Design, synthesis and antimicrobial activity of novel 2-aminothiophene containing cyclic and heterocyclic moieties

Asiri, Yahya I.; Muhsinah, Abdullatif Bin; Alsayari, Abdulrhman; Venkatesan, Kumar; Al‐Ghorbani, Mohammed; Mabkhot, Yahia N.

doi:10.1016/j.bmcl.2021.128117

Cited by 16 publications

(6 citation statements)

References 19 publications

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“…Thus, we speculated that both of the core nucleus and the groups on the core nucleus might be responsible for the antibacterial activity of STK-35/66, including the -NO 2 , -OOH and N-cyclopropyl groups. Similarly, these active groups have been previously reported as effective antibacterial active group (Zitko et al 2018;Zhang et al 2019b;Asiri et al 2021). In the present study, STK-35 and STK-66 showed the most effective antimicrobial activity against type strains and MDR clinical isolates of Gram-negative pathogens (A. baumannii, E. coli, K. pneumoniae and P. aeruginosa), with minimal inhibitory concentrations (MICs) ranging from 0Á0625 to 8 μg ml −1 and minimal bactericidal concentrations (MBCs) from 0Á125 to 16 μg ml −1 (Table 1 and Table S1).…”

Section: Resultsmentioning

confidence: 62%

“…2019b; Asiri et al . 2021). In the present study, STK‐35 and STK‐66 showed the most effective antimicrobial activity against type strains and MDR clinical isolates of Gram‐negative pathogens ( A. baumannii , E. coli , K. pneumoniae and P. aeruginosa ), with minimal inhibitory concentrations (MICs) ranging from 0·0625 to 8 μg ml −1 and minimal bactericidal concentrations (MBCs) from 0·125 to 16 μg ml −1 (Table 1 and Table S1).…”

Section: Resultsmentioning

confidence: 99%

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A novel bactericidal small molecule, STK-35, and its derivative, STK-66, as antibacterial agents against Gram-negative pathogenic bacteria in vitro and in vivo

She

Liu

et al. 2022

Letters in Applied Microbiology

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Significance and Impact of Study: The World Health Organization has considered Acinetobacter baumannii, Klebsiella pneumoniae, Pseudomonas aeruginosa and Escherichia coli as high-priority pathogens, and new antimicrobial agents are urgently needed to treat Gram-negative bacterial infections. In our study, we found STK-35 and STK-66 exhibited effective antibacterial and antibiofilm properties against a variety of Gram-negative pathogens with low levels of toxicity to mammalian cells. The compounds also showed synergistic antimicrobial effects with conventional antibiotics. In addition, STK-35 exhibited considerable efficacy in a mouse peritonitis model by E. coli infection. Thus, STK-35/66 could be considered as potential substitutes for the treatment of Gram-negative pathogenic infections after further structure optimization.

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Section: Resultsmentioning

confidence: 62%

Section: Resultsmentioning

confidence: 99%

A novel bactericidal small molecule, STK-35, and its derivative, STK-66, as antibacterial agents against Gram-negative pathogenic bacteria in vitro and in vivo

She

Liu

et al. 2022

Letters in Applied Microbiology

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“…These results are due to the presence of nitro (NO 2 ) group in the synthesized compound series unlike the others. In previous studies on this topic, compounds with similar structures were found to have significant antimicrobial activities 67 , 68 . In addition, compounds 4b and 6h have significant antimicrobial effects on S. aureus .…”

Section: Resultsmentioning

confidence: 96%

Synthesis, antimicrobial activity and molecular docking studies of spiroquinoline-indoline-dione and spiropyrazolo-indoline-dione derivatives

Gül

Çelikoğlu

İdil

et al. 2023

Sci Rep

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Spiro[benzo[h]quinoline-7,3′-indoline]diones and spiro[indoline-3,4′-pyrazolo[3,4-b]quinoline]diones were efficiently synthesized via one-pot multi-component reactions under ultrasound-promoted conditions. Spiro[benzo[h]quinoline-7,3′-indoline]dione derivatives were successfully developed by the reaction of isatins, naphthalene-1-amine and 1,3-dicarbonyl compounds. The spiro[indoline-3,4′-pyrazolo[3,4-b]quinoline]dione derivatives were prepared by the reaction of isatins, 5-amino-1-methyl-3-pheylpyrazole, and 1,3-dicarbonyl compounds by using ( ±)-camphor-10-sulfonic acid as a catalyst in H2O/EtOH (3:1 v/v) solvent mixture. The antibacterial activity of the synthesized compounds was evaluated against, Enterococcus faecalis, Staphylococcus aureus and Candida albicans. Compounds 4b, 4h, and 6h showed the strongest antimicrobial activity toward both bacteria. The MIC values of these compounds ranged from 375–3000 µg/mL. The effect of these compounds (4b, 4h, 6h) as a function of applied dose and time was investigated by a kinetic study, and the interaction with these antimicrobial results was simulated by a molecular docking study. We also used the docking approach with Covid-19 since secondary bacterial infections. Docking showed that indoline-quinoline hybrid compounds 4b and 4h exerted the strongest docking binding value against the active sites of 6LU7. In addition, the synthesized compounds had a moderate to good free radical scavenging activity.

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“…In the past decade, many heterocyclic compounds and their corresponding glycosides have been synthesized to obtain a novel antimicrobials drug, which would be able to treat infections caused by resistant bacteria and fungi strains. [50,51] Because of the above-mentioned, the main subject of our study is to synthesize the biologically important scaffold based on new spiro(cyclohexane-thiazolidine) derivatives and its corresponding glycosides with the assessment of their antibacterial and antifungal activity.…”

Section: Introductionmentioning

confidence: 99%

Boosting the antimicrobial performance based on new fused spirothiazolidine framework analogs

et al. 2022

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New spiro[cyclohexane-1,2'-thiazolo[4,5-b]pyridine derivatives (3–23) were investigated. Then there is in vitro antimicrobial potency against possible organisms Staphylococcus aurous ATCC-47,077, Bacillus cereus ATCC-12228, Escherichia coli ATCC-25922, Salmonella typhiATCC-15566, and Candida albicans ATCC-10231 were tested utilizing commercially available antibiotics ampicillin as a reference drug. A preliminary antimicrobial test represented that derivatives: (Aldoses) 3'-(4-fluorophenyl)-5'-(methyleneamino)-7'-(p-tolyl)-3'H-spiro[cyclohexane-1,2'-thiazolo[4,5-b]pyridine]-6'-carbonitrile (16–19) and (Acetyl aldoses) 3'-(4-fluorophenyl)-5'-(methyleneamino)-7'-(p-tolyl)-3'H-spiro [cyclohexane-1,2'-thiazolo[4,5-b]pyridine]-6'-carbonitrile (20–23) exhibited higher antifungal, and antibacterial performance with minimum inhibitory concentrations values of (39–67 µg/ml) toward all pathogenic strains compared to common reference drug ampicillin.

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Design, synthesis and antimicrobial activity of novel 2-aminothiophene containing cyclic and heterocyclic moieties

Cited by 16 publications

References 19 publications

A novel bactericidal small molecule, STK-35, and its derivative, STK-66, as antibacterial agents against Gram-negative pathogenic bacteria in vitro and in vivo

A novel bactericidal small molecule, STK-35, and its derivative, STK-66, as antibacterial agents against Gram-negative pathogenic bacteria in vitro and in vivo

Synthesis, antimicrobial activity and molecular docking studies of spiroquinoline-indoline-dione and spiropyrazolo-indoline-dione derivatives

Boosting the antimicrobial performance based on new fused spirothiazolidine framework analogs

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