Exploration of Nitroaromatic Antibiotics <i>via</i> Sanger’s Reagent: Synthesis, <i>In Silico</i>, and Antimicrobial Evaluation

Ayoup, Mohammed Salah; Rabee, Ahmed R.; Hamid, Hamida Abdel; Harras, Marwa F.; Menofy, Nagwan Galal El; Ismail, Magda M. F.

doi:10.1021/acsomega.1c06383

Cited by 12 publications

(9 citation statements)

References 37 publications

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“…To evaluate the antibacterial activity of the synthetized CTS-SB derivative, Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were selected as gram-negative and gram-positive bacteria, respectively [34]. Bacteria were firstly refreshed via their incubation in Luria Betani (LB) culture medium (pH 7) containing of peptone (1%), yeast extract (0.5%) and NaCl (1%).…”

Section: Antibacterial Activity Studiesmentioning

confidence: 99%

Novel Cytocompatible Chitosan Schiff Base Derivative as a Potent Antibacterial, Antidiabetic, and Anticancer Agent

et al. 2023

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This study intends to develop a novel bioactive chitosan Schiff base (CTS-SB) derivative via coupling of chitosan (CTS) with 4-((5, 5-dimethyl-3-oxocyclohex-1-en-1-yl) amino) benzene-sulfonamide. The alteration in the chemical structure of CTS-SB was verified using 1H NMR and FT-IR analysis, while the thermal and morphological properties were inspected by TGA and SEM characterization tools, respectively. Ion exchange capacity of the developed CTS-SB derivative recorded a maximal value of 12.1 meq/g compared to 10.1 meq/g for pristine CTS. In addition, antibacterial activity of CTS-SB derivative was greatly boosted against Escherichia coli (E coli) and Staphylococcus aureus (S. aureus) bacteria. Minimum inhibition concentration of CTS-SB derivative was perceived at 50 µg/mL, while the highest concentration (250 µg/mL) could inhibit the growth of S. aureus up to 91%. What’s more, enhanced antidiabetic activity by CTS-SB derivative, which displayed higher inhibitory values of α-amylase (57.9%) and α-glucosidase (63.9%), compared to those of pure CTS (49.8 and 53.4%), respectively Furthermore, cytotoxicity investigation on HepG-2 cell line revealed potential anticancer activity along with good safety margin against primary human skin fibroblasts (HSF cells) and decent cytocompatibility. Collectively, the gained results hypothesized that CTS-SB derivative could be effectively applied as a promising antibacterial, anticancer and antidiabetic agent for advanced biomedical applications.

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Section: Antibacterial Activity Studiesmentioning

confidence: 99%

Novel Cytocompatible Chitosan Schiff Base Derivative as a Potent Antibacterial, Antidiabetic, and Anticancer Agent

et al. 2023

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“…Thus, many pharmaceutical signi cant drug molecules contain 'Nitrogen' as a constituent in the molecule. Bioactive nitrogen containing components shows potent antimicrobial activity against gram-positive and gram-negative bacteria [10][11][12] . Advantage of having a nitrogen atom and proton-donating amine hydrogen atoms in the molecule is that it facilitates the formation of hydrogen bonds with enzymes, proteins and receptors 9 .…”

Section: Introductionmentioning

confidence: 99%

High antimicrobial effectiveness of acrylonitrile adducts and evaluation of their biological activity as haemolytic and thrombolytic agent

