CC BY 4.0 · SynOpen 2024; 08(01): 1-38
DOI: 10.1055/a-2212-0996
review

Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition

Nasrin Jahan
,
Arkadip Pal
,
Inul Ansary
We sincerely thank the Department of Science and Technology and Biotechnology (Government of West Bengal) for providing financial assistance until the year 2022. N. Jahan is grateful to the Government of West Bengal for her research fellowship, Swami Vivekananda Merit Cum Means Fellowship.


Abstract

A systematic highlight of syntheses reported since 2006 of 1,2,3-triazole-fused macrocycles possessing biological activities such as anticancer, antibacterial, antiviral, anti-inflammatory and antilarval action, is presented in this review. The well-renowned Cu-catalyzed azide-alkyne cycloaddition reaction was noted to be highly efficient and is one the most common methods utilized by scientists for the synthesis of 1,4-disubstituted triazole-fused macrocycles, whereas Ru-catalyzed cycloaddition is common for the formation of 1,5-disubstituted bioactive triazoles. This review would thus be extremely beneficial for both synthetic organic and medicinal chemists.

1 Introduction

2 Anticancer Derivatives

3 Antibacterial Derivatives

4 Derivatives with Dual Activity

5 Antilarval Derivatives

6 Anti-inflammatory Derivatives

7 Antiviral Derivatives

8 Anti-trypanosomal Derivatives

9 Derivatives with Miscellaneous Activities

10 Conclusion



Publication History

Received: 17 October 2023

Accepted after revision: 15 November 2023

Accepted Manuscript online:
16 November 2023

Article published online:
04 January 2024

© 2023. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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  • References

