The design of dipeptide helical mimetics: The synthesis, tachykinin receptor affinity and conformational analysis of 1,1,6-trisubstituted indanes

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 1, 1996, Pages 33-42

  Horwell, David C ^a   Howson, William ^a   Ratcliffe, Giles S ^a   Willems, Henriëtte M G ^a  

^a ADDENBROOKE S HOSPITAL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

INDAN DERIVATIVE; NEUROKININ 1 RECEPTOR; NEUROKININ 3 RECEPTOR; TACHYKININ RECEPTOR;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BLADDER; CHIRALITY; CHO CELL; COMPUTER SIMULATION; CONTROLLED STUDY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HAMSTER; HUMAN; HUMAN CELL; NEUROTRANSMISSION; NONHUMAN; X RAY CRYSTALLOGRAPHY;

AMINO ACID SEQUENCE; ANIMALS; BIOLOGICAL ASSAY; CRYSTALLOGRAPHY, X-RAY; DIPEPTIDES; HUMANS; INDANS; MODELS, MOLECULAR; MOLECULAR MIMICRY; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; NEUROKININ A; NEUROKININ B; PROTEIN CONFORMATION; RECEPTORS, TACHYKININ; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTANCE P;

EID: 0029972738     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(95)00169-7     Document Type: Article

References (25)

1. A preliminary account of this work has already been published: Horwell, D. C.; Howson, W.; Ratcliffe, G.; Willems, H. Bioorg. Med. Chem. Lett. 1994, 4, 2825.
2. Horwell, D. C.; Howson, W.; Rees, D. C. Drug Design & Discovery 1994, 12, 63.
3. See the following review articles: (a) Hölzemann, G. Kontakte (Darmstadt) 1991, 1, 3.
4. (b) Hölzemann, G. Kontakte (Darmstadt) 1991, 1, 55.
5. (c) Ball, J. B.; Alewood, P. F. J. Mol. Recognition 1990, 3, 55.
6. (d) Farmer, P. S. In Drug Design, Ariens, E. J., Ed.; Academic: London, 1980; Vol. X, pp 119-143.
7. Horwell, D. C.; Howson, W.; Nolan, W. P.; Ratcliffe, G. S.; Rees, D. C.; Willems, H. M. G. Tetrahedron 1995, 51, 203.
8. (a) Ikura, M.; Clore, M. G.; Gronenborn, A. M.; Zhu, G.; Klee, C. B.; Bax, A. Science 1992, 256, 632.
9. (b) Martin, P. D.; Robertson, W.; Turk, D.; Huber, R.; Bode, W.; Edwards, B. F. P. J. Biol. Chem. 1992, 267, 7911.
10. Nolan, W. P. ; Ratcliffe, G. S.; Rees. D. C. Tetrahedron Lett. 1992, 33, 6879.
11. Olson, G.; Bolin, D. R.; Bonner, M. P.; Bös, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039.
12. (a) Kemp, D. S.; Curran, T. P. Tetrahedron Lett. 1988, 29, 4931.
13. (b) Kemp, D. S.; Curran, T. P. Tetrahedron Lett. 1988, 29, 4935.
14. (c) Müller, K.; Obrecht, D.; Knierzinger, A.; Stankovic, C.; Spiegler, C.; Bannworth, W.; Trzeciak, A.; Englert, G.; Labhardt, A. M.; Schönhölzer, P. In Perspectives in Medicinal Chemistry; Testa, B.; Kyburz, F.; Fuhrer, W.; Giger, R., Eds.; VCH: Basel; 1993; pp 513-531.
15. Nongrum, F. M.; Myrboh, B. Synthesis, 1987, 845.
16. Aono, T.; Araki, Y.; Imanishi, M.; Noguchi, S. Chem. Pharm. Bull. 1978, 26, 1153.
17. (a) Boyle, S.; Guard, S.; Hodgson, J.; Horwell, D. C.; Howson, W.; Hughes, J.; McKnight, A. T.; Martin, K.; Pritchard, M. C.; Watling, K. J.; Woodruff, G. N. Bioorg. Med. Chem. 1994, 2, 101.
18. (b) Boyle, S.; Guard, S.; Higginbottom, M.; Horwell, D. C.; Howson, W.; Hughes, J.; McKnight, A. T.; Martin, K.; Pritchard, M. C.; O'Toole, J.; Raphy, J.; Rees, D. C.; Roberts, E.; Watling, K. J.; Woodruff, G. N. Bioorg. Med. Chem. 1994, 2, 357.
19. (c) Boden, P.; Eden, J. M.; Hodgson, J.; Horwell, D. C.; Howson, W.; Hughes, J.; McKnight, A. T.; Meecham, K.; Pritchard, M. C.; Raphy, J.; Ratcliffe, G. S.; Suman-Chauhan, N.; Woodruff, G. N. Bioorg. Med. Chem. Lett. 1994, 4, 1679.
20. Kollman, P. A. In Burger's Medicinal Chemistry and Drug Discovery; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; 5th Edition, Vol. 1, pp 399-416.
21. (a) Sheldrick, G. M. SHELX86, a computer program for crystal structure determination, University of Göttingen, 1986.
22. (b) Sheldrick, G. M. SHELX76, a computer program for crystal structure determination, University of Cambridge, 1976.
23. Compound 2 has been synthesised previously. See Haas, G.; Rossi, A. Ger. Offen. 2 505 106, 1975; Chem. Abs. 1976, 84, 105276g.
24. Compound 2 has been synthesised previously. See Haas, G.; Rossi, A. Ger. Offen. 2 505 106, 1975; Chem. Abs. 1976, 84, 105276g.
25. Geissman, T. A.; Armen, A. J. Am. Chem. Soc. 1952, 74, 3916.