Stereoselective synthesis and antioxidant activity of azabicycloadducts derived from 9, 10-Phenanthrenequinone

Heteroatom Chemistry

Volumn 20, Issue 7, 2009, Pages 379-392

  Arora, Komal ^a   Jose, D ^a   Singh, D ^a   Gupta, R S ^a   Pardasani, P ^a   Pardasani, R T ^a  

^a UNIVERSITY OF RAJASTHAN   (India)

Author keywords

[No Author keywords available]

Indexed keywords

9 ,10-PHENANTHRENEQUINONE; ANTIOXIDANT ACTIVITIES; AZOMETHINE YLIDES; CYCLIC AMINO ACIDS; CYCLOADDUCTS; DIPOLAROPHILES; ELECTRON-DEFICIENT; ELEMENTAL ANALYSIS; FACILE SYNTHESIS; L-PROLINE; NMR SPECTROSCOPY; PHENANTHRENEQUINONE; PYRROLIDINES; SPECTROSCOPIC TECHNIQUE; STEREOSELECTIVE SYNTHESIS; THIAZOLIDINE-4-CARBOXYLIC ACID;

AMINO ACIDS; CARBOXYLIC ACIDS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ORGANIC ACIDS;

EID: 77049108724     PISSN: 10427163     EISSN: 10981071     Source Type: Journal    
DOI: 10.1002/hc.20562     Document Type: Article

References (47)

