Synthesis of sulfur containing dihydro-pyrrolo derivatives and their biological evaluation as antioxidants

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 17, 2012, Pages 5103-5109

  Georgiou, Dimitra ^a,d   Toutountzoglou, Vasilios ^a   Muir, Kenneth W ^b   Hadjipavlou Litina, Dimitra ^c   Elemes, Yiannis ^a  

^a UNIVERSITY OF IOANNINA   (Greece)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

^c ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^d UNIVERSITY OF CYPRUS   (Cyprus)

Author keywords

1,3 Dipolar cycloadditions; Aminoacids; Antioxidant activity; Azomethine ylides; Dihydro pyrrole; Imines; Sulfides; Syn Diastereoselectivity; X ray

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 5H DIHYDROPYRROLO DERIVATIVE; ANTIOXIDANT; AZOMETHINE YLIDE; BENZYL 3 (METHYLTHIO) 4,6 DIOXO 5 PHENYL 1,3A,4,5,6,6A HEXAHYDROPYRROLO[3,4 C]PYRROLE 1 CARBOXYLIC ACID; DIHYDROPYRROLO DERIVATIVE; ETHYL 3 (METHYLTHIO) 4,6 DIOXO 5 PHENYL 1,3A,4,5,6,6A HEXAHYDROPYRROLO[3,4 C]PYRROLE 1 CARBOXYLIC ACID; GLYCINE; IMINE; LINOLEIC ACID; METHYL 3 (BENZYLLTHIO) 4,6 DIOXO 5 PHENYL 1,3A,4,5,6,6A HEXAHYDROPYRROLO[3,4 C]PYRROLE 1 CARBOXYLIC ACID; METHYL 3 (BUTYLTHIO) 4,6 DIOXO 5 PHENYL 1,3A,4,5,6,6A HEXAHYDROPYRROLO[3,4 C]PYRROLE 1 CARBOXYLIC ACID; METHYL 3 (ETHYLTHIO) 4,6 DIOXO 5 PHENYL 1,3A,4,5,6,6A HEXAHYDROPYRROLO[3,4 C]PYRROLE 1 CARBOXYLIC ACID; METHYL 3 (ISOPROPYLTHIO) 4,6 DIOXO 5 PHENYL 1,3A,4,5,6,6A HEXAHYDROPYRROLO[3,4 C]PYRROLE 1 CARBOXYLIC ACID; METHYL 3 (METHYLTHIO) 4,6 DIOXO 5 PHENYL 1,3A,4,5,6,6A HEXAHYDROPYRROLO[3,4 C]PYRROLE 1 CARBOXYLIC ACID; METHYL 4,6 DIOXO 5 PHENYL 3 (PROPYLTHIO) 1,3A,4,5,6,6A HEXAHYDROPYRROLO[3,4 C]PYRROLE 1 CARBOXYLIC ACID; N PHENYLMALEIMIDE; NORDIHYDROGUAIARETIC ACID; REACTIVE OXYGEN METABOLITE; SULFUR; TERT BUTYL 3 (METHYLTHIO) 4,6 DIOXO 5 PHENYL 1,3A,4,5,6,6A HEXAHYDROPYRROLO[3,4 C]PYRROLE 1 CARBOXYLIC ACID; TROLOX C; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYCLOADDITION; DIASTEREOISOMER; DRUG ISOLATION; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; LIPID PEROXIDATION; MICHAEL ADDITION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ANTIOXIDANTS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; LIPID PEROXIDATION; LIPOXYGENASE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRROLES; SOYBEANS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR;

EID: 84865011264     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.07.014     Document Type: Article

References (61)

