Peptidoglycan pathways: there are still more!

Helal, Ahmed; Sayed, Ahmed M.; Omara, Mariam; Elsebaei, Mohamed M.; Mayhoub, Abdelrahman S.

doi:10.1039/c9ra04518j

Cited by 6 publications

(4 citation statements)

References 125 publications

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“…Sulfonate esters appear as suitable starting compounds in the activation of the hydroxy group, [23,24] in many coupling reactions, [25][26][27] in the production of sulfonamides [27][28][29][30] which are synthetic antibiotics used as antibacterial agents. Along with this versatile use, it is of great interest to researchers to develop many new methods for the production of sulfonate esters, [21,28,[35][36][37][38][39] which possess important biological activity such as anticancer, [19,40] antibacterial, [18,35,41] some enzyme inhibitory, [20,42,43] anti-viral, [21] insecticidal activities. [22] Along with all these, the possible DNA effects of sulfonate esters should not be ignored.…”

Section: Inhibition Studiesmentioning

confidence: 99%

In Vitro and in Silico Studies of 3‐Hydroxyflavone‐Based Sulfonate Esters: Potent Acetylcholinesterase, Carbonic Anhydrase and α‐Glycosidase Inhibitors

Guney,

Aggul,

Erturk

et al. 2023

ChemistrySelect

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In this study, a novel series of sulfonate esters derived from 3‐hydroxyflavone was synthesized and their inhibitory effects on acetylcholinesterase (AChE), α‐glycosidase (AG), and carbonic anhydrase I and II (hCA I and II) enzymes were investigated using experimental and molecular docking analyses. The synthesis involved the reaction of 3‐hydroxyflavone with tosyl chloride, mesytl chloride, β‐naphthylsulfonyl chloride, and 8‐quinolinesulfonyl chloride. The characterization of each compound was confirmed by obtaining 1H NMR, 13C NMR and IR spectra. Furthermore, IC50 and Ki values for the synthesized compounds were calculated and compared to the clinical enzyme inhibitors. Our results showed that the synthesized compounds exhibited inhibition against the targeted enzymes, with Ki values ranging from 1.92 to 4.16 nM for AChE, 32.40 to 55.49 nM for AG, 9.45 to 65.53 nM for hCA I, and 76.62 to 163.33 nM for hCA II. The compound involved quinolinesulfonyl moiety demonstrated especially potent inhibition with IC50 values of 3.96 nM for AChE, 32.40 nM for AG, 9.50 nM for hCA I, and 76.62 nM for hCA II. The docking results aligned well with our experimental findings. The findings have promising implications for the development of novel inhibitors and drug discovery efforts in the future.

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Section: Inhibition Studiesmentioning

confidence: 99%

In Vitro and in Silico Studies of 3‐Hydroxyflavone‐Based Sulfonate Esters: Potent Acetylcholinesterase, Carbonic Anhydrase and α‐Glycosidase Inhibitors

Guney,

Aggul,

Erturk

et al. 2023

ChemistrySelect

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“…Phenylthiazoles were originally identified as a thiazole core with a guanidine head and an alkyl chain tail (Elsebaei, Mohammad et al 2018, Hosny, Abutaleb et al 2020 have undergone extensive research and optimization to improve their effectiveness and metabolic profile. While they showed anti-biofilm activity, the poor permeability of the early phenylthiazoles likely contributed to their narrow spectrum (Eid, Elsebaei et al 2017, Helal, Sayed et al 2019, Mancy, Abutaleb et al 2019, Elsebaie, El-Din et al 2022, Sayed, Abutaleb et al 2023. Consequently, changes to the tail led to the third generation, which showed intracellular effectiveness but required further optimization of the metabolic profile(El-Din, , Omara, Hagras et al 2023, Shahin, Mohamed et al 2023, Elbakry, Harras et al 2024).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New Azole Derivatives as Antibacterial Agents

Atwa,

Hagras,

Mayhoub

et al. 2024

Al-Azhar Journal of Pharmaceutical Sciences

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“…The pharmacophore phenylthiazole has been widely used in developing novel candidates having antibacterial action against multidrug‐resistant bacteria like MRSA and VRSA [15–36] . A study of the SAR of antibacterial phenylthiazoles uncovered that the thiazole ring should be enclosed within two major substituent groups.…”

Section: Introductionmentioning

confidence: 99%

New Phenylthiazoles: Design, Synthesis, and Biological Evaluation as Antibacterial, Antifungal, and Anti‐COVID‐19 Candidates

Shahin,

Mohamed,

Taher

et al. 2023

Chemistry & Biodiversity

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The combination of antibacterial and antiviral agents is becoming a very important aspect of dealing with resistant bacterial and viral infections. The N‐phenylthiazole scaffold was found to possess significant anti‐MRSA, antifungal, and anti‐COVID‐19 activities as previously published; hence, a slight refinement was proposed to attach various alkyne lipophilic tails to this promising scaffold, to investigate their effects on the antimicrobial activity of the newly synthesized compounds and to provide a valuable structure–activity relationship. Phenylthiazole 4 m exhibited the most potent anti‐MRSA activity with 8 μg/mL MIC value. Compounds 4 k and 4 m demonstrated potent activity against Clostridium difficile with MIC values of 2 μg/mL and moderate activity against Candida albicans with MIC value of 4 μg/mL. When analyzed for their anti‐COVID‐19 inhibitory effect, compound 4 b emerged with IC50=1269 nM and the highest selectivity of 138.86 and this was supported by its binding score of −5.21 kcal mol−1 when docked against SARS‐CoV‐2 M pro. Two H‐bonds were formed, one with His164 and the other with Met49 stabilizing phenylthiazole derivative 4 b, inside the binding pocket. Additionally, it created two arene‐H bonds with Asn142 and Glu166, through the phenylthiazole scaffold and one arene‐H bond with Leu141 via the phenyl ring of the lipophilic tail.

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Peptidoglycan pathways: there are still more!

Abstract: The discovery of 3rd and 4th generations of currently existing classes of antibiotics has not hindered bacterial resistance, which is escalating at an alarming global level.

Cited by 6 publications

References 125 publications

In Vitro and in Silico Studies of 3‐Hydroxyflavone‐Based Sulfonate Esters: Potent Acetylcholinesterase, Carbonic Anhydrase and α‐Glycosidase Inhibitors

In Vitro and in Silico Studies of 3‐Hydroxyflavone‐Based Sulfonate Esters: Potent Acetylcholinesterase, Carbonic Anhydrase and α‐Glycosidase Inhibitors

Synthesis of Some New Azole Derivatives as Antibacterial Agents

New Phenylthiazoles: Design, Synthesis, and Biological Evaluation as Antibacterial, Antifungal, and Anti‐COVID‐19 Candidates

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