Base-mediated decomposition of amide-substituted furfuryl tosylhydrazones: Synthesis and cytotoxic activities of enynyl-ketoamides

Journal of Organic Chemistry

Volumn 80, Issue 4, 2015, Pages 2092-2102

  Ji, Fanghua ^a   Peng, Hui ^a   Zhang, Xiaoting ^a   Lu, Wenhua ^b   Liu, Shubin ^c   Jiang, Huanfeng ^a   Liu, Bo ^d   Yin, Biaolin ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b SUN YAT SEN UNIVERSITY CANCER CENTER   (China)

^c UNIVERSITY OF NORTH CAROLINA   (United States)

^d Guangdong Provincial Academy of Chinese Medical Sciences   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CELL CULTURE;

CYTOTOXIC ACTIVITIES; FURAN RING; GROUP MIGRATION; HUMAN TUMOR CELL LINES; KETOAMIDES; MULTI-FUNCTIONALIZED; SYNTHETIC APPLICATION;

ORGANIC COMPOUNDS;

(5 BENZOYLFURAN 2 YL)(MORPHOLINO)METHANONE; 5 (2 CHLOROBENZOYL) N,N DIMETHYLFURAN 2 CARBOXAMIDE; 5 (2 NAPHTHOYL) N,N DIMETHYLFURAN 2 CARBOXAMIDE; 5 (3,5 DIMETHYLBENZOYL) N,N DIMETHYLFURAN 2 CARBOXAMIDE; 5 (4 METHOXYBENZOYL) N,N DIMETHYLFURAN 2 CARBOXAMIDE; 5 (FURAN 2 CARBONYL) N,N DIMETHYLFURAN 2 CARBOXAMIDE; 5 BENZOYL N (2 BROMOPHENYL) N ETHYLFURAN 2 CARBOXAMIDE; 5 BENZOYL N BENZYLFURAN 2 CARBOXAMIDE; 5 BENZOYL N METHYL N (3,4,5 TRIMETHOXYPHENYL)FURAN 2 CARBOXAMIDE; 5 BENZOYL N,N DIMETHYLFURAN 2 CARBOXAMIDE; 5 [(2 CHLOROPHENYL)(2 TOSYLHYDRAZONO)METHYL] N,N DIMETHYLFURAN 2 CARBOXAMIDE; 5 [(3,5 DIMETHYLPHENYL)(2 TOSYLHYDRAZONO)METHYL] N,N DIMETHYLFURAN 2 CARBOXAMIDE; 5 [(4 METHOXYPHENYL)(2 TOSYLHYDRAZONO)METHYL] N,N DIMETHYLFURAN 2 CARBOXAMIDE; AMIDE; ANTINEOPLASTIC AGENT; HYDRAZONE DERIVATIVE; METHYL 5 BENZOYLFURAN 2 CARBOXYLATE; N ALLYL 5 BENZOYL N METHYLFURAN 2 CARBOXAMIDE; N METHOXY N METHYL 5 (4 METHYLBENZOYL)FURAN 2 CARBOXAMIDE; N,N DIMETHYL 5 (4 (TRIFLUOROMETHYL)BENZOYL)FURAN 2 CARBOXAMIDE; N,N DIMETHYL 5 (4 METHYLBENZOYL)FURAN 2 CARBOXAMIDE; N,N DIMETHYL 5 (4 NITROBENZOYL)FURAN 2 CARBOXAMIDE; N,N DIMETHYL 5 (NAPHTHALEN 2 YL(2 TOSYLHYDRAZONO)METHYL)FURAN 2 CARBOXAMIDE; N,N DIMETHYL 5 (THIOPHEN 2 YL(2 TOSYLHYDRAZONO)METHYL)FURAN 2 CARBOXAMIDE; N,N DIMETHYL 5 (THIOPHENE 2 CARBONYL)FURAN 2 CARBOXAMIDE; N,N DIMETHYL 5 [(2 TOSYLHYDRAZONO)(4 (TRIFLUOROMETHYL)PHENYL)METHYL]FURAN 2 CARBOXAMIDE; N,N DIMETHYL 5 [(4 NITROPHENYL) TOSYLHYDRAZONO)METHYL]FURAN 2 CARBOXAMIDE; N,N DIMETHYL 5 [P TOLYL(2 TOSYLHYDRAZONO)METHYL]FURAN 2 CARBOXAMIDE; N,N DIMETHYL 5 [PHENYL(2 TOSYLHYDRAZONO)METHYL]FURAN 2 CARBOXAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AMIDATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHLORINATION; CYTOTOXICITY; DRUG DECOMPOSITION; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; HUMAN CELL; PH; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; THIN LAYER CHROMATOGRAPHY; TUMOR CELL LINE;

