Acetonide protection of dopamine for the synthesis of highly pure N-docosahexaenoyldopamine

Tetrahedron Letters

Volumn 51, Issue 18, 2010, Pages 2403-2405

  Liu, Zhongqiang ^a,b   Hu, Bi Huang ^a,b   Messersmith, Phillip B ^a,b  

^a Northwestern University   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2 DIMETHOXYPROPANE; ACETONE; CARBAMIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CERVONIC ACID; DOPAMINE; DOPAMINE DERIVATIVE; FLUORENYLMETHYLOXYCARBONYL CHLORIDE; ISOQUINOLINE DERIVATIVE; N CARBETHOXYPHTHALIMIDE; N DOCOSAHEXAENOYLDOPAMINE; PHTHALIMIDE DERIVATIVE; PROPANE; TOLUENESULFONIC ACID; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG PURITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 77950021346     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.089     Document Type: Article

References (29)

1. Benes F.M. Trends Pharmacol. Sci. 22 (2001) 46-47
2. Mendis T., Suchowersky O., Lang A., and Gauthier S. Can. J. Neurol. Sci. 26 (1999) 89-103
3. Shashoua V.E., and Hesse G.W. Life Sci. 58 (1996) 1347-1357
4. Shashoua, V. E. U.S. Pat. Appl. Publ. US2003050226A1, 2003.
5. Bezuglov V., Bobrov M., Gretskaya N., Gonchar A., Zinchenko G., Melck D., Bisogno T., Di Marzo V., Kuklev D., Rossi J.C., Vidal J.P., and Durand T. Bioorg. Med. Chem. Lett. 11 (2001) 447-449
6. LaVoie M.J., and Hastings T.G. J. Neurosci. 19 (1999) 1484-1491
7. Garcia-Gancedo A., Gil C., Roldan C.M., Perez S., and Vilas P. Chemotherapy 25 (1979) 83-90
8. Hu B.H., and Messersmith P.B. Tetrahedron Lett. 41 (2000) 5795-5798
9. Li G., Cheng G., Xue H., Chen S., Zhang F., and Jiang S. Biomaterials 29 (2008) 4592-4597
10. Liu Z., Hu B.-H., and Messersmith P.B. Tetrahedron Lett. 49 (2008) 5519-5521
11. Statz A.R., Meagher R.J., Barron A.E., and Messersmith P.B. J. Am. Chem. Soc. 127 (2005) 7972-7973
12. Nichols D.E., and Kostuba L.J. J. Med. Chem. 22 (1979) 1264-1267
13. Christian, S. T. PCT Int. Appl. WO2001079244A1, 2001.
14. Christian, S. T. Sundsmo, J. S. U.S. Pat. Appl. Publ. US2005250739A1, 2005.
15. Mark, C. PCT Int. Appl. WO2008006864, 2008.
16. Harwood H.J., and Cassidy H.G. J. Am. Chem. Soc. 79 (1957) 4360-4365
17. Fuller W.D., Verlander M.S., and Goodman M. Biopolymers 17 (1978) 2939-2943
18. Morita S., Ito T., and Tono T. Agric. Biol. Chem. 39 (1975) 547-549
19. Felder Flesch, D.; Steibel, J.; Bertin, A. PCT Int. Appl. WO2008043911, 2008.
20. Cai W., Kwok S.W., Taulane J.P., and Goodman M. J. Am. Chem. Soc. 126 (2004) 15030-15031
21. Cole E.R., Crank G., and Minh H.T.H. Aust. J. Chem. 33 (1980) 675-680
22. +, calcd 194.11756, found 194.11757.
23. Black T.D., Briggs B.S., Evans R., Muth W.L., Vangala S., and Zmijewski M.J. Biotechnol. Lett. 18 (1996) 875-880
24. Le Roy I., Mouysset D., Mignani S., Vuilhorgne M., and Stella L. Tetrahedron 59 (2003) 3719-3727
25. Delon L., Laurent P., and Blancou H. J. Fluorine Chem. 126 (2005) 1487-1492
26. Maryanoff B.E., Zhang H.C., Cohen J.H., Turchi I.J., and Maryanoff C.A. Chem. Rev. 104 (2004) 1431-1628
27. Babu V., Patil B., and Vasanthakumar G.-R. Synth. Commun. 35 (2005) 1795-1802
28. Niederstein Y., and Peter M.G. Liebigs Ann. Chem. (1989) 1189-1193
29. +, calcd 464.31592, found 464.31560.