Highly diastereoselective synthesis of new, carbostyril-based type of conformationally-constrained β-phenylserines

Tetrahedron

Volumn 59, Issue 37, 2003, Pages 7301-7306

  Ueki, Hisanori ^a   Ellis, Trevor K ^a   Khan, Masood A ^a   Soloshonok, Vadim A ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

Conformational and steric constrain; Diastereoselectivity; amino acids and derivatives

Indexed keywords

3 (1,3 DIHYDROISOINDOL 2 YL) 4 HYDROXY 4 PHENYL 3,4 DIHYDRO 1H QUINOLIN 2 ONE; 3 BENZYLAMINO 4 HYDROXY 4 PHENYL 3,4 DIHYDRO 1H QUINOLIN 2 ONE; 3 DIBENZYLAMINO 4 HYDROXY 4 PHENYL 3,4 DIHYDRO 1H QUINOLIN 2 ONE; 3 DIETHYLAMINO 4 HYDROXY 4 PHENYL 3,4 DIHYDRO 1H QUINOLIN 2 ONE; 4 HYDROXY 4 PHENYL 3 PIPERIDIN 1 YL 3,4 DIHYDRO 1H QUINOLIN 2 ONE; AMIDE; AMINO ACID DERIVATIVE; CARBONYL DERIVATIVE; GLYCINE DERIVATIVE; N (2 BENZOYLPHENYL) 2 (1,3 DIHYDROISOINDOL 2 YL)ACETAMIDE; N (2 BENZOYLPHENYL) 2 BENZYLAMINOACETAMIDE; N (2 BENZOYLPHENYL) 2 DIETHYLAMINOACETAMIDE; N (2 BENZOYLPHENYL) 2 PIPERIDIN 1 YLACETAMIDE; SERINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TANDEM MASS SPECTROMETRY; X RAY CRYSTALLOGRAPHY;

EID: 0041380988     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01172-4     Document Type: Article

References (52)

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13. For applications in peptide design of Atc-1, see: (a) Aldrich J.V., Zheng Q., Murray T.F. Chirality. 13:2001;125 (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
14. For applications in peptide design of Atc-1, see: (a) Aldrich J.V., Zheng Q., Murray T.F. Chirality. 13:2001;125 (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
15. For applications in peptide design of Atc-1, see: (a) Aldrich J.V., Zheng Q., Murray T.F. Chirality. 13:2001;125 (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
16. For applications in peptide design of Atc-1, see: (a) Aldrich J.V., Zheng Q., Murray T.F. Chirality. 13:2001;125 (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
17. For applications in peptide design of Atc-1, see: (a) Aldrich J.V., Zheng Q., Murray T.F. Chirality. 13:2001;125 (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
18. For applications in peptide design of Atc-1, see: (a) Aldrich J.V., Zheng Q., Murray T.F. Chirality. 13:2001;125 (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
19. For synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) ( 2 ), see: Majer P., Slaninova J., Lebl M. Int. J. Pept. Protein Res. 43:1994;62. (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
20. For synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) ( 2 ), see: Majer P., Slaninova J., Lebl M. Int. J. Pept. Protein Res. 43:1994;62. (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
21. For synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) ( 2 ), see: Majer P., Slaninova J., Lebl M. Int. J. Pept. Protein Res. 43:1994;62. (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
22. For synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) ( 2 ), see: Majer P., Slaninova J., Lebl M. Int. J. Pept. Protein Res. 43:1994;62. (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
23. For synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) ( 2 ), see: Majer P., Slaninova J., Lebl M. Int. J. Pept. Protein Res. 43:1994;62. (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
24. For synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) ( 2 ), see: Majer P., Slaninova J., Lebl M. Int. J. Pept. Protein Res. 43:1994;62. (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
25. For synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) ( 2 ), see: Majer P., Slaninova J., Lebl M. Int. J. Pept. Protein Res. 43:1994;62. (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
26. For synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) ( 2 ), see: Majer P., Slaninova J., Lebl M. Int. J. Pept. Protein Res. 43:1994;62. (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
27. For synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) ( 2 ), see: Majer P., Slaninova J., Lebl M. Int. J. Pept. Protein Res. 43:1994;62. (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
28. For synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) ( 2 ), see: Majer P., Slaninova J., Lebl M. Int. J. Pept. Protein Res. 43:1994;62. (b) Darula Z., Peter A., Toth G. J. Labelled Compd. Radiopharm. 39:1997;817 (c) Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., Marsden B.J., Wilkes B.C. J. Med. Chem. 34:1991;3125 (d) Deeks T., Crooks P.A., Waigh R.D. J. Pharm. Sci. 73:1984;457 (e) Cordi A.A., Lacoste J.-M., Descombes J.-J., Courchay C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056 (f) Denyer C.V., Turner-Brown S.J., Knowles R.G., Dawson J. Bioorg. Med Chem. Lett. 2:1992;1039 (g) Obrecht D., Altorfer M., Bohdal U., Daly J., Huber W., Labhardt A., Lehmann C., Muller K., Ruffieux R., Schonholzer P., Spiegler C., Zumbrunn C. Biopolymers. 42:1997;575.
