Synthesis of L-3, 4-Dihydroxyphenylalanie Derivative from L-Tyrosine by Microwave Irradiation

Authors

  • Ayan Bandyopadhyay  Department of Chemistry, Government General Degree College, Chapra, Village-Shikra, P.O.-Padmamala, District-Nadia, West Bengal, India

Keywords:

L-Tyrosine, L-DOPA, Parkinson's disease, Microwave Antitumor.

Abstract

A range of amide derivatives of L-dopa were synthesized and investigated for their enormous pharmacological activity and their capability to be converted into others natural and unnatural products of great biological interest. Herein, a microwave assisted rearrangement has been developed in the final step to produce much improved yield of L-DOPA derivative without any racemization with minimal byproducts and reduce the processing time also.

References

  1. Raper, S. H.; Biochem. J.1926, 20, 735.
  2. Tremmel, E.; Kuhn, C.; Kaltofen, T.; Vilsmaier, T.; Mayr, D.; Mahner, S.; Ditsch, N.; Jeschke, U.; Vattai, A. Int. J. Mol. Sci.2020, 21, 9565.
  3. Kofman, O. The Canadian Medical Association Journal Le Journal de1971, 104, 483-487.
  4. Sletzinger, M., Chemerda, M. J., Bolinger, W. F. J. Med. Chem. 1963, 6, 101. b) Porter, C.C. Biochem. Pharmacol.1962, 11, 1067.
  5. Cotizias, C.G., Papavasilion, S. P., Gellene, R. New. Engl. J. Med. 1969, 280, 337.
  6. Denora, N., Laquintana, V., Lopedota, A., Serra, M., Dazzi, L, Biggio, G., Pal, D., Mitra, K. A., Latrofa, A., Trapani, G., Liso, G. Pharm. Res. 2007, 7, 1309-24.
  7. Zhou, T., Hider, C. R., Jenner, P., Campbell, B., Hobbs, J. C., Rose, S.; Jairaj, M., Tayarani-Binazir, A. K., Syme, A. Biorg. Med. Chem. Lett.2013, 19, 5279-82.
  8. a) Sano, S.; Ikai, K. Yoshikawa, Y., Nakamura, T., Obayashi, A. J. Antibiot.1987, 40, 512. b) Yauzawa, T.; Shirahata, K.; Sano, H. J. Antibiot.1987, 40, 455-458. c) Nishiyama, S., Suzuki, Y.; Yamamura, S. Tetrahedron Lett. 1988, 29, 559. d) Boger, D. L.; Yohannes, D. J. Org. Chem.1990, 55, 6000-6017. e) Chattopadhyay, K. S., Bandyopadhyay, A; Pal B, K. Tetrahedron Lett.2007, 48, 3655-3659.
  9. Waser, E., Lewandowski, N. Helv. Chim. Acta.1921, 4, 657-666.
  10.  a) Knowles, S. W., Sabacky, J. M., Chem. Commun. 1966, 1445. b) Knowles, J.; Chem. Educ.1986, 63, 222-225. c) Vocke, W., Hanel, R.; Flother, U. F.; Chem. Technol.1987, 39, 123-125.
  11. Ooi, T., Kameda, M. Tannai, H., Maruoka, K. Tetrahedron Lett. 2000, 41, 8339-8342.
  12. Pecanha, P. E., Antunes, C. A. O., Tanuri, A. Quim. Nova2002, 25, 1108-1116.
  13. a) Gedye R.; Smith, F.; Westaway, K., Ali, H., Baldisera, L., Laberge, L., Rousell, J., Tetrahedron Lett.1986, 27, 279-282. b) Giguere, R. J.; Bray, L. T.; Duncan, M. S.; Majetick, G. Tetrahedron Lett. 1986, 27, 4945-4948, c) Lindstrom, P., Tierney, J., Warthy, B., Westman, J. Tetrahedron, 2001, 57, 9225-9283. d) Roberts, B. A.; Strauss, C. R. Acc. Chem. Res., 2005, 38, 653-661. e) Baghbanzadeh, M.; Carbon, L.; Cozzoli, P. D.; Kappe, C. O.; Angrew. Chem. Int, Ed. 2011, 50. f) Kappe, C. O.; Dallinger, D. Nat. Rev. Drug Discov., 2006, 5, 51-63.
  14.  Boger, L. D.; Yohannes, D. J. Org. Chem. 1987, 52, 5283-5286.
  15. a) Konda, M.; Shioire, T.; Yamada, S. Chem. Pharm.Bull. 1975, 23, 1063. b) Wilcox, M. E.; Wyler, H.; Mabry, T. J.; Dreiding, A. S. Helv. Chem. Acta1965, 48, 252.
  16. a) Kappe, C. O. Angrew. Chem. Int. Ed.2004, 43, 6250-6280. Angrew. Chem. 116, 6408-6443. b) Rodriguez, A. M.; Prieto, de la Hoz. A.; Diaz-Ortiz A.; Martin, D. R.; Garcia, J. I. Chemistry Open, 2015, 4, 308-307.
  17. a) Bose, K. A.; Manhas, S. M.; Banik, K. B. Res. Chem. Intermed1994, 20 ,1-11. b) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis1994, 741-760. c) Grieco, A.P. Aldrichimaca Acta, 1991, 24, 59-66.
  18. a) Laupy, A.; Petit, A.; Hamelin, F.; Texier-Boullet, P.; Jaquault, Mathe, D. Synthesis1998, 1213-1234. b) Das, K.; S. Synlett.2004, 915. c) Pistera, V.; Rescifina, A.; Chiacchio, A. M.; Corsaro, A. Curr. Org. Chem., 2014, 18, 417-445.

Downloads

Published

2018-04-30

Issue

Section

Research Articles

How to Cite

[1]
Ayan Bandyopadhyay, " Synthesis of L-3, 4-Dihydroxyphenylalanie Derivative from L-Tyrosine by Microwave Irradiation, International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 4, Issue 5, pp.1986-1990, March-April-2018.