Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy

Nasrin Jahan; Inul Ansary

doi:10.1055/s-0042-1751453

SynOpen, Inhaltsverzeichnis

CC BY 4.0 · SynOpen 2023; 07(02): 209-242
DOI: 10.1055/s-0042-1751453

review

Virtual Collection Click Chemistry and Drug Discovery

Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy

Authors

Nasrin Jahan
Inul Ansary ∗

Abstract

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Abstract

This review reports the synthesis of various bioactive macrocycles, involving ring-closing metathesis as a key step, developed since ca. 2000. These macrocycles exhibited biological activities such as antiviral, antifungal, antibacterial, and anticancer activities, and more. Thus, their syntheses and utilization are essential for both synthetic organic and medicinal chemists.

Key words

macrocycles - ring-closing metathesis - antiviral - antifungal - anticancer - antibiotic

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Referenzen

References
1 Jahan N, Das A, Ansary I. ChemistrySelect 2022; 7: e202201831
2 Malek F, Harit T, Cherfi M, Kim B. Molecules 2022; 27: 2123
3 Anketell MJ, Sharrock TM, Paterson I. Angew. Chem. Int. Ed. 2020; 59: 1572
4 Cheng-Sanchez I, Carrillo P, Sanchez-Ruiz A, Martínez-Poveda B, Quesada AR, Medina MA, Lopez-Romero JM, Sarabia F. J. Org. Chem. 2018; 83: 5365
5 Waser P, Altmann K. Angew. Chem. Int. Ed. 2020; 59: 17393
6 Cink RD, Lukin KA, Bishop RD, Zhao G, Pelc MJ, Towne TB, Gates BD, Ravn MM, Hill DR, Ding C, Cullen SC, Mei J, Leanna MR, Henle J, Napolitano JG, Nere NK, Chen S, Sheikh A, Kallemeyn JM. Org. Process Res. Dev. 2020; 24: 183
7 Chang C.-F, Flaxman HA, Woo C. Angew. Chem. Int. Ed. 2021; 60: 17045
8 Liniger M, Neuhaus CM, Altmann K.-H. Molecules 2020; 25: 4527
9 Sanguinetti M, Sanfilippo S, Castagnolo D, Sanglard D, Posteraro B, Donzellini G, Botta M. ACS Med. Chem. Lett. 2013; 4: 852
10 Sousbie M, Vivancos M, Brouillette RL, Besserer-Offroy É, Longpre J.-M, Leduc R, Sarret P, Marsault É. J. Med. Chem. 2018; 61: 7103
11 Mackman RL, Steadman VA, Dean DK, Jansa P, Poullennec KG, Appleby T, Austin C, Blakemore CA, Cai R, Cannizzaro C, Chin G, Chiva J.-YC, Dunbar NA, Fliri H, Highton AJ, Hui H, Ji M, Jin H, Karki K, Keats AJ, Lazarides L, Lee Y.-J, Liclican A, Mish M, Murray B, Pettit SB, Pyun P, Sangi M, Santos R, Sanvoisin J, Schmitz U, Schrier A, Siegel D, Sperandio D, Stepan G, Tian Y, Watt GM, Yang H, Schultz BE. J. Med. Chem. 2018; 61: 9473
12 Li H, Scott JP, Chen C.-y, Journet M, Belyk K, Balsells J, Kosjek B, Baxter CA, Stewart GW, Wise C, Alam M, Song ZJ, Tan L. Org. Lett. 2015; 17: 1533
13 Li Z, Partridge J, Silva-Garcia A, Rademacher P, Betz A, Xu Q, Sham H, Hu Y, Shan Y, Liu B, Zhang Y, Shi H, Xu Q, Ma X, Zhang L. ACS Med. Chem. Lett. 2017; 8: 185
14 Estrada-Ortiz N, Neochoritis CG, Twarda-Clapa A, Musielak B, Holak TA, Dömling A. ACS Med. Chem. Lett. 2017; 8: 1025
15 Zhou H, Liu L, Huang J, Bernard D, Karatas H, Navarro A, Lei M, Wang S. J. Med. Chem. 2013; 56: 1113

16a Hurd RN, Shah DH. J. Org. Chem. 1973; 38: 390
16b Tanabe Y, Makita A, Funakoshi S, Hamasaki R, Kawakusu T. Adv. Synth. Catal. 2002; 344: 507

17 Nicolaou KC, Winssinger N, Pastor J, Murphy F. Angew. Chem. Int. Ed. Engl. 1998; 37: 2534 ; Angew. Chem. 1998, 110, 2677

18a Porter NA, Magnin DR, Wright BT. J. Am. Chem. Soc. 1986; 108: 2787
18b Suginome H, Yamada S. Tetrahedron Lett. 1987; 28: 3963

19 Liu Y, Yeung Y.-Y. Org. Lett. 2017; 19: 1422
20 Rendina VL, Kaplan HZ, Kingsbury JS. Synthesis 2012; 44: 686
21 Rao HS. P, Rafi S, Kumar PR, Guravaiah C, Muthanna N. Tetrahedron Lett. 2012; 53: 6877
22 Garbaccio RM, Stachel SJ, Baeschlin DK, Danishefsky SJ. J. Am. Chem. Soc. 2001; 123: 10903
23 Louie J, Bielawski CW, Grubbs RH. J. Am. Chem. Soc. 2001; 123: 11312

