Bioisosteric group

Ertl, P. Cheminformatics analysis of organic substituents identification of the most common substituents, calculation of substituent properties, and automatic identification of dmg-like bioisosteric groups. J. Chem. Inf. 

Dabiri M, Salehi P, Baghbanzadeh M, Shakouri M, Otokesh S, Ekrami T, Doosti R (2007) Efficient and eco-friendly synthesis of dihydropyrimidinones, bis(indolyl) methanes, and N-alkyl and N-arylimides in ionic liquids. J Iran Chem Soc 4 393 01 Legeay JC, Eynde JJV, Bazureau JP (2008) Ionic liquid phase organic synthesis (loLiPOS) methodology applied to the preparation of new 3,4-dihydropyrimidine-2(lH)-ones bearing bioisostere group in N-3 position. Tetrahedron 64 5328-5335... 

P.H. Olesen, The use of bioisosteric groups in lead optimization, Curr. Opin. Drug Disc. Dev. 4 (2001) 471-478. 

An example of how bioisosteric groups have been used successfully is provided by the cholinergic drug bethanechol described in Chapter 11. 

Can the NH group be replaced by a CH2 group (b) (or any other possible bioisosteric group) ... 

Anzali, S., Barnickel, G., Krug, M., Wagener, M. and Gasteiger, J. (1997) Kohonen neural network a novel approach to search for bioisosteric groups, in Computer-Assisted Lead Finding and Optimization... 

In the histaminic H2 receptor antagonist series, the classical urea-thiourea-guanidine progression was successfully completed by the use of the V-nitro and V-cyanoguanidines and, later on, by l,l-diamino-2-nitroethylene groups (Fig. 13.19). Cyano amidines and carbamoyl amidines were also used, and structure-activity relationship patterns were rationalized in terms of dipole moment orientation of related bioisosteric groups. ... 

It is rare that the replacement of a part of a molecule by an isosteric or bioisosteric group leads to a strictly identical... 

Table 2.9. Classical Bioisosteres (Groups Within the Row Can Replace Each Other)...

Abstract This review first outlines general considerations on phosphinic acids and derivatives as bioisosteric groups. The next sections present key aspects of phosphinic acid-based molecules and include a brief description of the biological pathways involved for their activities. The synthetic aspects and the biological activities of such compounds reported in the literature between 2008 and 2013 are also described. 

Table 1.3 Some examples of classical bioisosteres - groups in each row are equivalent.

Xiaoqi, C. and Weibo, W. (2003) The use of bioisosteric groups in lead optimizatioiL Annual Reports in Medicinal Chemistry, 38. 333-346. 

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