Synthesis of a novel constrained α-amino acid with quinoxaline side chain : 7-Amino-6,7-dihydro-8H-cyclopenta[g]quinoxaline-7-carbox-ylic acid

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 9031-9034

  Kotha, Sambasivarao ^a   Brahmachary, Enugurthi ^a   Kuki, Atsuo ^b,d   Lang, Kamil ^b,e   Anglos, Demetrios ^b,f   Singaram, Bakthan ^c   Chrisman, William ^c  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b Department of Molecular Biology and Genetics   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d Alanex Corporation   (United States)

^e INSTITUTE OF INORGANIC CHEMISTRY   (Czech Republic)

^f INSTITUTE OF COMPUTER SCIENCE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMINO ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; QUINOXALINE;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS;

EID: 0030735486     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10427-0     Document Type: Article

References (20)

1. For some recent examples of unusual α-amino acids preparation, see: Ciapetti, P.; Soccolini, F.; Taddei, M. Tetrahedron 1997, 53, 1167; Zvilichovsky, G.; Gurvich, V. J. Chem. Soc., Perkin Trans. 1, 1997, 1069; Ma, D.; Ma, J, Dai, L. Tetrahedron Asymmetry 1997, 8, 825; Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561; Yuan, W.; Hruby, V. J. Tetrahedron Lett. 1997, 38, 3853; Yokum, T. S.; Bursavieh, M. G.; Piha-Paul, S.; Hall, D. A.; McLaughlin, M. L. Tetrahedron Lett. 1997, 38, 4013.
2. For some recent examples of unusual α-amino acids preparation, see: Ciapetti, P.; Soccolini, F.; Taddei, M. Tetrahedron 1997, 53, 1167; Zvilichovsky, G.; Gurvich, V. J. Chem. Soc., Perkin Trans. 1, 1997, 1069; Ma, D.; Ma, J, Dai, L. Tetrahedron Asymmetry 1997, 8, 825; Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561; Yuan, W.; Hruby, V. J. Tetrahedron Lett. 1997, 38, 3853; Yokum, T. S.; Bursavieh, M. G.; Piha-Paul, S.; Hall, D. A.; McLaughlin, M. L. Tetrahedron Lett. 1997, 38, 4013.
3. For some recent examples of unusual α-amino acids preparation, see: Ciapetti, P.; Soccolini, F.; Taddei, M. Tetrahedron 1997, 53, 1167; Zvilichovsky, G.; Gurvich, V. J. Chem. Soc., Perkin Trans. 1, 1997, 1069; Ma, D.; Ma, J, Dai, L. Tetrahedron Asymmetry 1997, 8, 825; Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561; Yuan, W.; Hruby, V. J. Tetrahedron Lett. 1997, 38, 3853; Yokum, T. S.; Bursavieh, M. G.; Piha-Paul, S.; Hall, D. A.; McLaughlin, M. L. Tetrahedron Lett. 1997, 38, 4013.
4. For some recent examples of unusual α-amino acids preparation, see: Ciapetti, P.; Soccolini, F.; Taddei, M. Tetrahedron 1997, 53, 1167; Zvilichovsky, G.; Gurvich, V. J. Chem. Soc., Perkin Trans. 1, 1997, 1069; Ma, D.; Ma, J, Dai, L. Tetrahedron Asymmetry 1997, 8, 825; Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561; Yuan, W.; Hruby, V. J. Tetrahedron Lett. 1997, 38, 3853; Yokum, T. S.; Bursavieh, M. G.; Piha-Paul, S.; Hall, D. A.; McLaughlin, M. L. Tetrahedron Lett. 1997, 38, 4013.
5. For some recent examples of unusual α-amino acids preparation, see: Ciapetti, P.; Soccolini, F.; Taddei, M. Tetrahedron 1997, 53, 1167; Zvilichovsky, G.; Gurvich, V. J. Chem. Soc., Perkin Trans. 1, 1997, 1069; Ma, D.; Ma, J, Dai, L. Tetrahedron Asymmetry 1997, 8, 825; Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561; Yuan, W.; Hruby, V. J. Tetrahedron Lett. 1997, 38, 3853; Yokum, T. S.; Bursavieh, M. G.; Piha-Paul, S.; Hall, D. A.; McLaughlin, M. L. Tetrahedron Lett. 1997, 38, 4013.
6. For some recent examples of unusual α-amino acids preparation, see: Ciapetti, P.; Soccolini, F.; Taddei, M. Tetrahedron 1997, 53, 1167; Zvilichovsky, G.; Gurvich, V. J. Chem. Soc., Perkin Trans. 1, 1997, 1069; Ma, D.; Ma, J, Dai, L. Tetrahedron Asymmetry 1997, 8, 825; Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561; Yuan, W.; Hruby, V. J. Tetrahedron Lett. 1997, 38, 3853; Yokum, T. S.; Bursavieh, M. G.; Piha-Paul, S.; Hall, D. A.; McLaughlin, M. L. Tetrahedron Lett. 1997, 38, 4013.
