Arylacetamide Kappa-selective opioid ligands

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 17, 1997, Pages 2271-2276

  Pechulis, Anthony D ^a,c   Archer, Sydney ^a   Wentland, Mark P ^a   Colasurdo, Ann M ^b   Bidlack, Jean M ^b  

^a Research Rensselaer Polytechnic Institute   (United States)

^b UNIVERSITY OF ROCHESTER SCHOOL OF MEDICINE AND DENTISTRY   (United States)

^c Albany Molecular Research Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; KAPPA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR AGONIST; N METHYL N [7 (1 PYRROLIDINYL) 1 OXASPIRO[4.5]DEC 8 YL]BENZENEACETAMIDE; NALTRINDOLE;

ANIMAL TISSUE; ARTICLE; BINDING SITE; BRAIN TISSUE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENANTIOMER; FLOW CYTOMETRY; FLUORESCENCE; GUINEA PIG; NONHUMAN; STEREOISOMERISM;

ANIMALIA; CAVIA PORCELLUS; SUS SCROFA;

EID: 0030985411     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0960-894x(97)00406-x     Document Type: Article

References (14)

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3. 1H NMR data matched literature values.
4. 3OH).
5. The racemic form of acetamide 4 has been synthesized. See Barlow, J. J.; Blackburn, T. P.; Costello, G. F.; James, R.; Le Count, D. J.; Main B. G.; Pearce, R. J.; Russell, K.; Shaw, J. S. J. Med. Chem. 1991, 34, 3149.
6. 2O: C, 61.99; H, 4.71; N, 6.88; S, 3.94; Cl, 8.72. Found: C, 61.58; H, 4.69; N, 6.65; S, 3.66; Cl, 8.49.
7. Compound (S)-(+)-5 has been synthesized using a different procedure, but was reported as containing triethylamine in a 1:1 molar ratio with the FITC derivative. See Chang, A. -C.; Chao, C. C.; Takemori, A. E.; Gekker, G.; Hu, S.; Peterson, P. K.; Portoghese, P. S. J. Med. Chem. 1996, 39, 1729.
8. It should be noted that, to our knowledge, none of the R-(-) analogs have been previously prepared.
9. 3OH).
10. 3OH + 1 drop triethylamine).
11. 3OH + 1 drop triethylamine).
12. Cheng, Y. C.; Prusoff, W. H. Biochem. Pharmacol., 1973, 22, 3099.
13. Ignatowski, T. A.; Bidlack, J. M. J. Pharmacol. Exp. Ther., in press.
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