Design, synthesis and fungicidal activity of isothiazole–thiazole derivatives

Wu, Qifan; Zhao, Bin; Fan, Zhijin; Zhao, Jia-Bao; Guo, Xiaofeng; Yang, Dongyan; Zhang, Nailou; Yu, Bin; Калинина, Т. А.; Глухарева, Т. В.

doi:10.1039/c8ra07619g

Cited by 29 publications

(22 citation statements)

References 37 publications

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“…Thiazoles and dihydropyrazoles are versatile ve membered heterocyclic compounds, which are widely used in the eld of medicinal chemistry, natural products and functional materials. Most of the thiazoles have been reported to exhibit vast pharmacological applications including antimicrobial [16,17], antivira [18 -20], antitubercular [21,22], anticancer [23 -26], anti-in ammatory [27 -29], antitrypanosomal [30,31] and anti fungal activity [32,33]. Pyrazoles represent another important nitrogen containing heterocycles that have attracted much more attention among the medicinal chemists due to their extensive applications in the eld of drug discovery [34 -40], agrochemicals [41] and materials [42 -45].…”

Section: Introductionmentioning

confidence: 99%

“ An Efficient One Pot Multicomponent Synthesis of Dihydro Pyrazolyl Bithiazole Derivatives as Potential Anticancer Agents and Their Molecular Docking Studies”

Anjaneyulu

Vaarla

Kesharwani

et al. 2022

Preprint

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A novel series of dihydropyrazolyl bithiazoles were efficiently synthesized through simple reaction conditions via one pot multicomponent reaction of 2-bromo-1-(4-methyl-2-phenyl thiazol-5-yl)ethan-1-one (1), thiosemicarbazide (2) and chalcones (3 a-k) in the presence of sodium hydroxide in ethanol under reflux condition. The reaction generates two potential five membered heterocylic pharmacophores i.e. Hantzsch thiazole and dihydropyrazole in one step through operational simplicity, shorter reaction time with high yields. The newly synthesized compounds were well characterized by IR, 1H, 13C NMR and Mass spectral data. All the newly synthesized compounds were evaluated for their anticancer activity against human cancer cell lines and calculated their binding energy values with respect to 3ert protein. The compounds 4f, 4g, 4h and 4j exhibited excellent activity against MCF-7 cancer cell line with IC50 Values of 3.47 ± 0.28, 1.36 ± 0.74, 3.76 ± 0.35 and 4.14 ± 0.26 µM concentrations and studied molecular interaction of probable target protein human Estrogen Receptor Alpha protein (3ert.pdb) using docking simulation.

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Section: Introductionmentioning

confidence: 99%

“ An Efficient One Pot Multicomponent Synthesis of Dihydro Pyrazolyl Bithiazole Derivatives as Potential Anticancer Agents and Their Molecular Docking Studies”

Anjaneyulu

Vaarla

Kesharwani

et al. 2022

Preprint

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“…Recently, thiazole derivatives have been strongly highlighted in consideration of their broad-spectrum pharmaceutical and pesticidal activities, such as insecticidal, herbicidal, antiviral, bactericidal, antimalarial, anti-cancer, antioxidant, and anti-tubercular functions [10][11][12][13][14][15][16]. Figure 1 illustrates some representative drugs containing the versatile thiazole scaffold including octhilinone, etridiazole (EC 50 � 0.006 µg/mL against Phytophthora nicotianae), amicarthiazol (EC 50 � 0.574 µg/mL against Xanthomonas oryzae pv.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Thiazolyl Hydrazine Derivatives and Their Antifungal Activity

Zhu

Chen

Fen

et al. 2021

Journal of Chemistry

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A series of novel thiazolyl hydrazine derivatives 3a–3o were synthesized and evaluated for their in vitro antifungal activity against six phytopathogenic strains, namely, Botryosphaeria dothidea (B. d.), Gibberella sanbinetti (G. s.), Fusarium oxysporum (F. o.), Thanatephorus cucumeris (T. c.), Sclerotinia sclerotiorum (S. s.), and Verticillium dahliae (V. d.), by the classical mycelial growth rate method. Biological assessment results showed that most of these target compounds showed good antifungal activity toward tested strains. Especially, compound 3l showed excellent antifungal activities against B. d. and G. s. with relatively lower EC50 values of 0.59 and 0.69 µg/mL, respectively, which were extremely superior to those of commercial fungicides fluopyram, boscalid, and hymexazol and were comparable to those of carbendazim. Given the excellent bioactivity of designed compounds, this kind of thiazolyl hydrazine framework can provide a suitable point for exploring highly efficient antifungal agents.

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“…They showed a wide range of useful properties which led researchers to study the synthesis and chemical transformations of its derivatives. Isothiazole derivatives are widely used in medicine mainly as antiviral, antimicrobial, and fungicidal agents, while data on antitumor activity is very scarce . Among isothiazoles, aminoisothiazole derivatives have been reported for their biological activity.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium(II) Complexes of Isothiazole Ligands: Crystal Structure, HSA/DNA Interactions, Cytotoxic Activity and Molecular Docking Simulations

et al. 2020

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Two new neutral ruthenium(II) complexes [Ru(η 6-p-cymene) Cl 2 (1)] (3) and [Ru(η 6-p-cymene)Cl 2 (2)] (4) (1 = 5-(phenylamino)-3-pyrrolidin-1-ylisothiazole-4-carbonitrile; 2 = 3-morpholin-4-yl-5-(phenylamino)isothiazole-4-carbonitrile) have been synthesized and characterized using elemental analysis, IR, UV-Vis and NMR spectroscopy. The crystal structure was confirmed for complex 3 and both ligands. Examination of the interactions of ligands and complexes with CT-DNA (Calf Thymus DNA), as well as with HSA (Human Serum Albumin) revealed that ligands and complexes could interact with CT-DNA through intercala-tion and could bind strongly with HSA. Docking experiments toward DNA dodecamer indicate excellent accordance with experimental ΔG values. The cytotoxic activity of ligands and complexes was evaluated by MTT assay against HCT116 and HeLa tumoral cells. The complexes 3 and 4 showed good activity and selectivity on HCT116 cells. Neither of the tested compounds shows cytotoxic activity against a healthy MRC-5 cell line. Flow cytometry analysis showed the apoptotic death of the HCT116 cells with a cell cycle arrest in the S-phase.

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Design, synthesis and fungicidal activity of isothiazole–thiazole derivatives

Abstract: Compound 6u exhibits ultrahigh fungicidal activity by acting at its potent target PcORP1 and induces systemic acquired resistance by activating the salicylic acid pathway.

Cited by 29 publications

References 37 publications

“ An Efficient One Pot Multicomponent Synthesis of Dihydro Pyrazolyl Bithiazole Derivatives as Potential Anticancer Agents and Their Molecular Docking Studies”

“ An Efficient One Pot Multicomponent Synthesis of Dihydro Pyrazolyl Bithiazole Derivatives as Potential Anticancer Agents and Their Molecular Docking Studies”

Synthesis of Novel Thiazolyl Hydrazine Derivatives and Their Antifungal Activity

Ruthenium(II) Complexes of Isothiazole Ligands: Crystal Structure, HSA/DNA Interactions, Cytotoxic Activity and Molecular Docking Simulations

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