Gallagher 1 Group

Another hybrid anatoxin-a/epibatidine, UB-165 (Fig. 7.4C), was synthesized by the Gallagher group (Wright et al. 1997). It was identified as a potent nicotinic ligand and showed a potency that was intermediate between anatoxin-a and epibatidine. Different derivatives of this compound have been synthesized lately (Gohlke et al. 2002 Sutherland et al. 2003 Karig et al. 2003). 

Figure 14-11 Schematic diagram of the active site of the pyruvoyl enzyme histidine decarboxylase showing key polar interactions between the pyruvoyl group and groups of the inhibitor O-methylhistidine and surrounding enzyme groups. Aspartate 63 appears to form an ion pair with the imidazolium group of the substrate.268 Hydrogen bonds are indicated by dotted lines. See Gallagher et al.269...

C. H. DELEGARD, G. S. BARNEY, and S. A. GALLAGHER Rockwell International, Energy Systems Group, Richland, WA 99352... 

Liang and Gallagher found that the inclusion of counting descriptors for OH, C = O, NH, COOH, NO2, and CN groups improved somewhat the correlation as expressed in Eq. [32]. 

Gallagher MP, Elall B, Craig J, Berry G, Tiller DJ, Erls J Australian Multicenter Trial of Cyclosporine Withdrawal Study Group and the ANZ Dialysis and Transplantation Registry. A randomized controlled trial of cyclosporine withdrawal in renal-transplant recipients 15-year results.Transplantation 2004 78 1653-1660. 

In another synthesis, Gallagher described a fruitful approach based on the use of a carbohydrate enolate, which takes advantage of the presence of the C7 keto group in the target compound [265-267]. In this approach, an enolate had to be formed at the anomeric position of the gluco chiron, stable toward (3-elimination. Moreover, the use of a strained system, as in 357, should force enolization to occur on the correct side. 

S. Siegel, H. R. Hoekstra, and F. X. Gallagher, J. Inorg. Nuclear Chem., 1969, 31, 3803 Platinum Group Metals and Compounds , American Chemical Society, Washington, D.C., 1971, Advances in Chemistry Series No. 98, p. 39. 

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