Synthesis of fluorescent ring-fused 2-pyridone peptidomimetics

Journal of Organic Chemistry

Volumn 78, Issue 23, 2013, Pages 12207-12213

  Krishnan, K Syam ^a   Bengtsson, Christoffer ^a   Good, James A D ^a   Mirkhanov, Shamil ^a   Chorell, Erik ^a   Johansson, Lennart B Å ^a   Almqvist, Fredrik ^a  

^a UMEÅ UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMYLOID FIBERS; CHEMICAL BIOLOGY; FIBER FORMATION; LITHIUM HALIDES; PEPTIDOMIMETICS; PHOTOPHYSICAL PROPERTIES; SYNTHETIC ROUTES; UROPATHOGENIC ESCHERICHIA COLI;

ESCHERICHIA COLI;

FLUORESCENCE;

2 BENZYL 7 (2 CARBOXY ETHYL) 8 CYCLOPROPYL 5 OXO 5H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID METHYL ESTER; 2 BENZYL 8 CYCLOPROPYL 7 (2 (1,3,5,7 TETRAMETHYL 4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE 8 YL)ETHYL] 5 OXO 5H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID; 2 BENZYL 8 CYCLOPROPYL 7 [2 (1,3,5,7 TETRAMETHYL 4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE 8 YL)ETHYL] 5 OXO 5H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID METHYL ESTER; 5 OXO 8 CYCLOPROPYL 7 [2 (1,3,5,7 TETRAMETHYL 4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE 8 YL)ETHYL] 3,5 DIHYDRO 2H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID; 5 OXO 8 CYCLOPROPYL 7 [2 (1,3,5,7 TETRAMETHYL 4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE 8 YL)ETHYL] 3,5 DIHYDRO 2H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID METHYL ESTER; 7 (2 CARBOXY ETHYL) 8 CYCLOPROPYL 2 METHYL 5 OXO 5H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID METHYL ESTER; 7 (2 CARBOXY ETHYL) 8 CYCLOPROPYL 5 OXO 2 PHENYL 5H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID METHYL ESTER; 7 (2 CARBOXY ETHYL) 8 CYCLOPROPYL 5 OXO 2,3 DIHYDRO 5H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID METHYL ESTER; 8 CYCLOPROPYL 7 (2 (1,3,5,7 TETRAMETHYL 4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE 8 YL)ETHYL] 2 METHYL 5 OXO 5H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID; 8 CYCLOPROPYL 7 [2 (1,3,5,7 TETRAMETHYL 4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE 8 YL)ETHY] 2 METHYL 5 OXO 5H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID METHYL ESTER; 8 CYCLOPROPYL 7 [2 (1,3,5,7 TETRAMETHYL 4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE 8 YL)ETHYL] 5 OXO 2 PHENYL 5H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID; 8 CYCLOPROPYL 7 [2 (1,3,5,7 TETRAMETHYL 4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE 8 YL)ETHYL] 5 OXO 2 PHENYL 5H THIAZOLO[3,2 A]PYRIDINE 3 CARBOXYLIC ACID METHYL ESTER; DIPYRONE; FLUORESCENT DYE; PEPTIDOMIMETIC AGENT; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; BACTERIAL VIRULENCE; BROMINATION; CATALYST; DEHALOGENATION; DERIVATIZATION; DRUG SOLUBILITY; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; HYDROLYSIS; LITHIATION; NONHUMAN; OLIGOMERIZATION; OXIDATION; QUANTUM YIELD; SONOGASHIRA REACTION; SUZUKI REACTION; UROPATHOGENIC ESCHERICHIA COLI;

FLUORESCENCE; FLUORESCENT DYES; MOLECULAR STRUCTURE; PEPTIDOMIMETICS; PYRIDONES; THIAZOLES;

EID: 84890202910     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401844y     Document Type: Article

References (28)

