Conformational analysis of phthalein derivatives acting as thymidylate synthase inhibitors by means of 1H NMR and quantum chemical calculations

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 10, 1996, Pages 1783-1794

  Ghelli, Stefano ^a   Rastelli, Giulio ^a   Barlocco, Daniela ^b   Rinaldi, Marcella ^a   Tondi, Donatella ^a   Pecorari, Piergiorgio ^a   Costi, Maria Paola ^a  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^b NONE

Author keywords

1H NMR; Conformational analysis; Enzyme inhibition; Phthalein derivatives; Quantum chemical calculations; Thymidylate synthase

Indexed keywords

ENZYME INHIBITOR; PHTHALEIN; THYMIDYLATE SYNTHASE;

ARTICLE; BINDING SITE; CONFORMATION; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

BACTERIA (MICROORGANISMS);

EID: 0030272851     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00193-9     Document Type: Article

References (21)

1. 1. Santi, D. V.; Danenberg, P. V. In Folate and Pteridines; Blakeley R. L.; Benkovic S. J., Eds.; Wiley: New York, 1984; pp 345-398.
2. 2. Douglas, K. T. Med. Res. 1987, 7, 441.
3. 3. Shoichet, B. K.; Perry, K. M.; Stroud, R. M.; Santi, D. V.; Kuntz, I. D. Science 1993, 259, 1445.
4. 4. Costi, M. P.; Pecorari, P.; Rinaldi, M.; Barlocco, D.; Shoichet, K. B.; Kuntz, I. .D.; Santi, D. V.; Stroud, R M. XII Symposium on Medicinal Chemistry, 19-23 September 1993, Parigi Abstr. P44.
5. 5. Costi, M. P., personal comunication.
6. 6. Sjoback, J.; Nygren, J.; Kubista, M. Spectros. Acta Part A 1995, 51, L7.
7. 7. Ozeki, T.; Morikawa, H.; Kihara, H. Comp. Aided Innoovation New Material II 1993, 925.
8. 8. Haubacher, M. J. Am. Chem. Soc. 1944, 66, 255.
9. 9. Blicke, F. F.; Patelski, R. A. J. Am. Chem. Soc. 1938, 69, 2283.
10. 10. Blicke, F. F.; Swisher, R. D. J. Am. Chem. Soc 1934, 56, 902.
11. 11. Aue, W. P.; Batholdi, E.; Ernst, R. R. J. Chem. Phys. 1976, 64, 2229.
12. 12. Jeener, J.; Meier B. H.; Bachmann P.; Ernst R. R. J. Chem. Phys. 1979, 71, 4546.
13. 13. (a) Redfield, A. G.; Kunz, S. D. J. Magn. Res. 1975, 19, 250.
14. (b) Bodenhausen, G.; Void, R. L.; Vold, R. R. J. Magn. Res. 1980, 37, 93.
15. 14. Bauer, C.; Freeman, R.; Frenkiel, T.; Keeler, J.; Shanka J. Magn. Res. 1984, 58, 442.
16. 15. Stewart, J. J. P. MOPAC 6.0, QCPE 455.
17. 16. Stewart, J. J. P. J. Comp. Chem. 1989, 10, 209.
18. 17. Climie, S. C.; Santi, D. V. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 633.
19. 18. Pogolotti, A. L.; Danenberg, P. U.; Santi, D. V. J. Med. Chem. 1986, 29, 478.
20. 19. (a) Segel, I. H. Enzyme Kinetics; Wiley: New York, 1975; p 172.
21. (b) ibidem, p 109.