New N,N,N',N'-tetradentate Pyrazoly Agents: Synthesis and Evaluation of their Antifungal and Antibacterial Activities

Abrigach, Farid; Bouchal, Btissam; Riant, Olivier; Macé, Yohan; Takfaoui, Abdelilah; Radi, Smaail; Oussaid, Adyl; Bellaoui, Mohammed; Touzani, Rachid

doi:10.2174/1573406411666150519111800

Cited by 27 publications

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“…In another sequence of pyrazole derivatives synthesized by Radi et al, a series of new N , N , N′ , N′ -tetradentate pyrazoly derivatives were screened for their antimicrobial activity. Among the compound 201 was exceedingly antifungal active against budding yeast ( Saccharomyces cerevisiae ) cells with MIC = 500 µM [ 105 ]. A series of quinoline derivatives bearing pyrazole moiety were synthesized and evaluated for their antibacterial and antifungal activities.…”

Section: Pharmacological Activitiesmentioning

confidence: 99%

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

et al. 2018

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Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. The presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antipsychotic CDPPB, the anti-obesity drug rimonabant, difenamizole, an analgesic, betazole, a H2-receptor agonist and the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Owing to this diversity in the biological field, this nucleus has attracted the attention of many researchers to study its skeleton chemically and biologically. This review highlights the different synthesis methods and the pharmacological properties of pyrazole derivatives. Studies on the synthesis and biological activity of pyrazole derivatives developed by many scientists around the globe are reported.

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Section: Pharmacological Activitiesmentioning

confidence: 99%

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

et al. 2018

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“…Antimicrobials are used to treat infections caused by pathogenic microorganisms , with specific types of antimicrobials used depending on the type of pathogenic microorganism . For example, acrylamide antimicrobials are antifungal drugs , aminoglycosides are especially effective against infections with members of the Enterobacteriaceae and Staphylococcus aureus and sulfonamides are broad‐spectrum antimicrobials . A large number of reports on clinical adverse reactions indicate that acrylamides, represented by terbinafine hydrochloride, can cause serious cutaneous side effects, such as pityriasis rosea .…”

Section: Introductionmentioning

confidence: 99%

Typical antimicrobials induce mast cell degranulation and anaphylactoid reactions via MRGPRX2 and its murine homologue MRGPRB2

et al. 2017

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Mast cells are unique immune cells that function as sentinels in host defence reactions, including immediate hypersensitivity responses and allergic responses. The mast cell-specific receptor named MAS-related G protein-coupled receptor X2 (MRGPRX2) triggers mast-cell degranulation, a key process in anaphylactoid reactions. It is widely observed that antimicrobials can induce pseudo-allergic reactions (i.e. IgE-independent mechanism) with symptoms ranging from skin inflammation to life-threatening systemic anaphylaxis. However, their direct involvement and the mechanisms underlying anaphylactoid reactions caused by antimicrobials have not been demonstrated. Structurally different antimicrobials were screened by Ca imaging using MRGPRX2 overexpressing HEK293 cells. MRGPRX2 related anaphylactoid reactions induced by these components were investigated by body temperature drop and mast cell degranulation assays. We showed that MRGPRX2 is involved in allergic-like reactions to three types of antimicrobials in a dose-dependent manner. However, mast cells lacking the receptor show reduced degranulation. Furthermore, mice without MAS-related G protein-coupled receptor B2 (the orthologous gene of MRGPRX2) exhibited reduced substance-induced inflammation. Interestingly, β-lactam and antiviral nucleoside analogues did not induce anaphylactic reactions, which were also observed in vitro. These results should alarm many clinicians that such drugs might induce anaphylactoid reactions and provide guidance on safe dosage of these drugs.

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“…Antibacterial activity was evaluated by an agar diffusion test, followed by the Abrigach et al's method [ 18 ]. Agar cultures were prepared with overnight bacterial cultures of 10 8 cells/mL.…”

Section: Methodsmentioning

confidence: 99%

Chemical Composition Related to Antimicrobial Activity of Moroccan Nigella sativa L. Extracts and Isolated Fractions

Tiji

Rokni

Benayad

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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Background. Nigella sativa L. (NS) is an aromatic and medicinal plant commonly used in Mediterranean cuisine. Its grains contain a large amount of fixed oil and have many therapeutic virtues and medicinal properties (antioxidant, antidiabetic, antimicrobial, and anticancer). Aim. The aim of this work is to study the antimicrobial activity of Nigella sativa L. extracts and separated fractions on various pathogenic strains and to correlate that with its chemical composition. Methods. Extracts from Moroccan Nigella sativa seeds were extracted using successive organic solvents, and their hexane and acetone extracts were separated by column chromatography. The chemical composition of extracts, fractions, and essential oil was determined by GC-MS and HPLC-DAD. Extracts and fractions were evaluated for antimicrobial activity through disk diffusion against Gram-positive bacteria (Staphylococcus aureus, Bacillus cereus, and Listeria innocua), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and yeast (Candida pelliculosa) for 1 mg/mL concentration. Bacterial strains were followed to study their behaviors over time in different concentrations. The minimum inhibitory concentration of Nigella sativa essential oil was determined against Staphylococcus aureus, Bacillus cereus, Escherichia coli, and Candida albicans. Results and Conclusion. Although hexane extract was active against both types of bacteria (Gram+ and Gram−), some of its fractions were specifically active against only one type. Fraction (SH4) had the highest activity (15 mm inhibitory diameter). Acetone extract was nonactive but surprisingly resulted in specific active fractions, and the most interesting one was (SA7) that had an inhibitory diameter of 13 mm. This antibacterial effect was related to fatty acids (linoleic and palmitic acids) in (SH4) and 17 pentatriacontene in (SA7). Moreover, the antifungal activity of hexane fractions (10–13 mm) was higher than hexane extract (8 mm), but for acetone, it was the opposite. Acetone extract had a higher activity (18 mm) than its fractions (8–12 mm), except for (SA7) (19 mm). Those inhibitions were attributed to gallic acid, cysteine, and apigenin in acetone extract and cysteine with ascorbic acid in fraction (SA7). Antifungal activity of the essential oil was more pronounced than the antibacterial one. Indeed, determined MICs in the first case were on the microgram scale (MIC = 8 μg/mL, Candida albicans), while in the second case, they were on the milligram scale (MIC = 0.96 mg/mL for Staphylococcus aureus, 0.5 mg/mL for Bacillus cereus, and 0.68 mg/mL for Escherichia coli). This antifungal activity was attributed to three major compounds beta-cymene, alpha-thujene, origanene, and thymoquinone. Results of strains behavior over time at different concentrations of the fractions showed all the curves went through a maximum around 20 hours and had a delay of expression of 5 hours at the start. Taking all results into count, Nigella sativa L. extracts and/or derived principles could form promising antimicrobial agents for therapeutical and industrial uses.

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New N,N,N',N'-tetradentate Pyrazoly Agents: Synthesis and Evaluation of their Antifungal and Antibacterial Activities

Cited by 27 publications

References 0 publications

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

Typical antimicrobials induce mast cell degranulation and anaphylactoid reactions via MRGPRX2 and its murine homologue MRGPRB2

Chemical Composition Related to Antimicrobial Activity of Moroccan Nigella sativa L. Extracts and Isolated Fractions

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