  • 1 Liang Y, Fang R, Rao Q. Molecules 2022; 27: 2837
    • 2a Marsault E, Peterson ML. J. Med. Chem. 2011; 54: 1961
    • 2b Cheekatla SR, Barik D, Anand G, Mol KM. R, Porel M. Organics 2023; 4: 333
    • 2c Medved’ko AV, Gaisen SV, Kalinin MA, Vatsadze SZ. Organics 2023; 4: 417
    • 2d Begnini F, Poongavanam V, Over B, Castaldo M, Geschwindner S, Johansson P, Tyagi M, Tyrchan C, Wissler L, Sjö P, Schiesser S, Kihlberg J. J. Med. Chem. 2021; 64: 1054
  • 3 Jahan N, Ansary I. SynOpen 2023; 7: 209
  • 4 Horne WS, Olsen CA, Beierle JM, Montero A, Ghadiri MR. Angew. Chem. Int. Ed. 2009; 48: 4718
  • 5 Day JE. H, Sharp SY, Rowlands MG, Aherne W, Workman P, Moody CJ. Chem. Eur. J. 2010; 16: 2758
  • 6 Duan X, Zhang Y, Ding Y, Lin J, Kong X, Zhang Q, Dong C, Luo G, Chen Y. Eur. J. Org. Chem. 2012; 500
  • 7 Prabhakaran P, Subaraja M, Rajakumar P. ChemistrySelect 2018; 3: 4687
  • 8 Anandhan R, Kannan A, Rajakumar P. Synth. Commun. 2017; 47: 671
  • 9 Mandadapu SR, Weerawarna PM, Prior AM, Uy RA. Z, Aravapalli S, Alliston KR, Lushington GH, Kim Y, Hua DH, Chang K, Groutas WC. Bioorg. Med. Chem. Lett. 2013; 23: 3709
  • 10 Rana R, Dolma SK, Maurya SK, Reddy SG. E. Toxin Rev. 2020; 39 (02) 197
  • 11 Bock VD, Speijer D, Hiemstra H, van Maarseveen JH. Org. Biomol. Chem. 2007; 5: 971
  • 12 Philkhana SC, Mehrotra S, Murray TF, Reddy DS. Org. Biomol. Chem. 2016; 14: 8457
    • 13a Ansary I, Roy H, Das A, Mitra D, Bandyopadhyay AK. ChemistrySelect 2019; 4: 3486
    • 13b Silvestri IP, Andemarian F, Khairallah GN, Yap SW, Quach T, Tsegay S, Williams CM, O’Hair RA. R, Donnelly PS, Williams SJ. Org. Biomol. Chem. 2011; 9: 6082
    • 13c Johansson JR, Beke-Somfai T, Stålsmeden AS, Kann N. Chem. Rev. 2016; 116: 14726
    • 13d Roshandel S, Suri SC, Marcischak JC, Rasul G, Surya Prakash GK. Green Chem. 2018; 20: 3700
    • 13e Dar BA, Bhowmik A, Sharma A, Sharma PR, Lazar A, Singh AP, Sharma M, Singh B. Appl. Clay Sci. 2013; 80–81: 351
  • 14 Jahan N, Das A, Ansary I. ChemistrySelect 2022; 7: e202201831
  • 15 Chen J, Nikolovska-Coleska Z, Yang C, Gomez C, Gao W, Krajewski K, Jiang S, Roller P, Wang S. Bioorg. Med. Chem. Lett. 2007; 17: 3939
  • 16 Singh EK, Nazarova LA, Lapera SA, Alexander LD, McAlpine SR. Tetrahedron Lett. 2010; 51: 4357
  • 17 Nahrwold M, Bogner T, Eissler S, Verma S, Sewald N. Org. Lett. 2010; 12: 1064
  • 18 Pirali T, Faccio V, Mossetti R, Grolla AA, Micco SD, Bifulco G, Genazzani AA, Tron GC. Mol. Diversity 2010; 14: 109
  • 19 Sun H, Liu L, Lu J, Qiu S, Yang C, Yi H, Wang S. Bioorg. Med. Chem. Lett. 2010; 20: 3043
  • 20 Ajay A, Sharma S, Gupt MP, Bajpai V, Hamidullah, Kumar B, Kaushik MP, Konwar R, Ampapathi RS, Tripathi RP. Org. Lett. 2012; 14: 4306
  • 21 Davis MR, Singh EK, Wahyudi H, Alexander LD, Kunicki JB, Nazarova LA, Fairweather KA, Giltrap AM, Jolliffe KA, McAlpine SR. Tetrahedron 2012; 68: 1029
  • 22 Neilsen PM, Pehere AD, Pishas KI, Callen DF, Abell AD. ACS Chem. Biol. 2013; 8: 353
  • 23 Tahoori F, Balalaie S, Sheikhnejad R, Sadjadi M, Boloori P. Amino Acids 2014; 46: 1033
  • 24 Goh WY. L, Chai CL. L, Chen A. Eur. J. Org. Chem. 2014; 7239
  • 25 Zhang Y, Seigal BA, Terrett NK, Talbott RL, Fargnoli J, Naglich JG, Chaudhry C, Posy SL, Vuppugalla R, Cornelius G, Lei M, Wang C, Zhang Y, Schmidt RJ, Wei DD, Miller MM, Allen MP, Li L, Carter PH, Vite GD, Borzilleri RM. ACS Med. Chem. Lett. 2015; 6: 770
