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Pregled bibliografske jedinice broj: 1194061

Design, synthesis, biological evaluation and QSAR analysis of novel N-substituted benzimidazole derived carboxamides


Beč, Anja; Mioč, Marija; Bertoša, Branimir; Kos, Marija; Debogović, Patricia; Kralj, Marijeta; Starčević, Kristina; Hranjec, Marijana
Design, synthesis, biological evaluation and QSAR analysis of novel N-substituted benzimidazole derived carboxamides // Journal of enzyme inhibition and medicinal chemistry, 37 (2022), 1; 1327-1339 doi:10.1080/14756366.2022.2070910 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1194061 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Design, synthesis, biological evaluation and QSAR analysis of novel N-substituted benzimidazole derived carboxamides

Autori
Beč, Anja ; Mioč, Marija ; Bertoša, Branimir ; Kos, Marija ; Debogović, Patricia ; Kralj, Marijeta ; Starčević, Kristina ; Hranjec, Marijana

Izvornik
Journal of enzyme inhibition and medicinal chemistry (1475-6366) 37 (2022), 1; 1327-1339

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
antioxidant activity ; antiproliferative activity ; benzimidazoles ; carboxamides ; QSAR ; ROS

Sažetak
As a result of our previous research focused on benzimidazole derivatives with potent antioxidative and antiproliferative activity, herein we present design, synthesis, QSAR analysis and biological activity of novel N-substituted benzimidazole derived carboxamides. The targeted carboxamides were designed in order to study the influence of the number of methoxy groups, the type of the substituent placed at the N atom of benzimidazole core as well as the type of the substituent placed at the benzimidazole core on biological activity. The most promising derivatives with pronounced antioxidative activity were unsubstituted derivative 28 (IC50 ≈ 3.78 mM, 538.81 mmolFe2+/mmolC) and dimetoxy substituted compound 34 (IC50 ≈ 5.68 mM, 618.10 mmolFe2+/mmolC) bearing methyl group at the N atom of benzimidazole core. On the other hand, trimethoxy substituted compound 43 and unsubstituted compound 40 both bearing isobutyl side chain at N atom at benzimidazole core showed strong activity in nanomolar concentrations against HCT116 (IC50 ≈ 0.6 µM, both) and H 460 cells (IC50 ≈ 2.5 µM and 0.4 µM, respectively), while being less cytotoxic toward non-tumour cell line HEK 293. In addition, antioxidative activity in cell generally confirmed relatively modest antioxidant capacity obtained in DPPH/FRAP assays of derivatives 34 and 40. Additionally, the 3D– QSAR models were generated to explore molecular properties that have the highest influence on antioxidative activity of studied compounds.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekti:
HRZZ-IP-2018-01-4379 - Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensa (AntioxPot) (Hranjec, Marijana, HRZZ - 2018-01) ( POIROT)
HRZZ-IP-2016-06-3163 - Lipidi hrane, spol i dob u patogenezi metaboličkog sindroma (DietMetSyn) (Starčević, Kristina, HRZZ - 2016-06) ( POIROT)

Ustanove:
Veterinarski fakultet, Zagreb,
Institut "Ruđer Bošković", Zagreb,
Prirodoslovno-matematički fakultet, Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Poveznice na cjeloviti tekst rada:

doi www.tandfonline.com dx.doi.org

Citiraj ovu publikaciju:

Beč, Anja; Mioč, Marija; Bertoša, Branimir; Kos, Marija; Debogović, Patricia; Kralj, Marijeta; Starčević, Kristina; Hranjec, Marijana
Design, synthesis, biological evaluation and QSAR analysis of novel N-substituted benzimidazole derived carboxamides // Journal of enzyme inhibition and medicinal chemistry, 37 (2022), 1; 1327-1339 doi:10.1080/14756366.2022.2070910 (međunarodna recenzija, članak, znanstveni)
Beč, A., Mioč, M., Bertoša, B., Kos, M., Debogović, P., Kralj, M., Starčević, K. & Hranjec, M. (2022) Design, synthesis, biological evaluation and QSAR analysis of novel N-substituted benzimidazole derived carboxamides. Journal of enzyme inhibition and medicinal chemistry, 37 (1), 1327-1339 doi:10.1080/14756366.2022.2070910.
@article{article, author = {Be\v{c}, Anja and Mio\v{c}, Marija and Berto\v{s}a, Branimir and Kos, Marija and Debogovi\'{c}, Patricia and Kralj, Marijeta and Star\v{c}evi\'{c}, Kristina and Hranjec, Marijana}, year = {2022}, pages = {1327-1339}, DOI = {10.1080/14756366.2022.2070910}, keywords = {antioxidant activity, antiproliferative activity, benzimidazoles, carboxamides, QSAR, ROS}, journal = {Journal of enzyme inhibition and medicinal chemistry}, doi = {10.1080/14756366.2022.2070910}, volume = {37}, number = {1}, issn = {1475-6366}, title = {Design, synthesis, biological evaluation and QSAR analysis of novel N-substituted benzimidazole derived carboxamides}, keyword = {antioxidant activity, antiproliferative activity, benzimidazoles, carboxamides, QSAR, ROS} }
@article{article, author = {Be\v{c}, Anja and Mio\v{c}, Marija and Berto\v{s}a, Branimir and Kos, Marija and Debogovi\'{c}, Patricia and Kralj, Marijeta and Star\v{c}evi\'{c}, Kristina and Hranjec, Marijana}, year = {2022}, pages = {1327-1339}, DOI = {10.1080/14756366.2022.2070910}, keywords = {antioxidant activity, antiproliferative activity, benzimidazoles, carboxamides, QSAR, ROS}, journal = {Journal of enzyme inhibition and medicinal chemistry}, doi = {10.1080/14756366.2022.2070910}, volume = {37}, number = {1}, issn = {1475-6366}, title = {Design, synthesis, biological evaluation and QSAR analysis of novel N-substituted benzimidazole derived carboxamides}, keyword = {antioxidant activity, antiproliferative activity, benzimidazoles, carboxamides, QSAR, ROS} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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  • CA Search (Chemical Abstracts)


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