Design, synthesis and biological evaluation of novel N,4-diphenylthiazol-2-amine derivatives

Nadaf, AfraQuasar A.; Barretto, Delicia A.; Najare, Mahesh S.; Mantur, Shivaraj; Garbhagudi, Manjunatha; Gaonkar, Supreet; Joshi, Shrinivas D.; Khazi, Imtiyaz Ahmed M.

doi:10.1007/s00044-019-02495-2

Cited by 7 publications

(2 citation statements)

References 24 publications

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“…Certain biological applications of thiazoles were first identified in 1887 by Hantzsch and Weber. Since this discovery, thiazoles are a notable moiety present in several modern compounds of interest for their antitubercular [17], antidiabetic [18], antimalarial [19], antibacterial [19][20][21][22][23][24][25][26][27][28][29][30][31], antiviral [26,[32][33][34], antifungal [22, 24-27, 29, 30, 33, 34], antioxidant [35], anti-inflammatory [30,35], anti-cancer [36,37], and anti-proliferative [27,[38][39][40], activities.…”

Section: Biological Applications Of Thiazolesmentioning

confidence: 99%

Synthetic Strategies and Biological Activities of 1,5-Disubstituted Pyrazoles and 2,5-Disubstituted Thiazoles

Lozano¹,

Lewis-Bakker²,

Kotra³

2023

Strategies for the Synthesis of Heterocycles and Their Applications

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Pyrazoles and thiazoles belong to 5-membered aromatic heterocycles called azoles. In addition to a nitrogen, pyrazoles contain an additional nitrogen in a 1,2 linkage and thiazoles contain a sulfur atom in a 1,3 linkage. These compounds are useful pharmacophores that offer a broad range of therapeutic applications. Pyrazoles can be synthesized by (i) the condensation of 1,3 dipolar compounds and alkenes/alkynes, (b) cyclocondensation of hydrazines and dicarbonyl reagents, and (c) multi-component reactions. Access to thiazoles is typically via (a) the condensation of α-haloketones with nucleophilic thioamides containing the N-C-S fragment, (b) a reaction between α-aminonitriles and various reactants containing an X-C-S fragment, and (c) a reaction of acylaminocarbonyls and phosphorus pentasulfide. This chapter will focus on the strategies and our perspectives on the synthesis of pyrazoles and thiazoles including derivatives at the 1,5 positions and 2, 4, 5 positions respectively, reported during 2015–2022. Additionally, their therapeutic and biological evaluations will be discussed.

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Section: Biological Applications Of Thiazolesmentioning

confidence: 99%

Synthetic Strategies and Biological Activities of 1,5-Disubstituted Pyrazoles and 2,5-Disubstituted Thiazoles

Lozano¹,

Lewis-Bakker²,

Kotra³

2023

Strategies for the Synthesis of Heterocycles and Their Applications

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“…1). [12][13][14][15][16][17] However, in all cases only in vitro assays were performed. Although of great importance for the initial selection of active substances, they do not accurately reflect in vivo conditions.…”

Section: Introductionmentioning

confidence: 99%

2‐Aminoselenazoles and 2‐aminothiazoles: One‐pot synthesis and control of the fungus Colletotrichum lindemuthianum in common beans

Pereira

Andrade

Souza

et al. 2022

Pest Management Science

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BACKGROUND: Anthracnose, caused by the fungus Colletotrichum lindemuthianum, increases losses in the production of common beans. As 1,3-diazoles can act against fungi by inhibiting the enzyme squalene epoxidase (SE), 2-aminoselenazoles and 2-aminothiazoles were synthesized and subjected to tests with the fungus. In addition, the interactions of the most promising substances with the enzyme SE were investigated in silico.RESULTS: Seventeen compounds (eight new) were prepared by a one-pot methodology. In vitro antifungal activities of these compounds against C. lindemuthianum were determined by the minimum inhibitory concentration (MIC) method. Most treatments differed from the control (water), and six azoles with the lowest MIC values underwent an assay employing common bean plants inoculated with the fungus. Among the best results were those from 2-(3-fluorophenyl)amino-4-phenyl-1,-3-thiazole (16; 2857 ∼g mL −1 ), which reduced the severity of anthracnose in common beans to values statistically comparable to the commercial fungicide thiophanate-methyl (700 ∼g mL −1 ). The in silico affinity of compound 16 for SE was statistically equal to those calculated for several inhibitors of this enzyme. CONCLUSIONS:The results suggested that 2-(3-fluorophenyl)amino-4-phenyl-1,3-thiazole ( 16) could be considered a potential fungicidal lead compound for further structural optimization, which according to the in silico study acts via SE inhibition.

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Thiazole-based analogues as potential antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA) and their SAR elucidation

Guo

Xie

Ruan

et al. 2023

European Journal of Medicinal Chemistry

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Design, synthesis and biological evaluation of novel N,4-diphenylthiazol-2-amine derivatives

Cited by 7 publications

References 24 publications

Synthetic Strategies and Biological Activities of 1,5-Disubstituted Pyrazoles and 2,5-Disubstituted Thiazoles

Synthetic Strategies and Biological Activities of 1,5-Disubstituted Pyrazoles and 2,5-Disubstituted Thiazoles

2‐Aminoselenazoles and 2‐aminothiazoles: One‐pot synthesis and control of the fungus Colletotrichum lindemuthianum in common beans

Thiazole-based analogues as potential antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA) and their SAR elucidation

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