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. 2020 Sep 21;25(18):4324.
doi: 10.3390/molecules25184324.

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

Ernestine Nicaise Djuidje  1 , Elisa Durini  1 , Sabrina Sciabica  2 , Elena Serra  3 , Jan Balzarini  4 , Sandra Liekens  4 , Stefano Manfredini  1 , Silvia Vertuani  1 , Anna Baldisserotto  1
Affiliations

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

Ernestine Nicaise Djuidje et al. Molecules. .

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.

Keywords: UV-filter; benzimidazole; melanoma.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Lead compound.
Scheme 1
Scheme 1
Synthesis of 3,4-diamino-benzene sulfonic acid, sulfate salt. Reagents and conditions: (i) H2SO4, reflux, 24 h.
Scheme 2
Scheme 2
Synthesis of 7–9 2-substituted benzimidazole-5-sulfonic acid. Reagents and conditions: (i) EtOH, NaHSO3 in H2O, reflux.
Scheme 3
Scheme 3
Synthesis of 10–15 benzimidazole derivatives. Reagents and conditions: (i) EtOH, NaHSO3 in H2O, reflux.
Figure 2
Figure 2
Transmittance profiles of formulations studied containing the benzimidazole derivatives 10 (panel A), 11 (panel B) and 12 (panel C) (1% w/w).
See this image and copyright information in PMC

References

    1. Afaq F., Adhami V.M., Mukhtar H. Photochemoprevention of ultraviolet B signalling and photocarcinogenesis. Mutat. Res. 2005;571:153–173. doi: 10.1016/j.mrfmmm.2004.07.019. - DOI - PubMed
    1. Wondrak G.T., Jacobson M.K., Jacobson E.L. Endogenous UVA photosensitizers: Mediators of skin photodamage and novel targets for skin photoprotection. Photochem. Photobiol. Sci. 2006;5:215–237. doi: 10.1039/B504573H. - DOI - PubMed
    1. Saewan N., Jimtaisong A. Photoprotection of natural flavonoids. J. Appl. Pharm. Sci. 2013;3:129–141.
    1. Laleh Farajia S.S. Synthesis of novel benzimidazole and benzothiazole derivatives bearing a 1,2,3-triazole ring system and their acetylcholinesterase inhibitory activity. J. Chem. Res. 2017;41:30–35. doi: 10.3184/174751917X14836231670980. - DOI
    1. Joule J.A., Mills K. Heterocyclic Chemistry. 5th ed. Wiley India Pvt. Ltd.; New Delhi, India: 2010. pp. 503–506.

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