Efficient and simple synthesis of novel 1,2,3-triazolyl-linked benzimidazolone, molecular docking and evaluation of their antimicrobial activity

References

• Taherian, E.; Khodarahmi, G.; Khajouei, M. R.; Hassanzadeh, F.; Dana, N. Synthesis and Cytotoxic Evaluation of Novel Quinozalinone Derivatives with Substituted Benzimidazole in Position 3. Res. Pharm. Sci. 2019, 14, 247–254. DOI: 10.4103/1735-5362.258493.
   PubMed Web of Science ®Google Scholar
• Song, D.; Ma, S. Recent Development of Benzimidazole-Containing Antibacterial Agents. ChemMedChem 2016, 11, 646–659. DOI: 10.1002/cmdc.201600041.
   PubMed Web of Science ®Google Scholar
• Xu, N.; Yang, C.; Gan, X.; Wei, S.; Ji, Z. Synthesis of 1-Isopropyl-3-Acyl-5-Methyl-Benzimidazolone Derivatives and Their Antimicrobial Activity. Int. J. Mol. Sci. 2013, 14, 6790–6804. DOI: 10.3390/ijms14046790.
   PubMed Web of Science ®Google Scholar
• Khodarahmi, G. A.; Chen, C. S.; Hakimelahi, G. H.; Tseng, C. T.; Chern, J. W. Design, Synthesis, and Cytotoxicity of 4-Sulfonamide Substituted Benzamidobenzimidazolones and an Acyl Benzimida-Zolone. JICS. 2005, 2, 124–134. DOI: 10.1007/BF03247203.
   Web of Science ®Google Scholar
• Nacak, S.; Doğruer, D. S.; Şahin, M. F. Synthesis and Antinociceptive Activity of (1-Benzyl-2(3H)-Benzimidazolon-3-yl) Acetic Acid Derivatives. II Farmaco 1999, 54, 768–772. DOI: 10.1016/S0014-827X(99)00100-7.
   PubMedGoogle Scholar
• Nale, D. B.; Bhanage, B. M. Copper-Catalyzed Efficient Synthesis of a 2-Benzimidazolone Scaffold from 2-Nitroaniline and Dimethyl Carbonate via a Hydrosilylation Reaction. Green Chem. 2015, 17, 2480–2486. DOI: 10.1039/C4GC02408G.
   Web of Science ®Google Scholar
• Zhang, P.; Terefenko, E. A.; Wrobel, J.; Zhang, Z.; Zhu, Y.; Cohen, J.; Marschke, K. B.; Mais, D. Synthesis and Progesterone Receptor Antagonist Activities of 6-Aryl Benzimidazolones and Benzothiazolones. Bioorg. Med. Chem. Lett. 2001, 11, 2747–2750. DOI: 10.1016/S0960-894X(01)00554-6.
   PubMed Web of Science ®Google Scholar
• Omura, H.; Kawai, M.; Shima, A.; Iwata, Y.; Ito, F.; Masuda, T.; Ohta, A.; Makita, N.; Omoto, K.; Sugimoto, H.; et al. Ando K. The SAR Studies of Novel CB2 Selective Agonists, Benzimidazolone Derivatives. Bioorg. Med. Chem. Lett. 2008, 18, 3310–3314. DOI: 10.1016/j.bmcl.2008.04.032.
   PubMed Web of Science ®Google Scholar
• Shingalapur, R. V.; Hosamani, K. M.; Keri, R. S.; Hugar, M. H. Derivatives of Benzimidazole Pharmacophore: Synthesis, Anticonvulsant, Antidiabetic and DNA Cleavage Studies. Eur. J. Med. Chem. 2010, 45, 1753–1759. DOI: 10.1016/j.ejmech.2010.01.007.
   PubMed Web of Science ®Google Scholar
• Messaoudi, S.; Sancelme, M.; Polard-Housset, V.; Aboab, B.; Moreau, P.; Prudhomme, M. Synthesis and Biological Evaluation of Oxindoles and Benzimidazolinones Derivatives. Eur. J. Med. Chem. 2004, 39, 453–458. DOI: 10.1016/j.ejmech.2004.01.001.
   PubMed Web of Science ®Google Scholar
• Gill, C.; Jadhav, G.; Shaikh, M.; Kale, R.; Ghawalkar, A.; Nagargoje, D.; Shiradkar, M. Clubbed [1,2,3] Triazoles by Fluorine Benzimidazole: A Novel Approach to H37Rv Inhibitors as a Potential Treatment for Tuberculosis. Bioorg. Med. Chem. Lett. 2008, 18, 6244–6247. DOI: 10.1016/j.bmcl.2008.09.096.
