Bioisosteric analogue

The hydrolytic accessibility of the ester bond in pTyr 1 (Scheme 1) to cellular protein-tyrosine phosphatases motivated numerous research groups to develop phosphatase-resistant bioisosteric analogues. It was soon recognized that the... 

Compounds 38 and 39 were synthesised as possible bioisosteric analogues for PHNO (27a) or one of its analogues. After changing the structure of the hexahydronaphthoxazines (27a, 75, 76) to the hexahydrothianaphthoxazines (38, 39) the position of the sulfur atom would suggest that the hexahydrothianaphthoxazines are bioisosteric analogues for tra s-7-hydroxy-4- -propyl-2,3,4a,5,6,1 Ob-hexahydro--///-naphth[l,2A][1,4]oxazine (75) which is not a potent dopamine... 

Wu, W.-L., et al. Dopamine D1/D5 receptor antagonists with improved pharmacokinetics Design, synthesis, and biological evaluation of phenol bioisosteric analogues of benzazepine D1/D5 antagonists. J. Med. Chem. 2005, 48, 680-693. 

Figure 3.6 Structures of the lead amide 9, and A2B adenosine receptor antagonist, and its bioisosteric analogues 10-13.

A number of organophosphonates have been synthesized as bioisosteric analogues for biochemically important non-nucleoside and nucleoside phosphates (3). For example, the S-enantiomer of 3,4-dihydroxybutyl-l-phos-phonic acid (DHBP) has been synthesized as the isosteric analogue of... 

---