Iodinated analogs of trimetoquinol as highly potent and selective β2- adrenoceptor ligands

Journal of Medicinal Chemistry

Volumn 39, Issue 19, 1996, Pages 3701-3711

  De Los Angeles, Joseph E ^a   Nikulin, Victor I ^a,d   Shams, Gamal ^c   Konkar, Anish A ^b   Mehta, Ratna ^b   Feller, Dennis R ^c   Miller, Duane D ^a  

^a UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^b OHIO STATE UNIVERSITY   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

^d INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ADRENERGIC RECEPTOR; ISOPRENALINE; TRETOQUINOL;

ARTICLE; BINDING AFFINITY; BRONCHODILATATION; DRUG POTENCY; LIGAND BINDING; RECEPTOR AFFINITY; STEREOSPECIFICITY;

ADRENERGIC BETA-AGONISTS; ANIMALS; BINDING, COMPETITIVE; BLOOD PLATELETS; CHO CELLS; CRICETINAE; HUMANS; IODINE; IODOCYANOPINDOLOL; LIGANDS; MOLECULAR STRUCTURE; PINDOLOL; RECEPTORS, ADRENERGIC, BETA; RECEPTORS, PROSTAGLANDIN; RECEPTORS, THROMBOXANE; RECEPTORS, THROMBOXANE A2, PROSTAGLANDIN H2; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; TRETOQUINOL;

EID: 0029815155     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960208o     Document Type: Article

References (22)

1. Iwasawa, Y.; Kiyomoto, A. Studies of tetrahydroisoquinolines (THI) 1. Bronchodilator activity and structure-activity relationships. Jpn. J. Pharmacol. 1967, 17, 143-152.
2. Yamamoto, E.; Hirakura, M.; Sugasawa, S. Synthesis of 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline derivatives. Tetrahedron Suppl. 1966, 8 (Part 1), 129-134.
3. Mayo, J. R.; Navaran, S. S.; Akbari H.; Miller, D. D.; Feller, D. R. Stereodependent inhibition of human platelet function by the optical isomers of trimethoquinol. Biochem. Pharmacol. 1981, 30, 2237-2241.
4. 2 receptor blockade. Biochem. Pharmacol. 1988, 37, 3023-3033.
5. 2 receptor sites by trimetoquinol isomers in human platelets, rat vascular endothelial cells and rat vascular smooth muscle cells. Pharmacol. Commun. 1993, 1, 303-312.
6. Clark, M. T.; Adejare, A.; Shams, G.; Feller, D. R.; Miller, D. D. 5-Fluoro- and 8-fluorotrimetoquinol: selective beta 2-adrenoceptor agonists. J. Med. Chem. 1987, 30, 86-90.
7. Fraundorfer, P. F. Functional and biochemical Characterization of trimetoquinol (TMQ) analog interactions with β-adrenergic receptor subtypes. Ph.D. Thesis, The Ohio State University, 1993.
8. Fraundorfer, P. F.; Fertel, R. H.; Miller, D. D.; Feller, D. R. Biochemical and pharmacological characterization of high-affinity trimetoquinol analogs on guinea pig and human beta adrenergic receptor subtypes: evidence for partial agonism. J. Pharmacol. Exp. Ther. 1994, 270, 665-674.
9. 2 receptors in human platelets, rat vascular endothelial cells and rat vascular smooth muscle cells. J. Pharmacol. Exp. Ther. 1993, 267, 1017-1023.
10. Harrold, M. W.; Gerhardt, M. A.; Romstedt, K.; Feller, D. R.; Miller, D. D. Synthesis and platelet antiaggregatory activity of trimetoquinol analogs as endoperoxide/thromboxane A2 antagonists. Drug Des. Delivery 1987, 1, 193-207.
11. Howe, R. Beta-3 adrenergic agonists. Drugs Future 1993, 18, 529-549.
12. 2 receptors by trimetoquinol analogs. Chirality 1991, 3, 112-117.
13. Adejare, A.; Miller, D. D.; Fedyna, J. S.; Ahn, C. H.; Feller, D. R. Syntheses and beta-adrenergic agonist and antiaggregatory properties of N-substituted trimetoquinol analogues. J. Med. Chem. 1986, 29, 1603-1609.
14. +). Bull. Chem. Soc. Jpn. 1968, 61, 600-602.
15. Ulffers, F.; von Janson, A. Diacetylderivate einger Amine der aromatischen Reihe. Ber. Otsch. Chem. Ges. 1894, 27, 93-101.
16. Lott, R. S.; Chauhan, V. S.; Stammer, C. H. Trimethylsilyl iodide as a peptide deblocking agent. J. Chem. Soc., Chem. Commun. 1979, 495-496.
17. Dalton, D. R.; Cava, M. P.; Buck, K. T. Hindered rotation in 1-benzyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolines. Tetrahedron Lett. 1965, 2687-2690.
18. Tomita, M.; Shingu, T.; Fujitani, K.; Furikawa, H. Studies on the alkaloids of menispermaceous plants. CCXVI. Nuclear magnetic resonance spectra of benzylisoquinoline derivatives. (1). N-Methylcoclaurine type bases. Chem. Pharm. Bull. 1965, 13, 921-926.
19. Iwasa, K.; Kamigauchi, M.; Takao, N. Metabolism of salsalinol by tissue cultures of some Papaveraceae. Phytochemistry 1991, 30, 2973-2975.
20. 2 receptor system. Section B: Approaches to the asymmetric synthesis of irreversibly binding iodinated derivatives of trimetoquinol. Ph.D. Thesis, The Ohio State University, 1993.
21. 2 receptors in human platelets. J. Pharmacol. Exp. Ther. 1988, 245, 786-792.
22. Viel, C.; Dorme, R.; Rumpf, P. Synthese et proprietes de nouvelles dimethoxy-6,7-dihydro-3,4-outetrahydr-1,2,3-isoquinoleines. Bull. Soc. Chim. Fr. 1966, 6, 1956-1966.