EID: 84923345612     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502328j     Document Type: Article

References (73)

1. Van Putten, R.-J.; van der Waal, J. C.; de Jong, E.; Rasrendra, C. B.; Heeres, H. J.; de Vries, J. G. Chem. Rev. 2013, 113, 1499
2. Gallezot, P. Chem. Soc. Rev. 2012, 41, 1538
3. Hu, L.; Zhao, G.; Hao, W.; Tang, X.; Sun, Y.; Lin, L.; Liu, S. RSC Adv. 2012, 2, 11184
4. Serrano-Ruiz, J. C.; Luque, R.; Sepulveda-Escribano, A. Chem. Soc. Rev. 2011, 40, 5266
5. Rosatella, A. A.; Simeonov, S. P.; Frade, R. F. M.; Afonso, C. A. M. Green Chem. 2011, 13, 754
6. Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411
7. Karinen, R.; Vilonen, K.; Niemalä, M. ChemSusChem 2011, 4, 1002
8. Martel, F.; Estrine, B.; Plantier-Royon, R.; Hoffmann, N.; Portella, C. Top. Curr. Chem. 2010, 294, 79
9. Geilen, F. M. A.; vom Stein, T.; Engendahl, B.; Winterle, S.; Liauw, M. A.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2011, 50, 6831
10. Buntara, T.; Noel, S.; Phua, P. H.; Melián-Cabrera, I.; de Vries, J. G.; Heeres, H. J. Angew. Chem., Int. Ed. 2011, 50, 7083
11. Kabro, A.; Escudero-Adán, E. C.; Grushin, V. V.; van Leeuwen, P. W. N. M. Org. Lett. 2012, 14, 4014
12. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5 th ed.; Wiley: Oxford, U.K., 2010; p 689.
13. Abaev, V. T.; Plieva, A. T.; Chalikidi, P. N.; Uchuskin, M. G.; Trushkov, I. V.; Butin, A. V. Org. Lett. 2014, 16, 4150-4153
14. Kuznetsov, A.; Makarov, A.; Rubtsov, A. E.; Butin, A. V.; Gevorgyan, V. J. Org. Chem. 2013, 78 (23) 12144-12153
15. Yin, B.; Lai, J.; Zhang, Z.; Jiang, H. Adv. Synth. Catal. 2011, 353, 1961
16. Yin, B.; Zeng, G.; Cai, C.; Ji, F.; Huang, L.; Li, Z.; Jiang, H. Org. Lett. 2012, 14, 616
17. Yin, B.; Cai, C.; Zeng, G.; Zhang, R.; Li, X.; Jiang, H. Org. Lett. 2012, 14, 1098
18. Yin, B.; Huang, L.; Wang, X.; Liu, J.; Jiang, H. Adv. Synth. Catal. 2013, 355, 370
19. Yin, B.; Zhang, X.; Liu, J.; Li, X.; Jiang, H. Chem. Commun. (Cambridge, U.K.) 2014, 50, 8113
20. Butin, A. V.; Nevolina, T. A.; Shcherbinin, V. A.; Trushkov, I. V.; Cheshkov, D. A.; Krapivin, G. D. Org. Biomol. Chem. 2010, 8 (14) 3316-3327
21. Trushkov, I. V.; Nevolina, T. A.; Shcherbinin, V. A.; Sorotskaya, L. N.; Butin, A. V. Tetrahedron Lett. 2013, 54 (30) 3974-3976
22. Uchuskin, M. G.; Pilipenko, A. S.; Serdyuk, O. V.; Trushkov, I. V.; Butin, A. V. Org. Biomol. Chem. 2012, 10 (36) 7262-7265
23. Lipshutz, B. H. Chem. Rev. 1986, 86, 795
