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

References

• Joule JA, Mills K, Heterocyclic chemistry. 5th ed. Chichester, West Sussex: Blackwell Publishing Ltd; 2010.
   Google Scholar
• Časar Z, Synthesis of heterocycles in contemporary medicinal chemistry (topics in heterocyclic chemistry, 44). 1st ed. Cham, Switzerland: Springer; 2016.
   Google Scholar
• Silakari O, Key heterocycle cores for designing multitargeting molecules. 1st ed. Amsterdam, Netherlands: Elsevier; 2018.
   Google Scholar
• Salahuddin Shaharyar M, Mazumder A. Benzimidazoles: a biologically active compounds. Arabian J Chem 2017;10:S157–73.
   Web of Science ®Google Scholar
• Bansal Y, Silakari O. The therapeutic journey of benzimidazoles: a review. Bioorg Med Chem 2012;20:6208–36.
   PubMed Web of Science ®Google Scholar
• Randaccio L, Geremia S, Demitri N, Wuerges J. Vitamin B12: unique metalorganic compounds and the most complex vitamins. Molecules 2010;15:3228–59.
   PubMed Web of Science ®Google Scholar
• Tahlan S, Kumar S, Kakkar S, Narasimhan B. Benzimidazole scaffolds as promising antiproliferative agents: a review. BMC Chemistry 2019;13:66.
   PubMed Web of Science ®Google Scholar
• Prasad PMK, S AK, S R. Potent biological agent benzimidazole – a review. Int J Pharm Pharm Sci 2016;8:22–33.
   Google Scholar
• Yadav G, Ganguly S. Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: a mini-review. Eur J Med Chem 2015;97:419–43.
   PubMed Web of Science ®Google Scholar
• Akhtar W, Faraz Khan M, Verma G, et al. Therapeutic evolution of benzimidazole derivatives in the last quinquennial period. Eur J Med Chem 2017;126:705–53.
   PubMed Web of Science ®Google Scholar
• Siva Kumar BV, Vaidya SD, Kumar RV, et al. Synthesis and anti-bacterial activity of some novel 2-(6-fluorochroman-2-yl)-1-alkyl/acyl/aroyl-1H-benzimidazoles. Eur J Med Chem 2006;41:599–604.
   PubMed Web of Science ®Google Scholar
• Monika G, Sarbjot S, Chander M. Benzimidazole: an emerging scaffold for analgesic and anti-inflammatory agents. Eur J Med Chem 2014;76:494–505.
   PubMed Web of Science ®Google Scholar
• Perin N, Starčević K, Perić M, et al. Synthesis and SAR study of novel amidino 2-substituted benzimidazoles as potential antibacterial agents. Croat Chem Acta 2017;90:145–54.
   Web of Science ®Google Scholar
• Bistrović A, Krstulović L, Stolić I, et al. Synthesis, anti-bacterial and anti-protozoal activities of amidinobenzimidazole derivatives and their interactions with DNA and RNA. J Enzyme Inhib Med Chem 2018;33:1323–34.
   PubMed Web of Science ®Google Scholar
• Danao KR, Mahapatra KD. Recent advances of benzimidazole derivatives as anti-hypertensive agents. In: Biochemistry, biophysics, and molecular chemistry. 1st ed. Washington DC: ACS Publications; 2020.
   Google Scholar
• Sović I, Cindrić M, Perin N, et al. Biological potential of novel methoxy and hydroxy substituted heteroaromatic amides designed as promising antioxidative agents: synthesis, 3D-QSAR analysis, and biological activity. Chem Res Toxicol 2019;32:1880–92.
   PubMed Web of Science ®Google Scholar
• Racané L, Cindrić M, Zlatar I, et al. Preclinical in vitro screening of newly synthesised amidino substituted benzimidazoles and benzothiazoles. J Enzyme Inhib Med Chem 2021;36:163–74.
   PubMed Web of Science ®Google Scholar
• Hranjec M, Kralj M, Piantanida I, et al. Novel cyano- and amidino-substituted derivatives of styryl-2-benzimidazoles and benzimidazo[1,2-a]quinolines. Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation, part 3. J Med Chem 2007;50:5696–711.
   PubMed Web of Science ®Google Scholar
• Cindrić M, Perić M, Kralj M, et al. Antibacterial and antiproliferative activity of novel 2-benzimidazolyl- and 2-benzothiazolyl-substituted benzo[b]thieno-2-carboxamides. Mol Divers 2018;22:637–46.
   PubMed Web of Science ®Google Scholar
• Tireli M, Starčević K, Martinović T, et al. Antioxidative and antiproliferative activities of novel pyrido[1,2-a]benzimidazoles. Mol Divers 2017;21:201–10.