24a Fustero S, Simón-Fuentes A, Barrio P, Haufe G. Chem. Rev. 2015; 115: 871
24b Vougioukalakis GC, Grubbs RH. Chem. Rev. 2010; 110: 1746

25a Deiters A, Martin SF. Chem. Rev. 2004; 104: 2199
25b McReynolds MD, Dougherty JM, Hanson PR. Chem. Rev. 2004; 104: 2239

26 Ogba OM, Warner NC, O’Leary DJ, Grubbs RH. Chem. Soc. Rev. 2018; 47: 4510
27 Sinclair F, Alkattan M, Prunet J, Shaver MP. Polym. Chem. 2017; 8: 3385
28 Lecourt C, Dhambri S, Allievi L, Sanogo Y, Zeghbib N, Othman RB, Lannou M.-I, Sorin G, Ardisson J. Nat. Prod. Rep. 2018; 35: 105
29 Yee NK, Farina V, Houpis IN, Haddad N, Frutos RP, Gallou F, Wang X, Wei X, Simpson RD, Feng X, Fuchs V, Xu Y, Tan J, Zhang L, Xu J, Smith-Keenan LL, Vitous J, Ridges MD, Spinelli EM, Johnson M. J. Org. Chem. 2006; 71: 7133
30 Velázquez F, Venkatraman S, Wu W, Blackman M, Prongay A, Girijavallabhan V, Shih N.-Y, Njoroge FG. Org. Lett. 2007; 9: 3061
31 Shu C, Zeng X, Hao M.-H, Wei X, Yee NK, Busacca CA, Han Z, Farina V, Senanayake CH. Org. Lett. 2008; 10: 1303
32 Randolph JT, Zhang X, Huang PP, Klein LL, Kurtz KA, Konstantinidis AK, He W, Kati WM, Kempf DJ. Bioorg. Med. Chem. Lett. 2008; 18: 2745
33 Wei X, Shu C, Haddad N, Zeng X, Patel ND, Tan Z, Liu J, Lee H, Shen S, Campbell S, Varsolona RJ, Busacca CA, Hossain A, Yee NK, Senanayake CH. Org. Lett. 2013; 15: 1016
34 Barluenga S, Lopez P, Moulin E, Winssinger N. Angew. Chem. Int. Ed. 2004; 43: 3467
35 Bouazza F, Renoux B, Bachmann C, Gesson J.-P. Org. Lett. 2003; 5: 4049
36 Balestri LJ. I, D’Agostino I, Rango E, Vagaggini C, Marchitiello R, Mariotti M, Casian A, Deodato D, Truglio GI, Orofino F, Sanguinetti M, Bugli F, Botta L, Dreass E. Mol. Diversity 2022; 26: 3399
37 Yasam BK, Pabbaraja S. SynOpen 2022; 6: 227
38 Content S, Dutton CJ, Roberts L. Bioorg. Med. Chem. Lett. 2003; 13: 321
39 Magauer T, Martin HJ, Mulzer J. Angew. Chem. Int. Ed. 2009; 48: 6032
40 Hattori H, Roesslein J, Caspers P, Zerbe K, Miyatake-Ondozabal H, Ritz D, Rueedi G, Gademann K. Angew. Chem. Int. Ed. 2018; 57: 11020
41 Trost BM, Yang H, Thiel OR, Frontier AJ, Brindle CS. J. Am. Chem. Soc. 2007; 129: 2206
42 Tao Z.-F, Sowin TJ, Lin N.-H. Synlett 2007; 2855
43 Ghosh AK, Anderson DD. Org. Lett. 2012; 14: 4730
44 Huang J, Wang Z. Org. Lett. 2016; 18: 4702
45 Reddy DP, Yu B. Chem Asian J. 2020; 15: 2467
46 Fürstner A, Grabowski J, Lehmann CW, Kataoka T, Nagai K. ChemBioChem 2001; 2: 60
47 Stymiest JL, Mitchell BF, Wong S, Vederas JC. Org. Lett. 2003; 5: 47
48 Wels B, Kruijtzer JA. W, Garner K, Nijenhuis WA. J, Gispen WH, Adan RA. H, Liskamp RM. J. Bioorg. Med. Chem. 2005; 13: 4221
49 Harris PW. R, Brimble MA. Org. Biomol. Chem. 2006; 4: 2696
50 Sliwa A, Dive G, Habib Jiwan J.-L, Marchand-Brynaert J. Tetrahedron 2010; 66: 9519
51 Biju P, Bitar R, Lim Y.-H, Wang Y, Berlin M, Aslanian R, McCormick K. Tetrahedron Lett. 2015; 56: 636
52 Kim D.-S, Endo A, Fang FG, Huang K.-C, Bao X, Choi H.-w, Majumder U, Shen YY, Mathieu S, Zhu X, Sanders K, Noland T, Hao M.-H, Chen Y, Wang JY, Yasui S, TenDyke K, Wu J, Ingersoll C, Loiacono KA, Hutz JE, Sarwar N. ChemMedChem 2021; 16: 1741