Synthesis and &lt;i&gt;in Vitro&lt;/i&gt; Antibacterial Evaluation of Novel 4-Substituted 1-Menthyl-1,2,3-triazoles

Khaligh, Pooneh; Salehi, Peyman; Bararjanian, Morteza; Aliahmadi, Atousa; Khavasi, Hamid Reza; Ebrahimi, Samad Nejad

doi:10.1248/cpb.c16-00463

Cited by 20 publications

(9 citation statements)

References 46 publications

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“…In other studies, menthyl 1,4-disubstituted 1,2,3-triazole derivatives of hydroxybenzaldehydes, phenols and bile acids showed a strong inhibitory effect against E. faecium with the minimum inhibitory concentration (MIC) values in the range of 1–3 μM [ 52 ]. Kant and co-workers reported that 1,2,3-triazole linked chalcone and flavone hybrids showed activity against Gram-positive bacteria ( Staphylococcus aureus , Enterococcus faecalis ) and Gram-negative bacteria ( Escherichia coli , Pseudomonas aeruginosa , Shigella boydii , Klebsiella pneumoniae ) with MIC values in the range of 6.25–100 µg/mL [ 53 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives

et al. 2018

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A new series of coumarin-1,2,3-triazole conjugates with varied alkyl, phenyl and heterocycle moieties at C-4 of the triazole nucleus were synthesized using a copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated coumarin (3) or N-propargylated coumarin (6) with alkyl or aryl azides. Based on their minimal inhibitory concentrations (MICs) against selected microorganisms, six out of twenty-six compounds showed significant antibacterial activity towards Enterococcus faecalis (MIC = 12.5–50 µg/mL). Moreover, the synthesized triazoles show relatively low toxicity against human erythrocytes.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives

et al. 2018

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“…CUR is a well-known natural product and has been proved to have a diverse range of biological activities [30]. Hybridization of bioactive compounds with heterocyclic rings is a trend for increasing their bioavailability and receptor selectivity [41,42]. 1,2,3-triazole ring is an interesting structure for medical chemists as an active moiety which is a bioisostere of amide group and with three nitrogen atoms may increase the solubility of its hybridized compounds.…”

Section: Discussionmentioning

confidence: 99%

Targeted Modulation of Inflammatory Lymphocytes and Neurogenesis/Neuroprotection Associated Genes by Curcumin and a Novel Derivative of Curcumin on Mice Experimental Autoimmune Encephalomyelitis Model

Khosropour

Noori

Salehi

et al. 2022

Preprint

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Multiple sclerosis (MS) is a chronic demyelinating disease that causes neurological disabilities mostly in young adults. Curcumin (CUR), a polyphenol found in Turmeric, has anti-inflammatory and neuroprotective properties in autoimmune diseases including MS, although it has low bioavailability and solubility. In the present study, administration of CUR and FCUR, a potent synthetic derivative of CUR, on experimental autoimmune encephalomyelitis (EAE), animal model of MS, was investigated. MOG-induced EAE mice were treated with placebo, 4 mg/Kg CUR, or 4 mg/Kg FCUR 10 days post immunization. After 20 days of treatment, mice were euthanized and subjected to ex-vivo examination. Protein was detected with ELISA and western blot. mRNA level was measured with qRT-PCR. The results showed that compared with the control group, in both CUR and FCUR treated groups, clinical score was improved. Histological H&E staining of spinal cord tissue demonstrated reduction in lymphocyte infiltration. Cytokine production of IL-6 and IL-17 decreased and TGF-β increased in the splenocytes and serum. Also the compounds stimulated mRNA expression of IL-4, IL-10, TGF-β, FOXP3, GATA3, MBP, and Olig2, and inhibited IL-1, IL-17, IFN-γ, RORγt, and T-bet genes in spinal cord lymphocytes. However, no considerable effect on PDGFRα, nestin, GAS6, Tyro3, and MERTK regulation was observed. The reported results were more significant in FCUR treated group. In conclusion, this study suggests that CUR and FCUR can alleviate neurological symptoms, reduce inflammation, and increase remyelination and neuroprotection. However, the stronger preliminary efficacy of FCUR would render this newly synthesized derivative as a potent therapeutic candidate against MS.

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“…Based on the attributes mentioned above, and in continuation of our interest in evaluating the overall impact of the combination between 1,2,3-triazole ring and natural products 26,27 here we report the synthesis of newly menthol analog containing 1,2,3-triazole and investigation of their antimicrobial activity.…”

Section: Structures Of Biologically Active Derivatives Of α-Aminonitr...mentioning

confidence: 99%

Synthesis of novel menthol derivatives containing 1,2,3-triazole group and their in vitro antibacterial activities

Karbasi

Salehi

Aliahmadi

et al. 2023

JSCS

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New N-substituted ?-aminonitrile derivatives from menthol were synthesized by consecutive succinic ester formation, propargylation, 1,3-dipolar Huisgen cycloaddition and Strecker reaction. The structures of the synthesized compounds were confirmed by diverse spectroscopic techniques including 1HNMR, 13C-NMR, ESI-MS, and IR. The novel synthesized compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus as Gram-positive and Escherichia coli as Gram-negative bacteria. These compounds demonstrated a strong inhibitory effect against S. aureus with the minimum inhibitory concentration (MIC) values ranged from 32-128 ?g mL-1. Derivatives 6a2, 6b1, 6b4, and 6b5 with a MIC value of 32 ?g mL-1 exhibited the best inhibitory effects.

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Synthesis and <i>in Vitro</i> Antibacterial Evaluation of Novel 4-Substituted 1-Menthyl-1,2,3-triazoles

Cited by 20 publications

References 46 publications

Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives

Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives

Targeted Modulation of Inflammatory Lymphocytes and Neurogenesis/Neuroprotection Associated Genes by Curcumin and a Novel Derivative of Curcumin on Mice Experimental Autoimmune Encephalomyelitis Model

Synthesis of novel menthol derivatives containing 1,2,3-triazole group and their in vitro antibacterial activities

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