7. Baudy, R. B.; Greenblatt, L. P.; Jirkovsky, I. L.; Conklin, M.; Russo, R. J.; Bramlett, D. R.; Emrey, T.A.; Simmonds, J. T.; Kowal, D. M.; Stein, R. P.; Tasse, R. P. J. Med Chem. 1992, 36, 331.
8. Anglos, D.; Bindra, V.; Kuki, A. J. Chem. Soc., Chem. Commun. 1994, 213. Quinoxaline and the tetrahydroquinoxaline 2 do not absorb at 355 nm (the acceptor molecule diketonaphthalene derivative 4 reported in this paper absorbs the excitation light at 355 nm). The resulting light induced charge-separated state features a broad peak at 435 nm.
9. Toniolo, C.; Benedetti, E. ISI Atlas of Science: Biochemistry 1988, 225; Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845; Hruby, V. J. Biopolymers 1993, 33, 1073; Liskamp R. M. Recl. Trav. Chim. Pyas-Bas. 1994, 113, 1; Bindra, V. A.; Kuki, A. Int. J, Peptide Protein Res. 1994, 44, 539; Augspurger, J. D.; Bindra, V. A.; Scheraga, H.; Kuki, A. Biochemistry 1995, 34, 2566.
10. Toniolo, C.; Benedetti, E. ISI Atlas of Science: Biochemistry 1988, 225; Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845; Hruby, V. J. Biopolymers 1993, 33, 1073; Liskamp R. M. Recl. Trav. Chim. Pyas-Bas. 1994, 113, 1; Bindra, V. A.; Kuki, A. Int. J, Peptide Protein Res. 1994, 44, 539; Augspurger, J. D.; Bindra, V. A.; Scheraga, H.; Kuki, A. Biochemistry 1995, 34, 2566.
11. Toniolo, C.; Benedetti, E. ISI Atlas of Science: Biochemistry 1988, 225; Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845; Hruby, V. J. Biopolymers 1993, 33, 1073; Liskamp R. M. Recl. Trav. Chim. Pyas-Bas. 1994, 113, 1; Bindra, V. A.; Kuki, A. Int. J, Peptide Protein Res. 1994, 44, 539; Augspurger, J. D.; Bindra, V. A.; Scheraga, H.; Kuki, A. Biochemistry 1995, 34, 2566.
12. Toniolo, C.; Benedetti, E. ISI Atlas of Science: Biochemistry 1988, 225; Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845; Hruby, V. J. Biopolymers 1993, 33, 1073; Liskamp R. M. Recl. Trav. Chim. Pyas-Bas. 1994, 113, 1; Bindra, V. A.; Kuki, A. Int. J, Peptide Protein Res. 1994, 44, 539; Augspurger, J. D.; Bindra, V. A.; Scheraga, H.; Kuki, A. Biochemistry 1995, 34, 2566.
13. Toniolo, C.; Benedetti, E. ISI Atlas of Science: Biochemistry 1988, 225; Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845; Hruby, V. J. Biopolymers 1993, 33, 1073; Liskamp R. M. Recl. Trav. Chim. Pyas-Bas. 1994, 113, 1; Bindra, V. A.; Kuki, A. Int. J, Peptide Protein Res. 1994, 44, 539; Augspurger, J. D.; Bindra, V. A.; Scheraga, H.; Kuki, A. Biochemistry 1995, 34, 2566.
14. Toniolo, C.; Benedetti, E. ISI Atlas of Science: Biochemistry 1988, 225; Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845; Hruby, V. J. Biopolymers 1993, 33, 1073; Liskamp R. M. Recl. Trav. Chim. Pyas-Bas. 1994, 113, 1; Bindra, V. A.; Kuki, A. Int. J, Peptide Protein Res. 1994, 44, 539; Augspurger, J. D.; Bindra, V. A.; Scheraga, H.; Kuki, A. Biochemistry 1995, 34, 2566.
15. Duthaler, R. O. Tetrahedron 1994, 50, 1539; William, R. M. Synthesis of Optically Active α-Amino Acids: Pergamon Press, Oxford, 1989.
16. Duthaler, R. O. Tetrahedron 1994, 50, 1539; William, R. M. Synthesis of Optically Active α-Amino Acids: Pergamon Press, Oxford, 1989.
17. Schollkopf, U.; Hoppe, D.; Jentsch, R. Chem. Ber. 1975, 108, 1580; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1974, 13, 789.
18. Schollkopf, U.; Hoppe, D.; Jentsch, R. Chem. Ber. 1975, 108, 1580; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1974, 13, 789.
19. 7. O'Donnell, M. J.; Wojciechowski, K. Synthesis 1983, 313.
20. 6, 500 MHz), δ 1.37 (s, 9H), 3.46 (part of ABq, J=17.5, 2H), 3.64 (part of ABq, J=17.0, 2H), 7.56 (s, 1H), 7.88 (s, 2H), 8.84 (s, 2H), 12.6 (br s, 1H).