   PubMed Web of Science ®Google Scholar
• Rossi, A.; Hunger, A.; Kebrle, J.; Hoffmann, K. Benzimidazol-Derivate und verwandte Heterocyclen VI Die Kondensation von o-Phenylendiamin mit aliphatischen und alicyclischen P-Ketoestern. Helv. Chim. Acta 1960, 43, 1298–1313. DOI: 10.1002/hlca.19600430515.
   Web of Science ®Google Scholar
• Adardour, M.; Zaballos-García, E.; Loughzail, M.; Dahaoui, S.; Baouid, A. Synthesis, Characterization and X-Ray Structure of Heterocyclic Systems Prepared via 1,3-Dipolar Cycloaddition of Nitrile Oxides with Benzimidazolone. J. Molecul. Struct. 2018, 1165, 153–161. DOI: 10.1016/j.molstruc.2018.03.128.
   Web of Science ®Google Scholar
• Subhashin, N. J. P.; Praveen, E. K.; Gurrapu, N.; Yerragunta, V. Design and Synthesis of Imidazolo-1, 2,3-Triazoles Hybrid Compounds by Microwave-Assisted Method: Evaluation as an Antioxidant and Antimicrobial Agents and Molecular Docking Studies. J. Molecul. Struct. 2019, 1180, 618–628. DOI: 10.1016/j.molstruc.2018.11.029.
   Web of Science ®Google Scholar
• Santosh, R.; Selvam, M. K.; Kanekar, S. U.; Nagaraja, G. K. Synthesis, Characterization, Antibacterial and Antioxidant Studies of Some Heterocyclic Compounds from Triazole-Linked Chalcone Derivatives. Chem. Select 2018, 3, 6338–6343. DOI: 10.1002/slct.201800905.
   Web of Science ®Google Scholar
• Kaushik, C. P.; Kumar, K.; Lal, K.; Narasimhan, B.; Kumar, A. Synthesis and Antimicrobial Evaluation of 1,4-Disubstituted 1,2,3-Triazoles Containing Benzo-Fused N-Heteroaromatic Moieties. Monatsh. Chem. 2016, 147, 817–828. DOI: 10.1007/s00706-015-1544-2.
   Web of Science ®Google Scholar
• Kuntala, N.; Rani Telu, J.; Banothu, V.; Babu, N. S.; Anireddy, J. S.; Pal, S. Novel Benzoxepine–1,2,3-Triazole Hybrids: Synthesis and Pharmacological Evaluation as Potential Antibacterial and Anticancer Agents. Med. Chem. Commun. 2015, 6, 1612–1619. DOI: 10.1016/j.ejmech.2018.05.055.
   Web of Science ®Google Scholar
• Kumar, A. K.; Sunitha, V.; Shankar, B.; Ramesh, M.; Krishna, T. M.; Jalapathi, P. Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel 1,2,3-Triazole Derivatives as Potent Anti-Inflammatory Agents. Russ. J. Gen. Chem. 2016, 86, 1154–1162. DOI: 10.1134/S1070363216050297.
   Web of Science ®Google Scholar
• Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. Studies on 1,2,3-Triazoles. 13. (Piperazinylalkoxy) [1]Benzopyrano[2,3-d]-1,2,3-Triazol-9(1H)-Ones with Combined H1-Antihistamine and Mast Cell Stabilizing Properties. J. Med. Chem. 1986, 29, 2262–2267. DOI: 10.1021/jm00161a022.
   PubMed Web of Science ®Google Scholar
• Khare, S. P.; Deshmukh, T. R.; Sangshetti, J. N.; Krishna, V. S.; Sriram, D.; Khedkar, V. M.; Shingate, B. B. Design, Synthesis and Molecular Docking Studies of Novel Triazole-Chromene Conjugates as Antitubercular. Antioxid. Antifungal Agents Chem. Select 2018, 3, 13113–13122. DOI: 10.1002/slct.201801859.
   Web of Science ®Google Scholar
• Ouahrouch, A.; Ighachane, H.; Taourirte, M.; Engels, J. W.; Sedra, M. H.; Lazrek, H. B. Benzimidazole-1,2,3-Triazole Hybrid Molecules: Synthesis and Evaluation for Antibacterial/Antifungal Activity. Arch. Pharm. Chem. Life. Sci. 2014, 347, 748–748. DOI: 10.1002/ardp.201400142.
   PubMed Web of Science ®Google Scholar
• Kumar, A.; Ahmad, I.; Chhikara, B. S.; Tiwari, R.; Mandal, D.; Parang, K. Synthesis of 3-Phenylpyrazolopyrimidine-1,2,3-Triazole Conjugates and Evaluation of Their Src Kinase Inhibitory and Anticancer Activities. Bioorg. Med. Chem. Lett. 2011, 21, 1342–1346. DOI: 10.1016/j.bmcl.2011.01.047.
