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Synthesis
DOI: 10.1055/a-2232-8240
DOI: 10.1055/a-2232-8240
paper
Special Issue PSRC-10 (10th Pacific Symposium on Radical Chemistry)
Synthesis of Anti-oxidant Steroids by Hybridisation with Nitroxides
We would like to thank the Queensland University of Technology (Centre for Genomics and Personalised Health) and the Australian Research Council (grant no. DP190100499) for their financial support.
Abstract
Steroidal–nitroxide hybrid molecules and non-radical controls were synthesised in good yields using simple carbodiimide coupling. An unexpected product arose from reactions between the nitroxide moiety and the solvent THF. Methoxyamine derivatives of the nitroxide drug hybrids were produced using Fenton chemistry without side reactions occurring on the steroid. The hybrid compounds bind to the glucocorticoid receptor and are relevant for the study of radical biological chemistry and redox-related disease processes.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2232-8240.
- Supporting Information
Publication History
Received: 31 October 2023
Accepted after revision: 19 December 2023
Accepted Manuscript online:
19 December 2023
Article published online:
26 February 2024
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References
- 1 Prescott C, Bottle SE. Cell Biochem. Biophys. 2017; 75: 227
- 2 Soule BP, Hyodo F, Matsumoto K, Simone NL, Cook JA, Krishna MC, Mitchell JB. Free Radical Biol. Med. 2007; 42: 1632
- 3 Haugland MM, Lovett JE, Anderson EA. Chem. Soc. Rev. 2018; 47: 668
- 4 Tebben L, Studer A. Angew. Chem. Int. Ed. 2011; 50: 5034
- 5 Hideg K, Kálai T, Sár CP. J. Heterocycl. Chem. 2005; 42: 437
- 6 Kálai T. Synthesis 1999; 973
- 7 Kálai T, Jekő J, Hideg K. Synthesis 2000; 831
- 8 Hideg K, Csekó J, Hankovszky HO. Synth. Commun. 1986; 16: 1839
- 9 Turnbull K, Kálai T, Kulcsár G, Õsz E, Jekõ J, Sümegi B, Hideg K. ARKIVOC 2004; (vii): 266
- 10 Hideg K, Sár CP, Hankovszky OH, Tamás T, Jerkovich G. Synthesis 1993; 390
- 11 Hankovszky HO, Hideg K, Jerkovich G. Synthesis 1989; 526
- 12 Rauckman EJ, Rosen GM, Abou-Donia MB. J. Org. Chem. 2002; 41: 564
- 13 Hideg K, Kálai T, Balog M, Jekő J, Hubbell WL. Synthesis 2002; 2365
- 14 Fairfull-Smith KE, Bottle SE. Eur. J. Org. Chem. 2008; 5391
- 15 Keddie DJ, Fairfull-Smith KE, Bottle SE. Org. Biomol. Chem. 2008; 6: 3135
- 16 Keddie DJ, Johnson TE, Arnold DP, Bottle SE. Org. Biomol. Chem. 2005; 3: 2593
- 17 Morris JC, McMurtrie JC, Bottle SE, Fairfull-Smith KE. J. Org. Chem. 2011; 76: 4964
- 18 Wang Z, Zhao J, Barbon A, Toffoletti A, Liu Y, An Y, Xu L, Karatay A, Yaglioglu HG, Yildiz EA, Hayvali M. J. Am. Chem. Soc. 2017; 139: 7831
- 19 Fall A, Sene M, Gaye M, Gómez G, Fall Y. Tetrahedron Lett. 2010; 51: 4501
- 20 Fairfull-Smith KE, Debele EA, Allen JP, Pfrunder MC, McMurtrie JC. Eur. J. Org. Chem. 2013; 4829
- 21 Hankovszky HO, Hideg K, Sár PC, Lovas MJ, Jerkovich G. Synthesis 1990; 59
- 22 Rajca A, Wang Y, Boska M, Paletta JT, Olankitwanit A, Swanson MA, Mitchell DG, Eaton SS, Eaton GR, Rajca S. J. Am. Chem. Soc. 2012; 134: 15724
- 23 Blinco JP, Chalmers BA, Chou A, Fairfull-Smith KE, Bottle SE. Chem. Sci. 2013; 4: 3411
- 24 Bolton R, Gillies DG, Sutcliffe LH, Wu X. J. Chem. Soc., Perkin Trans. 2 1993; 2049
- 25 Hideg K, Hankovszky HO, Halász HA, Sohár P. J. Chem. Soc., Perkin Trans. 1 1988; 2905
- 26 Thomas K, Moody TW, Jensen RT, Tong J, Rayner CL, Barnett NL, Fairfull-Smith KE, Ridnour LA, Wink DA, Bottle SE. Eur. J. Med. Chem. 2018; 147: 34
- 27 Karoui H, Moigne FL, Ouari O, Tordo P. Nitroxide Radicals: Properties, Synthesis and Applications . In Stable Radicals . Hicks RG. Wiley; Chichester: 2010: 173-229
- 28 Bottle SE, Gillies DG, Hughes DL, Micallef AS, Smirnov AI, Sutcliffe LH. J. Chem. Soc., Perkin Trans. 2 2000; 1285
- 29 Griffiths PG, Moad G, Rizzardo E. Aust. J. Chem. 1983; 36: 397