29. For the most recent papers on 'Quinapril' and its analogs ('Moexipril'), see: (a) Blumer J.L., Daniels S.R., Dreyer W.J., Batisky D., Walson P.D., Roman D., Ouellet D. J. Clin. Pharm. 43:2003;128 (b) Warnica J.W., Van Gilst W., Baillot R., Johnstone D., Block P., Myers M.G., Chocron S., Ave S.D., Martineau P., Rouleau J.-L. Can. J. Cardiol. 18:2002;1191 (c) Radauceanu A., Virion J.-M., Boivin J.-M., Zannad F. Fundam. Clin. Pharm. 16:2002;545 (d) Resnick L.M., Lester M.H. Am. J. Hypertens. 15:2002;1096 (e) Saran R., Dykstra D.M., Wolfe R.A., Gillespie B., Held P.J., Young E.W. Am. J. Kidney Dis. 40:2002;1255 (f) Okuguchi T., Osanai T., Fujiwara N., Kato T., Metoki N., Konta Y., Okumura K. Am. J. Hypertens. 15:2002;998 (g) Molinaro G., Cugno M., Perez M., Lepage Y., Gervais N., Agostoni A., Adam A. J. Pharm. Exp. Ther. 303:2002;232 (h) Sakata K., Yoshida H., Obayashi K., Ishikawa J., Tamekiyo H., Nawada R., Doi O. J. Hypertens. 20:2002;103 (i) Hlubocka Z., Umnerova V., Heller S., Peleska J., Jindra A., Jachymova M., Kvasnicka J., Horky K., Aschermann M. J. Human Hypertens. 16:2002;557 (j) Culy C.R., Jarvis B. Drugs. 62:2002;339.
30. For examples of application of 2′,6′-dimethyl-L-tyrosine (Dmt)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) pharmacophore, see: (a) Balboni G., Salvadori S., Guerrini R., Negri L., Giannini E., Jinsmaa Y., Bryant S.D., Lazarus L.H. J. Med. Chem. 45:2002;5556 (b) Bryant S.D., George C., Flippen-Anderson J.L., Deschamps J.R., Salvadori S., Balboni G., Guerrini R., Lazarus L.H. J. Med. Chem. 45:2002;5506 (c) Kumar V., Murray T.F., Aldrich J.V. J. Med. Chem. 45:2002;3820.
31. For examples of application of 2′,6′-dimethyl-L-tyrosine (Dmt)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) pharmacophore, see: (a) Balboni G., Salvadori S., Guerrini R., Negri L., Giannini E., Jinsmaa Y., Bryant S.D., Lazarus L.H. J. Med. Chem. 45:2002;5556 (b) Bryant S.D., George C., Flippen-Anderson J.L., Deschamps J.R., Salvadori S., Balboni G., Guerrini R., Lazarus L.H. J. Med. Chem. 45:2002;5506 (c) Kumar V., Murray T.F., Aldrich J.V. J. Med. Chem. 45:2002;3820.
32. For examples of application of 2′,6′-dimethyl-L-tyrosine (Dmt)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) pharmacophore, see: (a) Balboni G., Salvadori S., Guerrini R., Negri L., Giannini E., Jinsmaa Y., Bryant S.D., Lazarus L.H. J. Med. Chem. 45:2002;5556 (b) Bryant S.D., George C., Flippen-Anderson J.L., Deschamps J.R., Salvadori S., Balboni G., Guerrini R., Lazarus L.H. J. Med. Chem. 45:2002;5506 (c) Kumar V., Murray T.F., Aldrich J.V. J. Med. Chem. 45:2002;3820.
