Selective inhibitors of monoamine oxidase. 4. SAR of tricyclic N- methylcarboxamides and congeners binding at the tricyclics' hydrophilic binding site

Journal of Medicinal Chemistry

Volumn 40, Issue 16, 1997, Pages 2466-2473

  Harfenist, Morton ^a,b   Joseph, Diane M ^a   Spence, Sharon C ^a   Mcgee, Daniel P C ^a   Reeves, Mark D ^a   White, Helen L ^a  

^a GLAXOSMITHKLINE   (United States)

^b NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE OXIDASE (FLAVIN CONTAINING); MONOAMINE OXIDASE INHIBITOR; PHENELZINE; TYRAMINE;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANIMAL CELL; ARTICLE; BINDING SITE; ENZYME ACTIVITY; ENZYME SPECIFICITY; FOOD INTAKE; HYDROPHILICITY; HYPERTENSION; METHYLATION; NONHUMAN; RAT;

ANIMALS; ANTIDEPRESSIVE AGENTS, TRICYCLIC; BINDING SITES; CARBOXYLIC ACIDS; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; ISOENZYMES; LIVER; MALE; MONOAMINE OXIDASE INHIBITORS; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0030837494     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9608063     Document Type: Article

References (14)

1. Previous paper in this series: Harfenist, M.; Heuser, D. J.; Joyner, C. T.; Batchelor, J. F.; White, H. L. Selective Inhibitors of Monoamine Oxidase. 3. Structure-Activity Relationship of Tricyclics Bearing Imidazoline, Oxadiazole, or Tetrazole Groups. J. Med. Chem. 1996, 39, 1857-1863.
2. Johnston, J. P. Some Observations Upon a New Inhibitor of Monoamine Oxidase in Brain Tissue. Biochem. Pharmacol. 1968, 17, 1285-1297. Squires, R. F. Additional Evidence for the Existence of Several Forms of Mitochondrial Monoamine Oxidase in the Mouse. Biochem. Pharmacol. 1968, 17, 1401-1409.
3. Johnston, J. P. Some Observations Upon a New Inhibitor of Monoamine Oxidase in Brain Tissue. Biochem. Pharmacol. 1968, 17, 1285-1297. Squires, R. F. Additional Evidence for the Existence of Several Forms of Mitochondrial Monoamine Oxidase in the Mouse. Biochem. Pharmacol. 1968, 17, 1401-1409.
4. Bach, A. W. J.; Lan, N. C.; Johnson, D. L.; Abell, C. W.; Bembenek, M. E.; Kwan, S.-W;Seeburg, P. H.; Shih, J. C. cDNA Cloning of Human Liver Monoamine Oxidase A and B: Molecular Basis of Differences in Enzymatic Properties. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4934-4938.
5. Marley, E.; Blackwell, B. Interactions of Monoamine Oxidase Inhibitors,Amines and Foodstuffs. Adv. Pharmacol. Chemother. 1970, 8, 185-239.
6. Murphy, D. L.; Lipper, S.; Pickar, D.; Jimerson, D.; Cohen, R. M.; Garrick, N. A.; Alterman, I. S.; Campbell, I. C. Selective Inhibition of Monoamine Oxidase Type A: Clinical and Anti-depressant Effects and Metabolic Changes in Man. In Monoamine Oxidase Inhibitors - The State of the Art; Youdim, M., Paykil, E., Eds.; John Wiley and Sons: New York, 1981; pp 189-205. Cesura, A. M.; Pletscher, A. The New Generation of Monoamine Oxidase Inhibitors. Prog. Drug Res. 1992, 38, 171-297.
7. Murphy, D. L.; Lipper, S.; Pickar, D.; Jimerson, D.; Cohen, R. M.; Garrick, N. A.; Alterman, I. S.; Campbell, I. C. Selective Inhibition of Monoamine Oxidase Type A: Clinical and Anti-depressant Effects and Metabolic Changes in Man. In Monoamine Oxidase Inhibitors - The State of the Art; Youdim, M., Paykil, E., Eds.; John Wiley and Sons: New York, 1981; pp 189-205. Cesura, A. M.; Pletscher, A. The New Generation of Monoamine Oxidase Inhibitors. Prog. Drug Res. 1992, 38, 171-297.
8. Harfenist, M.; Joyner, C. T.; Mize, P. D.; White, H. L. Selective Inhibitors of Monoamine Oxidase. 2. Arylamide SAR. J. Med. Chem. 1994, 37, 2085-2089. For a more extensive discussion of arylamide carcinogenicity and lead references, see Harfenist, M. Prevention of Ames Test Mutagenicity by Chemical Modification in a Series of Monoamine Oxidase Inhibitors. J. Med. Chem. 1980, 23, 825-827.
9. Harfenist, M.; Joyner, C. T.; Mize, P. D.; White, H. L. Selective Inhibitors of Monoamine Oxidase. 2. Arylamide SAR. J. Med. Chem. 1994, 37, 2085-2089. For a more extensive discussion of arylamide carcinogenicity and lead references, see Harfenist, M. Prevention of Ames Test Mutagenicity by Chemical Modification in a Series of Monoamine Oxidase Inhibitors. J. Med. Chem. 1980, 23, 825-827.
10. Thull, U.; Testa, B. Screening of Unsubstituted Cyclic Compounds as Inhibitors of Monoamine Oxidases. Biochem. Pharmacol. 1994, 47, 2307-2310.
11. White, H. L.; Dren, A. T. Some Preclinical and Clinical Pharmacological Properties of BW-A616U, A Reversible MAO A Inhibitor. Clin. Neuropharmacol. 1986, 9, Supplement 4, 561-562. White, H. L.; Harfenist, M.; Beek, O; Soroko, F.: Cooper, B. R.; Maxwell, R. A. BWA-616U - A Selective Inhibitor of MAO-A With Negligible Tyramine-Potentiating Activity and Potential Antidepressant Activity. Abstr., Soc. Neurosci. 1985, 11 (Oct), 442.
12. White, H. L.; Dren, A. T. Some Preclinical and Clinical Pharmacological Properties of BW-A616U, A Reversible MAO A Inhibitor. Clin. Neuropharmacol. 1986, 9, Supplement 4, 561-562. White, H. L.; Harfenist, M.; Beek, O; Soroko, F.: Cooper, B. R.; Maxwell, R. A. BWA-616U - A Selective Inhibitor of MAO-A With Negligible Tyramine-Potentiating Activity and Potential Antidepressant Activity. Abstr., Soc. Neurosci. 1985, 11 (Oct), 442.
13. Harfenist, M.; Joyner, C. T.; Heuser, D. J. U.S. Patent 4737514, Apr 12, 1988.
14. Lawesson reagent is 2,4-bis(4-methoxyphenyl)cyclodiphosphathiane 2,4-disulfide. See: Yde, B.; Yousif, N. M.; Pedersen, U.; Thomsen, I.; Lawesson, S. O. Studies on Organophosphorus Compounds.XLVII. Preparation of Thiated Synthons of Amides, Lactams and Imides by Use of Some New Phosphorus- and Sulfur-containing Reagents. Tetrahedron 1984, 40, 2047-2052.