Browse > Article
http://dx.doi.org/10.5012/jkcs.2004.48.2.161

An Efficient Synthesis of γ-Aminobutyric Acid-Derived Phospholipase A2 Inhibitors from Acyl Cyanophosphoranes and Amine Derivatives  

Lee, Kie-Seung (Department of Chemistry, Woosuk University)
Kim, Dae-Keun (College of Pharmacy, Woosuk University)
Publication Information
Journal of the Korean Chemical Society / v.48, no.2, 2004 , pp. 161-170 More about this Journal
Abstract
A series of ${\gamma}$-aminobutyric acid-derived, potent human cytosolic phospholipase A$_2$ inhibitors have been prepared from acyl cyanophosphoranes and amine derivatives in a convergent manner. The ${\alpha}$-keto amide functionalities in the inhibitors have been introduced as electrophilic fragments via direct coupling reactions between the labile ${\alpha},{\beta}$-diketo nitriles and ${\gamma}$-aminobutyric acid t-butyl ester derivatives at -78 $^{\circ}C$ in moderate to good yields.
Keywords
Lipase Inhibition; Phospholipase A$_2$ Inhibitor; ${\alpha}$-Keto Amide; Acyl Cyanophosphorane;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Kokotos, G.; Kotsovolou,S.; Six, D. A.; Constantinou-Kokotou, V.; Beltzner, C.C.; Dennis, E. A. J. Med. Chem. 2002, 45, 2891.   DOI   ScienceOn
2 Hagihara, M.; Schreiber, S. L. J. Am. Chem. Soc.1992, 114, 6570.   DOI
3 Kobayashi, J.; Itagaki, F.; Shigemori, H.; Ishibashi,M.; Takahashi, K.; Ogura, M.; Nagasawa, S.;Nakamura, T.; Hirota, H.; Ohta, T.; Nozoe, S. J. Am.Chem. Soc. 1991, 113, 7812.   DOI
4 Toda,S.; Kotake, C.; Tsuno, T.; Narita, Y.; Yamasaki, T.;Konishi, M. J. Antibiot. 1992, 45, 1580.   DOI
5 Ocain, T. D.; Rich, D. H. J. Med. Chem. 1992, 35, 451.   DOI
6 Harbeson, S. L.; Abelleira, S. M.; Akiyama,A.; Barrett, R.; Carroll, R. M.; Straub, J. A.; Tkacz, J.N.; Wu, C.; Musso, G. F. J. Med. Chem. 1994, 37,2918.   DOI
7 Bryan, D. B.; Hall, R. F.; Holden, K. G.; Huffman, W.F.; Gleason, J. G. J. Am. Chem. Soc. 1977, 99, 2353.   DOI
8 Ohta, S.; Shimabayashi, A.; Aono,M.; Okamoto, M. Synthesis 1982, 833.
9 Luca, L. D.; Giacomelli. G.; Porcheddu,A. J. Org. Chem. 2001, 66, 7907.   DOI   ScienceOn
10 Frigerio, M.; Santagostino,M.; Sputore, S.; Palmisano, G. J. Org. Chem.1995, 60, 7272.   DOI   ScienceOn
11 Sieber, P.; Kamber, A.; Hartmann, A.; Joehl, A.; Riniker, B.; Rittel, W. Helv. Chim. Acta. 1977, 60, 27.   DOI   ScienceOn
12 Schiemenz, G. P.; Engelhard, H. Chem. Ber. 1961, 94, 578.   DOI
13 Li, Z.; Ortega-Vilain A.-C.; Patil, G. S.; Chu,D.-L.; Foreman, J. E.; Eveleth, D. D.; Powers, J. Med.Chem. 1996, 39, 4089.   DOI   ScienceOn
14 Windridge, G. C.; Jorgensen, E. C. J. Chem. Soc.,Chem. Commun. 1988, 419.
15 Wipf, P.; Kim, H. J. Org. Chem. 1993, 58,5592.   DOI
16 Fusetani, N.; Sugarawa, T.; Matsunaga,S.; Hirota, H. J. Am. Chem. Soc. 1991, 113,7811.   DOI
17 Greene, T. W.; Wuts, P. G. In Protective Groups inOrganic Synthesis, 2nd Ed.; John Wiley & Sons, Inc.:New York, 1991; pp 335-338.
