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Research Articles

Laccase-catalysed azide-alkyne cycloadditions: Synthesis of benzothiazole and benzimidazole fused 1,2,3-triazole derivatives by copper containing oxidoreductase enzymes

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Pages 140-150 | Received 07 Jun 2022, Accepted 21 Oct 2022, Published online: 08 Nov 2022

References

  • Aragão-Leoneti V, Campo VL, Gomes AS, Field RA, Carvalho I. 2010. Application of copper(I)-catalysed azide/alkyne cycloaddition (CuAAC) “click chemistry” in carbohydrate drug and neoglycopolymer synthesis. Tetrahedron. 66(49):9475–9492.
  • Bode ML, Van Rantwijk F, Sheldon RA. 2003. Crude aminoacylase from Aspergillus sp. is a mixture of hydrolases. Biotechnol Bioeng. 84(6):710–713.
  • Dervaux B, Du Prez FE. 2012. Heterogeneous azide-alkyne click chemistry: towards metal-free end products. Chem Sci. 3(4):959–966.
  • Faraji L, Shahkarami S, Nadri H, Moradi A, Saeedi M, Foroumadi A, Ramazani A, Haririan I, Ganjali MR, Shafiee A, et al. 2017. Synthesis of novel benzimidazole and benzothiazole derivatives bearing a 1,2,3-triazole ring system and their acetylcholinesterase inhibitory activity. J Chem Res. 41(1):30–35.
  • Gill C, Jadhav G, Shaikh M, Kale R, Ghawalkar A, Nagargoje D, Shiradkar M. 2008. Clubbed [1,2,3] triazoles by fluorine benzimidazole: a novel approach to H37Rv inhibitors as a potential treatment for tuberculosis. Bioorg Med Chem Lett. 18(23):6244–6247.
  • Harkala KJ, Eppakayala L, Maringanti TC. 2014. Synthesis and biological evaluation of benzimidazole-linked 1,2,3-triazole congeners as agents. Org Med Chem Lett. 4(1):14–17.
  • Hoegger PJ, Kilaru S, James TY, Thacker JR, Kües U. 2006. Phylogenetic comparison and classification of laccase and related multicopper oxidase protein sequences. FEBS J. 273(10):2308–2326.
  • Hult K, Berglund P. 2007. Enzyme promiscuity: mechanism and applications. Trends Biotechnol. 25(5):231–238.
  • Johansson JR, Beke-Somfai T, Said Stålsmeden A, Kann N. 2016. Ruthenium-catalyzed azide alkyne cycloaddition reaction: scope, mechanism, and applications. Chem Rev. 116(23):14726–14768.
  • Kumar SS, Kavitha HP. 2013. Synthesis and biological applications of triazole derivatives – a review. Mini Rev Org Chem. 10:40–65.
  • Lee Y-S, Cho Y-H, Lee S-J, Bin J-K, Yang J-H, Chae G, Cheon C-H. 2015. Significant facilitation of metal-free aerobic oxidative cyclization of imines with water in synthesis of benzimidazoles. Tetrahedron. 71(4):532–538.
  • Leutbecher H, Constantin MA, Mika S, Conrad J, Beifuss U. 2011. A new laccase-catalyzed domino process and its application to the efficient synthesis of 2-aryl-1H-benzimidazoles. Tetrahedron Lett. 52(5):605–608.
  • Lutz JF, Zarafshani Z. 2008. Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne “click” chemistry. Adv Drug Deliv Rev. 60(9):958–970.
  • Madhavi V, Lele SS. 2009. Laccase: properties and applications. BioRes. 4:1694–1717.
  • Maphupha M, Juma WP, de Koning CB, Brady D. 2018. A modern and practical laccase-catalysed route suitable for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles. RSC Adv. 8(69):39496–39510.
  • Maračić S, Kraljević TG, Paljetak HČ, Perić M, Matijašić M, Verbanac D, Cetina M, Raić-Malić S. 2015. 1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity. Bioorg Med Chem. 23(23):7448–7463.
  • Mate DM, Alcalde M. 2015. Laccase engineering: from rational design to directed evolution. Biotechnol Adv. 33(1):25–40.
  • McNulty J, Keskar K. 2012. Discovery of a robust and efficient homogeneous silver (I) catalyst for the cycloaddition of azides onto terminal alkynes. Eur J Org Chem. 2012(28):5462–5470.
