How to cite this paper
Cholewinski, G., Malachowska–Ugarte, M., Siebert, A., Prejs, M & Dzierzbicka, K. (2018). Modifications of total synthesis of mycophenolic acid.Current Chemistry Letters, 7(1), 9-16.
Refrences
1. Bentley R. (2000) A One Hundred Year Odyssey from Antibiotic to Immunosuppressant. Chem. Rev., 100 (10) 3801–3825.
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.
3. Hedstrom L. (2009) IMP dehydrogenase: structure, mechanism, and inhibition. Chem. Rev., 109 (7) 2903–2928.
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.
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.
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.
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) Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid. J. Med. Chem., 39 (21) 4181–4196.
8. 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.
9. Rohloff J. C., Gardner J. O., and Towne R. W. (1995) Mycophenolate dianions. Tetrahedron Lett., 36 (43) 7803–7806.
10. 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.
11. Lai G., and Anderson W. K. (2000) Synthesis of Novel Indole Analogues of Mycophenolic Acid as Potential Antineoplastic Agents. Tetrahedron, 56 (17) 2583–2590.
12. 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.
13. 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.
14. 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.
15. Felczak K., Vince R., and Pankiewicz K. W. (2014) NAD-based inhibitors with anticancer potential. Bioorg. Med. Chem. Lett., 24 (1) 332–336.
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.
18. Pankiewicz K. W., Petrelli L., Singh R., and Felczak K. (2015). Curr. Med. Chem., 22 3991–4028.
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.
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.
21. Patterson J. W. (1995) The Synthesis of Mycophenolic Acid from 2,4-Dihydroxybenzoic Acid. J. Org. Chem., 60 (14) 4542–4548.
22. Patterson J. W. (1993) The Synthesis of Mycophenolic Acid. Tetrahedron, 49 (22) 4789–4798.
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.
24. Launer P. J., and McCaulay D. A. (1951) Infared Absorption Spectrum for 1,2,3,4-Tetramethylbenzene. Anal. Chem., 23 (12) 1875–1876.
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.
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.
27. White W. N., and Wolfarth E. F. (1970) The o-Claisen rearrangement. VIII. Solvent effects. J. Org. Chem., 35 (7) 2196–2199.
28. Plé P. A., Hamon A., and Jones G. (1997) A convergent synthesis of Mycophenolic acid. Tetrahedron, 53 (9) 3395–3400.
29. Padwa A., and Murphree S. S. (2006) Epoxides and aziridines - a mini review. ARKIVOC, iii 6–33.
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.
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 . Acta Cryst., E67 (12) o3393.
32. Sklarz B. (1967) Organic chemistry of periodates. Q. Rev. Chem. Soc., 21, 3-28.
33. Nagarkatti J. P., and Ashley K. R. (1973) Periodic acid cleavage of epoxides in aqueous medium. Tetrahedron Lett., 14 (46) 4599–4600.
34. 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.
35. 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.
36. 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.
37. 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.
38. 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.
39. Covarrubias-Zúniga A., A. Gonzalez-Lucas A., and Dominguez M. M. (2003) Total synthesis of mycophenolic acid. Tetrahedron, 59 (11) 1989–1994.
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.
3. Hedstrom L. (2009) IMP dehydrogenase: structure, mechanism, and inhibition. Chem. Rev., 109 (7) 2903–2928.
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.
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.
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.
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) Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid. J. Med. Chem., 39 (21) 4181–4196.
8. 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.
9. Rohloff J. C., Gardner J. O., and Towne R. W. (1995) Mycophenolate dianions. Tetrahedron Lett., 36 (43) 7803–7806.
10. 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.
11. Lai G., and Anderson W. K. (2000) Synthesis of Novel Indole Analogues of Mycophenolic Acid as Potential Antineoplastic Agents. Tetrahedron, 56 (17) 2583–2590.
12. 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.
13. 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.
14. 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.
15. Felczak K., Vince R., and Pankiewicz K. W. (2014) NAD-based inhibitors with anticancer potential. Bioorg. Med. Chem. Lett., 24 (1) 332–336.
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.
18. Pankiewicz K. W., Petrelli L., Singh R., and Felczak K. (2015). Curr. Med. Chem., 22 3991–4028.
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.
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.
21. Patterson J. W. (1995) The Synthesis of Mycophenolic Acid from 2,4-Dihydroxybenzoic Acid. J. Org. Chem., 60 (14) 4542–4548.
22. Patterson J. W. (1993) The Synthesis of Mycophenolic Acid. Tetrahedron, 49 (22) 4789–4798.
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.
24. Launer P. J., and McCaulay D. A. (1951) Infared Absorption Spectrum for 1,2,3,4-Tetramethylbenzene. Anal. Chem., 23 (12) 1875–1876.
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.
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.
27. White W. N., and Wolfarth E. F. (1970) The o-Claisen rearrangement. VIII. Solvent effects. J. Org. Chem., 35 (7) 2196–2199.
28. Plé P. A., Hamon A., and Jones G. (1997) A convergent synthesis of Mycophenolic acid. Tetrahedron, 53 (9) 3395–3400.
29. Padwa A., and Murphree S. S. (2006) Epoxides and aziridines - a mini review. ARKIVOC, iii 6–33.
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.
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 . Acta Cryst., E67 (12) o3393.
32. Sklarz B. (1967) Organic chemistry of periodates. Q. Rev. Chem. Soc., 21, 3-28.
33. Nagarkatti J. P., and Ashley K. R. (1973) Periodic acid cleavage of epoxides in aqueous medium. Tetrahedron Lett., 14 (46) 4599–4600.
34. 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.
35. 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.
36. 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.
37. 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.
38. 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.
39. Covarrubias-Zúniga A., A. Gonzalez-Lucas A., and Dominguez M. M. (2003) Total synthesis of mycophenolic acid. Tetrahedron, 59 (11) 1989–1994.