   PubMed Web of Science ®Google Scholar
• Perin N, Nhili R, Cindrić M, et al. Amino substituted benzimidazo[1,2-a]quinolines: Antiproliferative potency, 3D QSAR study and DNA binding properties. Eur J Med Chem 2016;122:530–45.
   PubMed Web of Science ®Google Scholar
• Perin N, Bobanović K, Zlatar I, et al. Antiproliferative activity of amino substituted benzo[b]thieno[2,3-b]pyrido[1,2-a]benzimidazoles explored by 2D and 3D cell culture system. Eur J Med Chem 2017;125:722–35.
   PubMed Web of Science ®Google Scholar
• Cindrić M, Jambon S, Harej A, et al. Novel amidino substituted benzimidazole and benzothiazole benzo[b]thieno-2-carboxamides exert strong antiproliferative and DNA binding properties. Eur J Med Chem 2017;136:468–79.
   PubMed Web of Science ®Google Scholar
• Perin N, Hok L, Beč A, et al. N-substituted benzimidazole acrylonitriles as in vitro tubulin polymerization inhibitors: synthesis, biological activity and computational analysis. Eur J Med Chem 2021;211:113003.
   PubMed Web of Science ®Google Scholar
• Hranjec M, Starčević K, Kraljević Pavelić S, et al. Synthesis, spectroscopic characterization and antiproliferative evaluation in vitro of novel Schiff bases related to benzimidazoles. Eur J Med Chem 2011;46:2274–9.
   PubMed Web of Science ®Google Scholar
• Cindrić M, Sović I, Mioč M, et al. Experimental and computational study of the antioxidative potential of novel nitro and amino substituted benzimidazole/benzothiazole-2-carboxamides with antiproliferative activity. Antioxidants 2019;8:477–99.
   Web of Science ®Google Scholar
• Cindrić M, Sović I, Martin-Kleiner I, et al. Synthesis, antioxidative and antiproliferative activity of methoxy amidino substituted benzamides and benzimidazoles. Med Chem Res 2017;26:2024–37.
   Web of Science ®Google Scholar
• Sosa V, Moliné T, Somoza R, et al. Oxidative stress and cancer: an overview. Ageing Res Rev 2013;12:376–90.
   PubMed Web of Science ®Google Scholar
• Imran M, Al Kury LT, Nadeem H, et al. Benzimidazole containing acetamide derivatives attenuate neuroinflammation and oxidative stress in ethanol-induced neurodegeneration. Biomolecules 2020;10:108.
   PubMed Web of Science ®Google Scholar
• Vomund S, Schäfer A, Parnham M, et al. Nrf2, the master regulator of anti-oxidative responses. Int J Mol Sci 2017;18:2772.
   PubMed Web of Science ®Google Scholar
• Liu L, Shen LY, Hu Y, Lu YF. Antiviral effect of 7-(4-benzimidazole-butoxy)-coumarin on rhabdoviral clearance via Nrf2 activation regulated by PKCα/β phosphorylation. Fish Shellfish Immunol 2018;83:386–96.
   PubMed Web of Science ®Google Scholar
• Cruciani G, Crivori P, Carrupt PA, Testa B. Molecular fields in quantitative structure-permeation relationships: the VolSurf approach. J Mol Struct THEOCHEM 2000;503:17–30.
   Web of Science ®Google Scholar
• Cruciani G, Pastor M, Guba W. VolSurf: a new tool for pharmacokinetic optimization of lead compounds. Eur J Pharm Sci 2000;11:S29–S39.
   PubMed Web of Science ®Google Scholar
• Bryan HK, Olayanju A, Goldring CE, Park K. The Nrf2 cell defence pathway: Keap1-dependent and -independent mechanisms of regulation. Biochem Pharmacol 2013;85:705–17.
   PubMed Web of Science ®Google Scholar
• Li Y, Paonessa JD, Zhang Y. Mechanism of chemical activation of Nrf2. PloS One 2012;7:e35122.
   PubMed Web of Science ®Google Scholar
• Jing P, Zhao SJ, Jian WJ, et al. Quantitative studies on structure-DPPH• scavenging activity relationships of food phenolic acids. Molecules 2012;17:12910–24.
   PubMed Web of Science ®Google Scholar
• Spiegel M, Kapusta K, Kołodziejczyk W, et al. Antioxidant activity of selected phenolicacids-ferric reducing antioxidant power assay and QSAR analysis of the structural features. Molecules 2020;25:3088.
   PubMed Web of Science ®Google Scholar