1. Kaper, J. B.; Nataro, J. P.; Mobley, H. L. T. Nat. Rev. Micro. 2004, 2, 123
2. Waksman, G.; Hultgren, S. J. Nat. Rev. Micro. 2009, 7, 765
3. Pinkner, J. S.; Remaut, H.; Buelens, F.; Miller, E.; Åberg, V.; Pemberton, N.; Hedenström, M.; Larsson, A.; Seed, P.; Waksman, G.; Hultgren, S. J.; Almqvist, F. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 17897
4. Chorell, E.; Pinkner, J. S.; Phan, G.; Edvinsson, S.; Buelens, F.; Remaut, H.; Waksman, G.; Hultgren, S. J.; Almqvist, F. J. Med. Chem. 2010, 53, 5690
5. Chorell, E.; Pinkner, J. S.; Bengtsson, C.; Edvinsson, S.; Cusumano, C. K.; Rosenbaum, E.; Johansson, L. B. Å.; Hultgren, S. J.; Almqvist, F. Chem.-Eur. J. 2012, 18, 4522
6. Cegelski, L.; Pinkner, J. S.; Hammer, N. D.; Cusumano, C. K.; Hung, C. S.; Chorell, E.; Åberg, V.; Walker, J. N.; Seed, P. C.; Almqvist, F.; Chapman, M. R.; Hultgren, S. J. Nat. Chem. Biol. 2009, 5, 913
7. Horvath, I.; Weise, C. F.; Andersson, E. K.; Chorell, E.; Sellstedt, M.; Bengtsson, C.; Olofsson, A.; Hultgren, S. J.; Chapman, M.; Wolf-Watz, M.; Almqvist, F.; Wittung-Stafshede, P. J. Am. Chem. Soc. 2012, 134, 3439
8. Horvath, I.; Sellstedt, M.; Weise, C.; Nordvall, L.-M.; Krishna Prasad, G.; Olofsson, A.; Larsson, G.; Almqvist, F.; Wittung-Stafshede, P. Arch. Biochem. Biophys. 2013, 532, 84
9. Zhang, J.; Campbell, R. E.; Ting, A. Y.; Tsien, R. Y. Nat. Rev. Mol. Cell Biol. 2002, 3, 906
10. Lavis, L. D.; Raines, R. T. ACS Chem. Biol. 2008, 3, 142
11. Chorell, E.; Das, P.; Almqvist, F. J. Org. Chem. 2007, 72, 4917
12. Lumbierres, M.; Palomo, J. M.; Kragol, G.; Roehrs, S.; Müller, O.; Waldmann, H. Chem.-Eur. J. 2005, 11, 7405
13. Crawford, S. M.; Thompson, A. Org. Lett. 2010, 12, 1424
14. Liras, M.; Bañuelos Prieto, J.; Pintado-Sierra, M.; García-Moreno, I.; Costela, á.; Infantes, L.; Sastre, R.; Amat-Guerri, F. Org. Lett. 2007, 9, 4183
15. Chorell, E.; Edvinsson, S.; Almqvist, F. Tetrahedron Lett. 2010, 51, 2461
16. Bengtsson, C.; Almqvist, F. J. Org. Chem. 2011, 76, 9817
17. Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891
18. Li, Z.; Mintzer, E.; Bittman, R. J. Org. Chem. 2006, 71, 1718
19. West, R.; Panagabko, C.; Atkinson, J. J. Org. Chem. 2010, 75, 2883
20. Åberg, V.; Hedenstrom, M.; Pinkner, J. S.; Hultgren, S. J.; Almqvist, F. Org. Biomol. Chem 2005, 3, 3886
21. Elsinger, F.; Schreiber, J.; Eschenmoser, A. Helv. Chim. Acta 1960, 43, 113
22. Dean, P. D. G. J. Chem. Soc. 1965, 6655
23. Karolin, J.; Johansson, L. B. A.; Strandberg, L.; Ny, T. J. Am. Chem. Soc. 1994, 116, 7801
24. Bergström, F.; Mikhalyov, I.; Hägglöf, P.; Wortmann, R.; Ny, T.; Johansson, L. B. Å. J. Am. Chem. Soc. 2001, 124, 196
25. Emtenäs, H.; Taflin, C.; Almqvist, F. Mol. Diversity 2003, 7, 165
26. Isomura, S.; Wirsching, P.; Janda, K. D. J. Org. Chem. 2001, 66, 4115
27. Weber, G.; Teale, F. W. J. J. Chem. Soc., Faraday Trans. 1958, 54, 640
28. Levenberg, K. Q. Appl. Math. 1944, 2, 164