  • 26 Seigal BA, Connors WH, Fraley A, Borzilleri RM, Carter PH, Emanuel SL, Fargnoli J, Kim K, Lei M, Naglich JG, Pokross ME, Posy SL, Shen H, Surti N, Talbott R, Zhang Y, Terrett NK. J. Med. Chem. 2015; 58: 2855
  • 27 Cao G, Yang K, Li Y, Huang L, Teng D. Molecules 2016; 21: 212
  • 28 Gabba A, Robakiewicz S, Taciak B, Ulewicz K, Broggoni G, Rastelli G, Krol M, Murphy P, Passarella D. Eur. J. Org. Chem. 2017; 60
  • 29 Raj PJ, Bahulayan D. Tetrahedron Lett. 2017; 58: 2122
  • 30 Hernandez-Vazquez E, Chvez-Riveros A, Romo-Perez A, Ramirez-Apan MT, Blanco AD. C, Morales-Barcenas R, Duenas-Gonzalez A, Miranda LD. ChemMedChem 2018; 13: 1193
  • 31 Cruz-Lopez O, Temps C, Longo B, Myers SH, Franco-Montalban F, Unciti-Broceta A. ACS Omega 2019; 4: 21620
  • 32 Rahman A, Sharma P, Kaur N, Shanavas AK, Neelakandan PP. ChemistrySelect 2020; 5: 5473
  • 33 Srinivas A, Rao EK. Acta Chim. Slov. 2021; 68: 404
  • 34 Hernandez-Vazquez E, Amador-Sanchez YA, Cruz-Mendoza MA, Ramírez-Apan MT, Miranda LD. Bioorg. Med. Chem. Lett. 2021; 40: 127899
  • 35 Isidro-Llobet A, Murillo T, Bello P, Cilibrizzi A, Hodgkinson JT, Galloway WR. J. D, Bender A, Welch M, Spring DR. Proc. Natl. Acad. Sci. USA 2011; 108: 6793
  • 36 Noor A, Huff GS, Kumar SV, Lewis JE. M, Paterson BM, Schieber C, Donnelly PS, Brooks HJ. L, Gordon KC, Moratti SC, Crowley JD. Organometallics 2014; 33: 7031
  • 37 Guo Y, Liu C, Song H, Wang F, Zou Y, Wu Q, Hu H. RSC Adv. 2017; 7: 2110
  • 38 Singh K, Sharma G, Shukla M, Kant R, Chopra S, Shukla SK, Tripathi RP. J. Org. Chem. 2018; 83: 14882
  • 39 Yang X, Kemmink J, Rijkers DT. S, Liskamp RM. J. Bioorg. Med. Chem. Lett. 2022; 73: 128887
  • 40 Selvarani S, Rajakumar P, Nagaraj S, Choudhury M, Velmurugan D. New J. Chem. 2018; 42: 12684
  • 41 Maurya SK, Rana R. Beilstein J. Org. Chem. 2017; 13: 1106
  • 42 Weerawarna PM, Kim Y, Kankanamalage AC. G, Damalanka VC, Lushington GH, Alliston KR, Mehzabeen N, Battaile KP, Lovell S, Chang K, Groutas WC. Eur. J. Med. Chem. 2016; 119: 300
  • 43 Kankanamalage AC. G, Weerawarna PM, Rathnayake AD, Kim Y, Mehzabeen N, Battaile KP, Lovell S, Chang K, Groutas WC. Proteins Struct. Funct. Bioinform. 2019; 87: 579
  • 44 Campo VL, Ivanova IM, Carvalho I, Lopes CD, Carneiro ZA, Saalbach G, Schenkman S, da Silva JS, Nepogodiev SA, Field RA. Tetrahedron 2015; 71: 7344
  • 45 Choi WJ, Shi Z, Worthy KM, Bindu L, Karki RG, Nicklaus MC, Fisher RJ, Burke TR. Jr. Bioorg. Med. Chem. Lett. 2006; 16: 5265
  • 46 Ingale S, Dawson PE. Org. Lett. 2011; 13: 2822
  • 47 Empting M, Avrutina O, Meusinger R, Fabritz S, Reinwarth M, Biesalski M, Voigt S, Buntkowsky G, Kolmar H. Angew. Chem. Int. Ed. 2011; 50: 5207
  • 48 Pehere AD, Pietsch M, Gütschow M, Neilsen PM, Pedersen DS, Nguyen S, Zvarec O, Sykes MJ, Callen DF, Abell AD. Chem. Eur. J. 2013; 19: 7975
  • 49 Jogula S, Soorneedi AR, Gaddam J, Chamakuri S, Deora GS, Indarapu RK, Ramgopal MK, Dravida S, Arya P. Eur. J. Med. Chem. 2017; 135: 110
  • 50 Tala SR, Singh A, Lensing CJ, Schnell SM, Freeman KT, Rocca JR, Haskell-Luevano C. ACS Chem. Neurosci. 2017; 9: 1001
  • 51 White AM, De Veer SJ, Wu G, Harvey PJ, Yap K, King GJ, Swedberg JE, Wang CK, Law RH. P, Durek T, Craik DJ. Angew. Chem. Int. Ed. 2020; 59: 11273
  • 52 Kulsi G, Sannigrahi A, Mishra S, Saha KD, Datta S, Chattopadhyay P, Chattopadhyay K. ACS Omega 2020; 5: 16395
  • 53 Cheekatla SR, Thurakkal L, Jose A, Barik D, Porel M. Molecules 2022; 27: 3409
  • 54 Thurakkal L, Mol R, Porel M. Chem. Commun. 2023; 59: 7399