The use of 3,6-pyridazinediones in organic synthesis and chemical biology

Journal of Chemical Research

Volumn 40, Issue 1, 2016, Pages 1-9

  Lee, Maximillian T W ^a   Maruani, Antoine ^a   Chudasama, Vijay ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Cysteine modification; Diels Alder; Disulfide modification; Drug like molecules; Multi component reactions; Protein modification; Pyridazindiones

Indexed keywords

EID: 84954478474     PISSN: 17475198     EISSN: 20476507     Source Type: Journal    
DOI: 10.3184/174751916X14495034614855     Document Type: Review

References (65)

1. W. Hofer, F. Maurer, H.J. Riehel, L. Rohe and R. Schroeder, Germ. Offen. 2,534,893
2. Chem. Abstr., 1977, 87, 233139.
3. R.A. Fuchs, F. Maurer, H.J. Riebel, R. Schroeder, I. Hammonn, W. Behrenz and B. Homeyer, Germ. Offen. 2,537,353
4. Chem. Abstr., 1977, 87, 233314r.
5. W. Hofer, F. Maurer, H.J. Riebel, I. Hammonn and W. Stendel, Germ. Offen. 2,531,340
6. Chem. Abstr., 1977, 86, 171601b.
7. K. Nitonia, T. Ito, O. Morikawa and S. Ogawa, Chem. Abstr., 1974, 80, 14950y.
8. K. Nitonia, T. Ito, O. Morikawa and S. Ogawa, Chem. Abstr., 1974, 80, 14951z.
9. W. Hofer, F. Maurer, H.J. Riebel and W. Stendel, Germ. Offen. 2,737,486
10. Chem. Abstr., 1977, 87, 233155s.
11. M. Yoshihara, T. Eda, Y. Matsubara and T. Maeshima, Nippon Kagaku Kaishi, 1975, 4, 720-723
12. Chem. Abstr., 1975, 83, 43857.
13. D. C. Allport, Chem. Abstr., 1967, 66, 116270e.
14. R. Ozegawski and H. Dom, Chem. Abstr., 1988, 109, 6532r.
15. R. Sivakumar, N. Anbalagan, V. Gunasekaran and J.T. Leonard, Biol. Pharm. Bull., 2003, 26, 1407.
16. B. Wanno and V. Ruangpornvisuti, Chem. Phys. Lett., 2005, 415, 176.
17. R. J. Greenwood, H.R. Capper, D.R. Allan and G.A.R. Johnston, Internet J. Chem., 1998, 1, 21.
18. H. Feuer, E.H. White and J.E. Wyman, J. Am. Chem. Soc., 1958, 80, 3790.
19. R.H. Mizzoni and P.E. Spoerri, J. Am. Chem. Soc., 1951, 73, 1873.
20. M.J. Edelmann, J.-M. Raimundo, N.F. Utesch, F. Diederich, C. Boudon, J.-P. Gisselbrecht and M. Gross, Helv. Chim. Acta, 2002, 85, 2195.
21. R. Sun, Y. Zhang, F. Bi and Q. Wang, J. Agric. Food Chem., 2009, 57, 6356.
22. V. Chudasama, M.E.B. Smith, F.F. Schumacher, D. Papaioannou, G. Waksman, J.R. Baker and S. Caddick, Chem. Commun., 2011, 47, 8781.
23. L. Castañeda, Z.V.F. Wright, C. Marculescu, T.M. Tran, V. Chudasama, A. Maruani, E. A. Hull, J.P.M. Nunes, R.J. Fitzmaurice, M.E.B. Smith, L. Jones, S. Caddick and J.R. Baker, Tetrahedron Lett., 2013, 54, 3493.
24. T.J. Kealy, J. Am. Chem. Soc., 1962, 84, 966.
25. C.D. Mayer and F. Bracher, Eur. J. Med. Chem., 2011, 46, 3227.
26. J. Zhu and H. Bienayme, Multicomponent reactions. Wiley-VCH: Weinheim, 2005.
27. E.C. Franklin, Chem. Rev., 1935, 16, 305.
28. F.W. Bergstrom, Chem. Rev., 1944, 35, 77.
29. F.W. Lichtenthaler, Acc. Chem. Res., 2002, 35, 728.
30. V.P. Litvinov, Russ. Chem. Rev., 2003, 72, 69.
31. Y. Xu and Q.X. Guo, Heterocycles, 2004, 63, 903.
32. T. Modeer and T. Yucel-Lindberg, Acta Odont. Scand., 1999, 57, 40.
33. L. Mosti, G. Menozzi, P. Schenone, L. Molinario, F. Conte, C. Montanario and E. Marmoe, Il Farmaco, 1988, 43, 763.
34. L. Mosti, G. Menozzi, P. Fossa, P. Schenone, E. Lampa, C. Parrillo, M. Damisco and F. Rossi, Il Farmaco, 1992, 47, 567.