1. Huisgen, R. Angew Chem 1963, 75(13), 604.
2. (a) Pandey, G.; Banerjee, P.; Gadre, S. R. Chem Rev 2006, 106(11), 4484;
3. (b) Gothelf, Kurt V. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen, K. A.; (Eds.); Wiley-VCH; Weinheim, Germany, 2002; Ch. 6, p. 211;
4. (c) Gothelf, K. V.; Jorgensen, K. A. Chem Rev 1998, 98(2), 863;
5. (d) Gribble, G. W. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W.; Scriver, E. F. V.; (Eds.); Pergamon; Oxford, UK, 1996; Vol. 2, p. 207.
6. (a) Harwood, L. M.; Vickers, R. J. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H. (Eds.); Wiley: New York, 2003; Ch. 3, p. 169;
7. (b) Najera, C.; Sansano, J. M. Curr Org Chem 2003, 7(11), 1105;
8. (c) Tsuge, O.; Kanesmasa, S. In Advances in Cycloaddition; Curran, D. P.; (Ed.); JAI Press; Greenwich, CT, 1993; Vol. 3, p. 99;
9. (d) Pearson, W. H.; Stoy, P. SynLett 2003, 903.
10. (a) Londhe, A. V.; Gupta, B.; Kohli, S.; Pardasani, P.; Pardasani, R. T. Z Naturoforsch B 2006, 61b, 213;
11. (b) Pardasani, R. T.; Pardasani, P.; Jain, A.; Arora, K. Indian J Chem B 2005, 44, 1204;
12. (c) Pardasani, R. T.; Pardasani, P.; Chaturvedi, V.; Yadav, S. K.; Saxena, A.; Sharma, I. Heteroatom Chem 2003, 14, 36;
13. (d) Pardasani, R. T.; Pardasani, P.; Yadav, S. K.; Bharatam, P. V. J Heterocycl Chem 2003, 40, 557;
14. (e) Pardasani, R. T.; Pardasani, P.; Sherry, D.; Chaturvedi, V. K. Synth Commun 2002, 40, 435.
15. (a) Zhu, Y. Z.; Huang, S. H.; Tan, K. H.; Sun, J.; Whiteman, M.; Zhu, Y. C. Nat Prod Rep 2004, 21, 478;
16. (b) Ip, Sui Po; Yang, H.; Sun, H.-D.; Che, C.-T. Planta Med 2002, 68, 1077;
17. (c) Cao, E. H.; Liu, X. Q.; Wang, J. J.; Xu, N. F. Free radical Biol Med 1996, 20 (6), 801;
18. (d) Jiang, W.; Zhao, Y.; Zhao, B.; Wan, Q.; Xin, W. Acta Biophys Sinica 1994, 10, 685;
19. (e) Wu, T. W.; Zeng, L.-H.; Fung, K.-P.; Wu, J.; Pang, H.; Grey, A. A.; Weisel, R. D.; Wang, J. Y. Biochem Pharmacol 1993, 46 (12), 2327.
20. (a) Pranham, M. J. Biochem Pharmacol 1999, 58, 209;
21. (b) Kamal, A. J Org Chem 1991, 56, 2237;
22. (c) Dressman, B. A.; Fritz, J. E.; Hammond, M.; Hornback, W. J.; Kaldor, S. W.; Kalish, V. J.; Munroe, J. E.; Reich, S. H.; Tatlock, J. H. PCT Int. Appl. WO 95, 1995, 09, 843, US Appl 133, 543 Chem Abstr 1998, 123, 256539v;
23. (d) Vicchietti, V.; Colle, R.; Dondio, G.; Giordani, A. Eur Pat Appl 1991, EP 447, 704.
24. Navarro, A.; Sanchez Pino, M.-J.; Gomez, C.; Bandez, M. J.; Cadenas, E.; Boveris, A. Antioxid Redox Signal 2007, 9, 131.
25. De la Funte, M.; Ferrandez, D.; Munoz, F.; de Juan, E.; Miquel, J. Mech Ageing Dev 1993, 68(1-3), 27.
26. (a) De la Funte, M.; Miquel, J.; Catalan, M. P.; Victor, V. M.; Guayerbas, N.; Free Radical Research 2002, 36, 119;
27. (b) De la Fuente, M.; Ferrandez, M. D.; Del Rio, M.; Sol Burgos, M.; Miquel, J. Mech Ageing Dev 1998, 104, 213.
28. Del Rio, M.; Ruedas, G.; Medina, S.; Victor, V. M.; De la Fuente, M. Life Sci, 1998, 63, 871.
29. Correa, R.; Blanco, B.; Del Rio, M.; Victor, V.; Guayerbas, N.; Medina, S.; De La Fuente, M. Bio Factors, 1999, 10, 195.
30. Amornaksa, K.; Grigg, R.; Gunaratne, H. Q. N.; Kemp, J.; Sridharan, V.; J Chem Soc, Perkin Trans I 1987, 2285.
31. Coulter, T.; Grigg, R; Malone, J. F.; Sridharan, V. Tetrahedron Lett 1991, 32, 5417.
32. Ardill, H.; Dorrity, M. J. R.; Grigg, R.; Leon-Ling, M. S.; Malone, J. F.; Sridharan, V.; Thianpatanagul, S. Tetrahedron Lett 1990, 46(18), 6433.
33. Yeler, H.; Tahtabas, F.; Candan, F. Cell Biochem Funct 2005, 23(2), 137.
34. Weber, L. W. D.; Boll, M.; Stampfl, A. Crit Rev Toxicol 2003, 33, 105.
35. Youdim, K. A.; Joseph, J. A. Free Radical Biol Med 2001, 30, 583.
36. Recknagel, R. O. Life Sci 1983, 33 (5), 401.
37. Thabrew, M. I.; Joice, P. D. T. M.; Rajatissa, W.; Planta Med 1987, 53, 239.
38. Ploa, G. L.; Hewitt, W. R.; Wallace, H. A. (Ed.) Principle and Methods of Toxicology, Vol II; Raven Press: New York, 1989; p. 399.
39. Kamalakkannan, N.; Rukkumani, R.; Varma, P. S.; Viswanathan, P.; Rajasekharan, K. N.; Menon, V. P. Basic Clin Pharmacol Toxicol 2005, 97(1), 15.
40. Fieser, L. F. J Org Chem 1929, 3101.
41. Pessayre, D.; Larrey, D.; Brentano, F. C.; Benhamon, J. P. J Antimicrob Chemother 1985, 16, 181.
42. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 2nd ed.; Pergamon Press: Oxford, 1998.
43. Vogel, A. I. Vogel's Text Book of Practical Organic Chemistry, 4th ed.; ELBS Longman: London, 1984.
44. Marklund, S.; Marklund, G. Eur J Biochem 1974, 47, 469.
45. Aebi, H.; Colowick, S. P.; Kaplan, N. O. Eds. In Methods in Enzymology. Academic Press: New York, 1984; Vol. 105, p. 121.
46. Moron, M. S.; De Pierre, J. W.; Mannervick, B. Biochim Biophys Acta 1979, 582, 6778.
47. Ohkawa, H.; Ohishi, N.; Yagi, K. Anal Biochem 1979, 95(2), 351.