  • Mogharabi-Manzari M, Heydari M, Sadeghian-Abadi S, Yousefi-Mokri M, Faramarzi MA. 2019. Enzymatic dimerization of phenylacetylene by laccase immobilized on magnetic nanoparticles via click chemistry. Biocatal Biotransform. 37(6):455–465.
  • Nicotra S, Intra A, Ottolina G, Riva S, Danieli B. 2004. Laccase-mediated oxidation of the steroid hormone 17β-estradiol in organic solvents. Tetrahedron Asymmetry. 15(18):2927–2931.
  • Ouahrouch A, Ighachane H, Taourirte M, Engels JW, Sedra MH, Lazrek HB. 2014. Benzimidazole-1,2,3-triazole hybrid molecules: synthesis and evaluation for antibacterial/antifungal activity. Arch Pharm. 347(10):748–755.
  • Padalkar VS, Gupta VD, Phatangare KR, Patil VS, Umape PG, Sekar N. 2012. Indion 190 resin: efficient, environmentally friendly, and reusable catalyst for synthesis of benzimidazoles, benzoxazoles, and benzothiazoles. Green Chem Lett Rev. 5(2):139–145.
  • Peyton LR, Gallagher S, Hashemzadeh M. 2015. Triazole antifungals: a review. Drugs Today. 51(12):705–718.
  • Pradere U, Roy V, McBrayer TR, Schinazi RF, Agrofoglio LA. 2008. Preparation of ribavirin analogues by copper- and ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloaddition. Tetrahedron. 64(38):9044–9051.
  • Sarode PB, Bahekar SP, Chandak HS. 2016. DABCO/AcOH jointly accelerated copper(I)-catalysed cycloaddition of azides and alkynes on water at room temperature. Synlett. 27(19):2681–2684.
  • Sato S, Nakane K, Nakamura HA. 2020. A laccase-catalysed tyrosine click reaction. Org Biomol Chem. 18(19):3664–3668.
  • Schulze B, Schubert US. 2014. Beyond click chemistry-supramolecular interactions of 1,2,3-triazoles. Chem Soc Rev. 43(8):2522–2571.
  • Shaikh MH, Subhedar DD, Arkile M, Khedkar VM, Jadhav N, Sarkar D, Shingate BB. 2016. Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent. Bioorg Med Chem Lett. 26(2):561–569.
  • Sharma A, Agrahari AK, Rajkhowa S, Tiwari VK. 2022. Emerging impact of triazoles as anti-tubercular agent. Eur J Med Chem. 238:114454.
  • Shaveta, Mishra S, Singh P. 2016. Hybrid molecules: the privileged scaffolds for various pharmaceuticals. Eur J Med Chem. 124:500–536.
  • Singh MS, Chowdhury S, Koley S. 2016. Advances of azide-alkyne cycloaddition-click chemistry over the recent decade. Tetrahedron. 72(35):5257–5283.
  • Singh S, Mandal MK, Masih A, Saha A, Ghosh SK, Bhat HR, Singh UP. 2021. 1,3,5-Triazine: a versatile pharmacophore with diverse biological activities. Arch Pharm. 354(6):2000363.
  • Thurston CF. 1994. The structure and function of fungal laccases. Microbiology. 140(1):19–26.
  • Totobenazara J, Burke AJ. 2015. New click-chemistry methods for 1,2,3-triazoles synthesis: recent advances and applications. Tetrahedron Lett. 56(22):2853–2859.
  • Wellington KW. 2011. Application of laccases in organic synthesis: a review. In: Green chemistry. Nova Science Publishers, Inc. New York; p. 167–212.
  • WHO. 2021. World Health Organisation, global tuberculosis report. Geneva, ISBN 978-92-4-003702-1
  • Zhang L, Chen X, Xue P, Sun HH, Williams ID, Sharpless KB, Fokin VV, Jia G. 2005. Ruthenium-catalyzed cycloaddition of alkynes and organic azides. J Am Chem Soc. 127(46):15998–15999.
  • Zhang S, Xu Z, Gao C, Ren QC, Chang L, Lv ZS, Feng LS. 2017. Triazole derivatives and their anti-tubercular activity. Eur J Med Chem. 138:501–513.
  • Zhang X, Zhang Y. 2013. Applications of azide-based bioorthogonal click chemistry in glycobiology. Molecules. 18(6):7145–7159.

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