24. Bur, S. K.; Padwa, A. Chem. Rev. 2004, 104, 2401
25. Röser, C.; Albers, R.; Sander, W. Eur. J. Org. Chem. 2001, 269
26. Hoffman, R. V.; Shechter, H. J. Am. Chem. Soc. 1978, 100, 7934
27. Hoffman, R. V.; Orphanides, G. G.; Shechter, H. J. Am. Chem. Soc. 1978, 100, 7927
28. Hoffman, R. V.; Shechter, H. J. Org. Chem. 1974, 39, 2939
29. Hoffman, R. V.; Shechter, H. J. Am. Chem. Soc. 1971, 93, 5940
30. Pharr, C. R.; Kopff, L. A.; Bennett, B.; Reid, S. A.; McMahon, R. J. J. Am. Chem. Soc. 2012, 134, 6443
31. Shirtcliff, L. D.; McClintock, S. P.; Haley, M. M. Chem. Soc. Rev. 2008, 37, 343
32. Sheridan, R. S. Chem. Rev. 2013, 113, 7179
33. Guilford, W. J.; Bauman, J. G.; Skuballa, W.; Bauer, S.; Wei, G. P.; Davey, D.; Schaefer, C.; Mallari, C.; Terkelsen, J.; Tseng, J.-L.; Shen, J.; Subramanyam, B.; Schottelius, A. J.; Parkinson, J. F. J. Med. Chem. 2004, 47, 2157
34. Konish, M.; Ohkuma, H.; Matsumoto, K.; Tsuno, T.; Kamei, H.; Miyake, T.; Oki, T.; Kawaguchi, H.; Van Duyne, G. D.; Clardy, J. J. Antibiot. 1989, 42, 1449
35. Nussbaumer, P.; Leitner, L.; Marz, K.; Stutz, A. J. Med. Chem. 1995, 38, 1831
36. Neuhaus, C. M.; Liniger, M.; Stieger, M.; Altmann, K.-H. Angew. Chem., Int. Ed. 2013, 52, 5866
37. Lee, S.; Lee, T.; Lee, Y. M.; Kim, D.; Kim, S. Angew. Chem., Int. Ed. 2007, 46, 8422
38. Sorg, A.; Brückner, R. Angew. Chem., Int. Ed. 2004, 43, 4523
39. Xie, H.; Zhang, S.; Li, H.; Zhang, X.; Zhao, S.; Xu, Z.; Song, X.; Yu, X.; Wang, W. Chem.-Eur. J. 2012, 18, 2230
40. Sorg, A.; Siegel, K.; Brückner, R. Chem.-Eur. J. 2005, 11, 1610
41. Speed, T. J.; Thamattoor, D. M. Tetrahedron Lett. 2002, 43, 367
42. Kuroda, H.; Hanaki, E.; Izawa, H.; Kano, M.; Itahashi, H. Tetrahedron 2004, 60, 1913
43. Hadi, V.; Yoo, K. S.; Jeong, M.; Jung, K. W. Tetrahedron Lett. 2009, 50, 2370
44. Chen, J.; Fan, G.; Liu, Y. Org. Biomol. Chem. 2010, 8, 4806
45. Fu, X.; Zhang, S.; Yin, J.; Schumacher, D. P. Tetrahedron Lett. 2002, 43, 6673
46. Martins, M. A. P.; Rossatto, M.; Rosa, F. A.; Machado, P.; Zanatta, N.; Bonacorso, H. G. ARKIVOC (Gainesville, FL, U.S.) 2007, 205
47. Geyer, M.; Bauer, J.; Burschka, C.; Kraft, P.; Tacke, R. Eur. J. Inorg. Chem. 2011, 2011, 2769
48. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236
49. Barluenga, J.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 7486
50. Zhao, X.; Zhang, Y.; Wang, J. Chem. Commun. (Cambridge, U.K.) 2012, 48, 10162
51. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560
