ArticleMolecular diversity2020
Synthesis and anthelmintic activity of benzopyrano[2,3-c]pyrazol-4(2H)-one derivatives.
Article in Molecular diversity, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 21 citations in OpenAlex.
- Green synthesis of diazo-pyrazole derivatives and their application as functional disperse dyes for dyeing polyester fabric.Scientific reports · 2026Article
- Recent Synthetic Advances in C-H/N-H Functionalization of 1H-Pyrazoles: Diverse Strategies Across Variously Substituted Scaffolds.Chemical record (New York, N.Y.) · 2025Review
- Multicomponent Synthesis of New Fluorescent Boron Complexes Derived from 3-Hydroxy-1-phenyl-1Molecules (Basel, Switzerland) · 2024Article
- Advanced screening methods for assessing motility and hatching in plant-parasitic nematodes.Plant methods · 2024Article
- Synthesis and Characterization of New Pyrano[2,3-Molecules (Basel, Switzerland) · 2023Article
- Pyrazole-based lamellarin O analogues: synthesis, biological evaluation and structure-activity relationships.RSC advances · 2023Article
- Convenient Synthesis ofMolecules (Basel, Switzerland) · 2022Article
- Synthesis and Characterization of Novel Heterocyclic Chalcones from 1-Phenyl-1Molecules (Basel, Switzerland) · 2022Article
- Anthelmintic Effect ofMolecules (Basel, Switzerland) · 2022Article
- Synthesis and Antiproliferative Activity of 2,4,6,7-Tetrasubstituted-2Molecules (Basel, Switzerland) · 2021Article
- Convenient Synthesis of Pyrazolo[4',3':5,6]pyrano[4,3-Molecules (Basel, Switzerland) · 2021Article
- Drug discovery: Insights from the invertebrate Caenorhabditis elegans.Pharmacology research & perspectives · 2021Review
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Authors and funding
9 authors at 4 institutions in 3 countries.
Funding
Abstract
A series of benzopyrano[2,3-c]pyrazol-4(2H)-one derivatives were synthesized from readily available 1-phenyl- and 1-methyl-1H-pyrazol-3-ols by sequentially employing O-acylation, Fries rearrangement and potassium carbonate-induced cyclization. The anthelmintic properties of the obtained compounds were investigated in vivo in a model nematode, Caenorhabditis elegans. Five compounds, namely 2-phenyl[1]benzopyrano[2,3-c]pyrazol-4(2H)-one 33 and its 7-fluoro, 7-chloro-, 7-bromo- and 8-fluoro-analogues, 36, 38, 40 and 43, respectively, altered the development of C. elegans. While the activities of 33 and 43 were rather modest, compounds 36, 38 and 40 inhibited the growth of the worms at concentrations of approximately 1-3 µM. At these concentrations, the compounds did not kill the worms, but they strongly inhibited their development, with the majority of larvae never progressing past the L1 stage. Moreover, testing in non-cancer human cell lines showed that, with exception of 7-bromo derivative 40, the active compounds have favourable toxicity profiles.
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