Microwave-enhanced α-arylation of a protected glycine in water: Evaluation of 3-phenylglycine derivatives as inhibitors of the tuberculosis enzyme, glutamine synthetase

Combinatorial Chemistry and High Throughput Screening

Volumn 10, Issue 9, 2007, Pages 783-789

  Lagerlund, Olof ^a   Odell, Luke R ^a   Mowbray, Sherry L ^b   Nilsson, Mikael T ^a   Krajewski, Wojciech W ^a   Nordqvist, Anneli ^a   Karlén, Anders ^a   Larhed, Mats ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

Author keywords

Arylation; Glutamine synthetase; Microwave; Palladium; Tuberculosis; Water

Indexed keywords

3 PHENYLGLYCINE DERIVATIVE; ARYL L METHIONINE SULFOXIMINE DERIVATIVE; GLUTAMATE AMMONIA LIGASE; GLYCINE; IMINE; PALLADIUM; UNCLASSIFIED DRUG; WATER;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL STRUCTURE; ENZYME INHIBITION; MICROWAVE IRRADIATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; TUBERCULOSIS;

CATALYSIS; ENZYME INHIBITORS; GLUTAMATE-AMMONIA LIGASE; GLYCINE; HYDROCARBONS, CYCLIC; METHIONINE SULFOXIMINE; MICROWAVES; MODELS, CHEMICAL; MYCOBACTERIUM TUBERCULOSIS; PALLADIUM; WATER;

MYCOBACTERIUM TUBERCULOSIS;

EID: 37049032876     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/138620707783018478     Document Type: Article

References (30)

1. Kappe, C.O. Angew. Chem. Int. Ed., 2004, 43, 6250.
2. de la Hoz, A.; Díaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev., 2005, 34, 164.
3. Mavandadi, F.; Pilotti, A. Drug Discov. Today, 2006, 11, 165.
4. Kappe, C.O.; Dallinger, D. Nat. Rev. Drug Discov., 2006, 5, 51.
5. Wannberg, J.; Ersmark, K.; Larhed, M. Top. Curr. Chem., 2006, 266, 167.
6. Wu, X.; Larhed, M. Org. Lett., 2005, 7, 3327.
7. Wu, X.; Ekegren, J.K.; Larhed, M. Organometallics, 2006, 25, 1434.
8. Pierre Genet, J.; Savignac, M. J. Organomet. Chem., 1999, 576, 305.
9. Strauss, C.; Trainor, R. Aust. J. Chem., 1995, 48, 1665.
10. Harth, G.; Horwitz, M.A. Infect. Immun., 2003, 71, 456.
11. Global Tuberculosis Control: Surveillance, Planning, Financing. WHO Report 2006. Geneva, World Health Organization (WHO/HTM/TB/2006.362).
12. Berlicki, L.; Obojska, A.; Forlani, G.; Kafarski, P. J. Med. Chem., 2005, 48, 6340.
13. Harth, G.; Horwitz, M.A. J. Exp. Med., 1999, 189, 1425.
14. Duncan, K. Curr. Pharm. Des., 2004, 10, 3185.
15. Berlicki, L.; Kafarski, P. Bioorg. Med. Chem., 2006, 14, 4578.
16. Logusch, E.W.; Walker, D.M.; McDonald, J.F.; Franz, J.E. Biochemistry, 1989, 28, 3043.
17. Forlani, G.; Obojska, A.; Berlicki, L.; Kafarski, P. J. Agric. Food Chem., 2006, 54, 796.
18. Griffith, O. W.; Horwitz, M.; Harth, G. PCT. Int. Appl., 2004, WO 2004045539 A2, 40 pp.
19. Krajewski, W.W.; Jones, T.A.; Mowbray, S.L. Proc. Natl. Acad. Sci. USA, 2005, 102, 10499.
20. Lee, S.; Beare, N.A.; Hartwig, J.F. J. Am. Chem. Soc., 2001, 123, 8410.
21. Gaertzen, O.; Buchwald, S.L. J. Org. Chem., 2002, 67, 465.
22. Culkin, D.A.; Hartwig, J.F. Acc. Chem. Res., 2003, 36, 234.
23. Ikeda, D.; Kawatsura, M.; Uenishi, J. Tetrahedron Lett., 2005, 46, 6663.
24. Nilsson, P.; Olofsson, K.; Larhed, M. Top. Curr. Chem., 2006, 266, 103.
25. Xu, W.L.; Li, Y.Z.; Zhang, Q.S.; Zhu, H. S. Synthesis, 2004, 227.
26. Okamura, H.; Bolm, C. Org. Lett., 2004, 6, 1305.
27. Rarey, M.; Kramer, B.; Lengauer, T.; Klebe, G. J. Mol. Biol., 1996, 261, 470.
28. Tripos Inc. FlexX, 1.13.5, 1699 South Hanley Rd., St. Louis, Missouri, 63144, USA.
29. Schrödinger LLC. Maestro, 6.5, 120 West 45th Street, 32nd floor, New York, NY 10036-4041, USA.
30. Gawronski, J.D.; Benson, D.R. Anal. Biochem., 2004, 327, 114.