- 30 Blinco JP, Hodgson JL, Morrow BJ, Walker JR, Will GD, Coote ML, Bottle SE. J. Org. Chem. 2008; 73: 6763
- 31 Rychnovsky SD, Beauchamp T, Vaidyanathan R, Kwan T. J. Org. Chem. 1998; 63: 6363
- 32 Hussain H, Al-Harrasi A, Green IR, Ahmed I, Abbas G, Rehman NU. RSC Adv. 2014; 4: 12882
- 33 Payne GB, Williams PH. J. Org. Chem. 1959; 24: 54
- 34 Sato K, Aoki M, Takagi J, Zimmermann K, Noyori R. Bull. Chem. Soc. Jpn. 1999; 72: 2287
- 35 Chong KL, Chalmers BA, Cullen JK, Kaur A, Kolanowski JL, Morrow BJ, Fairfull-Smith KE, Lavin MJ, Barnett NL, New EJ, Murphy MP, Bottle SE. Free Radical Biol. Med. 2018; 128: 97
- 36 Hosokawa K, Chen P, Lavin FM, Bottle ES. Free Radical Biol. Med. 2004; 37: 946
- 37 Morrow BJ, Keddie DJ, Gueven N, Lavin MF, Bottle SE. Free Radical Biol. Med. 2010; 49: 67
- 38 Rayner CL, Bottle SE, Gole GA, Ward MS, Barnett NL. Neurochem. Int. 2016; 92: 1
- 39 Baraldi PG, Romagnoli R, Del Carmen NunezM, Perretti M, Paul-Clark MJ, Ferrario M, Govoni M, Benedini F, Ongini E. J. Med. Chem. 2004; 47: 711
- 40 Galassi F, Masini E, Giambene B, Fabrizi F, Uliva C, Bolla M, Ongini E. Br. J. Ophthalmol. 2006; 90: 1414
- 41 Kosutova P, Kolomaznik M, Calkovska A, Mokra D, Mikolka P. Pharmaceutics 2021; 13: 2092
- 42 Paul-Clark M, Del Soldato P, Fiorucci S, Flower RJ, Perretti M. Br. J. Pharmacol. 2000; 131: 1345
- 43 Paul-Clark MJ, Mancini L, Del Soldato P, Flower RJ, Perretti M. Proc. Natl. Acad. Sci. U.S.A. 2002; 99: 1677
- 44 Tallet D, Del Soldato P, Oudart N, Burgaud JL. Biochem. Biophys. Res. Commun. 2002; 290: 125
- 45 Turner DL, Ferrari N, Ford WR, Kidd EJ, Paquet L, Renzi P, Broadley KJ. Eur. J. Pharmacol. 2010; 641, 213
- 46 Yang Y, Li H, Sun H, Gong L, Guo L, Shi Y, Cai C, Gu H, Song Z, Yang L, Tong Y, Wei C, Zou Q, Zeng H. Sci. Rep. 2016; 6: 20307
- 47 Benson WR, Maienthal M. J. Med. Chem. 1977; 20: 1308
- 48 Lam MA, Pattison DI, Bottle SE, Keddie DJ, Davies MJ. Chem. Res. Toxicol. 2008; 21: 2111
- 49 Ruiz JF, Radics G, Windle H, Serra HO, Simplicio AL, Kedziora K, Fallon PG, Kelleher DP, Gilmer JF. J. Med. Chem. 2009; 52: 3205
- 50 Crielaard BJ, Rijcken CJ, Quan L, van de Wal S, Altintas I, van der Pot M, Kruijtzer JA, Liskamp RM, Schiffelers RM, van Nostrum CF, Hennink WE, Wang D, Lammers T, Storm G. Angew. Chem. Int. Ed. 2012; 51: 7254
- 51 Matsubara H, Suzuki S, Hirano S. Org. Biomol. Chem. 2015; 13: 4686
- 52 Gao Y, Liu J, Wei C, Li Y, Zhang K, Song L, Cai L. Nat. Commun. 2022; 13: 7450
- 53 Straub T, Koskinen AM. P. Inorg. Chem. Commun. 2002; 5: 1052
- 54 Wei J, Tang Y, Yang Q, Li H, He D, Cai Y. Org. Lett. 2022; 24: 7928
- 55 Vil VA, Grishin SS, Baberkina EP, Kostyagina VA, Kovalenko AE, Terent’ev AO. Tetrahedron Lett. 2020; 61: 152150
- 56 Ciriano MV, Korth H.-G, van Scheppingen WB, Mulder P. J. Am. Chem. Soc. 1999; 121: 6375
- 57 Chalmers BA, Morris JC, Fairfull-Smith KE, Grainger RS, Bottle SE. Chem. Commun. 2013; 49: 10382
- 58 Soltau CP, Brown ZE, Brock AJ, Martyn AP, Blinco JP, Miljevic B, McMurtrie JC, Bottle SE. Chem. Commun. 2022; 58: 10416
- 59 Ponec M, Kempenaar J, Shroot B, Caron JC. J. Pharm. Sci. 1986; 75: 973
- 60 Lewis BW, Ford ML, Rogers LK, Britt RD. Jr. Antioxidants 2021; 10: 1335
- 61 Bjelakovic G, Beninati S, Pavlovic D, Kocic G, Jevtovic T, Kamenov B, Saranac LJ, Bjelakovic B, Stojanovic I, Basic J. J. Basic Clin. Physiol. Pharmacol. 2007; 18: 115
- 62 Torres RL, Torres IL, Laste G, Ferreira MB, Cardoso PF, Bello-Klein A. J. Bras. Pneumol. 2014; 40: 238
- 63 Tiwari P, Singh N, Sharma B. Indian J. Clin. Biochem. 2023; 1
- 64 Feng YL, Tang XL. Chem. Biol. Interact. 2014; 207: 26
- 65 Lohan SB, Saeidpour S, Colombo M, Staufenbiel S, Unbehauen M, Wolde-Kidan A, Netz RR, Bodmeier R, Haag R, Teutloff C, Bittl R, Meinke MC. Pharmaceutics 2020; 12: 400
- 66 Muller P, Herrmann A. Biophys. J. 2002; 82: 1418