Unanticipated stereoselectivity in the reaction of primaquine α-aminoamides with substituted benzaldehydes: A computational and experimental study

Journal of Organic Chemistry

Volumn 72, Issue 11, 2007, Pages 4189-4197

  Ferraz, Ricardo ^a,b   Gomes, José R B ^a   De Oliveira, Eliandre ^c   Moreira, Rui ^d   Gomes, Paula ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b POLYTECHNIC INSTITUTE OF PORTO   (Portugal)

^c UNIVERSITY OF BARCELONA   (Spain)

^d RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; COMPUTATIONAL METHODS; HYDROLYSIS; REACTION KINETICS; STEREOSELECTIVITY; SUBSTITUTION REACTIONS;

AMINOPEPTIDASE; BENZALDEHYDES; BIOACTIVE OLIGOPEPTIDES;

AMIDES;

ALDEHYDE; AMIDE; AMINE; AMINO ACID; AMINOPEPTIDASE; BENZALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; IMIDAZOLINE DERIVATIVE; IMINE; KETONE; OLIGOPEPTIDE; PRIMAQUINE DERIVATIVE; PROLINE; PROTEINASE;

ARTICLE; CYCLIZATION; ENZYME MECHANISM; HYDROGEN BOND; HYDROLYSIS; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

AMIDES; ANTIMALARIALS; BENZALDEHYDES; CATALYSIS; COMPUTATIONAL BIOLOGY; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PRIMAQUINE; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; STEREOISOMERISM;

EID: 34249810396     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0703202     Document Type: Article

References (31)

1. Klixbull, U.; Bundgaard, H. Int. J. Pharm. 1984, 20, 273.
2. Rasmussen, G. J.; Bundgaard, H. Int. J. Pharm. 1991, 71, 45.
3. Rasmussen, G. J.; Bundgaard, H. Int. J. Pharm. 1991, 76, 113.
4. Bak, A.; Fich, M.; Larsen, B. D.; Frokjaer, S.; Friis, G. J. Eur. J. Pharm. Sci. 1999, 7, 317.
5. Gomes, P.; Araújo, M. J.; Rodrigues. M.; Vale, N.; Azevedo, Z.; Iley, J.; Chambel, P.; Morais, J.; Moreira, R. Tetrahedron 2004, 60, 5551.
6. Araújo, M. J.; Bom, J.; Capela, R.; Casimiro, C.; Chambel, P.; Gomes, P.; Iley, J.; Lopes, F.; Morais, J.; Moreira, R.; de Oliveira, E.; do Rosário, V.; Vale, N. J. Med. Chem. 2005, 48, 888.
7. Chambel, P.; Capela, R.; Lopes, F.; Iley, J.; Morais, J.; Gouveia, L.; Gomes, J. R. B.; Gomes, P.; Moreira, R. Tetrahedron 2006, 62, 9883.
8. Heck, A. J. R.; Bonnici, P. J.; Breukink, E.; Morris, D.; Wills, M. Chem.-Eur. J 2001, 7, 910.
9. Pinza, M.; Farina, C.; Cerri, A.; Pfeiffer, U.; Riccaboni, M. T.; Banfi, S.; Biagetti, R.; Pozzi, O.; Magnani, M.; Dorigotti, L. J. Med. Chem. 1993, 36, 4214.
10. Pinza, M.; Riccaboni, M. T.; Cerri, A.; Farina, C. Eur. Pat. Appl. EP 335483 A2, 1989. Chem. Abstr. 1990, 112, 158246.
11. Farina, C.; Gagliardi, S.; Parini, C.; Martinelli, M.; Ghelardini, C. PCT Int. Appl. WO 2004085438 A2, 2004; Chem. Abstr. 2004, 141, 332191.
12. Satoh, A.; Kato, T.; Ooi, N.; Iwasawa, Y. PCT Int. Appi. WO 2001096337 A1; Chem. Abstr. 2001, 136, 37608.
13. Flautt, T. J.; Erman. W. F. J. Am. Chem. Soc. 1963, 85, 3212.
14. Laszlo, P.; von Ragué, Schleyer, P. J. Am. Chem. Soc. 1964, 86, 1171.
15. Rassat, A.; Jefford, C. W.; Lehn, J. M.; Waegell, B. Tetrahedron Lett. 1964, 5, 233.
16. Chmielewski, P. J.; Latos-Grażyński. L. J. Chem. Soc. Perkin Trans. 2 1995, 503.
17. Meinwald, J.; Lewis, A. J. Am. Chem. Soc. 1963, 85, 2514.
18. Osawa, Y.; Neeman, N. J. Am. Chem. Soc. 1963, 85, 2856.
19. Perry, N. B.; Blunt, J. W.; Munro. M. H. G.; Higa, T.; Sakai, R. J. Org. Chem. 1988, 53, 4127.
20. Hesse, M.; Meier, H.; Zeeh, B. Spectroscopic Methods in Organic Chemistry; Enders, D., Noyori, R., Trost. B. M., Eds.; Foundations of Organic Chemistry Series, Translated by Linden, A., Murray, M.; Thieme; New York. 1997; pp 110-111.
21. Yajima, T.; Okada, K.; Nagano. H. Tetrahedron 2004, 60, 5683.
22. Nagano, H.; Ohkouchi, H.; Yajima. T. Tetrahedron 2003, 59, 3649.
23. Freccero, M.; Gandolfi, R.; Sarzi-Amadè, M. Tetrahedron 1999, 55, 11309.
24. Lee, E. C.; Hodous, B. L.; Bergin, E.; Shih, C.; Fu. G. C. J. Am. Chem. Soc. 2005, 127, 11586.
25. Jiao, L.; Liang, Y.; Xu, J. J. Am. Chem. Soc. 2006, 128, 6060.
26. Clemente, F. R.; Houk, K. N. J. Am. Chem. Soc. 2005, 127, 11294.
27. Fu. A.; List, B.; Thiel. W. J. Org. Chem. 2006, 71, 320.
28. Katritzky, A. R.; Xu, Y.-J.; He, H.-Y.; Steel, P. J. J. Chem. Soc. Perkin Trans. I 2001, 1767.
29. García-Martínez, C.; Cervantes-Cuevas, H.; Escalante-García. J. Chirality 2003, 15, S74.
30. Frisch, M. J.; Tracks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Milian, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adammo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, C.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, C.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham. M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Rev. A.3,;Gaussian, Inc.: Pittsburgh PA, 1998.
31. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.