(α-aminoacyl)amino-substituted heterocycles and related compounds

Journal of Organic Chemistry

Volumn 73, Issue 14, 2008, Pages 5442-5445

  Katritzky, Alan R ^a   El Gendy, Bahaa El Dien M ^a   Todadze, Ekaterina ^a   Abdel Fattah, Ashraf A A ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; ARSENIC COMPOUNDS; CHEMICAL REACTIONS; MICROWAVE IRRADIATION; MICROWAVES; ORGANIC COMPOUNDS;

AMERICAN CHEMICAL SOCIETY (ACS); AMINOACYL; BENZIMIDAZOLES; BENZOTHIAZOLES; BENZOTRIAZOLES; CHEMICAL EQUATIONS; HETERO-CYCLES; HETEROCYCLIC AMINES; PYRAZOLES; RELATED COMPOUNDS; THIADIAZOLES;

AMIDES;

AMIDE; AMINE; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; BENZYL N [1 (1H INDOL 3 YLMETHYL) 2 OXO 2 (1,3 THIAZOL 2 YLAMINO)ETHYL]CARBAMATE; BENZYL[1 [1 (6 METHOXYBENZOTHIAZOL 2 YLCARBAMOYL)ETHYLCARBAMOYL] 2 PHENYLETHYL]CARBAMATE; CARBAMIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; PYRAZOLE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINONE DERIVATIVE; THIADIAZOLE DERIVATIVE; THIAZOLE DERIVATIVE;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICROWAVE RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION;

AMINES; AMINOACYLATION; BENZENE; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; SULFHYDRYL COMPOUNDS;

EID: 48249092646     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8007379     Document Type: Article

References (48)

