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Document Page 509 The correlation of potency with logP might suggest that A rings with the lowest hydrogen-bonding potential would be the most potent. This has not been shown to be true. In fact, rings with heterocyclic nitrogen atoms are preferred to furan and thiophene rings, which would be expected to have less hydrogen-bonding potential [86,87]. This observation even extends to tetrazole rings, which have often been used in pharmaceutical design to replace hydrophilic groups such as carboxylates or esters. Explanations for the variability in potency due to A-ring changes have not been satisfactory. These heterocycles lack any consistent pattern of hydrogen bonds with the pocket residues (Table 6) [88]. Like QSAR analysis, structural analysis has not been able to show any relationship between hydrogenbonding groups in the A ring, or dipole moment, and potency [80,85]. Extensive structural characterization of many different A-ring heterocycles has not yet been done. Difficulties predicting relative potency of these compounds a priori stem from the lack of understanding of solvation/desolvation effects as well as difficulties in characterizing the low-intensity hydrophobic interactions. Consequently, it seems likely that new structure—activity relationships about the A-ring heterocycle will continue to be determined <strong>based</strong> on empirical findings. Hydrogen-Bonding Requirements Capsid-binding compounds with a hydrogen-bond accepting atom in the region of the drug that binds to the VP1 pocket heel appear to demonstrate greater potency than do their non-hydrogen-bonding counterparts (Table 7) [55,89]. Studies using HRV14 where Asn1219, a hydrogen-bond donor in the pore region, has been mutated to Ala have shown that the compounds bind as well in the mutated virus as in the native virus [27]. This might suggest that the hydrogen bonding to Asn1219 at the pocket pore is unimportant. Recent structures of compounds in HRV14 have shown that other hydrogen-bond donors can function in place of Asn1219, even if Asn1219 is still present. These groups in HRV14 are the hydroxyl of Ser1107 and the backbone nitrogen of Leu1106. Other hydrogen-bonding groups are present in other rhinoviruses that coordinate to tightly bound waters, which can also act as hydrogen-bond donors [55,56]. This provides a flexible hydrogen-bonding network that can then http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_509.html [4/9/2004 12:42:48 AM]
Document accommodate a variety of different hydrogen-bonding groups in the C ring of the drug (Figure 10). Page 510 This hydrogen-bonding network has also been observed in all classes of capsid-binding compounds that have had their structures determined in HRVs [58,62]. Reports of compounds that bind to the capsid and inhibit picornavirus uncoating, but would seem to have little hydrogen-bonding potential (e.g., dichloroflavan) have not been structurally examined [60]. The effect of adding a hydrogen-bonding group to these compounds near the pocket pore is unknown, but one might expect that the potency of the compound would improve. Remember that WIN compounds without a hydrogen-bonding group at the pore region still have antiviral activity, albeit this activity is much weaker than that of an analogous drug with the hydrogen-bonding group present. http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_510.html (1 of 2) [4/9/2004 12:43:03 AM]
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Structure-based Drug Design 14 Stru
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Document 4 Bradykinin Receptor Anta
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Page 589 and 590: Document Page 476 nM, respectively.
Page 591 and 592: Document Page 478 lished—was asso
Page 593 and 594: Document VI. Conclusion Page 480 It
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Page 611 and 612: Document A. The Canyon Page 491 The
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Page 617 and 618: Document Figure 4 A ribbon diagram
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Document D ddI, 152 tumour necrosis
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