A Facile Synthesis of 2,4-Disubstituted Thiazoles Using MnO2

Yu, Yanbo; Chen, Hongliang; Wang, Li-Yi; Chen, Xin-Zheng; Fu, Bin

doi:10.3390/molecules14124858

Cited by 19 publications

(8 citation statements)

References 22 publications

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“…Recent surveys showed that thiazole compounds play important role as antibacterial, anti-inflammatory, anticonvulsant and anticancer agents [10,11]. Structural activity relationship (SAR) study based on thiazole revealed that substituents on a particular position at position 2 and 4 of the 1,3-thiazole ring affect the biological behavior [12,13]. Other than that, molecular docking study is a computer-assisted drug design (CADD) that is used to predict eligible orientation of ligand towards specific receptor.…”

Section: Introductionmentioning

confidence: 99%

New 2,4,5-Trisubstituted-1,3-Thiazole Derivatives: Synthesis, in Vitro Antimicrobial Activity and in Silico Study

et al. 2020

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A series of thiazole derivatives 1-4 were synthesized employing simple one-pot reaction pathway and characterized via Fourier Transform Infrared (FTIR), Proton Nuclear Magnetic Resonance (1H NMR), Ultraviolet-Visible (UV-Vis) and Gas Chromatography-Mass Spectrometry (GC-MS). The newly synthesized compounds were evaluated for their in vitro antimicrobial properties against several bacterial strains including Gram-positive and Gram-negative as well as fungus using broth microdilution method. The results revealed that all of the compounds exhibited good activity with a range of MIC values between 1.25-5.0 mg/mL. From the MIC and MBC results, compound 1 exhibited good activities with same MIC value of 1.25 mg/mL and MBC value of 5 mg/mL against B. cereus and S. flexneri. In order to support antimicrobial results, the molecular docking studies were carried out for inhibition of the GlcN-6-P synthase as the target. Out of four compounds underwent for molecular docking studies, 5-acetyl-4-methyl-2-(4-aminobiphenyl)-1,3-thiazole (1) shows the lowest minimum binding energy at -7.32 kcal/mol as compared to 2, 3 and 4 with -7.31, -7.20 and -6.76 kcal/mol, respectively which are in agreement with antimicrobial assay results. In conclusion, 2, 4, 5-trisubstituted- 1,3- thiazole derivatives could be considered as promising antimicrobial in drug discovery candidates.

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Section: Introductionmentioning

confidence: 99%

New 2,4,5-Trisubstituted-1,3-Thiazole Derivatives: Synthesis, in Vitro Antimicrobial Activity and in Silico Study

et al. 2020

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“…The crude product was purified using column chromatography on silica gel G60, eluting with hexane-EtOAc (3:2) to give, as a yellowish, fluffy solid, 4-phenyl-2-styrylthiazole (4a) (0.109 g, 82.6%), mp 130-132 ºC (Lit. [39][40][41] …”

Section: Methodsmentioning

confidence: 99%

Synthesis and biological evaluation of (E)-cinnamic acid, (E)-2-styrylthiazole and (E)-2-[2-(naphthalen-1-yl)vinyl]thiazole derivatives

Olawode¹,

Tandlich²,

Prinsloo³

et al. 2017

Arkivoc

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Cinnamyl-and thiazole-based compounds have been shown to exhibit diverse medicinal properties and a series of twelve (E)-2-styrylthiazole and (E)-2-[(naphthalen-1-yl)vinyl]thiazole derivatives, which are conjugates of both systems and which satisfy the "Lipinski rule of 5", have been synthesised and subjected to in vitro biological screening. While insignificant inhibition (60-98% viability at 10 µM) of HeLa (cervical cancer) cells was noted, all five of the (E)-2-[naphthalen-1-yl)vinyl]thiazole derivatives proved remarkably active against SH-SY5Y (neuroblastoma) cells with IC50 values ranging from 2.09 to 8.64 µM. Two of the seven (E)-2-styrylthiazoles were found to be moderately active (with IC50 values of 10.8 and 11.7 mM), whereas the remaining five analogues exhibit significant proliferation of SH-SY5Y cells (with IC50 values of 180-1000 mM). The results warrant further studies on the effects of styrylthiazoles on the differentiation and extension of SH-SY5Y cells in order to assess their activity in neurological degenerative diseases.

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“…Molecular entities bearing thiazole ring system(s) form an important class of natural and synthetic compounds because of their physicochemical properties [ 1 , 2 , 3 , 4 ].Furthermore, they exhibit a wide range of biological activities such as cardiotonic [ 5 ], antifungal [ 6 , 7 ], analgesic [ 8 ], anticonvulsant [ 9 ], antituberculosis [ 10 ], antiviral [ 11 ], anti-inflammatory [ 12 ], anti-HIV [ 13 , 14 ], and anticancer activities [ 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New Substituted Hantzsch Thiazole Derivatives from Environmentally Benign One-Pot Synthesis Using Silica Supported Tungstosilisic Acid as Reusable Catalyst

et al. 2017

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An efficient and green method has been developed for the synthesis of new substituted Hantzsch thiazole derivatives in 79%–90% yield, via the one-pot multi-component procedure, by the reaction of 3-(bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, thiourea and substituted benzaldehydes in the presence of silica supported tungstosilisic acid, as a reusable catalyst, under conventional heating or under ultrasonic irradiation. The catalyst is recoverable by a simple filtration and can be reused in the subsequent reactions. Most of the thiazoles exhibited significant antibacterial activity compared toamoxicillin and ciprofloxacin as positive controls. In addition, the new compounds showed moderate to good antioxidant (DPPH) radical scavenging activity.

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A Facile Synthesis of 2,4-Disubstituted Thiazoles Using MnO2

Cited by 19 publications

References 22 publications

New 2,4,5-Trisubstituted-1,3-Thiazole Derivatives: Synthesis, in Vitro Antimicrobial Activity and in Silico Study

New 2,4,5-Trisubstituted-1,3-Thiazole Derivatives: Synthesis, in Vitro Antimicrobial Activity and in Silico Study

Synthesis and biological evaluation of (E)-cinnamic acid, (E)-2-styrylthiazole and (E)-2-[2-(naphthalen-1-yl)vinyl]thiazole derivatives

Synthesis and Biological Evaluation of New Substituted Hantzsch Thiazole Derivatives from Environmentally Benign One-Pot Synthesis Using Silica Supported Tungstosilisic Acid as Reusable Catalyst

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