The stereochemical requirements of the novel δ-opioid selective dipeptide antagonist TMT-Tic

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 23, 1997, Pages 3049-3052

  Liao, Subo ^a   Lin, Jun ^a,c   Shenderovich, Mark D ^a   Han, Yinglin ^a,d   Hasohata, Keiko ^b   Davis, Peg ^b   Qiu, Wei ^a   Porreca, Frank ^b   Yamamura, Henry I ^b   Hruby, Victor J ^a  

^a University of Arizona ^*  (United States)

^b UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

^c YUNNAN UNIVERSITY   (China)

^d NANJING TECH UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 (BETA METHYL 2',6' DIMETHYLTYROSYL) 1,2,3,4 TETRAHYDRO 3 ISOQUINOLINECARBOXYLIC ACID; DELTA OPIATE RECEPTOR; DIPEPTIDE; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; ENKEPHALIN[2,5 DEXTRO PENICILLAMINE]; MU OPIATE RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CHIRALITY; CONTROLLED STUDY; DRUG PURIFICATION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0030725590     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10145-7     Document Type: Article

References (19)

1. (a) Schiller, P. W.; Nguyen, T. M.-D.; Weltrowska, G.; Wilkes, B. C.; Marsden, B. J.; Lemieux, C.; Chung, N. N. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 11871.
2. (b) Schiller, P. W.; Waltroswka, G.; Naguyen, T. M.-D.; Wilkes, B. C.; Chung, N. N.; Lemieux, C. J. Med. Chem. 1993, 36, 3182.
3. Temussi, P. A.; Salvadori, S.; Amodeo, P.; Bianchi, C.; Guerrini, R.; Tomatis, R.; Lazarus, L. H.; Picone, D.; Tancredi, T. Biochem. Biophys. Res. Commun. 1994, 198, 933.
4. Tancredi, T.; Salvadori, S.; Amodeo, P.; Picone, D.; Lazarus, L. H.; Bryant, S. D.; Guerrini, R.; Marzola, G.; Temussi, P. A. Eur. J. Biochem. 1994, 224, 241.
5. Salvadori, S.; Attila, M.; Balboni, G.; Bianchi, C.; Bryant, S. D.; Crescenzi, O.; Guerrini, R.; Picone, D.; Tancredi, T.; Temussi, P. A.; Lazarus, L. H. Mol. Medicine 1995, 1, 678.
6. (a) Qian, X.; Kövér, K. E.; Shenderovich, M. D.; Lou, B.-S.; Misicka, A.; Zalewska, T.; Horváth, R.; Davis, P.; Bilsky, E. J.; Porreca, F.; Yamamura, H. I.; Hruby, V. J. J. Med. Chem. 1994, 37, 1746.
7. (b) Qian, X.; Shenderovich, M. D.; Kövér, K. E.; Davis, P.; Horváth, R.; Zalewaska, T.; Yamamura, H. I.; Porreca, F.; Hruby, V. J. J. Am. Chem. Soc. 1996, 118, 7280.
8. Qian, X.; Russell, K. C.; Boteju, L. W.; Hruby, V. J. Tetrahedron 1995, 51, 1033.
9. Bocchi, V.; Casnati, G.; Dossena, A.; Marchelli, R. Synthesis 1979, 957.
10. (a) Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397.
11. (b) Carpino, L. A.; El-Faham, A.; Albericio, F. Tetrahedron Lett. 1994, 55, 2279.
12. Vaughn, L. K.; Knapp, R. J.; Toth, G.; Wan, J.-P.; Hruby, V. J.; Yamamura, H. I. Life Sci. 1989, 45, 1001.
13. Sagan, S.; Charpentier, S.; Delfour, A.; Amiche, M.; Nicolas, P. Biochem. Biophys. Res. Comm. 1992, 187, 1203.
14. Shook, J. E.; Pelton, J. T.; Wire, W. S.; Herning, L. D.; Hruby, V. J.; Burks, T. F. J. Pharmacol. Exp.Ther. 1987, 240, 772.
15. Kazmierski, W. M.; Hruby, V. J. Tetrahedron 1988, 44, 697.
16. Amodeo, P.; Balhoni, G.; Crescenzi, O.; Guerrini, R.; Picone, D.; Salvadori, S.; Tancredi, T.; Temussi, P. A. FEBS Lett. 1995, 377, 363.
17. (a) Portoghese, P. S., Larson, D. L.; Sultana, M.; Takemori, A. E. J. Med. Chem. 1992, 35, 4325.
18. (b) Portoghese, P. S.; Sultana, M., Moe, S. T.; Takemori, A. E. J. Med. Chem. 1990, 33, 1714.
19. +).