Asymmetric synthesis of isobenzofuranone derivatives and their unique character as protein kinase Cα (PKCα) activators

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3609-3612

  Hirai, Go ^a   Ogoshi, Yosuke ^b   Ohkubo, Megumi ^a,b   Tamura, Yuki ^a   Watanabe, Toru ^a,b   Shimizu, Tadashi ^a   Sodeoka, Mikiko ^a  

^a RIKEN   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

Asymmetric dihydroxylation; Bleb forming assay; Isobenzofuranone; Protein kinase C

Indexed keywords

BENZOFURAN DERIVATIVE; GAMMA LACTONE DERIVATIVE; ISOBENZOFURANONE DERIVATIVE; PROTEIN KINASE C ALPHA; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; BINDING AFFINITY; BIOLOGICAL ACTIVITY; CARBOXYLATION; CELL STRAIN K 562; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); CONFORMATIONAL TRANSITION; ENANTIOSELECTIVITY; HUMAN; HUMAN CELL; HYDROXYLATION; LITHIATION; PHENOTYPE;

EID: 65549129275     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.069     Document Type: Article

References (38)

1. Nishizuka Y. Science 258 (1992) 607-614
2. Yang C., and Kazanietz M.G. Trends Pharmacol. Sci. 24 (2003) 602-608
3. Newton A.C. Chem. Rev. 101 (2001) 2353-2364
4. Kishi Y., and Rando R.R. Acc. Chem. Res. 31 (1998) 163-172
5. Castagna M., Takai Y., Kaibuchi K., Sano K., Kikkawa U., and Nishizuka Y. J. Biol. Chem. 257 (1982) 7847-7851
6. Fujiki H., Tanaka Y., Miyake R., Kikkawa U., Nishizuka Y., and Sugimura T. Biochem. Biophys. Res. Commun. 120 (1984) 339-343
7. Smith J.B., Smith L., and Pettit G.R. Biochem. Biophys. Res. Commun. 132 (1985) 939-945
8. Berkow R.L., and Kraft A.S. Biochem. Biophys. Res. Commun. 131 (1985) 1109-1116
9. Teicher B.A. Clin. Cancer Res. 12 (2006) 5336-5345
10. Newman D.J., and Cragg G.M. J. Nat. Prod. 67 (2004) 1216-1238
11. Selected recent reports:. Yanagita R.C., Nakagawa Y., Yamanaka N., Kashiwagi K., Saito N., and Irie K. J. Med. Chem. 51 (2008) 46-56
12. Wender P.A., and Verma V.A. Org. Lett. 10 (2008) 3331-3334
13. Keck G.E., Kraft M.B., Truong A.P., Li W., Sanchez C.C., Kedei N., Lewin N.E., and Blumberg P.M. J. Am. Chem. Soc. 130 (2008) 6660-6661
14. Mach U.R., Lewin N.E., Blumberg P.M., and Kozikowski A.P. ChemMedChem 1 (2006) 307-314
15. Bertolini T.M., Giorgione J., Harvey D.F., and Newton A.C. J. Org. Chem. 68 (2003) 5028-5036
16. Marquez V.E., and Blumberg P.M. Acc. Chem. Res. 36 (2003) 434-443
17. Selected recent reports:. El Kazzouli S., Lewin N.E., Blumberg P.M., and Marquez V.E. J. Med. Chem. 51 (2008) 5371-5386 and references therein
18. Lee J., Lee J.-H., Kim S.Y., Perry N.A., Lewin N.E., Ayres J.A., and Blumberg P.M. Bioorg. Med. Chem. 14 (2006) 2022-2031
19. Baba Y., Ogoshi Y., Hirai G., Yanagisawa T., Nagamatsu K., Mayumi S., Hashimoto Y., and Sodeoka M. Bioorg. Med. Chem. Lett. 14 (2004) 2963-2967
20. Baba Y., Mayumi S., Hirai G., Kawasaki H., Ogoshi Y., Yanagisawa T., Hashimoto Y., and Sodeoka M. Bioorg. Med. Chem. Lett. 14 (2004) 2969-2972
21. Hirai G., Shimizu T., Watanabe T., Ogoshi Y., Ohkubo M., and Sodeoka M. ChemMedChem 2 (2007) 1006-1009
22. Marquez and co-workers reported that DAG and DAG-lactone derivatives with bulky hydrophobic substituents were potent ligands with low nanomolar binding affinity. See:. Nacro K., Sigano D.M., Yan S., Nicklaus M.C., Pearce L.L., Lewin N.E., Garfield S.H., Blumberg P.M., and Marquez V.E. J. Med. Chem. 44 (2001) 1892-1904
23. Nacro K., Bienfait B., Lee J., Han K.-C., Kang J.-H., Benzaria S., Lewin N.E., Bhattacharyya D.K., Blumberg P.M., and Marquez V.E. J. Med. Chem. 43 (2000) 921-944
24. Wang Z.-M., and Sharpless K.B. Synlett (1993) 603-604
25. Bennani Y.L., and Sharpless K.B. Tetrahedron Lett. 34 (1993) 2079-2082
26. A carboxymethyl group at the ortho-position did not disturb asymmetric dihydroxylation:. Ohzeki T., and Mori K. Biosci. Biotechnol. Biochem. 67 (2003) 2240-2244
27. Moderate ee was observed in the case of a highly substituted styrene derivative:. Ohzeki T., and Mori K. Biosci. Biotechnol. Biochem. 67 (2003) 2584-2590
28. Uemura M., Tokuyama S., and Sakan T. Chem. Lett. (1975) 1195-1198
29. Trost B.M., Rivers G.T., and Gold J.M. J. Org. Chem. 45 (1980) 1835-1838
30. Olah G.A., Wu A., and Farooq O. Synthesis (1989) 566-567
31. The complete characterization for all new compounds has been done using NMR and MALDI-TOFMS.
32. Assay protocol is described in Ref. 8c.
33. Tanaka Y., Miyake R., Kikkawa U., and Nishizuka Y. J. Biochem. 99 (1986) 257-261
34. Ananthanarayanan B., Stahelin R.V., Digman M.A., and Cho W. J. Biol. Chem. 278 (2003) 46886-46894
35. i value of 2d determined with this system was 11.2 nM
36. 21 Another possibility is that 2d has an alternative binding mode, in which the lactone carbonyl group instead of the side chain carbonyl group makes critical hydrogen bond with Gly124. If this is the case, the hydrogen bonding with Gly124 would be missing in the compound 2e causing drastic decrease in affinity to PKCα.
37. The importance of the both carbonyl groups in DAG-lactone was discussed in the following literature:. Kang J.-H., Peach M.L., Pu Y., Lewin N.E., Nicklaus M.C., Blumberg P.M., and Marquez V.E. J. Med. Chem. 48 (2005) 5738-5748
38. Osada H., Magae J., Watanabe C., and Isono K. J. Antibiot. 41 (1988) 925-931