18 Kobayashi, T.; Tanaka, M. J.Organometal. Chem. 1982, 233, C64.   DOI   ScienceOn
19 Rodriguez, M.; Liinares, M.; Doulut, S.; Heitz, A.;Martinez, J. Tetrahedron. Lett. 1991, 32, 923.   DOI   ScienceOn
20 Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem.1978, 43, 2480.   DOI
21 Cirino, G. Biochem. Pharmacol. 1998, 55, 105.   DOI   ScienceOn
22 Ghomashchi, F.; Loo, R.; Balsinde, J.; Bartoli,F.; Apitz-Castro, R.; Clark, J. D.; Dennis, E. A.;Gelb, M. H. Biochim. Biophys. Acta 1999, 1420, 45.   DOI   ScienceOn
23 Balsinde, J.; Dennis, E, A. J. Biol. Chem. 1996, 271, 6758   DOI
24 Khim, S.-K.;Nuss, J. M. Tetrahedron. Lett. 1999, 49, 1827.
25 Yang, Z.; Zhang, Z.; Meanwell, N. A.; Kadow, J. F.;Wang, T. Org. Lett. 2002, 1103.
26 Sibi, M. P.; Marvin,M.; Sharma, R. J. Org. Chem. 1995, 60, 5016.   DOI   ScienceOn
27 Wasserman, H. H.; Petersen, A. K. Tetrahedron.Lett. 1997, 38, 953.   DOI   ScienceOn
28 Wasserman, H. H.; Petersen, A.K. J. Org. Chem. 1997, 62, 8972.   DOI   ScienceOn
29 Lee, K. Bull. Kor. Chem. Soc. 2002, 23, 351.   DOI   ScienceOn
30 Fosker, A. P.; Law, H. D. J. Chem. Soc. 1965, 7305.   DOI
31 Ozawa, F.; Yamamoto, A. Chem. Lett. 1982, 865.
32 Conde-Frieboes, K.; Reynolds, L. J.; Lio, Y.-C.; Hale,M. R.; Wasserman, H. H.; Dennis, E. A. J. Am. Chem.Soc. 1996, 118, 5519.   DOI   ScienceOn
33 Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem.1999, 64, 4537.   DOI   ScienceOn
34 Inanaga, J.;Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull.Chem. Soc. Jpn. 1979, 52, 1989.   DOI
35 Kokotos, G.; Constantinou-kokotu, V.; Noula, C.; Nicolaou, A.; Gibbons,W. A. Int. J. Peptide Protein Res. 1996, 48, 160.   DOI   ScienceOn
36 Seno, K.; Okuno, T.; Nishi,K.; Murakami, Y.; Watanabe, F.; Matsuura, T.; Wada,M.; Fujii, Y.; Yamada, M.; Ogawa, T.; Okada, T.; Hashizume,H.; Kii, M.; Hara, S.-I.; Hagishita, S.; Nakamoto,S.; Yamada, K.; Chikazawa, Y.; Ueno, M.; Teshirogi,I.; Ono, T.; Ohtani, M. J. Med. Chem. 2000, 43, 1041.   DOI   ScienceOn
37 Wasserman,H. H.; Wang, J. J. Org. Chem. 1998, 63, 5581.   DOI   ScienceOn
38 Ghomashchi, F.; Stewart, A.; Hefner, Y.; Ramanadham,S.; Turk, J.; Leslie, C. C.; Gelb, M. H. Biochim.Biophys. Acta 2001, 1513, 160.   DOI   ScienceOn
39 Street, I. P.; Lin, H.-K.; Laliberte, F.; Ghomashchi, F.; Wang, Z.; Perrier, H.; Tremblay, N. M.; Huang, Z.; Weech, P. K.; Gelb, M. H. Biochemistry 1993, 32, 5935.   DOI   ScienceOn
40 Dhaon, M.; Olsen, R. K.; Ramasamy, K. J. Org. Chem.1982, 47, 1962.   DOI
41 Wasserman, H. H.; Ho, W.-B. J. Org. Chem. 1994, 59,4364.   DOI   ScienceOn
42 Wasserman, H. H.; Lee, K.; Xia, M. Tetrahedron. Lett.2000, 41, 2511.   DOI   ScienceOn
43 Aoyagi, T.; Nagai, M.;Ogawa, K.; Kojima, F.; Okada, M.; Ikeda, T.; Hamada,M.; Takeuchi, T. J. Antibiot. 1991, 44, 949.   DOI
44 Wasserman, H.H.; Xia, M.; Petersen, A. K.; Jorgensen, M. R.; Curtis,E. A. Tetrahedron. Lett. 1999, 40, 6163.   DOI   ScienceOn
45 Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem.1969, 34, 2543.   DOI
46 Ackerman, E. J.; Conde-Frieboes, K.; Dennis, E. A.J. Biol. Chem. 1995, 270, 445.   DOI   ScienceOn