Synthesis of 5-arylated N-arylthiazole-2-amines as potential skeletal muscle cell differentiation promoters

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 7, 2011, Pages 2149-2154

  Schnürch, Michael ^a   Waldner, Birgit ^a   Hilber, Karlheinz ^b   Mihovilovic, Marko D ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^b MEDICAL UNIVERSITY OF VIENNA   (Austria)

Author keywords

Bioactive compound; Cell differentiation; CH activation; Heterocycles

Indexed keywords

AMINE; N (3 BENZYLTHIAZOLE 2[3H]YLIDENE)ANILINE; N ARYLTHIAZOLE 2 AMINE DERIVATIVE; N BENZYL N PHENYLTHIAZOLEAMINE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; BIOLOGICAL ACTIVITY; CELL DIFFERENTIATION; CYCLIZATION; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; MUSCLE CELL; SKELETAL MUSCLE; SUBSTITUTION REACTION;

CELL DIFFERENTIATION; MUSCLE, SKELETAL; THIAZOLES;

EID: 79952484201     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.01.123     Document Type: Article

References (73)

1. (a) Biagetti, M.; Leslie, C. P.; Mazzali, A.; Seri, C.; Pizzi, D. A.; Bentley, J.; Genski, T.; Di Fabio, R.; Zonzini, L.; Caberlotto, L. Bioorg. Med. Chem. Lett. 2010, 20, 4741;
2. (b) Mahboobi, S.; Dove, S.; Sellmer, A.; Winkler, M.; Eichhorn, E.; Pongratz, H.; Ciossek, T.; Baer, T.; Maier, T.; Beckers, T. J. Med. Chem. 2009, 52, 2265;
3. (c) Andersen, C. B.; Wan, Y.; Chang, J. W.; Riggs, B.; Lee, C.; Liu, Y.; Sessa, F.; Villa, F.; Kwiatkowski, N.; Suzuki, M.; Nallan, L.; Heald, R.; Musacchio, A.; Gray, N. S. ACS Chem. Biol. 2008, 3, 180;
4. (d) Hay, M. P.; Turcotte, S.; Flanagan, J. U.; Bonnet, M.; Chan, D. A.; Sutphin, P. D.; Nguyen, P.; Giaccia, A. J.; Denny, W. A. J. Med. Chem. 2010, 53, 787;
5. (e) Satoh, A.; Nagatomi, Y.; Hirata, Y.; Ito, S.; Suzuki, G.; Kimura, T.; Maehara, S.; Hikichi, H.; Satow, A.; Hata, M.; Ohta, H.; Kawamoto, H. Bioorg. Med. Chem. Lett. 2009, 19, 5464;
6. (f) Susnik, M. P.; Schnürch, M.; Mihovilovic, M. D.; Mereiter, K.; Stanetty, P. Monatsh. Chem. 2009, 140, 423.
7. Warashina, M.; Min, K. H.; Kuwabara, T.; Huynh, A.; Gage, F. H.; Schultz, P. G.; Ding, S. Angew. Chem., Int. Ed. 2006, 45, 591.
8. Graf, T.; Enver, T. Nature 2009, 462, 587.
9. Davis, R. L.; Weintraub, H.; Lasser, A. B. Cell 1987, 51, 987;
10. Kulessa, H.; Frampton, J.; Graf, T. Genes Dev. 1995, 9, 1250.
11. (a) Gurdon, J. B.; Byrne, J. A. Proc. Natl Acad. Sci. U.S.A. 2003, 100, 8048;
12. (b) Wilmut, I.; Schnieke, A. E.; McWhir, J.; Kind, A. J.; Campbell, K. H. Nature 1997, 385, 810;
13. (c) Gurdon, J. B.; Melton, D. A. Science 2008, 322, 1811;
14. (d) Hochedlinger, K.; Jaenisch, R. Nature 2002, 415, 1035.
15. (a) Takahashi, K.; Yamanaka, S. Cell 2006, 126, 663;
16. (b) Maherali, N.; Hochedlinger, K. Cell Stem Cell 2008, 3, 595;
17. (c) Lowry, W. E.; Richter, L.; Yachechko, R.; Pyle, A. D.; Tchieu, J.; Sridharan, R.; Clark, A. T.; Plath, K. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 2883;
