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Document Table 1 Inhibitor Constants of Selected COMT Inhibitors K i (nM) Human b K i (nM)Pig c Nitecapone 1.0 700 Entacapone 0.3 N.D. Tolcapone 0.3 N.D. Vinylphenylketone 4.0 a 200 a T. Lotta, unpublished results b Reference 19. c Reference 41. N.D.: not determined Page 353 used as in vitro tools to investigate COMT inhibition, but because of the lack of potency and selectivity and because they were toxic, they were not clinically useful [2]. These inhibitors have inhibition constants (K i values) in the micromolar range. Many of them contain the catechol structure and are also substrates of COMT. B. Second-Generation Inhibitors The invention of a new structural family of COMT inhibitors in the late 1980s lead the COMT research into a new active epoch [25,26]. The most potent second-generation inhibitors are nitrocatechol derivatives; some examples are shown in Figure 11. Entacapone (OR-611) and tolcapone (RO-40-7592) are now in clinical trials for the treatment of Parkinson's disease, and have been extensively studied [27–40]. Both compounds are very potent and selective tightbinding inhibitors of human COMT with K i values of 0.3 nM [19]. They differ mainly in their pharmacokinetic properties. Entacapone acts peripherally while tolcapone inhibits COMT both peripherally and centrally. Recently it was reported that 2-((3,4-dihydroxy-2-nitrophenyl)vinyl) phenylketone is a tight-binding inhibitor of pig COMT [41], and it is also a potent inhibitor of human COMT (Table 1). This inhibitor has a vinylphenylketone group at position 4 of the catechol ring, i.e., in the position ortho to the nitro group. V. Enzyme Inhibitor Interactions A. Background http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_353.html (1 of 2) [4/5/2004 5:28:31 PM]
Document From quantitative structure activity relationship studies (QSAR) of COMT inhibitors it became evident that the acidity of the catechol hydroxyl group is the most important factor that influences the inhibitory activity of catechol http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_353.html (2 of 2) [4/5/2004 5:28:31 PM]
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Structure-based Drug Design 14 Stru
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Document Table 3 HIV-1 RT Amino Aci
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Document ever, once an NNRTI is bou
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Document dine) and didanosine (dide
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Document 163. Lacey SF, Larder BA.
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Document 4 Bradykinin Receptor Anta
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Document Figure 9 Composition of te
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Document We determined the structur
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Document large solvent channels and
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Document IV. Drug Design Progressio
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Document Table 1 Inhibition Data fo
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Document References 1. Parks RE Jr.
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Document 17. Ealick SE, Rule SA, Ca
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Document 6 Structural Implications
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Document Important for the validity
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Page 395 and 396: Document 13 Rational Design of Reni
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Page 411 and 412: Document IV. Rational Drug Design F
Page 413 and 414: Document 2. Blundell TL, Cooper J,
Page 415 and 416: Document 17. Szelke M. Chemistry of
Page 417 and 418: Document 34. Rosenberg SH, Plattner
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Page 421 and 422: Document Page 343 14 Structural Asp
Page 423 and 424: Document Figure 2 The reaction cata
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Document Table 1 Approval Indicatio
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Document Page 476 nM, respectively.
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Document A. The Canyon Page 491 The
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Document Page 495 of the RNA and pr
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Document Figure 5 Some compounds wh
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Document Cyclotheonamide A (CtA), 2
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Document D ddI, 152 tumour necrosis
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Document antistasin peptides, 281 c
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Document fragment-based programs, 5
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Document [Human immunodeficiency vi
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Document antagonistic activity, 416
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Document Kininogen, 119 high molecu
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Document RT inhibitor, 41, 56 Nonpe
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Document Phosphoglycerate kinase (P
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Document [Protease targets] serinyl
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