Design, synthesis and molecular modeling studies of new series of s-triazine derivatives as antimicrobial agents against multi-drug resistant clinical isolates

Haiba, Nesreen S.; Khalil, Hosam H.; Moniem, Mohamed Abdel; El-Wakil, Marwa H.; Bekhit, Adnan A.; Khattab, Sherine N.

doi:10.1016/j.bioorg.2019.103013

Cited by 31 publications

(17 citation statements)

References 40 publications

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“…Among chemotherapeutics, we can find compounds which contain the hydrazidehydrazone moiety in their chemical structure (i.e., nitrofurazone, furazolidone, and nitrofurantoin) [12] (Figure 1). As can be seen from the literature review, the compounds with an azomethine group (-NH-N=CH-) show a significant and broad spectrum of bioactivity, mainly antibacterial [13][14][15][16][17][18][19][20], antifungal [21], antitubercular [22], antimycobacterial [23], anticancer [24][25][26][27], anti-inflammatory [28], anticonvulsant [29], and antiviral activity [30]. Several previously published articles by our research team proved that hydrazide-hydrazones can exhibit significant antimicrobial and anticancer activity [12,[31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 88%

Novel Derivatives of 4-Methyl-1,2,3-Thiadiazole-5-Carboxylic Acid Hydrazide: Synthesis, Lipophilicity, and In Vitro Antimicrobial Activity Screening

et al. 2021

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Bacterial infections, especially those caused by strains resistant to commonly used antibiotics and chemotherapeutics, are still a current threat to public health. Therefore, the search for new molecules with potential antimicrobial activity is an important research goal. In this article, we present the synthesis and evaluation of the in vitro antimicrobial activity of a series of 15 new derivatives of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. The potential antimicrobial effect of the new compounds was observed mainly against Gram-positive bacteria. Compound 15, with the 5-nitro-2-furoyl moiety, showed the highest bioactivity: minimum inhibitory concentration (MIC) = 1.95–15.62 µg/mL and minimum bactericidal concentration (MBC)/MIC = 1–4 µg/mL.

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Section: Introductionmentioning

confidence: 88%

Novel Derivatives of 4-Methyl-1,2,3-Thiadiazole-5-Carboxylic Acid Hydrazide: Synthesis, Lipophilicity, and In Vitro Antimicrobial Activity Screening

et al. 2021

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“…In medicinal chemistry, the s-triazine ring has proved to be a privileged structure, and, therefore, its derivatives have been extensively studied against a broad number of biological targets. In this respect, s-triazine derivatives have shown antiprotozoal [11], anti-HIV [12], anticancer [13,14], antimalarial [15,16], antibacterial [17][18][19], antifungal [20][21][22], and antileishmanial activity [23], carbonic anhydrase inhibitors [24,25], and human monoamine oxidase (MAO) inhibitors [26].…”

Section: Introductionmentioning

confidence: 99%

Novel 4,6-Disubstituted s-Triazin-2-yl Amino Acid Derivatives as Promising Antifungal Agents

Alhameed

Almarhoon

Sholkamy

et al. 2020

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A novel series of 4,6-disubstituted s-triazin-2-yl amino acid derivatives was prepared and characterized. Most of them showed antifungal activity against Candida albicans compared to clotrimazole (standard drug). Compounds bearing aniline derivatives, piperidine and glycine on the triazine core showed the highest inhibition zones at concentrations of 50, 100, 200, and 300 μg per disc. In addition, docking studies revealed that all the compounds accommodated well in the active site residues of N-myristoltransferase (NMT) and exhibited complementarity, which explains the observed antifungal activity. Interestingly, none of these compounds showed antibacterial activity.

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“…Similarly, s-triazine is one of the constituent molecular scaffolds found in natural products and synthetic drugs [16,17]. The s-triazine ring-based compounds have been proven to display different pharmaceutical targets for example MAO inhibitors [18], anticancer [19], antiviral [20], drug delivery systems [21], antimalarial [22], antiprotozoal [23], antimicrobial [24], antifungal [25], and antileishmanial activity [26]. The s-triazine moiety linked with other groups is of a lipophilic character and is already reported to have remarkable antifungal and antibacterial activities [27][28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-S-Triazine Derivative as a New Class of Urease Inhibitor

et al. 2019

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The one-pot fashion of three multi-component reaction provides the desired hydroacridinone-based hydrazino-s-triazine scaffold 4. Compound 4 was crystallized in an orthorhombic crystal system and Pbca space group with a = 11.6271(2) Å, b = 18.2018(4) Å, c = 32.4721(6) Å, and α = β = γ = 90° with one formula unit per asymmetric unit and eight molecules per unit cell. Additionally, structural features, Hirshfeld surfaces, and DFT studies were also investigated. Its packing in the crystal is controlled by H…H (63.4%), O…H (12.7%), Cl…H (7.2%), N…H (4.7%), and C…H (10.2%) contacts, where the O…H and Cl…H contacts were found the strongest. In vitro urease inhibition evaluation showed that the hydroacridinone-based hydrazino-s-triazine is more active (IC50 = 17.9 ± 0.47 µM) than the standard acetohydroxamic acid (IC50 = 20.3 ± 0.43 µM).

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Design, synthesis and molecular modeling studies of new series of s-triazine derivatives as antimicrobial agents against multi-drug resistant clinical isolates

Cited by 31 publications

References 40 publications

Novel Derivatives of 4-Methyl-1,2,3-Thiadiazole-5-Carboxylic Acid Hydrazide: Synthesis, Lipophilicity, and In Vitro Antimicrobial Activity Screening

Novel Derivatives of 4-Methyl-1,2,3-Thiadiazole-5-Carboxylic Acid Hydrazide: Synthesis, Lipophilicity, and In Vitro Antimicrobial Activity Screening

Novel 4,6-Disubstituted s-Triazin-2-yl Amino Acid Derivatives as Promising Antifungal Agents

Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-S-Triazine Derivative as a New Class of Urease Inhibitor

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