33. For synthesis of 3-amino-3,4-dihydro-1H-quinolin-2-one ( 3 ), see: (a) Juarez-Gordiano C., Hernandez-Campos A., Castillo R. Synth. Commun. 32: 2002;2959 (b) Minin P.L., Walton J.C. J. Org. Chem. 68:2002;2960.
34. For synthesis of 3-amino-3,4-dihydro-1H-quinolin-2-one ( 3 ), see: (a) Juarez-Gordiano C., Hernandez-Campos A., Castillo R. Synth. Commun. 32: 2002;2959 (b) Minin P.L., Walton J.C. J. Org. Chem. 68:2002;2960.
35. For application of model 3 in peptide design, see: (a) Patel M., McHugh R.J., Cordova B.C., Klabe R.M., Bacheler L.T., Erickson-Viitanen S., Rodgers J.D. Bioorg. Med. Chem. Lett. 11:2001;1943 (b) Zhao H., Thurkauf A., Braun J., Brodbeck R., Kieltyka A. Bioorg. Med. Chem. Lett. 10:2000;2119 (c) Shono T., Motoyama M., Tatsumi K., Ulbrich N., Iwamoto Y., Kuwano M., Ono M. Angiogenesis. 2:1999;319 (d) Iki K., Tsutsumi M., Kido A., Sakitani H., Takahama M., Yoshimoto M., Motoyama M., Tatsumi K., Tsunoda T., Konishi Y. Carcinogenesis. 20:1999;1323 (e) Kido A., Tsutsumi M., Iki K., Motoyama M., Takahama M., Tsujiuchi T., Morishita T., Tatsumi K., Tamai S., Konishi Y. Jpn. J. Cancer Res. 90:1999;333 (f) Lewis R.J., Francis C.A., Lehr R.E., LeRoy Blank C. Tetrahedron. 56:2000;5345 (g) Masubuchi K., Taniguchi M., Umeda I., Hattori K., Suda H., Kohchi Y., Isshiki Y., Sakai T., Kohchi M., Shirai M., Okabe H., Sudoh M., Yamazaki T., Shimma N. Bioorg. Med. Chem. Lett. 10:2000;1459 (h) Tamura S.Y., Goldman E.A., Bergum P.W., Semple J.E. Bioorg. Med. Chem. Lett. 9:1999;2573.
36. For examples of application of 2′,6′-dimethyl-L-tyrosine (Dmt)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) pharmacophore, see: (a) Balboni G., Salvadori S., Guerrini R., Negri L., Giannini E., Jinsmaa Y., Bryant S.D., Lazarus L.H. J. Med. Chem. 45:2002;5556 (b) Bryant S.D., George C., Flippen-Anderson J.L., Deschamps J.R., Salvadori S., Balboni G., Guerrini R., Lazarus L.H. J. Med. Chem. 45:2002;5506 (c) Kumar V., Murray T.F., Aldrich J.V. J. Med. Chem. 45:2002;3820.
37. For examples of application of 2′,6′-dimethyl-L-tyrosine (Dmt)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) pharmacophore, see: (a) Balboni G., Salvadori S., Guerrini R., Negri L., Giannini E., Jinsmaa Y., Bryant S.D., Lazarus L.H. J. Med. Chem. 45:2002;5556 (b) Bryant S.D., George C., Flippen-Anderson J.L., Deschamps J.R., Salvadori S., Balboni G., Guerrini R., Lazarus L.H. J. Med. Chem. 45:2002;5506 (c) Kumar V., Murray T.F., Aldrich J.V. J. Med. Chem. 45:2002;3820.
38. For examples of application of 2′,6′-dimethyl-L-tyrosine (Dmt)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) pharmacophore, see: (a) Balboni G., Salvadori S., Guerrini R., Negri L., Giannini E., Jinsmaa Y., Bryant S.D., Lazarus L.H. J. Med. Chem. 45:2002;5556 (b) Bryant S.D., George C., Flippen-Anderson J.L., Deschamps J.R., Salvadori S., Balboni G., Guerrini R., Lazarus L.H. J. Med. Chem. 45:2002;5506 (c) Kumar V., Murray T.F., Aldrich J.V. J. Med. Chem. 45:2002;3820.
