A topological function based on spectral moments for predicting affinity toward A3 adenosine receptors.

The spectral moment descriptors have been applied to the study of affinity for A(3) adenosine receptors of 32 adenosine analogues. A model, able to describe more than 95% of the variance in the experimental activity, was developed with the use of the above-mentioned approach. The fragment contributions to the activity carried out show that the sulfonamido moiety at the N(6) position and hydrogen bonding play an important role in the interaction with the receptor.

[1]  Maykel Pérez González,et al.  TOPS-MODE Based QSARs Derived from Heterogeneous Series of Compounds. Applications to the Design of New Herbicides , 2003, J. Chem. Inf. Comput. Sci..

[2]  G. Spalluto,et al.  Synthesis and biological activity of a new series of N6-arylcarbamoyl, 2-(Ar)alkynyl-N6-arylcarbamoyl, and N6-carboxamido derivatives of adenosine-5'-N-ethyluronamide as A1 and A3 adenosine receptor agonists. , 1998, Journal of medicinal chemistry.

[3]  J. Gálvez,et al.  New bronchodilators selected by molecular topology. , 1998, Bioorganic & medicinal chemistry letters.

[4]  B. Fredholm,et al.  International Union of Pharmacology. XXV. Nomenclature and classification of adenosine receptors. , 2001, Pharmacological reviews.

[5]  Maykel Pérez González,et al.  A radial distribution function approach to predict A(2B) agonist effect of adenosine analogues. , 2005, Bioorganic & medicinal chemistry.

[6]  H. Akaike,et al.  Information Theory and an Extension of the Maximum Likelihood Principle , 1973 .

[7]  R A Pearlstein,et al.  Comparative molecular field analysis of selective A3 adenosine receptor agonists. , 1995, Bioorganic & medicinal chemistry.

[8]  Ernesto Estrada,et al.  Spectral Moments of the Edge-Adjacency Matrix of Molecular Graphs, 2. Molecules Containing Heteroatoms and QSAR Applications , 1997, J. Chem. Inf. Comput. Sci..

[9]  Maykel Pérez González,et al.  A TOPS-MODE approach to predict affinity for A1 adenosine receptors. 2-(Arylamino)adenosine analogues. , 2004, Bioorganic & medicinal chemistry.

[10]  K. Jacobson,et al.  N6-substituted D-4'-thioadenosine-5'-methyluronamides: potent and selective agonists at the human A3 adenosine receptor. , 2003, Journal of medicinal chemistry.

[11]  C. Müller Adenosine receptor ligands-recent developments part I. Agonists. , 2000 .

[12]  K. Jacobson,et al.  (N)-methanocarba 2,N6-disubstituted adenine nucleosides as highly potent and selective A3 adenosine receptor agonists. , 2005, Journal of medicinal chemistry.

[13]  Milan Randic,et al.  Resolution of ambiguities in structure-property studies by use of orthogonal descriptors , 1991, J. Chem. Inf. Comput. Sci..

[14]  C. Müller Medicinal chemistry of adenosine A3 receptor ligands. , 2003, Current topics in medicinal chemistry.

[15]  Milan Randic,et al.  Orthogonal molecular descriptors , 1991 .

[16]  K. Varani,et al.  Synthesis and biological evaluation of novel N6-[4-(substituted)sulfonamidophenylcarbamoyl]adenosine-5'-uronamides as A3 adenosine receptor agonists. , 2004, Journal of medicinal chemistry.

[17]  Miguel A. Cabrera,et al.  TOPS-MODE approach for the prediction of blood-brain barrier permeation. , 2004, Journal of pharmaceutical sciences.

[18]  Maykel Pérez González,et al.  A TOPS-MODE approach to predict adenosine kinase inhibition. , 2004, Bioorganic & medicinal chemistry letters.

[19]  Ernesto Estrada,et al.  Edge Adjacency Relationships and a Novel Topological Index Related to Molecular Volume , 1995, J. Chem. Inf. Comput. Sci..

[20]  Ram Sagar,et al.  CP-MLR directed QSAR studies on the antimycobacterial activity of functionalized alkenols--topological descriptors in modeling the activity. , 2005, Bioorganic & medicinal chemistry.

[21]  G. Spalluto,et al.  Novel N6-(substituted-phenylcarbamoyl)adenosine-5'-uronamides as potent agonists for A3 adenosine receptors. , 1996, Journal of medicinal chemistry.

[22]  K. Jacobson,et al.  125I-4-aminobenzyl-5'-N-methylcarboxamidoadenosine, a high affinity radioligand for the rat A3 adenosine receptor. , 1994, Molecular pharmacology.

[23]  Maykel Pérez González,et al.  Designing Antibacterial Compounds through a Topological Substructural Approach , 2004, J. Chem. Inf. Model..

[24]  Aliuska Morales Helguera,et al.  TOPS-MODE based QSARs derived from heterogeneous series of compounds. Applications to the design of new anti-inflammatory compounds. , 2004, Bioorganic & medicinal chemistry.

[25]  Maykel Pérez González,et al.  QSAR study of N6-(substituted-phenylcarbamoyl) adenosine-5′-uronamides as agonist for A1 adenosine receptors , 2004 .

[26]  Maykel Pérez González,et al.  BCUT descriptors to predicting affinity toward A3 adenosine receptors. , 2005, Bioorganic & medicinal chemistry letters.

[27]  Milan Randić,et al.  Correlation of enthalphy of octanes with orthogonal connectivity indices , 1991 .

[28]  H. Akaike A new look at the statistical model identification , 1974 .

[29]  N6,5'-Disubstituted adenosine derivatives as partial agonists for the human adenosine A3 receptor. , 1999 .

[30]  Ernesto Estrada,et al.  Spectral Moments of the Edge Adjacency Matrix in Molecular Graphs, 1. Definition and Applications to the Prediction of Physical Properties of Alkanes , 1996, J. Chem. Inf. Comput. Sci..