18. (d) Park, I. H.; Zhao, R.; West, J. A.; Yabuuchi, A.; Huo, H.; Ince, T. A.; Lerou, P. H.; Lensch, M. W.; Daley, G. Q. Nature 2008, 451, 141;
19. (e) Takahashi, K.; Tanabe, K.; Ohnuki, M.; Narita, M.; Ichisaka, T.; Tomoda, K.; Yamanaka, S. Cell 2007, 131, 861;
20. (f) Yu, J.; Vodyanik, M. A.; Smuga-Otto, K.; Antosiewicz-Bourget, J.; Frane, J. L.; Tian, S.; Nie, J.; Jonsdottir, G. A.; Ruotti, V.; Stewart, R.; Slukvin, I. I.; Thomson, J. A. Science 2007, 318, 1917.
21. Feng, B.; Jiang, J.; Kraus, P.; Ng, J. H.; Heng, J. C.; Chan, Y. S.; Yaw, L. P.; Zhang, W.; Loh, Y. H.; Han, J.; Vega, V. B.; Cacheux-Rataboul, V.; Lim, B.; Lufkin, T.; Ng, H.-H. Nat. Cell Biol. 2009, 11, 197.
22. (a) Wu, X.; Ding, S.; Ding, Q.; Gray, N. S.; Schultz, P. G. J. Am. Chem. Soc. 2004, 126, 1590;
23. (b) Wu, X.; Ding, S.; Schultz, P. G. PCT Int. Appl. 2005, WO 2005068437; CAN 143:172888.;
24. (c) Willems, E.; Bushway, P. J.; Mercola, M. Pediatr. Cardiol. 2009, 30, 635.
25. (a) Barnard, J. H.; Collings, J. C.; Whiting, A.; Przyborski, S. A.; Marder, T. B. Chem. Eur. J. 2009 2009, 15, 11430;
26. (b) Williams, D. R.; Lee, M. R.; Song, Y. A.; Ko, S. K.; Kim, G. H.; Shin, I. J. Am. Chem. Soc. 2007, 129, 9258.
27. (a) Chen, S.; Zhang, Q.; Wu, X.; Schultz, P. G.; Ding, S. J. Am. Chem. Soc. 2004, 126, 410;
28. (b) Chen, S.; Ding, S.; Schultz, P. G. PCT Int. Appl. 2005, WO, 2005047524 A2 20050526.
29. Feng, B.; Ng, J. H.; Heng, J. C.; Ng, H. H. Cell Stem Cell 2009, 4, 301;
30. Chen, J. K.; Firestone, A. J.; Morgan, T. C.; Lee, M.-H.; Kimble J. Nat. Chem. Biol. 2010, 6, 102;
31. Kim, N. R.; kang, S. K.; Ahn, H. H.; Kwon, S. W.; Park, W. S.; Kim, K. S.; Kim, S. S.; Jung, H. J.; Choi, S. U.; Ahn, J. H.; Kim, K. R. J. Med. Chem. 2009, 52, 7931;
32. De Medina, P.; Paillasse, M. R.; Payre, B.; Silvente-Poirot, S.; Poirot, M. J. Med. Chem. 2009, 52, 7765;
33. Firestone, A. J.; Chen, J. K. ACS Chem. Biol. 2010, 5, 15.
34. Hoshino, M.; Tsujimoto, T.; Yamazoe, S.; Uesugi, M.; Terada, S. Biochem. J. 2010, 427, 297.
35. Jung, D.; Shimogawa, H.; Kwon, Y.; Mao, Q.; Sato, S.-i.; Kamisuki, S.; Kigoshi, H.; Uesugi, M. J. Am. Chem. Soc. 2009, 131, 4774.
36. (a) Hantzsch, A. Ber. Dtsch. Chem. Ges. 1888, 21, 942;
37. (b) Prakash, R.; Kumar, A.; Aggarwal, R.; Prakash, O.; Singh, S. P. Synth. Commun. 2007, 37, 2501;
38. (c) Egan, R. S.; Tadanier, J.; Garmaise, D. L.; Gaunce, A. P. J. Org. Chem. 1968, 33, 4422;
39. (d) Babadjamian, A.; Metzger, J.; Chanon, M. J. J. Heterocycl. Chem. 1975, 12, 643.
40. Zhao, M.; Yin, J.; Huffman, M. A.; McNamara, J. M. Tetrahedron 2006, 62, 1110.
41. Schnürch, M.; Khan, A. F.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2009, 3228.
42. (a) Khan, A. F.; Schnürch, M.; Mihovilovic, M. D.; Stanetty, P. Lett. Org. Chem. 2009, 6, 171;
43. (b) Stanetty, P.; Schnürch, M.; Mereiter, K.; Mihovilovic, M. D. J. Org. Chem. 2005, 70, 567.
44. (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046;
