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Modifications of total synthesis of mycophenolic acid

Abstract

The total synthesis of mycophenolic acid (MPA), a potent immunosuppressant, was modified. The obtained mycophenolic acid was suitable for further preparation of new prospective immunosuppressants with improved therapeutic properties.

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Category:
Articles
Type:
artykuły w czasopismach recenzowanych i innych wydawnictwach ciągłych
Published in:
Current Chemistry Letters no. 7, edition 1, pages 9 - 16,
ISSN: 1927-7296
Language:
English
Publication year:
2018
Bibliographic description:
Cholewiński G., Małachowska - Ugarte M., Siebert A., Prejs M., Dzierzbicka K.: Modifications of total synthesis of mycophenolic acid// Current Chemistry Letters. -Vol. 7., iss. 1 (2018), s.9-16
DOI:
Digital Object Identifier (open in new tab) 10.5267/j.ccl.2018.1.001
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  1. Bentley R. (2000) A One Hundred Year Odyssey from Antibiotic to Immunosuppressant. Chem. Rev., 100 (10) 3801-3825. open in new tab
  2. Kaplan B. (2006) Mycophenolic acid trough level monitoring in solid organ transplant recipients treated with mycophenolate mofetil: Association with clinical outcomes. Curr. Med. Res. Opin., 22 (12) 2355-2364. open in new tab
  3. Hedstrom L. (2009) IMP dehydrogenase: structure, mechanism, and inhibition. Chem. Rev., 109 (7) 2903-2928. open in new tab
  4. Siebert A., Prejs M., G. Cholewiński G., and Dzierzbicka K. (2017) New Analogues of Mycophenolic Acid. Mini Rev. Med. Chem., 17 (9) 734-745. open in new tab
  5. Ghioa L., Ferraresso M., Zacchelloc G., Murerc L., Ginevrid F., Belingheria M., Peruzzie L., Zanonf F. Perfumod F., Berardinellib L., Tirellig S., Strologoh L. D.,Fontanai I. Valentei U. Cardilloj M., and Edefontia A. (2009) Longitudinal evaluation of mycophenolic acid pharmacokinetics in pediatric kidney transplant recipients. The role of post-transplant clinical and therapeutic variables. Clin. Transplant., 23 (2) 264-270. open in new tab
  6. Jablecki J., Kaczmarzyk L., Patrzałek D., Domanasiewicz A., and Boratynska Z. (2009) First Polish forearm transplantation: report after 17 months. Transplant. Proc., 41 (2) 549-553. open in new tab
  7. Nelson P. H., Carr S. F., Devens B. H., Eugui E. M., Franco F., Gonzalez C., Havley R. C., Loghhead R. G., Milan D. J., Papp E., Patterson J. W., Rouhafza S., Sjogren E. B., Smith D. B., Stephenson R. A., Talamas F. X., Waltos A. N., Weikert R. J., and Wu J.C. (1996) open in new tab
  8. Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid. J. Med. Chem., 39 (21) 4181-4196. open in new tab
  9. Watkins W. J., Chen J. M., Cho A., Chong L., Collins N., Fardis M., Huang W., Hung M., Kirschberg T., Lee W. A., Liu X., Thomas W., Xu X., Zeynalzadegan A., and Zhang J. (2006) Phosphonic acid- containing analogues of mycophenolic acid as inhibitors of IMPDH. Bioorg. Med. Chem. Lett., 16 (13) 3479-3483. open in new tab
  10. Rohloff J. C., Gardner J. O., and Towne R. W. (1995) Mycophenolate dianions. Tetrahedron Lett., 36 (43) 7803-7806. open in new tab
  11. Chen L., Wilson D., Jayaram H. N., and Pankiewicz K. W. (2007) Dual inhibitors of IMP- dehydrogenase and histone deacetylases for cancer treatment. J. Med. Chem., 50 (26) 6685-6691. open in new tab
  12. Lai G., and Anderson W. K. (2000) Synthesis of Novel Indole Analogues of Mycophenolic Acid as Potential Antineoplastic Agents. Tetrahedron, 56 (17) 2583-2590. open in new tab
  13. Meza-Aviña M. E., Ordoñez M., Fernández-Zertuche M., Rodríguez-Fragoso L., Reyes-Esparza J., and Martínez de los Ríos-Corsino A. A. (2005) Synthesis of some monocyclic analogues of mycophenolic acid via the Johnson ortho ester Claisen rearrangement. Bioorg. Med. Chem., 13 (23) 6521-6528. open in new tab
  14. Pankiewicz K. W., Lesiak-Watanabe K. B., Watanabe K. A., Patterson S. E., Jayaram H. N., Yalowitz J. A., Miller M. D., Seidman M., Majumdar A. G., Prehna G., and Goldstein B. M. (2002) Novel mycophenolic adeninę bis(phosphonate) analogues as potential differentiation agents against human leukemia. J. Med. Chem., 45 (3) 703-712. open in new tab
  15. Cholewiński G., Malachowska-Ugarte M., and Dzierzbicka K. (2010) The chemistry of mycophenolic acid -synthesis and modifications towards desired biological activity. Curr. Med. Chem., 17 (18) 1926-1941. open in new tab