35. E. Tse, L. Butner, Y. Huang and I.H. Hall, Arch. Pharmacol., 1996, 329, 35.
36. E.A.M. Badawey and I.M. El-Ashmawey, Eur. J. Med. Chem. Chim. Ther., 1998, 33, 349.
37. M.M. Badran, M.A. Ismail, K.A. Youssef and M. Abdel-Hakeem, Alex. J. Pharm. Sci., 1999, 13, 68.
38. M.M. Badran, M.A. Ismail, K.A. Youssef and M. Abdel-Hakeem, Alex. J. Pharm. Sci., 1999, 13, 73.
39. K.A.M. Abouzid and H.S. El-Abhar, Arch. Pharm. Res., 2003, 26, 1.
40. F. Al'-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan and B.A. Chakchir, Pharm. Chem. J., 2002, 36, 598.
41. M.B. Teimouri and F. Mansouri, J. Chem. Res., 2009, 552.
42. X. Shi, J. Li, W. Zhong and J. Li, J. Chem. Res., 2012, 36, 17.
43. M.B. Teimouri, F. Mansouri and R. Bazhrang, Tetrahedron, 2010, 66, 259.
44. S. Keshipour, S. Shojaei and A. Shaabani, Tetrahedron, 2012, 68, 6141.
45. S. Baloniak and A. Ostrowicz, Pol. J. Chem., 1991, 65, 1085.
46. M.E.B. Smith, M.B. Caspersen, E. Robinson, M. Morais, A. Maruani, J.P.M. Nunes, K. Nicholls, M.J. Saxton, S. Caddick, J.R. Baker and V. Chudasama, Org. Biomol. Chem., 2015, 13, 7946.
47. R.E. Morgan, V. Chudasama, P. Moody, M.E.B. Smith and S. Caddick, Org. Biomol. Chem., 2015, 13, 4165.
48. L. Spasser and A. Brik, Angew. Chem. Int. Ed., 2012, 51, 6840.
49. T. Schneider, D. Schneider, D. Rösner, S. Malhotra, F. Mortensen, T.U. Mayer, M. Scheffner and A. Marx, Angew. Chem. Int. Ed., 2014, 53, 12925.
50. A. Maruani, M.E.B. Smith, E. Miranda, K.A. Chester, V. Chudasama and S. Caddick, Nat. Commun., 2015, 6, 6645.
51. M.F. Debets, J.C.M. van Hest and F.P.J.T. Rutjes, Org. Biomol. Chem., 2013, 11, 6439.
52. A. Maruani, H. Savoie, F. Bryden, S. Caddick, R. Boyle and V. Chudasama, Chem. Commun., 2015, 51, 15304.
53. M.T.W. Lee, A. Maruani, J.R. Baker, S. Caddick and V. Chudasama, Chem. Sci., 2016, doi: 10.1039/C5SC02666K.
54. A. Maruani, S. Alom, P. Canavelli, M.T.W. Lee, R.E. Morgan, V. Chudasama and S. Caddick, Chem. Commun., 2015, 51, 5279.
55. M. Schmitt, J.X. de Araujo-Junior, S, Oumouch and J.-J. Bourguignon, Molec. Divers., 2006, 10, 429.
56. P. Kowalski, T. Kowalska, M.J. Mokrosz, A.J. Bojarski and S. Charakchieva-Minol, Molecules, 2001, 6, 784.
57. A.J. Bojarski, P. Kowalski, T. Kowalska, B. Duszynska, S. Charakchieva-Minol, E. Tatarczynska, A. Kodzinskac and E. Chojnacka-Wojcik, Bioorg. Med. Chem., 2002, 10, 3817.
58. W.-Y Choi, S.-D. Cho, S.-K Kim and Y.-J. Yoon, J. Heterocyclic Chem., 1997, 34, 1307.
59. G.G. Furin, E.L. Zhuzhgov, K.-V. Chi and N.-A. Kim, Russ. J. Org. Chem., 2005, 75, 394.
60. T.R. Akopyan and E.G. Paronikyan, Chem. Heterocycl. Compd., 1997, 33, 1466.
61. K. Exner, M. Heizmann, F. Yang, M. Kegel, M. Keller, L. Knothe, B. Großmann, J. Heinze and H. Prinzbach, Eur. J. Org. Chem., 2005, 70, 1311.
62. J. Holz, O. Zayas, H. Jiao, W. Baumann, A. Spannenberg, A. Monsees, T. H. Riermeier, J. Almena, R. Kadyrov and A. Borner, Chem. Eur. J., 2006, 12, 5001.
63. A.A. Nada, N.K. El-din, S.T. Gaballah and M.F. Zayed, Phosphorus Sulfur Silicon Relat. Elem., 2000, 156, 213.
64. A. Ostrowicz, S. Baloniak, M. Makosza and A. Rykowski, Tetrahedron Lett., 1992, 33, 4787.
65. A.A. Nada, N.K. El-din, S.T. Gaballah and M.F. Zayed, Phosphorus Sulfur Silicon Relat. Elem., 1996, 119, 27.