Semicarbazone, thiosemicarbazone tailed isoxazoline-pyrazole: synthesis, DFT, biological and computational assessment.

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  • Additional Information
    • Source:
      Publisher: Taylor & Francis Country of Publication: England NLM ID: 101511162 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1756-8927 (Electronic) Linking ISSN: 17568919 NLM ISO Abbreviation: Future Med Chem Subsets: MEDLINE
    • Publication Information:
      Publication: 2024- : [Milton Park, Oxfordshire] : Taylor & Francis
      Original Publication: London : Future Science, 2009-
    • Subject Terms:
      Thiosemicarbazones*/chemistry ; Thiosemicarbazones*/pharmacology ; Thiosemicarbazones*/chemical synthesis ; Antineoplastic Agents*/pharmacology ; Antineoplastic Agents*/chemistry ; Antineoplastic Agents*/chemical synthesis ; Semicarbazones*/chemistry ; Semicarbazones*/pharmacology ; Semicarbazones*/chemical synthesis ; Pyrazoles*/chemistry ; Pyrazoles*/pharmacology ; Pyrazoles*/chemical synthesis ; Density Functional Theory* ; Molecular Docking Simulation* ; Drug Screening Assays, Antitumor* ; Apoptosis*/drug effects; Humans ; Cell Line, Tumor ; Isoxazoles/chemistry ; Isoxazoles/pharmacology ; Isoxazoles/chemical synthesis ; Molecular Structure ; Cell Proliferation/drug effects ; Structure-Activity Relationship
    • Abstract:
      Aim: A series of semicarbazone and thiosemicarbazone-tailed hybrids comprising pyrazole and acetylisoxazoline were prepared from (R)-carvone and characterized by technique spectroscopies Nuclear Magnetic Resonance (NMR), IR and High-Resolution Mass Spectrometry. Density Functional Theory (DFT) determined the structural parameters. Their cytotoxic activity was evaluated in vitro against four human cancer cell lines. Methods & results: All the studied semi and thiosemicarbazone demonstrate a promising potential as anticancer agents. The mechanism of action of these compounds involves apoptosis in HT-1080 cells, supported by an increase in the level of caspase-3/7 activity, which also arrests the cell cycle in the G0/G1 phase. Molecular docking studies were performed to establish the potential of the most active compounds 4a and 5a . ADMET analysis showed appropriate pharmacokinetic properties, allowing structure prediction for anticancer activity.
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    • Contributed Indexing:
      Keywords: caspase-3/7; in silico; molecular docking; semicarbazone; thiosemicarbazone
      Local Abstract: [plain-language-summary] [Box: see text].
    • Accession Number:
      0 (Thiosemicarbazones)
      0 (Antineoplastic Agents)
      0 (Semicarbazones)
      0 (Pyrazoles)
      0 (Isoxazoles)
      3QD5KJZ7ZJ (pyrazole)
    • Publication Date:
      Date Created: 20240918 Date Completed: 20241112 Latest Revision: 20241115
    • Publication Date:
      20250114
    • Accession Number:
      PMC11559363
    • Accession Number:
      10.1080/17568919.2024.2394011
    • Accession Number:
      39291612