Stereoselective synthesis of β-substituted phenylalanine-β-phenylisoserine-derived tripeptides using N-cinnamoyl-L-proline as template: Synthesis of structural analogues of HIV protease inhibitors

Journal of Organic Chemistry

Volumn 67, Issue 22, 2002, Pages 7858-7860

  Saha, Biswajit ^a   Prokash Nandy, Jyoti ^a   Shukla, Shalini ^a   Siddiqui, Iffat ^a   Iqbal, Javed ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSELECTIVE SYNTHESIS;

BIOSYNTHESIS; ENZYMES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; VIRUSES;

AMINO ACIDS;

BETA PHENYLISOSERINE; N CINNAMOYLPROLINE; PHENYLALANINE; PROLINE DERIVATIVE; PROTEINASE INHIBITOR; SERINE DERIVATIVE; TRIPEPTIDE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS; NONHUMAN; PEPTIDE ANALYSIS; PROTEINASE INHIBITION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

CINNAMATES; CRYSTALLOGRAPHY, X-RAY; HIV PROTEASE INHIBITORS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PEPTIDES; PHENYLALANINE; PROLINE; SERINE; STEREOISOMERISM;

EID: 0036827572     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0109826     Document Type: Article

References (27)

1. (a) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1.
2. (b) Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244.
3. (c) Wiley: R. A.; Rich, D. A. Med. Res. Rev. 1993, 13, 327.
4. (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
5. (e) Hruby, V. J. Biopolymers 1993, 33, 1073.
6. (f) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367.
7. (g) Jiao, D.; Russel, K. C.; Hruby, V. J. Tetrahedron 1993, 49, 3511.
8. (h) Moree, W. J.; van Gent, L. C.; van der Marcel, G. A.; Liskamp, R. M. J. Tetrahedron 1993, 49, 1133.
9. (i) Gordon, T.; Hansen, P.; Morgan, B.; Singh, J.; Baizman, E.; Ward, S. Biorg. Med. Chem. Lett. 1991, 1, 653.
10. (j) Xu, T.; Werner, R. M.; Lee, K.-C.; Fittenger, C.; Davis, J. T.; Coward, J. K. J. Org. Chem. 1998, 63, 4767.
11. (k) Saladino, R.; Mezetti, M.; Mincicone, E.; Torrini, I.; Paradisi, M. P.; Mastropietro, G. J. Org. Chem. 1999, 64, 8468.
12. (l) Benmer, R.; Bubert, C.; Cabrele, C.; Vielhaner, O.; Pietzsch, M.; Reiser, O. J. Org. Chem. 2000, 65, 8960.
13. (m) Smith, A. B., III; Wang, W.; Springler, P. A.; Hrischmann, R. J. Am. Chem. Soc. 2000, 122, 11037.
14. (a) For pyrrolidine-containing HIV protease inhibitors, see: Slee, D. H.; Laslo, K. L.; Elder, J. H.; Ollmann, I. R.; Gustchina, A.; Kervinen, J.; Zdanov, A.; Wlodawer, A.; Wong, C. J. Am. Chem. Soc. 1995, 117, 11867.
15. (b) Smith, A. B., III; Hrischmann, R.; Pasternak, A.; Yao, W.; Springler, P. A.; Holloway, M. K.; Kuo, L. C.; Chen, Z.; Darke, P. L.; Schlief, W. A. J. Med. Chem. 1997, 40, 2440.
16. (c) For some recent advances, also see: Edmonds, M. K.; Abell, A. D. J. Org. Chem. 2001, 66, 3747-3752. Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc, 2001, 123, 7207-7219. Hagen S. H.; et al. J. Med. Chem. 2001, 44, 2319-1332.
17. (c) For some recent advances, also see: Edmonds, M. K.; Abell, A. D. J. Org. Chem. 2001, 66, 3747-3752. Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc, 2001, 123, 7207-7219. Hagen S. H.; et al. J. Med. Chem. 2001, 44, 2319-1332.
18. (c) For some recent advances, also see: Edmonds, M. K.; Abell, A. D. J. Org. Chem. 2001, 66, 3747-3752. Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc, 2001, 123, 7207-7219. Hagen S. H.; et al. J. Med. Chem. 2001, 44, 2319-1332.
19. (a) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 469.
20. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
21. The racemic aziridine ester 2 was synthesised from ethyl glycidate according to the following protocol:
22. Zwanenburg, B. Pure Appl. Chem. 1999, 71, 423.
23. For polyaniline supported cobalt catalysed epoxidation see: (a) Das, B. C.; Iqbal, J. Tetrahedron Lett. 1997, 38, 2903. (b) Punniyamurthy, T.; Iqbal, J. Tetrahedron Lett. 1997, 38, 4463. (c) De, A.; Basak, P.; Iqbal, J. Tetrahedron Lett. 1997, 38, 8383.
24. For polyaniline supported cobalt catalysed epoxidation see: (a) Das, B. C.; Iqbal, J. Tetrahedron Lett. 1997, 38, 2903. (b) Punniyamurthy, T.; Iqbal, J. Tetrahedron Lett. 1997, 38, 4463. (c) De, A.; Basak, P.; Iqbal, J. Tetrahedron Lett. 1997, 38, 8383.
25. For polyaniline supported cobalt catalysed epoxidation see: (a) Das, B. C.; Iqbal, J. Tetrahedron Lett. 1997, 38, 2903. (b) Punniyamurthy, T.; Iqbal, J. Tetrahedron Lett. 1997, 38, 4463. (c) De, A.; Basak, P.; Iqbal, J. Tetrahedron Lett. 1997, 38, 8383.
26. Prabhakaran, E. N.; Nandy, J. P.; Shukla, S.; Iqbal, J. Tetrahedron Lett. 2001, 42, 333.
27. Bhatia, B.; Jain, S.; De, A.; Bagchi, I.; Iqbal, J. Tetrahedron Lett. 1996, 37, 7311.