52. Liu, Z.; Wang, J. J. Org. Chem. 2013, 78, 10024
53. Xia, Y.; Zhang, Y.; Wang, J. ACS Catal. 2013, 3, 2586
54. Sheha, M. M.; Mahfouz, N. M.; Hassan, H. Y.; Youssef, A. F.; Mimoto, T.; Kiso, Y. Eur. J. Med. Chem. 2000, 35, 887
55. Han, W.; Hu, Z.; Jiang, X.; Wasserman, Z. R.; Decicco, C. P. Bioorg. Med. Chem. Lett. 2003, 13, 1111
56. Donkor, I. O.; Han, J.; Zheng, X. J. Med. Chem. 2004, 47, 72
57. Lee, K. S.; Seo, S. H.; Lee, Y. H.; Kim, H. D.; Son, M. H.; Chung, B. Y.; Lee, J. Y.; Jin, C.; Lee, Y. S. Bioorg. Med. Chem. Lett. 2005, 15, 2857
58. Steuer, C.; Gege, C.; Fischl, W.; Heinonen, K. H.; Bartenschlager, R.; Klein, C. D. Bioorg. Med. Chem. 2011, 19, 4067
59. Kher, S. S.; Penzo, M.; Fulle, S.; Finn, P. W.; Blackman, M. J.; Jirgensons, A. Bioorg. Med. Chem. Lett. 2014, 24, 4486
60. Sai, K. K. S.; Esteves, P. M.; da Penha, E. T.; Klumpp, D. A. J. Org. Chem. 2008, 73, 6506
61. Tomita, D.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 6946
62. Yang, L.; Wang, D.-X.; Huang, Z.-T.; Wang, M.-X. J. Am. Chem. Soc. 2009, 131, 10390
63. Coffinier, D.; Kaim, L. E.; Grimaud, L. Org. Lett. 2009, 11, 1825
64. Liu, Q.; Perreault, S.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14066
65. Natarajan, A.; Wang, K.; Ramamurthy, V.; Scheffer, J. R.; Patrick, B. Org. Lett. 2002, 4, 1443
66. For the preparation of keto ester: Fernandez, P. A.; Bellamy, T.; Kling, M.; Madge, D. J.; Selwood, D. L. Heterocycles 2001, 55, 1813
67. Sakya, S. M.; Hou, X.; Minich, M. L.; Rast, B.; Shavnya, A.; DeMello, K. M. L.; Cheng, H.; Li, J.; Jaynes, B. H.; Mann, D. W.; Petras, C. F.; Seibel, S. B.; Haven, M. L. Bioorg. Med. Chem. Lett. 2007, 17, 1067
68. Di Santo, R.; Costi, R.; Artico, M.; Ragno, R.; Lavecchia, A.; Novellino, E.; Gavuzzo, E.; La Torre, F.; Cirilli, R.; Cancio, R.; Maga, G. ChemMedChem 2006, 1, 82
69. Kolodziej, S. A.; Hockerman, S. L.; DeCrescenzo, G. A.; McDonald, J. J.; Mischke, D. A.; Munie, G. E.; Fletcher, T. R.; Stehle, N.; Swearingen, C.; Becker, D. P. Bioorg. Med. Chem. Lett. 2010, 20, 3561
70. Sasikumar, T. K.; Qiang, L.; Burnett, D. A.; Cole, D.; Xu, R.; Li, H.; Greenlee, W. J.; Clader, J.; Zhang, L.; Hyde, L. Bioorg. Med. Chem. Lett. 2010, 20, 3632
71. Feng, X.-W.; Wang, J.; Zhang, J.; Yang, J.; Wang, N.; Yu, X.-Q. Org. Lett. 2010, 12, 4408
72. Sha, Q.; Wei, Y. Tetrahedron 2013, 69, 3829
73. Bartrum, H. E.; Blakemore, D. C.; Moody, C. J.; Hayes, C. J. Tetrahedron 2013, 69, 2276