Development of novel antioxidants: Design, synthesis, and reactivity

Journal of Organic Chemistry

Volumn 68, Issue 18, 2003, Pages 7023-7032

  Hussain, Helmi H ^a   Babic, Gordana ^a   Durst, Tony ^a   Wright, James S ^b   Flueraru, Mihaela ^b   Chichirau, Alexandru ^b   Chepelev, Leonid L ^b  

^a UNIVERSITY OF OTTAWA   (Canada)

^b CARLETON UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ENTHALPY; FREE RADICALS; NITROGEN; PHENOLS; RATE CONSTANTS; SYNTHESIS (CHEMICAL);

SYNTHETIC ANTIOXIDANTS;

ANTIOXIDANTS;

2 HYDROXYMETHYL 4 METHOXYPHENOL; 2,6,7 TRIMETHYL 2,3 DIHYDROBENZOFURAN 4,5 DIOL; 2,7,8 TRIMETHYL 2 (4,8,12 TRIMETHYLTRIDECYL) 3,4 DIHYDRO 2H CHROMENE 5,6 DIOL; 3 METHYL 4 METHOXY 1,2 DIHYDROXYBENZENE; 4 METHOXY 3,4,6 TRIMETHYLBENZENE 1,2 DIOL; 4 METHYLBENZO[1,3]DIOXOLE 5,6 DIOL; ALPHA TOCOPHEROL; ANTIOXIDANT; BENZILIC ACID DERIVATIVE; BENZO[1,3]DIOXOLE 5,6 DIOL; CATECHOL DERIVATIVE; MEQUINOL; OXYGEN RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; DRUG ACTIVITY; DRUG DESIGN; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; ENTHALPY; STRUCTURE ANALYSIS; THEORY;

ANTIOXIDANTS; CATECHOLS; DRUG DESIGN; INDICATORS AND REAGENTS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NAPHTHALENES; PICRATES; THERMODYNAMICS;

EID: 0041837376     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0301090     Document Type: Article

References (26)

1. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine; Oxford University Press: Oxford, UK, 1999.
2. Burton, G.; Ingold, K. U. Acc. Chem. Res. 1986, 194, 194-201.
3. Mukai, K.; Okabe, K.; Hosose, H. J. Org. Chem. 1989, 54, 557-560.
4. Thomas, C. E. In Handbook of synthetic antioxidants; Packer, L., Cadenas, E., Eds.; Marcel Dekker: New York, 1997; pp 1-52.
5. Noguchi, N.; Niki, E. Free Radicals Biol. Med. 2000, 28, 1538-1546.
6. Foti, M. C.; Johnson, E. R.; Vinqvist, M. R.; Wright, J. S.; Barclay, L. R. C.; Ingold, K. U. J. Org. Chem. 2002, 67, 5190-5196.
7. Wright, J. S. Chem. Br. 2003, 39, 25-27.
8. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1976, 9, 13-19.
9. Scaiano, J. C.; Martin, A.; Yap, G. P. A.; Ingold, K. U. Org. Lett. 2000, 2, 899-901.
10. Wright, J. S.; Chepelev, L. Unpublished results.
11. DiLabio, G. A.; Wright, J. S. Free Radicals Biol. Med. 2000, 29, 480-485.
12. DiLabio, G. A.; Pratt, D. A.; LoFaro, A. D.; Wright, J. S. J. Phys. Chem. A 1999, 103, 1653-1661.
13. Wright, J. S.; Carpenter, D. J.; McKay, D. J.; Ingold, K. U. J. Am. Chem. Soc. 1997, 119, 4245-4252.
14. Wright, J. S.; Johnson, E. R.; DiLabio, G. A. J. Am. Chem. Soc. 2001, 123, 1173-1183.
15. (a) Wayner, D. D. M.; Lusztyk, E.; Page, D.; Ingold, K. U.; Mulder, P.; Laarhoven, L. J. J. A.; Aldrich, H. S. J. Am. Chem. Soc. 1995, 117, 8737-8744.
16. (b) Lucarini, M.; Pedulli, G. F.; Cipollone, M. J. Org. Chem. 1994, 59, 5063.
17. Burton, G. W.; LePage, Y.; Gabe, E. J.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 7791-7792.
18. Burton, G. W.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1983, 105, 5950-51.
19. Valgimigli, L.; Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 9966-9971.
20. Valgimigli, L.; Banks, J. T.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1999, 64, 3381-3383.
21. Spartan '02 for Windows, Wavefunction, Inc.: Irvine, CA, 2002.
22. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh PA, 1998.
23. Bolton, J. L.; Trush, M. A.; Penning, T. M.; Dryhurst, G.; Monks, T. J. Chem. Res. Toxicol. 2000, 13, 135-160.
24. Nelson, S. D.; Pearson, P. G. Annu. Rev. Pharmacol. Toxicol. 1990, 30, 169-195.
25. K. U. Ingold, personal communication.
26. DiLabio, G. A.; Pratt, D. A.; Wright, J. S. Chem. Phys. Lett. 1999, 311, 215-220.