   PubMed Web of Science ®Google Scholar
• Huisgen, R. 1,3-Dipolar Cycloaddition Chemistry; Wiley: New York, 1984; Vol. 1, pp 1–176.
   Google Scholar
• Kolb, H. C.; Finn, M. G.; Sharpless, K. R. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew. Chem. Int. Ed. 2001, 40, 2004–2021. DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5.
   PubMed Web of Science ®Google Scholar
• Bakherad, M.; Karami, S.; Keivanloo, A.; Sepehri, S. Synthesis of New Derivatives of 1,2,3-Triazole-LinkedPhthalazine-1,4-Dione in Water: Experimental Aspects and Molecular Docking Calculations. Chem. Select 2018, 3, 11042–11047. DOI: 10.1002/slct.201802096.
   Web of Science ®Google Scholar
• Lee, J. H.; Gupta, S.; Jeong, W.; Rhee, Y. H.; Park, J. Characterization and Utility of N-Unsubstituted Imines Synthesized from Alkyl Azides by Ruthenium Catalysis. Angew. Chem. Int. Ed. Engl. 2012, 51, 10851–10855. DOI: 10.1002/anie.201204483.
   PubMed Web of Science ®Google Scholar
• Noelting, E.; Michel, O. Direkte Ueberführung von Aminen in Diazoimide mittels Stickstoffwasserstoffsäure Ber. Ber. Dtsch. Chem. Ges. 1893, 26, 86–87. DOI: 10.1002/cber.18930260119.
   Google Scholar
• Hooper, N.; Beeching, L. J.; Dyke, J. M.; Morris, A.; Ogden, J. S.; Dias, A. A.; Costa, M. L.; Barros, M. T.; Cabral, M. H.; Moutinho, A. M. C. A Study of the Thermal Decomposition of 2-Azidoethanol and 2-Azidoethyl Acetate by Ultraviolet Photoelectron Spectroscopy and Matrix Isolation Infrared Spectroscopy. J. Phys. Chem. A 2002, 106, 9968–9975. DOI: 10.1021/jp020625e.
   Web of Science ®Google Scholar
• Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper (Ι)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes. Angew. Chem. Int. Ed. 2002, 41, 2596–2599. DOI: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4.
   PubMed Web of Science ®Google Scholar
• Saraei, M.; Eftekhari-Sis, B.; Faramarzi, M.; Hossienzadeh, R. Synthesis of New 1,2,3-Triazole Derivatives Possessing 4H-Pyran-4-One Moiety by 1,3-Dipolar Cycloaddition Reaction of Azidomethyl Phenylpyrone with Various Alkynes. J. Heterocyclic Chem. 2014, 51, 1500–1503. DOI: 10.1002/jhet.1743.
   Web of Science ®Google Scholar
• Adardour, M.; Loughzail, M.; Dahaoui, S.; Baouid, A.; Berraho, M. UCrData. 2017, 2, x170907. DOI: 10.1107/S2414314617009075.
   Google Scholar
• Hein, J. E.; Fokin, V. V. Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) and Beyond: New Reactivity of Copper(I) Acetylides. Chem. Soc. Rev. 2010, 39, 1302–1315. DOI: 10.1039/b904091a.
   PubMed Web of Science ®Google Scholar
• NCCLS. Performance Standards for Antimicrobial Susceptibility Testing; Ninth Informational Supplement. NCCLS Document M100-S9. National Committee for Clinical Laboratory Standard: Wayne, PA, 2008; pp 120–126.
   Google Scholar
• Lee, J.-H.; Kim, J.; Gludish, D.; Roach, R. R.; Saunders, A. H.; Barrios, J.; Woo, A. J.; Chen, H.; Conner, D. A.; Fujiwara, Y.; et al. Surfactant Protein–C Chromatin-Bound Green Fluorescence Protein Reporter Mice Reveal Heterogeneity of Surfactant Protein C–Expressing Lung Cells. Am. J. Respir. Cell Mol. Biol. 2013, 48, 288–298. DOI: 10.1165/rcmb.2011-0403OC.
   PubMed Web of Science ®Google Scholar
• Ansari, K. F.; Lal, C. Synthesis, Physicochemical Properties and Antimicrobial Activity of Some New Benzimidazole Derivatives. Eur. J. Med. Chem. 2009, 44, 4028–4033. DOI: 10.1016/j.ejmech.2009.04.037.
   PubMed Web of Science ®Google Scholar
• Hoshi, T.; Yamada, K.; Yoshizawa, Y.; Oh, K. Structure-Activity Relationship Study for Fungicidal Activity of 1-(4-Phenoxymethyl-2-Phenyl-[1, 3] Dioxolan-2-Ylmethyl)-1H-1, 2, 4-Triazole Derivatives against Rice Blast. J. Plant. Protect. Res. 2015, 55, 383–388. DOI: 10.1515/jppr-2015-0051.
   Google Scholar