Synthesis, Reactions and Biological Evaluation of Some New Naphtho[2,1-b]furan Derivatives Bearing a Pyrazole Nucleus

El‐Wahab, Ashraf Hassan Fekry Abd; Al-Fifi, Zarrag; Bedair, A. H.; Ali, Fawzy M.; Halawa, Ahmed H.; El‐Agrody, Ahmed M.

doi:10.3390/molecules16010307

Cited by 23 publications

(4 citation statements)

References 15 publications

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“…Pyrazole derivatives play an important role in the development of pesticides and medicines, which have become hot topics in recent years. Dozens of pyrazole products are available and widely used as fungicides, antiviral agents, analgesic agents, insecticides and herbicides [15][16][17]. In order to discover novel active compounds for use in agriculture, we sought to combine the active structures of thiourea and pyrazole to design and synthesize a class of novel pyrazole acyl thiourea derivatives.…”

Section: Open Accessmentioning

confidence: 99%

Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives

Shi

Chen

et al. 2012

Molecules

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Sixteen novel pyrazole acyl thiourea derivatives 6 were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl chloride intermediates 4 were first generated in four steps through cyclization, formylation, oxidation and acylation. Thess were then reacted with ammonium thiocyanate in the presence of PEG-400 to afford 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl isothiocyanates 5. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds. The synthesized compound were unequivocally characterized by IR, 1 H-NMR, 13 C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica and anti-TMV activity in preliminary antifungal activity tests.

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Section: Open Accessmentioning

confidence: 99%

Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives

Shi

Chen

et al. 2012

Molecules

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“…Thus, the reaction of compound 83a with phenacyl bromide and/or chloroacetone in refluxing ethanol in the presence of sodium acetate afforded the thiazole derivatives (84a,b), respectively, while with ethyl bromoacetate afforded thiazolidin-4-one (85). Condensation of thiazolidin-4-one (85) with p-methoxybenzaldehyde and/or pchlorobenzaldehyde in ethanol containing piperidine as a base gave arylidene derivatives (86a,b), respectively (Scheme 19) [55].…”

Section: From 2-styrylfuranmentioning

confidence: 99%

Synthesis, reactions and applications of naphthofurans: A review

Abdelwahab

Fekry

2021

Eur J Chem

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Considering the highly important biological and medicinal properties of naphthofurans, the synthesis of these heterocycles has attracted the interest of medicinal and organic chemists. This review aims to describe the different strategies developed so far for the synthesis of naphthofurans and their applications and the literature reports for the period of 2000 to early 2020. After a brief introduction of the types of naphthofurans and their biological activities, the different synthetic approaches such as chemical and photochemical, methods are described and organized on the basis of the catalysts and the other reagents employed in the syntheses. Some of the reactions have been applied successfully to the synthesis of biologically important compounds.

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“…Recently, the synthesis of naphtho [1,2-b]furans using In(OTf) 3 and Fe-Pd bimetallic nanoparticlescatalyzed reactions was reported [29,30]. Although a number of methods for the synthesis of these compounds have been reported, there have been few biological evaluations of naphtho [1,2-b]furans [31][32][33][34][35][36]. In particular, there are no reports of a biological study of naphtho [1,2-b]furan-3-carboxamides.…”

Section: Introductionmentioning

confidence: 98%

$$\hbox {Re}_{2}\hbox {O}_{7}$$ Re 2 O 7 -catalyzed formal [3 + 2] cycloaddition for diverse naphtho[1,2-b]furan-3-carboxamides and their biological evaluation

2015

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Diverse naphtho[1,2-b]furan-3-carboxamide derivatives 12a-12q were synthesized in high yield via the novel Re2O7-catalyzed formal [3 + 2] cycloaddition of 1,4-naphthoquinones with β-ketoamides as the key step. This methodology offers several advantages, such as environmentally benign character, the use of a mild catalyst, high yields, and ease of handling. The synthesized compounds were screened for their tyrosinase inhibitory, antioxidant, and antibacterial activities. The results showed that compound 12c exhibited excellent tyrosinase inhibitory activity with an IC50 of 13.48 μg/mL, which is comparable to that of kojic acid (IC50 = 19.45 μg/mL). Compounds 12a, 12b, and 12i displayed moderate antioxidant activities in a DPPH assay. Compound 12m showed good activity against S. aureus (MIC = 16 μg/mL), and compound 12p was found to be active against E. coli (MIC = 16 μg/mL).

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Synthesis, Reactions and Biological Evaluation of Some New Naphtho[2,1-b]furan Derivatives Bearing a Pyrazole Nucleus

Cited by 23 publications

References 15 publications

Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives

Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives

Synthesis, reactions and applications of naphthofurans: A review

$$\hbox {Re}_{2}\hbox {O}_{7}$$ Re 2 O 7 -catalyzed formal [3 + 2] cycloaddition for diverse naphtho[1,2-b]furan-3-carboxamides and their biological evaluation

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