; Abdellatif, Khaled R.A.; Abdelgawad, Mohamed A.; Attia, Khadiga M.; Georghiou, Paris E.

doi:10.1002/slct.201800174

Cited by 25 publications

(8 citation statements)

References 20 publications

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“…Oraby and teammates [34] synthesized 2,4-disubstituted phenylhydrazonopyrazolone and isoxazolone analogues as antibacterial agents. The results of antibacterial test suggested that the compounds contain the scaffold of pyrazolone like 51 and 52 ( Fig.…”

Section: Pyrazolones As Antimicrobial Agents and Their Sarmentioning

confidence: 99%

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Zhao

Dai

et al. 2020

European Journal of Medicinal Chemistry

136

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a b s t r a c tThe pyrazolone structural motif is a critical element of drugs aimed at different biological end-points. Medicinal chemistry researches have synthesized drug-like pyrazolone candidates with several medicinal features including antimicrobial, antitumor, CNS (central nervous system) effect, anti-inflammatory activities and so on. Meanwhile, SAR (Structure-Activity Relationship) investigations have drawn attentions among medicinal chemists, along with a plenty of analogues have been derived for multiple targets. In this review, we comprehensively summarize the biological activity and SAR for pyrazolone analogues, wishing to give an overall retrospect and prospect on the pyrazolone derivatives.

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Section: Pyrazolones As Antimicrobial Agents and Their Sarmentioning

confidence: 99%

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Zhao

Dai

et al. 2020

European Journal of Medicinal Chemistry

136

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“…We recently applied an MCR to the synthesis of isoxazol-5(4 H )-one (ISX) derivatives, an important class of heterocyclics with potential and diverse biological activities [ 161 , 162 , 163 , 164 , 165 , 166 ], by using a synthetic enzyme (synzyme) that we had previously reported [ 167 ] as an efficient catalyst to perform ISX syntheses ( Scheme 11 ) [ 168 ]. Some of these MCR adducts had fluorescent properties and could be applied in cell-imaging experiments as selective bioprobes.…”

Section: The Combined Role Of Catalysis and Solvent Effects In Mcrsmentioning

confidence: 99%

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

2021

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In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields and shortening reaction times, catalysis is vital to achieving greener protocols and to furthering the MCR field of research. Considering that MCRs typically have two or more possible reaction pathways to explain the transformation, catalysis is essential for selecting a reaction route and avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts and reagent quantities, were analyzed. Solvent effects, which are likely the most neglected topic in MCRs, as well as their combined roles with catalysis, are critically discussed. Stereocontrolled MCRs, rarely observed without the presence of a catalytic system, are also presented and discussed in this review. Perspectives on the use of catalytic systems for improved and greener MCRs are finally presented.

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“…In consideration of the aforementioned background and with the extension of our former investigations on benzoxazole moiety and its innate pharmacological activities [14,[29][30][31][32][33], we describe the preparation of a new series of compounds with 3-benzoxazolyl aniline scaffold ( Figure 2). All the analogs were screened for their antimicrobial, antimalarial, antileishmanial, and antitrypanosomal activities.…”

Section: Introductionmentioning

confidence: 99%

New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation

Abdelgawad

Al-Sanea

Zaki

et al. 2021

Journal of Chemistry

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Background. Benzoxazole derivatives have different biological activities. In pursuit of designing novel chemical entities with antiprotozoal and antimicrobial activities, benzoxazolyl aniline was utilized as a privileged scaffold of a series of (3-benzoxazole-2-yl) phenylamine derivatives, 3-benzoxazoloyl acetamide, and butyramide derivatives. Methods. These novel analogs were synthesized in straightforward simple chemistry without any quantitative chromatographic separations in reasonable yields. The biological evaluation of all target compounds as potential antimalarial, antileishmanial, antitrypanosomal, and antimicrobial agents was performed by various well-established cell-based methods. Results. Compounds 6d and 5a showed promising biological screening data. The amidation of 3-benzoxazolyl aniline 1 with the chloroacetyl functional group resulted in a good antimalarial activity and showed moderate inhibitory activities against leishmanial and trypanosomal spp. Moreover, chloroacetyl functionalization of benzoxazolyl aniline serves as a good early goal for constructing and synthesizing new antimicrobial and antiprotozoal agents. The molecular docking study rationalizes the relative inhibitory activity of compound 5a as an antimalarial agent with the deregulation of PfPNP activity which has emerged as a major mechanism of these targets.

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2,4‐Disubstituted Phenylhydrazonopyrazolone and Isoxazolone Derivatives as Antibacterial Agents: Synthesis, Preliminary Biological Evaluation and Docking Studies

Cited by 25 publications

References 20 publications

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation

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