ArticleMolecules (Basel, Switzerland)2020
Synthesis, Crystal Structure, and Biological Activity of a Multidentate Calix[4]arene Ligand Doubly Functionalized by 2-Hydroxybenzeledene-Thiosemicarbazone.
Article in Molecules (Basel, Switzerland), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed.
- Functionalized Calixarenes as Promising Antibacterial Drugs to Face Antimicrobial Resistance.Molecules (Basel, Switzerland) · 2023Review
- Biological investigation ofJournal of enzyme inhibition and medicinal chemistry · 2022Article
- Fluorescein-Labeled Thiacalix[4]arenes as Potential Theranostic Molecules: Synthesis, Self-Association, and Antitumor Activity.Pharmaceutics · 2022Article
- Functionalized graphene oxide nanosheets with folic acid and silk fibroin as a novel nanobiocomposite for biomedical applications.Scientific reports · 2022Article
- Catechol-Containing Schiff Bases on Thiacalixarene: Synthesis, Copper (II) Recognition, and Formation of Organic-Inorganic Copper-Based Materials.Molecules (Basel, Switzerland) · 2021Article
- Antimicrobial Activity of Calixarenes and Related Macrocycles.Molecules (Basel, Switzerland) · 2020Review
- Synthesis of novel calix[4]areneRSC advances · 2020Article
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6 authors.
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Abstract
The design and synthesis of a novel tert-butyl-calix[4]arene functionalized at 1, 3 positions of the lower rim with two terminal 2-hydroxybenzeledene-thiosemicarbazone moieties is reported. The new ligand with multi-dentate chelating properties was fully characterized by several techniques: ESI-Mass spectroscopy, FT-IR, 1H-NMR, and single crystal X-ray diffraction. The solid state structure confirms that the calix[4]arene macrocycle has the expected open cone conformation, with two opposite phenyl rings inclined outwards with large angles. The conformation of the two alkoxythiosemicarbazone arms produces a molecule with a C2 point group symmetry. An interesting chiral helicity is observed, with the two thiosemicarbazone groups oriented in opposite directions like a two-blade propeller. A water molecule is encapsulated in the center of the two-blade propeller through multiple H-bond coordinations. The antibacterial, antifungal, anticancer, and cytotoxic activities of the calix[4]arene-thiosemicarbazone ligand and its metal derivatives (Co2+, Ni2+, Cu2+, and Zn2+) were investigated. A considerable antibacterial activity (in particular against
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