39. For application of model 3 in peptide design, see: (a) Patel M., McHugh R.J., Cordova B.C., Klabe R.M., Bacheler L.T., Erickson-Viitanen S., Rodgers J.D. Bioorg. Med. Chem. Lett. 11:2001;1943 (b) Zhao H., Thurkauf A., Braun J., Brodbeck R., Kieltyka A. Bioorg. Med. Chem. Lett. 10:2000;2119 (c) Shono T., Motoyama M., Tatsumi K., Ulbrich N., Iwamoto Y., Kuwano M., Ono M. Angiogenesis. 2:1999;319 (d) Iki K., Tsutsumi M., Kido A., Sakitani H., Takahama M., Yoshimoto M., Motoyama M., Tatsumi K., Tsunoda T., Konishi Y. Carcinogenesis. 20:1999;1323 (e) Kido A., Tsutsumi M., Iki K., Motoyama M., Takahama M., Tsujiuchi T., Morishita T., Tatsumi K., Tamai S., Konishi Y. Jpn. J. Cancer Res. 90:1999;333 (f) Lewis R.J., Francis C.A., Lehr R.E., LeRoy Blank C. Tetrahedron. 56:2000;5345 (g) Masubuchi K., Taniguchi M., Umeda I., Hattori K., Suda H., Kohchi Y., Isshiki Y., Sakai T., Kohchi M., Shirai M., Okabe H., Sudoh M., Yamazaki T., Shimma N. Bioorg. Med. Chem. Lett. 10:2000;1459 (h) Tamura S.Y., Goldman E.A., Bergum P.W., Semple J.E. Bioorg. Med. Chem. Lett. 9:1999;2573.
40. For application of model 3 in peptide design, see: (a) Patel M., McHugh R.J., Cordova B.C., Klabe R.M., Bacheler L.T., Erickson-Viitanen S., Rodgers J.D. Bioorg. Med. Chem. Lett. 11:2001;1943 (b) Zhao H., Thurkauf A., Braun J., Brodbeck R., Kieltyka A. Bioorg. Med. Chem. Lett. 10:2000;2119 (c) Shono T., Motoyama M., Tatsumi K., Ulbrich N., Iwamoto Y., Kuwano M., Ono M. Angiogenesis. 2:1999;319 (d) Iki K., Tsutsumi M., Kido A., Sakitani H., Takahama M., Yoshimoto M., Motoyama M., Tatsumi K., Tsunoda T., Konishi Y. Carcinogenesis. 20:1999;1323 (e) Kido A., Tsutsumi M., Iki K., Motoyama M., Takahama M., Tsujiuchi T., Morishita T., Tatsumi K., Tamai S., Konishi Y. Jpn. J. Cancer Res. 90:1999;333 (f) Lewis R.J., Francis C.A., Lehr R.E., LeRoy Blank C. Tetrahedron. 56:2000;5345 (g) Masubuchi K., Taniguchi M., Umeda I., Hattori K., Suda H., Kohchi Y., Isshiki Y., Sakai T., Kohchi M., Shirai M., Okabe H., Sudoh M., Yamazaki T., Shimma N. Bioorg. Med. Chem. Lett. 10:2000;1459 (h) Tamura S.Y., Goldman E.A., Bergum P.W., Semple J.E. Bioorg. Med. Chem. Lett. 9:1999;2573.
41. For application of model 3 in peptide design, see: (a) Patel M., McHugh R.J., Cordova B.C., Klabe R.M., Bacheler L.T., Erickson-Viitanen S., Rodgers J.D. Bioorg. Med. Chem. Lett. 11:2001;1943 (b) Zhao H., Thurkauf A., Braun J., Brodbeck R., Kieltyka A. Bioorg. Med. Chem. Lett. 10:2000;2119 (c) Shono T., Motoyama M., Tatsumi K., Ulbrich N., Iwamoto Y., Kuwano M., Ono M. Angiogenesis. 2:1999;319 (d) Iki K., Tsutsumi M., Kido A., Sakitani H., Takahama M., Yoshimoto M., Motoyama M., Tatsumi K., Tsunoda T., Konishi Y. Carcinogenesis. 20:1999;1323 (e) Kido A., Tsutsumi M., Iki K., Motoyama M., Takahama M., Tsujiuchi T., Morishita T., Tatsumi K., Tamai S., Konishi Y. Jpn. J. Cancer Res. 90:1999;333 (f) Lewis R.J., Francis C.A., Lehr R.E., LeRoy Blank C. Tetrahedron. 56:2000;5345 (g) Masubuchi K., Taniguchi M., Umeda I., Hattori K., Suda H., Kohchi Y., Isshiki Y., Sakai T., Kohchi M., Shirai M., Okabe H., Sudoh M., Yamazaki T., Shimma N. Bioorg. Med. Chem. Lett. 10:2000;1459 (h) Tamura S.Y., Goldman E.A., Bergum P.W., Semple J.E. Bioorg. Med. Chem. Lett. 9:1999;2573.