45. (b) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969;
46. (c) Hill, L. L.; Moore, L. R.; Huang, R.; Craciun, R.; Vincent, A. J.; Dixon, D. A.; Chou, J.; Woltermann, C. J.; Shaughnessy, K. H. J. Org. Chem. 2006, 71, 5117;
47. (d) Yin, J.; Zhao Matthew, M.; Huffman Mark, A.; McNamara James, M. Org. Lett. 2002, 4, 3481;
48. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144;
49. (f) Doherty, S.; Knight, J. G.; Smyth, C. H.; Sore, N. T.; Rath, R. K.; McFarlane, W.; Harrington, R. W.; Clegg, W. Organometallics 2006, 25, 4341;
50. (g) Liu, Y.; Bai, Y.; Zhang, J.; Li, Y.; Jiao, J.; Qi, X. Eur. J. Org. Chem. 2007, 6084;
51. (h) Lipshutz, B. H.; Nihan, D. M.; Vinogradova, E.; Taft, B. R.; Boskovic, Z. V. Org. Lett. 2008, 10, 4279.
52. 3 solution and brine followed by general work-up. Purification was carried out by Kugelrohr distillation.
53. (a) Parisien, M.; Valette, D.; Fagnou, K. J. Org. Chem. 2005, 70, 7578;
54. (b) Liegault, B.; Lapointe, D.; Caron, L.; Vlassova, A.; Fagnou, K. J. Org. Chem. 2009, 74, 1826.
55. Primas, N.; Bouillon, A.; Lancelot, J.-C.; El-Kashef, H.; Rault, S. Tetrahedron 2009, 65, 5739.
56. Miyaoku, T.; Mori, A. Heterocycles 2009, 77, 151.
57. (a) Roger, J.; Pozgan, F.; Doucet, H. J. Org. Chem. 2009, 74, 1179;
58. (b) Pozgan, F.; Roger, J.; Doucet, H. ChemSusChem 2008, 1, 404.
59. Greene, T. W. W., 3rd ed. In Protective groups in Organic Synthesis; Wiley-Interscience, 1999.
60. 2S requires 267.0950.
61. 2S requires 267.0950.
62. (a) Oegretir, C.; Demirayak, S.; Tay, N. F.; Duran, M. J. Chem. Eng. Data 2008, 53, 422;
63. (b) Mohamed, A. A.; El-Harby, A. W. Theochem 2007, 817, 125;
64. (c) Mohamed, A. A.; El-Harby, A. W. Theochem 2008, 849, 52;
65. (d) Zeng, Y.; Ren, Y. Int. J. Quantum Chem. 2006, 107, 247;
66. (e) Remko, M.; Swart, M.; Bickelhaupt, F. M. Bioorg. Med. Chem. 2006, 14, 1715.
67. 2 were charged into the reaction vessel in that same order. Dimethylacetamide was added and the reaction vial was evacuated and purged with argon three times. The reaction mixture was then stirred at 120 °C until the reaction was complete. The solution was diluted with ethyl acetate, silica gel was added, and this mixture was concentrated in vacuo, followed by MPLC purification.
68. (a) Hansen, J. M.; Klass, M.; Harris, C.; Csete, M. Cell Biol. Int. 2007, 31, 546;
69. (b) Chen, S. E.; Jin, B.; Li, Y. P. Am. J. Physiol. Cell Physiol. 2007, 292, C1660;
70. (c) Li, Y.; Li, J.; Zhu, J.; Sun, B.; Branca, M.; Tang, Y.; Foster, W.; Xiao, X.; Huard, J. Mol. Ther. 2007, 15, 1616.
71. Zebedin, E.; Sandtner, W.; Galler, S.; Szendroedi, J.; Just, H.; Todt, H.; Hilber, K. Am. J. Physiol. Cell Physiol. 2004, 287, C270.
72. (a) Nguyen, T. H.; Bertrand, M. J.; Sterpin, C.; Achouri, Y.; De Backer, O. R. BMC Cell Biol. 2010, 11, 57;
73. (b) Deponti, D.; François, S.; Baesso, S.; Sciorati, C.; Innocenzi, A.; Broccoli, V.; Muscatelli, F.; Meneveri, R.; Clementi, E.; Cossu, G.; Brunelli, S. J. Cell Biol. 2007, 179, 305.