1. Zablocki, J. A.; Tarlton, E.; Rizzi, J. P.; Manto,N. B. PCT Int. Appl. 9822457 1998; Chem. Abstr. 1998, 129, 27933.
2. Hoffmann, M.; Grauert, M.; Brandl, T.; Steegmaier, M.; Hauptmann, R. U.S. Patent 009457 2006; Chem. Abstr. 2006, 144, 1299006.
3. Klein, S. I.; Molino, B. F.; Czekaj, M.; Gardner, C. J. U.S. Patent 5780590 1998; Chem. Abstr. 1998, 129, 122869.
4. Giori, P.; Vertuani, G.; Mazzotta, D.; Guarneri, M.; Pancaldi, d.; Brunelli, A. Farmaco 1982, 37, 450-458.
5. Brodney, M. A.; Coffman, K. J.; Kleinman, E. F.; O'neill, B. T.; Chen, Y. L. U.S. Patent 066613 1998; Chem. Abstr. 2007, 146, 359172.
6. Hagmann, W. D.; Delaszlo, S. E.; Doherty, G.; Chang, L. L.; Yang, G. X. PCT Int. Appl. 012183 2001; Chem. Abstr. 2001, 134, 193737.
7. Bowles, S. A.; Floyd, C. D.; Miller, A.; Whittaker, M.; Wood, L. M. PCT Int. Appl. 9314069 1993; Chem. Abstr. 1993, 120, 77276.
8. Kubo, A.; Imashiro, R.; Sakurai, H.; Miyoshi, H.; Ogasawara, A.; Hiramatsu, H. PCT Int. Appl. 035638 2003; Chem. Abstr. 2003, 138, 353990.
9. Dhanak, D.; Knight, S. D.; Lu, P.; Morgans, D.; Yao, B. PCT Int. Appl. 10.575 2003; Chem. Abstr. 2003, 140, 42200.
10. Fujita, Y.; Tsuda, Y.; Li, T.; Motoyama, T.; Takahashi, M.; Shimizu, Y.; Yokoi, T.; Sasaki, Y.; Ambo, A.; Kita, A.; Jinsmaa, Y.; Bryant, S. D.; Lazarus, L. H.; Okada, Y. J. Med. Chem. 2004, 47, 3591-3599.
11. Watkins, W. J.; Landaverry, Y.; Leger, R.; Litman, R.; Renau, T. E.; Williams, N.; Yen, R.; Zhang, J. Z.; Chamberland, S.; Madsen, D.; Griffith, D.; Tembe, V.; Huie, K.; Dudley, M. N. Bioorg. Med. Chem. Lett. 2003, 13, 4241-4244.
12. Renau, T. E.; Léger, R.; Filonova, L.; Flamme, E. M.; Wang, M.; Yen, R.; Madsen, D.; Griffith, D.; Chamberland, S.; Dudley, M. N.; Lee, V. J.; Lomovskaya, O. L.; Watkins, W. J.; Ohta, T.; Nakayama, K.; Ishida, Y. Bioorg. Med. Chem. Lett. 2003, 13, 2755-2758.
13. Fuwa, H.; Okamura, Y.; Morohashi, Y.; Tomita, T.; Iwatsubo, T.; Kan, T.; Fukuyama, T.; Natsugari, H. Tetrahedron Lett. 2004, 45, 2323-2326.
14. Rabinowitz, M. H.; Andrews, R. C.; Becherer, J. D.; Bickett, D. M.; Bubacz, D. G.; Conway, J. G.; Cowan, D. J.; Gaul, M.; Glennon, K.; Lambert, M. H.; Leesnitzer, M. A.; McDougald, D. L.; Moss, M. L.; Musso, D. L.; Rizzolio, M. C. J. Med. Chem. 2001, 44, 4252-4267.
15. Katritzky, A. R.; Suzuki, K.; Wang, Z. Synlett 2005, 11, 1656-1665.
16. Katritzky, A. R.; Khelashvili, L.; Mohapatra, P. P.; Steel, P. J Synth. 2007, 23, 3673-3677.
17. Katritzky, A. R.; He, H.-Y.; Suzuki, K. J. Org. Chem. 2000, 65, 8210-8213.
18. Katritzky, A. R.; Yang, H.; Zhang, S.; Wang, M. ARKIVOC 2002, xi, 39-44.
19. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Wang, M. J. Org. Chem. 2003, 68, 1443-1446.
20. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Wang, M. J. Org. Chem. 2003, 68, 4932-4934.
21. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Gromova, A.; Witek, R.; Steel, J. S. J. Org. Chem. 2005, 70, 9211-9214.
22. Katritzky, A. R.; Khanh, N., B.; Le, Khelashvili, L.; Mohapatra, P. P. J. Org. Chem. 2006, 71, 9861-9864.
23. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Akhmedova, R. G. ARKIVOC 2005, vi, 329-338.
24. Katritzky, A. R.; Pastor, A.; Voronkov, M. V. J. Heterocycl. Chem. 1999, 36, 777-781.
25. Katritzky, A. R.; Angrish, P. Steroids 2006, 71, 660-669.
26. Katritzky, A. R.; Wang, M.; Yang, H.; Zhang, S.; Akhmedov, N. G. ARKIVOC 2002, viii, 134-142.
27. (a) Katritzky, A. R.; Todadze, E.; Angrish, P.; Draghici, B. J. Org. Chem. 2007, 72, 5794-5801.
28. (b) Katritzky, A. R.; Suzuki, K.; Singh, S. K. Synthesis 2004, 2645-2652.
29. Katritzky, A. R.; Zhang, Y.; Singh, S. K. Synthesis 2003, 2795-2798.
30. Katritzky, A. R.; Angrish, P.; Suzuki, K. Synthesis 2006, 411-424.
31. Quelever, G.; Burlet, S.; Garino, C.; Pietrancosta, N.; Laras, Y.; Kraus, J. J. Comb. Chem. 2004, 6, 695-698.
32. Laras, Y.; Quelever, G.; Garino, C.; Pietrancosta, N.; Sheha, M.; Bihel, F.; Wolfe, M. S.; Kraus, J. Org. Biomol. Chem 2005, 3, 612-618.
33. Leung-Toung, R.; Wodzinska, J.; Li, W.; Lowrie, J.; Kukreja, R.; Desilets, D.; Karimian, K.; Tam, T. F. Bioorg. Med. Chem. 2003, 11, 5529-5537.
34. Camplo, M.; Niddam, V.; Barthelemy, P.; Faury, P.; Mourier, N.; Simon, V.; Charvet, A. S.; Trabaud, C.; Graciet, J. C. Eur. J. Med. Chem. 1995, 30, 789-800.
35. Manfredini, S.; Marastoni, M.; Tomatis, R.: Durini, E.; Spisani, S.; Pani, A.; Marceddu, T.; Musiu, C.; Marongiu, M. E.; La Colla, P. Bioorg. Med. Chem. 2000, 8, 539-547.
36. Balajthy, Z.; Aradi, J.; Kiss, I. T.; Elodi, P. J. Med. Chem. 1992, 35, 3344-3349.
37. Kenner, G. W.; Reese, C. B.; Todd, A. R. J. Chem. Soc. 1955, 855-859.
38. (a) Daidone, G.; Bajardi, M. L.; Plescia, S.; Raffa, D.; Schillaci, D.; Maggio, B.; Benetollo, F.; Bombieri, G. Eur. J. Med. Chem. 1996, 31, 461-468.
39. (b) Daidone, G.; Maggio, B.; Plescia, S.; Raffa, D.; Musiu, C.; Milia, C.; Perra, G.; Marongiu, M. Eur. J. Med. Chem. 1998, 33, 375-382.
40. (a) Carpino, L. A.; Sadat-Aalaee, D.; Chao, H. G.; DeSelms, R. H. J. Am. Chem. Soc. 1990, 112, 9651-9652.
41. (b) Bertho, J.-N.; Loffet, A.; Pinel, C.; Reuther, F.; Sennyey, G. Tetrahedron Lett. 1991, 32, 1303-1306.
42. Rzepecki, P.; Gallmeier, H.; Geib, N.; Cernovska, K.; Koenig, B.; Schrader, T. J. Org. Chem. 2004, 69, 5168-5178.
43. Molard, Y.; Parrot-Lopez, H. Tetrahedron Lett. 2001, 42, 4799-4802.
44. Pratt, L. M.; Beckett, R. P.; Bellamy, C. L.; Corkill, D. J.; Cossins, J.; Courtney, P. F.; Davies, S. J.; Davidson, A. H.; Drummond, A. H.; Helfrich, K.; Lewis, C. N.; Mangan, M.; Martin, F. M.; Miller, K.; Nayee, P.; Ricketts, M. L.; Thomas, W.; Todd, R. S.; Whittaker, M. Bioorg. Med. Chem. Lett. 1998, 8, 1359-1364.
45. Duflos, M.; Courant, J.; Le Baut, G.; Grimaud, N.; Renard, P.; Manechez, D.; Caignard, D.-H. Eur. J. Med. Chem. 1998, 33, 635-645.
46. He, L. Acta Crystallogr. 2006, E62, o3947-o3948.
47. (a) Vaughan, J.; Smith, P. A. S. J. Org. Chem. 1958, 23, 1909-1912.
48. (b) Jozwiak, A.; Brzezinski, J. Z.; Plotka, M. W.; Szczesniak, A. K.; Malinowski, Z.; Epsztajn, J. Eur. J. Org. Chem. 2004, 33, 3254-3261.