1. S. Kobayashi, and K.A. Jorgensen Cycloaddition Reaction in Organic Synthesis 2001 Wiley New York
2. W. Carruthers Cycloaddition Reactions in Organic Synthesis 1990 Pergamon Oxford
3. A. Padwa 1,3-Dipolar Cycloaddition in Chemistry 1984 Wiley New York
4. K.V. Gothelf, and K.A. Jorgensen Chem. Rev. 98 1998 863
5. I. Coldham, and R. Hufton Chem. Rev. 105 2005 2765
6. D.H. Ess, and K.N. Houk J. Am. Chem. Soc. 129 2007 10646
7. D.H. Ess, and K.N. Houk J. Am. Chem. Soc. 130 2008 10187
8. L.M. Harwood, and R.J. Vickers A. Padwa, W.H. Pearson, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products 2002 Wiley New York Chapter 3
9. O. Tsuge, and S. Kanemasa Adv. Heterocycl. Chem. 45 1989 231
10. J.W. Lown A. Padwa, 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley New York Chapter 6
11. O. Tsuge, S. Kanemasa, M. Ohe, K. Yorozu, S. Takenaka, and K. Ueno Bull. Chem. Soc. Jpn. 60 1987 4067
12. P. Prassana, K. Palamurugan, S. Perumal, P. Vogeeswari, and D. Sriram Eur. J. Med. Chem. 45 2010 5653
13. A. Dandia, A.K. Jain, and D.S. Bhati Tetrahedron Lett. 52 2011 5333
14. S.U. Maheswari, S. Perumal, and A.I. Almansur Tetrahedron Lett. 53 2012 349
15. S.U. Maheswari, K. Balamurugan, S. Perumal, P. Vogeeswari, and D. Sriram Bioorg. Med. Chem. Lett. 20 2010 7278
16. Q.-H. Li, Z.-Y. Xue, H.-Y. Tao, and C.-J. Wang Tetrahedron Lett. 53 2012 3650
17. H. Wo, B. Wang, H. Liu, and L. Wang Tetrahedron 67 2012 1210
18. M. Martin-Rodriguez, C. Najera, J.M. Sansano, and F-L. Wu Tetrahedron: Asymmetry 21 2010 1184
19. C. Nájera, and J.M. Sansano Curr. Org. Chem. 7 2003 1105
20. K. Gothelf, and K.A. Jorgensen Chem. Rev. 98 1998 863
21. K.V. Gothelf S. Kobayashi, K.A. Jorgensen, Cycloaddition Reactions in Organic Synthesis 2002 Wiley-VCH Weinheim 211 245
22. S. Kanemasa Synlett 2002 1371
23. R. Huisgen, W. Scheer, and H. Huber J. Am. Chem. Soc. 89 1967 1753
24. R. Grigg, G. Donegan, and H.Q.N. Gunaratne Tetrahedron 45 1989 1723
25. R. Grigg, J. Montgomery, and A. Somasunderam Tetrahedron 48 1992 10431
26. D.M. Copper, R. Grigg, S. Hargreaves, P. Kennewell, and J. Redpath Tetrahedron 51 1995 7791
27. S. Kanemasa, T. Hayashi, J. Tanaka, H. Yamamoto, and T. Sakurai J. Org. Chem. 56 1991 4473
28. P. Allway, and R. Grigg Tetrahedron Lett. 32 1991 5817
29. R. Grigg, C. Kilner, M.B.M. Sarker, C. Orgaz de la Cierva, and H.A. Dondas Tetrahedron 64 2008 8974
30. P. Garner, and H.Ü. Kaniskan J. Org. Chem. 70 2005 10868
31. L.M. Stanley, and M.P. Sibi Chem. Rev. 108 2008 2887
32. M. Naodovic, and H. Yamamoto Chem. Rev. 108 2008 3132
33. M. Álvarez-Corral, M. Muñoz-Dorado, and I. Rodriguez-García Chem. Rev. 108 2008 3174
34. N.T. Patil, and Y. Yamamoto Chem. Rev. 108 2008 3395
35. H. Pellissier Tetrahedron 63 2007 3235
36. A. Awata, and T. Arai Chem. Eur. J. 18 2012 8278
37. M.-C. Tong, J. Li, H.-Y. Tao, Y.-X. Li, and C-J. Wang Chem. Eur. J. 17 2011 12922
38. M. Rodriguez-Martin, C. Nacera, J.M. Mansano, A. de Gozar, and F.P. Cosio Chem. Eur. J. 17 2011 14224
39. C. Najera, and J. Sansano Org. Biobol. Chem. 7 2009 4567
40. L. Huck, J.F. Conzalez, E. de la Guesta, J.C. Menendez, and C. Avandano Org. Biomol. Chem. 9 2011 4567
41. J. Yu, F. Shi, and L-Z. Gong Acc. Chem. Res. 44 2011 1156
42. D. Hoppe, and L. Beckmann Liebigs Ann. Chem. 1979 2066
43. L. Lankiewicz, B. Nyasse, B. Fransson, L. Grehn, and U. Ragnarsson J. Chem. Soc., Perkin Trans. 1 1994 2503
44. W. Oppolzer, R. Moretti, and S. Thomi Tetrahedron Lett. 30 1989 6009
45. W. Oppolzer, R. Moretti, and C. Zhou Helv. Chim. Acta 77 1994 2363
46. Y. Elemes, and U. Ragnarsson J. Chem. Soc., Perkin Trans. 1 1996 537
47. Y. Elemes, and U. Ragnarsson Chem. Commun. 1996 935
48. G. Naxakis, P. Sofou, and Y. Elemes Fullerenes Nanot. Carbon Nanostruct. 12 2004 781
49. P. Sofou, Y. Elemes, E. Panou-Pomonis, A. Stavrakoudis, V. Tsikaris, C. Sakarellos, M. Sakarellos-Daitsiotis, M. Maggini, F. Formaggio, and C. Toniolo Tetrahedron 60 2004 2823
50. E. Ioannou, A. Hirsch, and Y. Elemes Tetrahedron 63 2007 7070
51. L.A. Damani Sulphur containing drugs and related compounds: Chemistry, Biochemistry and Toxicology Part A: Metabolism of Sulfur Functional Groups Vol. 1 1989 Ellis Horwood Limited
52. H.R. Hoveyda, and D.G. Hall Org. Lett. 3 2001 3491
53. R. Grigg, D.A. Basanagoudar, D.A. Kennedy, J.F. Malone, and S. Thianpatanagul Tetrahedron Lett. 23 1982 2803
54. R.L. Prior, X. Wu, and K. Schaich J. Agric. Food Chem. 53 2005 4290
55. E. Niki Chem. Phys. Lipids 44 1987 227
56. C. Liegois, G. Lermusieau, and S. Colin J. Agric. Food Chem. 48 2000 1129
57. D. Huang, B. Ou, and R.L. Prior J. Agric. Food Chem. 53 2005 1841 and references cited therein
58. D.V. Jovanovic, J.C. Fermandes, J. Martel-Pelletier, F.C. Jolicoeur, P. Reboul, S. Laufer, S. Tries, and J.P. Pelletier Arthritis Rheum. 2001 2001 2320
59. D. Hadjipavlou-Litina, T. Garnelis, C.M. Athanassopoulos, and D. Papaioannou J. Enzyme Inhib. Med. Chem. 24 2009 1188
60. Biobyte Corp., C-QSAR Database 201 West 4th Str., Suite 204, Claremont CA, California 91711, USA.
61. W.L.F. Armarego, and D.D. Perrin Purification of Laboratory Chemicals 1996 Reed Educational and Profesional Publishing Oxford