42. For application of model 3 in peptide design, see: (a) Patel M., McHugh R.J., Cordova B.C., Klabe R.M., Bacheler L.T., Erickson-Viitanen S., Rodgers J.D. Bioorg. Med. Chem. Lett. 11:2001;1943 (b) Zhao H., Thurkauf A., Braun J., Brodbeck R., Kieltyka A. Bioorg. Med. Chem. Lett. 10:2000;2119 (c) Shono T., Motoyama M., Tatsumi K., Ulbrich N., Iwamoto Y., Kuwano M., Ono M. Angiogenesis. 2:1999;319 (d) Iki K., Tsutsumi M., Kido A., Sakitani H., Takahama M., Yoshimoto M., Motoyama M., Tatsumi K., Tsunoda T., Konishi Y. Carcinogenesis. 20:1999;1323 (e) Kido A., Tsutsumi M., Iki K., Motoyama M., Takahama M., Tsujiuchi T., Morishita T., Tatsumi K., Tamai S., Konishi Y. Jpn. J. Cancer Res. 90:1999;333 (f) Lewis R.J., Francis C.A., Lehr R.E., LeRoy Blank C. Tetrahedron. 56:2000;5345 (g) Masubuchi K., Taniguchi M., Umeda I., Hattori K., Suda H., Kohchi Y., Isshiki Y., Sakai T., Kohchi M., Shirai M., Okabe H., Sudoh M., Yamazaki T., Shimma N. Bioorg. Med. Chem. Lett. 10:2000;1459 (h) Tamura S.Y., Goldman E.A., Bergum P.W., Semple J.E. Bioorg. Med. Chem. Lett. 9:1999;2573.
43. -3, respectively. The complete X-ray data were deposited with Cambridge Crystallographic Data Centre.
44. Suzuki K., Seebach D. Liebigs Ann. Chem. 1992;51.
45. (a) Beier N., Labitzke E., Medeski W.K.R., Radunz H.-E. Heterocycles. 39:1994;117 (b) Hino K., Kawashima K., Oka M., Nagai Y., Uno H., Matsumoto J. Chem. Pharm. Bull. 37:1989;110 (c) Hino K., Furukawa K., Nagai Y., Uno H. Chem. Pharm. Bull. 28:1980;2618 (d) Buckle D.R., Cantello B.C.C., Smith H., Spicer B.A. J. Med. Chem. 18:1975;726 (e) Torisawa Y., Nishi T., Minamikawa J. Bioorg. Med. Chem. Lett. 12:2002;387 (f) Uray G., Niederreiter K.S., Belaj F., Fabian W.M.F. Helv. Chem. Acta. 82:1999;1408 (g) Fabian W.M.F., Niederreiter K.S., Uray G., Stadlbauer W. J. Mol. Struct. 477:1999;209. and references there in.
46. (a) Beier N., Labitzke E., Medeski W.K.R., Radunz H.-E. Heterocycles. 39:1994;117 (b) Hino K., Kawashima K., Oka M., Nagai Y., Uno H., Matsumoto J. Chem. Pharm. Bull. 37:1989;110 (c) Hino K., Furukawa K., Nagai Y., Uno H. Chem. Pharm. Bull. 28:1980;2618 (d) Buckle D.R., Cantello B.C.C., Smith H., Spicer B.A. J. Med. Chem. 18:1975;726 (e) Torisawa Y., Nishi T., Minamikawa J. Bioorg. Med. Chem. Lett. 12:2002;387 (f) Uray G., Niederreiter K.S., Belaj F., Fabian W.M.F. Helv. Chem. Acta. 82:1999;1408 (g) Fabian W.M.F., Niederreiter K.S., Uray G., Stadlbauer W. J. Mol. Struct. 477:1999;209. and references there in.
