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Synthesis 2016; 48(21): 3763-3772
DOI: 10.1055/s-0035-1562437
DOI: 10.1055/s-0035-1562437
paper
Toward the Efficient Synthesis of New Phosphopantothenate Derivatives by Using Chlorophosphate Reagents
Weitere Informationen
Publikationsverlauf
Received: 15. April 2016
Accepted after revision: 09. Mai 2016
Publikationsdatum:
22. Juni 2016 (online)
Abstract
Seven new masked analogues of phosphopantothenate, suitable for an evaluation of their potential ability to restore intracellular coenzyme A (CoA) levels, were successfully synthesized in good to moderate yields. The preparation of derivatives masked with (acyloxy)alkyl groups was studied particularly in terms of synthetic efficiency, and the possibility of applying different chlorophosphate reagents for the preparation of a variety of masked derivatives was also investigated. Using this methodology, we have successfully synthesized a new chlorophosphate reagent, suitable for the introduction of the (isobutyryloxy)methyl functionality into the prodrug. Additionally, special attention was given to finding mild and economical reaction conditions for phosphorylation of biological molecules.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562437.
- Supporting Information
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References
- 1a Theodoulou FL, Sibon OC. M, Jackowski S, Gout I. Biochem. Soc. Trans. 2014; 42: 1025
- 1b Leonardi R, Zhang Y.-M, Rock CO, Jackowski S. Prog. Lipid Res. 2005; 44: 125
- 2 Srinivasan B, Sibon OC. M. Biochem. Soc. Trans. 2014; 42: 1075
- 3a Zhou B, Westaway SK, Levinson B, Johnson MA, Gitschier J, Hayflick SJ. Nat. Genet. 2001; 28: 345
- 3b Dusi S, Valletta L, Haack Tobias B, Tsuchiya Y, Venco P, Pasqualato S, Goffrini P, Tigano M, Demchenko N, Wieland T, Schwarzmayr T, Strom Tim M, Invernizzi F, Garavaglia B, Gregory A, Sanford L, Hamada J, Bettencourt C, Houlden H, Chiapparini L, Zorzi G, Kurian Manju A, Nardocci N, Prokisch H, Hayflick S, Gout I, Tiranti V. Am. J. Hum. Genet. 2014; 94: 11
- 3c Hayflick SJ. Biochem. Soc. Trans. 2014; 42: 1063
- 4 Zorzi G, Nardocci N. Int. Rev. Neurobiol. 2013; 110: 153
- 5 Srinivasan B, Baratashvili M, van der Zwaag M, Kanon B, Colombelli C, Lambrechts RA, Schaap O, Nollen EA, Podgorsek A, Kosec G, Petkovic H, Hayflick S, Tiranti V, Reijngoud D.-J, Grzeschik NA, Sibon OC. M. Nat. Chem. Biol. 2015; 11: 784
- 6 Zano SP, Pate C, Frank M, Rock CO, Jackowski S. Mol. Genet. Metab. 2015; 116: 281
- 7a King TE, Strong FM. Science 1950; 112: 562
- 7b King TE, Strong FM. J. Biol. Chem. 1951; 189: 315
- 7c King TE, Strong FM. J. Biol. Chem. 1951; 191: 515
- 8a Moffatt JG, Khorana HG. J. Am. Chem. Soc. 1959; 81: 1265
- 8b Baddiley J, Thain EM. J. Chem. Soc. 1953; 1610
- 8c Moffatt JG, Khorana HG. J. Am. Chem. Soc. 1961; 83: 663
- 8d Michelson AM. Biochim. Biophys. Acta 1964; 93: 71