Das

Devi

Gaur

et al. 2023

Preprint

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In this work, five acrylonitrile adducts were screened for antibacterial activity against Gram-positive Bacillus subtilis (MTCC 1305) and Gram-negative Escherichia coli (MTCC 443). Synthesis was followed by aza-Michael addition reaction, where the acrylonitrile accepts an electron pair from the respective amines and results in the formation of n-alkyliminobis-propionitrile and n-alkyliminopropionitrile under microwave irradiation. Characterization of the compounds were performed using FTIR, 1H NMR and ESI-MS. The particle size characterization was done by DLS technique. The antibacterial study showed higher inhibition rate for both Gram-positive and Gram-negative bacteria. The antibacterial ability was found to be dose dependent. The minimum inhibitory concentration against both bacteria were found to be 1, 3, 0.4, 1, 3 µl/ml for E. coli and 6, 6, 0.9, 0.5, 5 µl/ml for B. subtilis. Time-kill kinetics evaluation showed that the adducts possess bacteriostatic action. Further it was evaluated for high-throughput in vitro assays to determine the compatibility of the adducts for drug delivery. The haemolytic and thrombolytic activity was analysed against normal mouse erythrocytes. The haemolytic activity showed prominent results, and thereby projecting this acrylonitrile adducts as potent antimicrobial and haemolytic agent.

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“…The triazoloquinoxaline scaffold is considered a versatile moiety, and an important structural template for the design and synthesis of novel biologically relevant compounds such as antibacterial, anti-HIV, antitrypanosomal, antiallergic, antifungal, cardiovascular, antileishmanial, and chemotherapeutic agents ( Amer et al, 2010 ; El-Sagheer and Brown, 2012 ; Ayoup et al, 2016 ; Nagavelli et al, 2016 ; Zhang et al, 2017 ; Ayoup et al, 2022 ). Despite several applications of this scaffold in medicinal chemistry and its special features and potentiality of derivatization, little has been done with respect to the search of versatile and potentially ecofriendly synthetic protocols ( Baashen et al, 2016 ).…”

Section: Introductionmentioning

confidence: 99%

Rejuvenating the [1, 2, 3]-triazolo [1,5-a]quinoxalin-4(5H)-one scaffold: Synthesis and derivatization in a sustainable guise and preliminary antimicrobial evaluation

Pelliccia

Alfano²,

Assunção³

et al. 2023

Front. Chem.

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The [1,2,3]-triazolo [1,5-a] quinoxalin-4(5H)-one scaffold and its analogues triazole-fused heterocyclic compounds are relevant structural templates in both natural and synthetic biologically active compounds. However, their medicinal chemistry applications are often limited due to the lack of synthetic protocols combining straightforward generation of the central core while also allowing extensive decoration activity for drug discovery purposes. Herein, we report a “refreshed” synthesis of the [1,2,3]-triazolo [1,5-a]quinoxalin-4(5H)-one core, encompassing the use of eco-compatible catalysts and reaction conditions. We have also performed a sustainable and extensive derivatization campaign at both the endocyclic amide nitrogen and the ester functionality, comprehensively exploring the reaction scope and overcoming some of the previously reported difficulties in introducing functional groups on this structural template. Finally, we unveiled a preliminary biological investigation for the newly generated chemical entities. Our assessment of the compounds on different bacterial species (two S. aureus strains, three P. aeruginosa strains, K. pneumonia), and two fungal C. albicans strains, as well as the evaluation of their activity on S. epidermidis biofilm formation, foster further optimization for the retrieved hit compounds 9, 14, and 20.

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Exploration of Nitroaromatic Antibiotics via Sanger’s Reagent: Synthesis, In Silico, and Antimicrobial Evaluation

Cited by 12 publications

References 37 publications

Novel Cytocompatible Chitosan Schiff Base Derivative as a Potent Antibacterial, Antidiabetic, and Anticancer Agent

Novel Cytocompatible Chitosan Schiff Base Derivative as a Potent Antibacterial, Antidiabetic, and Anticancer Agent

High antimicrobial effectiveness of acrylonitrile adducts and evaluation of their biological activity as haemolytic and thrombolytic agent

Rejuvenating the [1, 2, 3]-triazolo [1,5-a]quinoxalin-4(5H)-one scaffold: Synthesis and derivatization in a sustainable guise and preliminary antimicrobial evaluation

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