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Cited by 19Synthesis and biological activitySynthesis and Characterization of Heterocyclic CompoundsSynthesis and Biological Evaluation

Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System

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Djuidje, Ernestine Nicaise, Durini, Elisa, Sciabica, Sabrina, Serra, Elena, Balzarini, Jan, Liekens, Sandra, Manfredini, Stefano, Vertuani, Silvia +1 more·2020·Molecules
DOI 10.3390/molecules25184324PMC PMC7570844
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Abstract

In the search for scaffolds for multifunctional compounds we investigated the structure activity relationship of a class of benzimidazole derivatives bearing 5-membered ring. The newly synthesized and the already known compounds were divided into three classes that present different substituent at 5 position of the benzimidazole ring (-H, -COOH or –SO3H) and different heterocycle at position 2 (thiophene, furan or pyrrole). All the derivatives were synthesized and tested to determine their photoprotective profile against UV rays, in vitro antioxidant capacity against different radicals (DPPH and FRAP test), antifungal inhibitory activity (dermatophytes and Candida albicans), antiviral and antiproliferative activity. A Structure-Activity Relationship study indicated compound 10, bearing a pyrrole heterocycle on the benzimidazole ring, as the best multifunctional derivative of the series and as potential candidate for the development of drugs especially in case of melanoma.

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  • Among 5-membered ring-benzimidazole derivatives, the thiophene derivative 89 was the most photostable, followed by pyrrole derivative 87 and furan derivative 88.

    “Among these, the most photostable was the thiophene derivative 89, followed by pyrrole derivative 87, and the furan derivative 88 [135].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [135]

    Section 2.2.3 states the photostability order as thiophene > pyrrole > furan, supporting the ranking. The source identifies the tested compounds as 12, 10, and 11, respectively; our copy does not establish whether these correspond to derivatives 89, 87, and 88 in the citing document. (LLM, conf=0.85)

    Experimental — accuracy not yet measured

  • New 5-membered ring-benzimidazole derivatives (87-89) with pyrrole (87), furan (88), and thiophene (89) moieties were the most promising regarding antioxidant, photostability, and photoprotective activities.

    “Additionally, new 5-membered ring-benzimidazole derivatives (87–89) were also prepared, being compounds with pyrrole (87), furan (88), and thiophene (89) moieties which were the most promising regarding their antioxidant, photostability, and photoprotective activities [135].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [135]

    The Results and Discussion sections (pp. not supplied) identify the pyrrole, furan, and thiophene derivatives and report promising properties across the group. But they do not support calling all three promising for each listed activity: the furan compound was photoinstable, and the antioxidant findings favored the pyrrole and furan compounds rather than thiophene. The paper numbers these compounds 10–12; 87–89 appear to be the citing document’s numbering. (LLM, conf=0.90)

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Authors
Djuidje, E. N., Durini, E., Sciabica, S., Serra, E., Balzarini, J., Liekens, S., Manfredini, S., Vertuani, S., & Baldisserotto, A.
Affiliations
  • University of Ferrara (IT)
  • Aptuit (Italy) (IT)
  • Rega Institute for Medical Research (BE)
Corresponding author
Baldisserotto, Anna
ORCID
Venue
Molecules
Publisher
MDPI AG
Published
2020-09-21
Volume
25
Issue
18
Pages
4324
ISSN
1420-3049 (ISSN-L)
DOI
10.3390/molecules25184324
PMC
PMC7570844
OpenAlex
W3087716092
Cited by
19
References
35
Citations by year
2026: 1 · 2025: 4 · 2023: 6 · 2022: 5 · 2021: 3
FWCI
1.36
Type
journal article
Language
en
Open access
Licence
Locations
  • Molecules (publishedVersion, cc-by)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • Lirias (KU Leuven) (submittedVersion, cc-by)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
  • Institutional Research Information System University of Ferrara (University of Ferrara) (submittedVersion, cc-by)
Funders
  • PRIN 2017 (Prot. No. 2010E84AA4_002)
  • Grant FAR 2019 (Anna Baldisserotto)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Characterization of Heterocyclic Compounds
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Biological Evaluation
Keywords
benzimidazole derivatives, structure-activity relationship, photoprotection, ultraviolet radiation, antioxidant activity, antifungal activity, dermatophytes, Candida albicans, antiviral activity, antiproliferative activity, melanoma, thiophene, furan, carboxylic acid substituents
MeSH terms
Antifungal Agents, Antineoplastic Agents, Antiviral Agents, Benzimidazoles, Candida albicans, Humans, Radiation-Protective Agents, Skin, Structure-Activity Relationship, Ultraviolet Rays, Free Radical Scavengers, Cell Line, Tumor, Cell Proliferation

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