{
  "abstract": "Benzimidazole-based Schiff bases, (Z)-2-(((1H-benzo[d]imidazol-2-yl)imino)methyl)phenol monohydrate (HL1·H₂O) and (Z)-1-(((1H-benzo[d]imidazol-2-yl)imino)methyl)naphthalen-2-ol monohydrate (HL2·H₂O) were synthesized and characterized by IR, UV-vis, EI-mass, ¹H NMR spectroscopy, and single-crystal X-ray diffraction studies. Molecular structure determination suggested the presence of crystal water in the unit cell of each compound. The structure adopted a usual enol-imine form, with an intramolecular hydrogen bond between the phenolate-oxygen and the imine-nitrogen atoms. Supramolecular packing indicated that the structure was assembled and stabilized by several significant intermolecular non-covalent interactions between symmetrically related lattice water and the molecules, as supported by quantitative Hirshfeld surface analyses. DSC analyses revealed an irreversible phase transition from solid-crystal to isotropic liquid. Computational modeling by DFT/TD-DFT supported the experimental results of the molecular and electronic structures of the compounds. Molecular orbital (MO) calculations revealed a relatively lower HOMO-LUMO energy gap for HL2 (ΔE g = 2.41 eV) compared with HL1 (2.65 eV), suggesting the former had enhanced charge delocalization due to the extended π-electrons conjugation system, in parallel with molecular electrostatic potential (MEP) surface maps. Biological activities were assessed using cytotoxicity, antioxidant, α-amylase, and antibacterial tests. HL1 possessed more pronounced cytotoxic effects on cervical cancer (HeLa) cells (IC₅₀ = 75.53 ± 3.10 µM) than HL2 (IC₅₀ = 462.61 ± 5.24 µM). DPPH radical-scavenging studies revealed moderate antioxidant activity for HL2 (IC₅₀ = 168 ± 4 µM) and weaker activity for HL1 (IC₅₀ = 233 ± 5 µM) compared with the standard ascorbic acid (IC₅₀ = 106 ± 1 µM). HL1 showed moderately the inhibit α-amylase enzyme (IC₅₀ = 399 ± 2.7 µM), while no inhibitory activity for HL2 was noted. Both compounds were moderately active against selected bacterial strains in a concentration-dependent manner. Computational analyses on Escherichia coli BepA metalloprotease (6SAR) and human DNA topoisomerase IIα (5GWK) using molecular docking exhibited favorable predicted protein-ligand interactions, involving hydrogen-bonding, hydrophobic and π-stacking interactions. HL1 had a more favorable predicted binding affinity towards BepA metalloprotease, whereas HL2 had a more favorable predicted binding affinity towards human DNA topoisomerase IIα, which was associated with enhanced hydrophobic interactions.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry, Jahangirnagar University Dhaka 1342 Bangladesh enamullah@juniv.edu.",
    "Hajee Mohammad Danesh Science & Technology University (HSTU) Dinajpur Bangladesh.",
    "Department of Pharmacy, Jahangirnagar University Dhaka 1342 Bangladesh.",
    "Department of Chemistry, University of Manitoba Winnipeg Manitoba R3T 2N2 Canada.",
    "Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität Düsseldorf Universitätsstr. 1 D-40225 Düsseldorf Germany."
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 8,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Mohammed Enamullah",
      "orcid": "0000-0002-6905-3210"
    },
    {
      "affs": [
        0
      ],
      "name": "Imdadul Haque",
      "orcid": "0000-0003-0550-8797"
    },
    {
      "affs": [
        2
      ],
      "name": "Taslima Akter"
    },
    {
      "affs": [
        0
      ],
      "name": "Tarek Aziz",
      "orcid": "0009-0003-2034-7159"
    },
    {
      "affs": [
        3
      ],
      "name": "Amelia Kacperkiewicz",
      "orcid": "0009-0004-3689-4250"
    },
    {
      "affs": [
        3
      ],
      "name": "David E Herbert",
      "orcid": "0000-0001-8190-2468"
    },
    {
      "affs": [
        4
      ],
      "name": "Takin Haj Hassani Sohi",
      "orcid": "0000-0001-6902-077X"
    },
    {
      "affs": [
        4
      ],
      "name": "Christoph Janiak",
      "orcid": "0000-0002-6288-9605"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/d0q02ae0v9h3z.bib",
  "cited_by": 0,
  "doi": "10.1039/d6ra07753f",
  "fulltext_url": "https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13717624/?tool=EBI",
  "id": "d0q02ae0v9h3z",
  "issns": [
    "2046-2069"
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  "landing_url": "https://europepmc.org/article/PMC/PMC13717624",
  "language": "eng",
  "licence": "CC-BY-NC",
  "licence_label": "CC BY-NC",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by-nc/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "heading",
      "Chemistry"
    ],
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      "openalex",
      "1604|Crystal structures of chemical compounds"
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  "openalex": "W7224394010",
  "pdf_url": "https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13717624/pdf/?tool=EBI",
  "pmcid": "PMC13717624",
  "pmid": "42959800",
  "published": "2026-10-29",
  "publisher": "Royal Society of Chemistry",
  "ris": "https://research.draconitic.com/paper/d0q02ae0v9h3z.ris",
  "sources": [
    {
      "first_seen": "2026-10-31T00:20:37Z",
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    {
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      "native_id": "PMC13717624",
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      "url": "https://doi.org/10.1039/d6ra07753f"
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  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1604|Crystal structures of chemical compounds",
      "subfield": "inorganic"
    }
  ],
  "title": "Synthesis, molecular structure, supramolecular and biological evaluation of benzimidazole-based Schiff bases",
  "title_text": "Synthesis, molecular structure, supramolecular and biological evaluation of benzimidazole-based Schiff bases",
  "type": "peer-reviewed",
  "updated_at": "2026-11-02T12:21:54Z",
  "url": "https://research.draconitic.com/paper/d0q02ae0v9h3z",
  "venue": "RSC advances",
  "versions": []
}