Solid phase organic synthesis of piperazinone containing enkephalin mimetics: A readily derivatized, traceless scaffold

Journal of Combinatorial Chemistry

Volumn 1, Issue 5, 1999, Pages 383-387

  Shreder, Kevin ^a   Zhang, Li ^a   Gleeson, Jean Paul ^a   Ericsson, Jens A ^a   Yalamoori, Venkatachalapathi V ^a   Goodman, Murray ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; LEUCINE ENKEPHALIN; PEPTIDE LIBRARY; PIPERAZINE DERIVATIVE; PLANT RESIN;

ARTICLE; CHEMISTRY; DRUG DESIGN; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

DRUG DESIGN; ENKEPHALIN, LEUCINE; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE LIBRARY; PIPERAZINES; RESINS, PLANT; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 0033186498     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc9900100     Document Type: Article

References (19)

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9. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
10. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
11. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
12. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
13. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
14. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
15. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
16. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
17. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
18. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
19. For various syntheses of piperazinones in solution, see: (a)Pohlmann, A.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1997, 62, 1016-1022. (b) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315-318. (c) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Lett. 1996, 37, 2083-2084. (d) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. (e) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988. (f) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120. (g) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elsevier Science: New York; 1989; pp 294-296. (h) Lai, J. T. J. Org. Chem. 1.980, 45, 754-755. (i) Masuzawa, K.; Masaki, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 2078-2081. (j) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Jpn. 1963, 36, 922-925. (k) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.