- 8e Hashimoto M, Mukaiyama T. Chem. Lett. 1972; 1: 595
- 8f Gao F, Yan X, Shakya T, Baettig OM, Ait-Mohand-Brunet S, Berghuis AM, Wright GD, Auclair K. J. Med. Chem. 2006; 49: 5273
- 9a Okada S, Nagase O, Shimizu M. Chem. Pharm. Bull. 1967; 15: 713
- 9b Shimizu M, Nagase O, Hosokawa Y, Tagawa H. Tetrahedron 1968; 24: 5241
- 10a Khalil EM, De Angelis J, Ishii M, Cole PA. Proc. Natl. Acad. Sci. U.S.A. 1999; 96: 12418
- 10b Mandel AL, La Clair JJ, Burkart MD. Org. Lett. 2004; 6: 4801
- 10c Tautz L, Rétey J. Eur. J. Org. Chem. 2010; 1728
- 11a Hecker SJ, Erion MD. J. Med. Chem. 2008; 51: 2328
- 11b Schultz C. Bioorg. Med. Chem. 2003; 11: 885
- 12 Rautio J, Kumpulainen H, Heimbach T, Oliyai R, Oh D, Jaervinen T, Savolainen J. Nat. Rev. Drug Discov. 2008; 7: 255
- 13 Schinazi RF, Cho JH, Zhou L, Zhang H, Pradere U, Coats SJ. WO2012158811, 2012
- 14a Parry RJ, Burns MR, Skae PN, Hoyt JC, Pal B. Bioorg. Med. Chem. 1996; 4: 1077
- 14b Soliveri G, Bertolotti A, Panza L, Poletti L, Jones C, Lay L. J. Chem. Soc., Perkin Trans. 1 2002; 2174
- 14c Walker SR, Jiao W, Parker EJ. Bioorg. Med. Chem. Lett. 2011; 21: 5092
- 15a Farquhar D, Srivastva DN, Kuttesch NJ, Saunders PP. J. Pharm. Sci. 1983; 72: 324
- 15b Sastry JK, Nehete PN, Khan S, Nowak BJ, Plunkett W, Arlinghaus RB, Farquhar D. Mol. Pharmacol. 1992; 41: 441
- 15c Farquhar D, Khan S, Srivastva DN, Saunders PP. J. Med. Chem. 1994; 37: 3902
- 15d Farquhar D, Chen R, Khan S. J. Med. Chem. 1995; 38: 488
- 15e Kang SH, Sinhababu AK, Cory JG, Mitchell BS, Thakker DR, Cho MJ. Pharm. Res. 1997; 14: 706
- 15f Rose JD, Parker WB, Someya H, Shaddix SC, Montgomery JA, Secrist JA. J. Med. Chem. 2002; 45: 4505
- 15g Khan SR, Kumar SK, Farquhar D. Pharm. Res. 2005; 22: 390
- 15h Zhao S, Etzkorn FA. Bioorg. Med. Chem. Lett. 2007; 17: 6615
- 15i Seo S, Onizuka K, Nishioka C, Takahashi E, Tsuneda S, Abe H, Ito Y. Org. Biomol. Chem. 2015; 13: 4589
- 16 FDA Approved Drugs, 2002, Herpesa (adefovir dipivoxil), http://www.centerwatch.com/drug-information/fda-approved-drugs/drug/797/hepsera-adefovir-dipivoxil (accessed February 2016).
- 17a Cebrat M, Kim CM, Thompson PR, Daugherty M, Cole PA. Bioorg. Med. Chem. 2003; 11: 3307
- 17b Hwang Y, Cole PA. Org. Lett. 2004; 6: 1555
- 18 Rutschow S, Thiem J, Kranz C, Marquardt T. Bioorg. Med. Chem. 2002; 10: 4043
- 19 Jenko B, Kosec G, Petkovic H, Podgorsek Berke A, Pahor J, Cusak A, Sibon OC. M, Srinivasan B. WO2015063177, 2015
- 20a Hwang Y, Ganguly S, Ho AK, Klein DC, Cole PA. Bioorg. Med. Chem. 2007; 15: 2147
- 20b Ruda GF, Alibu VP, Mitsos C, Bidet O, Kaiser M, Brun R, Barrett MP, Gilbert IH. ChemMedChem 2007; 2: 1169
- 21 DrugBank, Pivampicillin, http://www.drugbank.ca/drugs/DB01604 (accessed January 2016).
- 22 Srivastva DN, Farquhar D. Bioorg. Chem. 1984; 12: 118
- 23 Dhineshkumar J, Prabhu KR. Org. Lett. 2013; 15: 6062