Design, synthesis, fungicidal activities and structure–activity relationship studies of (−)-borneol derivatives containing 2-aryl-thiazole scaffold

Huang, Danling; Zheng, Suiping; Zhang, Tianyuan; Cheng, Yong‐Xian

doi:10.1016/j.bmcl.2021.128006

Cited by 5 publications

(4 citation statements)

References 20 publications

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“…Most saccharin derivatives are important in medicinal chemistry ( Huang et al, 2021 ; Abdel-Rahman et al, 2013 and Al Bayati et al, 2015 ). Furthermore, Schiff bases have a broad spectrum of biological activities, such as anti-inflammatory, anticonvulsant, and anti-HIV.…”

Section: Resultsmentioning

confidence: 99%

“…Another advantage of saccharine was using it as a catalyst in synthesizing some dihydro-2-oxypyrrole derivatives ( Mohamadpour et al, 2016 ). So, in connection ( Huang et al, 2021 , Abdel-Rahman et al, 2013 , and Al Bayati et al, 2015 ; Magda et al, 2016 ) with our ongoing interest, the goal was to develop new synthetic strategies for constructing systems involving saccharin or its derivatives due to its significant biological and pharmacological activities. Furthermore, Schiff bases have been reported to exhibit a broad range of biological and pharmacological properties.…”

Section: Introductionmentioning

confidence: 99%

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Novel saccharin analogs as promising antibacterial and anticancer agents: synthesis, DFT, POM analysis, molecular docking, molecular dynamic simulations, and cell-based assay

et al. 2022

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Saccharine is a pharmacologically significant active scaffold for various biological activities, including antibacterial and anticancer activities. Herein, saccharinyl hydrazide (1) was synthesized and converted into 2-[(2Z)-2-(1,1-dioxo-1,2-dihydro-3H-1λ6,2- benzothiazole-3-ylidene) hydrazinyl] acetohydrazide (5), which was employed as a key precursor for synthesizing a novel series of small molecules bearing different moieties of monosaccharides, aldehydes, and anhydrides. Potent biological activities were found against Staphylococcus and Escherichia coli, and the results indicated that compounds 6c and 10a were the most active analogs with an inhibition zone diameter of 30–35 mm. In cell-based anticancer assay over Ovcar-3 and M-14 cell lines, compound 10a was the most potent analog with IC50 values of 7.64 ± 0.01 and 8.66 ± 0.01 µM, respectively. The Petra Orisis Molinspiration (POM) theoretical method was used to calculate the drug score of tested compounds and compare them with their experimental screening data. Theoretical DFT calculations were carried out in a gas phase in a set of B3LYP 6-311G (d,p). Molecular docking studies utilizing the MOE indicated the best binding mode with the highest energy interaction within the binding sites. The molecular docking for Ovcar-3 was carried out on the ovarian cancer protein (3W2S), while the molecular docking for M-14 melanoma was carried out on the melanoma cancer protein (2OPZ). The MD performed about 2ns simulations to validate selected compounds’ theoretical studies.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Novel saccharin analogs as promising antibacterial and anticancer agents: synthesis, DFT, POM analysis, molecular docking, molecular dynamic simulations, and cell-based assay

et al. 2022

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“…F131 possesses the l -borneol instead of l -menthol fragment and demonstrates higher antimicrobial activity. Interestingly, many previous studies reported the anti-inflammatory and antimicrobial activity of borneol derivatives [ 73 , 74 , 75 ]. Some aromatic borneol compounds were significantly active with MIC 50 = 125 µg/mL for both S. aureus and C. albicans [ 76 ].…”

Section: Discussionmentioning

confidence: 99%

Antimicrobial and Biofilm-Preventing Activity of l-Borneol Possessing 2(5H)-Furanone Derivative F131 against S. aureus—C. albicans Mixed Cultures

et al. 2022

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Candida albicans and Staphylococcus aureus are human pathogens that are able to form mixed biofilms on the surface of mucous membranes, implants and catheters. In biofilms, these pathogens have increased resistance to antimicrobials, leading to extreme difficulties in the treatment of mixed infections. The growing frequency of mixed infections caused by S. aureus and C. albicans requires either the development of new antimicrobials or the proposal of alternative approaches to increase the efficiency of conventional ones. Here, we show the antimicrobial, biofilm-preventing and biofilm-eradicating activity of 2(5H)-furanone derivative F131, containing an l-borneol fragment against S. aureus–C. albicans mixed biofilms. Furanone F131 is also capable of inhibiting the formation of monospecies and mixed biofilms by S. aureus and C. albicans. The minimal biofilm-prevention concentration (MBPC) of this compound was 8–16 μg/mL for S. aureus and C. albicans mono- and two-species biofilms. While the compound demonstrates slightly lower activity compared to conventional antimicrobials (gentamicin, amikacin, fluconazole, terbinafine and benzalkonium chloride), F131 also increases the antimicrobial activity of fluconazole–gentamicin and benzalkonium chloride against mixed biofilms of S. aureus–C. albicans, thus reducing MBPC of fluconazole–gentamicin by 4–16 times and benzalkonium chloride twofold. F131 does not affect the transcription of the MDR1, CDR1 and CDR2 genes, thus suggesting a low risk of micromycete resistance to this compound. Altogether, combined use of antibiotics with a F131 could be a promising option to reduce the concentration of fluconazole used in antiseptic compositions and reduce the toxic effect of benzalkonium chloride and gentamicin. This makes them an attractive starting point for the development of alternative antimicrobials for the treatment of skin infections caused by S. aureus–C. albicans mixed biofilms.

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“…As a typical heteroaromatic motif, the thiazole ring has been proved to be a pivotal structure in numerous pharmaceutical molecules, natural products as well as organic molecules possessing other versatile functions. 1 Rather recent works have revealed many more interesting thiazole compounds possessing attractive biological activities, such as anti-inflammatory, 2 antimicrobial, 3 anticancer, 4 antitumor, 5 antiproliferative, 6 fungicidal 7 activity etc. , which keeps enriching the application frontiers of thiazole scaffolds in discovering valuable lead compounds and drug candidates.…”

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confidence: 99%

Electrochemical enaminone C–H thiolation/C–N amination cascade for thiazole synthesis and its diastereoselective dearomatization

et al. 2022

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Design, synthesis, fungicidal activities and structure–activity relationship studies of (−)-borneol derivatives containing 2-aryl-thiazole scaffold

Cited by 5 publications

References 20 publications

Novel saccharin analogs as promising antibacterial and anticancer agents: synthesis, DFT, POM analysis, molecular docking, molecular dynamic simulations, and cell-based assay

Novel saccharin analogs as promising antibacterial and anticancer agents: synthesis, DFT, POM analysis, molecular docking, molecular dynamic simulations, and cell-based assay

Antimicrobial and Biofilm-Preventing Activity of l-Borneol Possessing 2(5H)-Furanone Derivative F131 against S. aureus—C. albicans Mixed Cultures

Electrochemical enaminone C–H thiolation/C–N amination cascade for thiazole synthesis and its diastereoselective dearomatization

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