  16. Felczak K., Vince R., and Pankiewicz K. W. (2014) NAD-based inhibitors with anticancer potential. Bioorg. Med. Chem. Lett., 24 (1) 332-336. open in new tab
  17. Pankiewicz K. W., and Felczak K. (2015) From ribavirin to NAD analogues and back to ribavirin in search for anticancer agents. Heterocycl. Commun., 21 (1) 249-257. open in new tab
  18. Pankiewicz K. W., Petrelli L., Singh R., and Felczak K. (2015). Curr. Med. Chem., 22 3991-4028. open in new tab
  19. Cholewinski G., Iwaszkiewicz-Grzes D., Prejs M., Glowacka A., and Dzierzbicka K. (2015) Synthesis of the inosine 5'-monophosphate dehydrogenase (IMPDH) Inhibitors. J. Enzyme Inhib. Med. Chem., 30 (4) 550-563. open in new tab
  20. Alani F., Grove J. A., Anderson W. A., and Moo-Young M. (2009) Mycophenolic acid production in solid-state fermentation using a packed-bed bioreactor. Biochem. Eng. J., 44 (2-3) 106-110. open in new tab
  21. Patterson J. W. (1995) The Synthesis of Mycophenolic Acid from 2,4-Dihydroxybenzoic Acid. J. Org. Chem., 60 (14) 4542-4548. open in new tab
  22. Patterson J. W. (1993) The Synthesis of Mycophenolic Acid. Tetrahedron, 49 (22) 4789-4798. open in new tab
  23. Patterson J. W., and Huang G. T. (1991) The orthoester Claisen rearrangement in the synthesis of mycophenolic acid. J. Chem. Soc., Chem. Commun., (21) 1579-1580. open in new tab
  24. Launer P. J., and McCaulay D. A. (1951) Infared Absorption Spectrum for 1,2,3,4- Tetramethylbenzene. Anal. Chem., 23 (12) 1875-1876. open in new tab
  25. Aliev M. I., Kozeiko T. A., and Fisher S. I. (1970) Capillary chromatography of C8-C122 alkylbenzenes and dependence of their volumes of retention on the boiling point. Chem. Tech. Fuels Oil., 6 (10) 781-786. open in new tab
  26. Krichko A. A., Skvortsov D. V., Titova T. A., Filippov B. S., and Dogadkina N. E. (1969) Production of tetralin by the hydrogenation of naphthalene-containing fractions. Chem. Tech. Fuels Oil., 5 (1) 18-22. open in new tab
  27. White W. N., and Wolfarth E. F. (1970) The o-Claisen rearrangement. VIII. Solvent effects. J. Org. Chem., 35 (7) 2196-2199. open in new tab
  28. Plé P. A., Hamon A., and Jones G. (1997) A convergent synthesis of Mycophenolic acid. Tetrahedron, 53 (9) 3395-3400. open in new tab
  29. Padwa A., and Murphree S. S. (2006) Epoxides and aziridines -a mini review. ARKIVOC, iii 6- 33. open in new tab
  30. Binder C. M., Dixon D. D., Almaraz E., Tius M. A., and Singaram B. (2008) A Simple Procedure for C-C Bond Cleavage of Aromatic and Aliphatic Epoxides with Aqueous Sodium Periodate Under Ambient Conditions. Tetrahedron Lett., 49 (17) 2764-2767. open in new tab
  31. Malachowska-Ugarte M., Cholewinski G., Chojnacki J., and Dzierzbicka K. (2011) 4-[(tert- Butyldimethylsilyl)oxy]-6-methoxy-7-methyl-5-(oxiran-2-ylmethyl)-2-benzofuran-3(1H)-one . open in new tab
  32. Acta Cryst., E67 (12) o3393. open in new tab
  33. Sklarz B. (1967) Organic chemistry of periodates. Q. Rev. Chem. Soc., 21, 3-28. open in new tab
  34. Nagarkatti J. P., and Ashley K. R. (1973) Periodic acid cleavage of epoxides in aqueous medium. Tetrahedron Lett., 14 (46) 4599-4600. open in new tab
  35. Gillies C. W., Gillies J. Z., Suenram R. D., Lovas F. J., Kraka E., and Cremer D. (1991) Van der Waals complexes in 1,3-dipolar cycloaddition reactions: ozone-ethylene. J. Am. Chem. Soc., 113 (7) 2412-2421. open in new tab
  36. Malachowska-Ugarte M., Cholewinski G., Dzierzbicka K., and Trzonkowski P. (2012) Synthesis and biological activity of novel mycophenolic acid conjugates containing nitro-acridine/acridone derivatives. Eur. J. Med. Chem., 54 197-201. open in new tab
  37. Iwaszkiewicz-Grzes D., Cholewinski G., Kot-Wasik A., Trzonkowski P., and Dzierzbicka K. (2013) Synthesis and biological activity of mycophenolic acid-amino acid derivatives. Eur. J. Med. Chem., 69, 863-871. open in new tab
  38. Cholewinski G., Iwaszkiewicz-Grzes D., Trzonkowski P., and Dzierzbicka K. (2016) Synthesis and biological activity of ester derivatives of mycophenolic aci and acridines/acridones as potential immunosuppressive agents. J. Enzyme Inhib. Med. Chem., 31 (6) 974-982. open in new tab
  39. Prejs M., Cholewinski G., Siebert A., Trzonkowski P., and Dzierzbicka K. (2016) New conjugates of mycophenolic acid and their antiproliferative activity. J. Asian. Nat. Prod. Res., 18 (11) 1057- 1062. open in new tab
  40. Covarrubias-Zúniga A., A. Gonzalez-Lucas A., and Dominguez M. M. (2003) Total synthesis of mycophenolic acid. Tetrahedron, 59 (11) 1989-1994. open in new tab
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