Sulfonamide-based non-alkyne LpxC inhibitors as Gram-negative antibacterial agents

Kawai, Toshiyuki; Kazuhiko, Iwase; Takaya, Noriko; Yamaguchi, Yûko; Kishii, Ryuta; Kohno, Yasushi; Kurasaki, Haruaki

doi:10.1016/j.bmcl.2016.12.059

Cited by 24 publications

(11 citation statements)

References 22 publications

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“…Sulfonamides exhibit antibacterial activity by competitively inhibiting the dihydropteroate synthase enzyme, which is very important for folate synthesis. Thus, they inhibit DNA replication of bacteria .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial and Antioxidant Activities of Sulfonamide Derivatives Containing Tetrazole and Oxadiazole Rings

Özkan

Demirci

2019

Journal of Heterocyclic Chem

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In the present work, we synthesized new sulfonamide derivatives with 1,3,4‐oxadiazole moiety and tetrazole ring. The synthesized derivatives of sulfonamides were characterized through Fourier transform infrared, 13C‐APT‐NMR, 1H‐NMR, and high‐resolution liquid chromatography–mass spectrometry. The biological activities of resulting compound were also investigated and observed that the compounds reveal strong antimicrobial activity over some important bacterial strains including Bacillus subtilis ATCC 6633, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 13883, and Staphylococcus aureus ATCC 29213. The in vitro antifungal properties of synthesized compounds were also a target using Candida albicans NRRL Y‐477 and Saccharomyces cerevisiae fungal strains. We have provided a useful guideline for future studies about the effect of the chemical structures of sulfonamide compounds on the biological activities. Among the target compounds, 7b, 7c, 7d, and 7e demonstrated surprisingly high antimicrobial activities than did others.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial and Antioxidant Activities of Sulfonamide Derivatives Containing Tetrazole and Oxadiazole Rings

Özkan

Demirci

2019

Journal of Heterocyclic Chem

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“…Organic sulfur compounds are ubiquitous structural elements in numerous natural products and widely used as various artificial chemicals [1][2][3]. In particular, sulfonyl chlorides are the most prevalent reagents for the installation of the sulfonyl protecting group [4], which could be converted into numerous different sulfonyl derivatives [5][6][7][8][9], undergo diverse desulfitative cross-couplings [10,11] or serve as arylating agents [12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Sulfonyl Chlorides/Bromides from Sulfonyl Hydrazides

Chen¹,

Xu²,

Shen³

et al. 2021

Preprint

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A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups has been described. A variety of nucleophiles could be engaged in this transformation thus permitting the synthesis of complex sulfonamides, sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields.

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“…Sulfonamides (SNs), as synthetic antibacterial veterinary drugs, have been widely used in clinics. It has a broad‐spectrum antibacterial property with chemical stability and ease of use (Kawai et al, ; Zessel, Mohring, Hamscher, Kietzmann, & Stahl, ). Moreover, the combined use of SNs and other drugs, such as trimethoprim (TMP), can synergistically enhance the antibacterial effect and expand the treatment range (Economou, Petraki, Tsipi, & Botitsi, ; Li, Sun, Zhang, & Pang, ).…”

Section: Introductionmentioning

confidence: 99%

Comparison of three different lipid removal cleanup techniques prior to the analysis of sulfonamide drug residues in porcine tissues

Wang

Fang

et al. 2019

Food Science & Nutrition

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A number of 17 sulfonamides (SNs) determination in porcine tissues using two new materials including Enhanced Matrix Removal for Lipid (EMR‐L) and Oasis PRiME hydrophilic‐lipophilic balance (HLB), and the conventional liquid–liquid extraction with n‐hexane (LLE) sample preparation methods were evaluated and compared. Samples were extracted uniformly with acidified acetonitrile and cleaned up by the three sample preparation methods, and then, analytes were further separated by ultrahigh‐performance liquid chromatography (UHPLC) and detected by a triple quadrupole mass spectrometry (MS/MS) or a quadrupole‐time‐of‐flight tandem mass spectrometry (Q‐TOF/MS). The results showed that the matrix effects from the EMR‐L and HLB were significantly lower than that from LLE, suggesting that these two new materials are superior to n‐hexane in the precipitation of proteins and the adsorption of lipids. Moreover, the recoveries of 17 SNs were quantified by the matrix‐matched calibration curve at spiked level of 5, 10, and 20 μg/kg, and 97.0% of the results satisfied method validation requirements. The samples cleaned up by EMR‐L and HLB achieved the highest average recovery in liver and kidney with high moisture content, and muscle which is high in fat, respectively. In addition, Q‐TOF/MS could play a good role in aided verification based on the result of repeated validation test. In summary, either combination of approaches could be used to achieve monitoring purposes; it is still worthwhile to adopt a specific sample preparation method and MS detector for the quantification in a specific matrix.

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Sulfonamide-based non-alkyne LpxC inhibitors as Gram-negative antibacterial agents

Cited by 24 publications

References 22 publications

Synthesis and Antimicrobial and Antioxidant Activities of Sulfonamide Derivatives Containing Tetrazole and Oxadiazole Rings

Synthesis and Antimicrobial and Antioxidant Activities of Sulfonamide Derivatives Containing Tetrazole and Oxadiazole Rings

Facile Synthesis of Sulfonyl Chlorides/Bromides from Sulfonyl Hydrazides

Comparison of three different lipid removal cleanup techniques prior to the analysis of sulfonamide drug residues in porcine tissues

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