47. (a) Beier N., Labitzke E., Medeski W.K.R., Radunz H.-E. Heterocycles. 39:1994;117 (b) Hino K., Kawashima K., Oka M., Nagai Y., Uno H., Matsumoto J. Chem. Pharm. Bull. 37:1989;110 (c) Hino K., Furukawa K., Nagai Y., Uno H. Chem. Pharm. Bull. 28:1980;2618 (d) Buckle D.R., Cantello B.C.C., Smith H., Spicer B.A. J. Med. Chem. 18:1975;726 (e) Torisawa Y., Nishi T., Minamikawa J. Bioorg. Med. Chem. Lett. 12:2002;387 (f) Uray G., Niederreiter K.S., Belaj F., Fabian W.M.F. Helv. Chem. Acta. 82:1999;1408 (g) Fabian W.M.F., Niederreiter K.S., Uray G., Stadlbauer W. J. Mol. Struct. 477:1999;209. and references there in.
48. (a) Beier N., Labitzke E., Medeski W.K.R., Radunz H.-E. Heterocycles. 39:1994;117 (b) Hino K., Kawashima K., Oka M., Nagai Y., Uno H., Matsumoto J. Chem. Pharm. Bull. 37:1989;110 (c) Hino K., Furukawa K., Nagai Y., Uno H. Chem. Pharm. Bull. 28:1980;2618 (d) Buckle D.R., Cantello B.C.C., Smith H., Spicer B.A. J. Med. Chem. 18:1975;726 (e) Torisawa Y., Nishi T., Minamikawa J. Bioorg. Med. Chem. Lett. 12:2002;387 (f) Uray G., Niederreiter K.S., Belaj F., Fabian W.M.F. Helv. Chem. Acta. 82:1999;1408 (g) Fabian W.M.F., Niederreiter K.S., Uray G., Stadlbauer W. J. Mol. Struct. 477:1999;209. and references there in.
49. (a) Beier N., Labitzke E., Medeski W.K.R., Radunz H.-E. Heterocycles. 39:1994;117 (b) Hino K., Kawashima K., Oka M., Nagai Y., Uno H., Matsumoto J. Chem. Pharm. Bull. 37:1989;110 (c) Hino K., Furukawa K., Nagai Y., Uno H. Chem. Pharm. Bull. 28:1980;2618 (d) Buckle D.R., Cantello B.C.C., Smith H., Spicer B.A. J. Med. Chem. 18:1975;726 (e) Torisawa Y., Nishi T., Minamikawa J. Bioorg. Med. Chem. Lett. 12:2002;387 (f) Uray G., Niederreiter K.S., Belaj F., Fabian W.M.F. Helv. Chem. Acta. 82:1999;1408 (g) Fabian W.M.F., Niederreiter K.S., Uray G., Stadlbauer W. J. Mol. Struct. 477:1999;209. and references there in.
50. (a) Beier N., Labitzke E., Medeski W.K.R., Radunz H.-E. Heterocycles. 39:1994;117 (b) Hino K., Kawashima K., Oka M., Nagai Y., Uno H., Matsumoto J. Chem. Pharm. Bull. 37:1989;110 (c) Hino K., Furukawa K., Nagai Y., Uno H. Chem. Pharm. Bull. 28:1980;2618 (d) Buckle D.R., Cantello B.C.C., Smith H., Spicer B.A. J. Med. Chem. 18:1975;726 (e) Torisawa Y., Nishi T., Minamikawa J. Bioorg. Med. Chem. Lett. 12:2002;387 (f) Uray G., Niederreiter K.S., Belaj F., Fabian W.M.F. Helv. Chem. Acta. 82:1999;1408 (g) Fabian W.M.F., Niederreiter K.S., Uray G., Stadlbauer W. J. Mol. Struct. 477:1999;209. and references there in.
51. (a) Beier N., Labitzke E., Medeski W.K.R., Radunz H.-E. Heterocycles. 39:1994;117 (b) Hino K., Kawashima K., Oka M., Nagai Y., Uno H., Matsumoto J. Chem. Pharm. Bull. 37:1989;110 (c) Hino K., Furukawa K., Nagai Y., Uno H. Chem. Pharm. Bull. 28:1980;2618 (d) Buckle D.R., Cantello B.C.C., Smith H., Spicer B.A. J. Med. Chem. 18:1975;726 (e) Torisawa Y., Nishi T., Minamikawa J. Bioorg. Med. Chem. Lett. 12:2002;387 (f) Uray G., Niederreiter K.S., Belaj F., Fabian W.M.F. Helv. Chem. Acta. 82:1999;1408 (g) Fabian W.M.F., Niederreiter K.S., Uray G., Stadlbauer W. J. Mol. Struct. 477:1999;209. and references there in.
52. Mancilla T., Carrillo L., Zamudio-Rivera L.S., Beltran H.I., Farfan N. Org. Prep. Proced. Int. 33:2001;341.