chemaxon properties: pi interactions

The Chemaxon's properties 'pKa' and 'charges' of
selected atoms normally correlate with the strength of hydrogen bonding
capacity.

Are there similar Chemaxon's properties which correlate with strength of
pi interacting capacity of fragments, for instance properties such as
polarizability, orbital electronegativity? Are there any case studies
from chemaxon's users where such properties
were used to analyze the pi-interaction capacity of fragments.



For instance 'bosutinib_complete' which contains the hinge binding
fragment 'Bosutinib_fragment' preferentially inhibits a set of
kinases (which do not have an aromatic hinge residue) and 'erlotinib_complete' which contains the
hinge binding fragment 'Erlotinib_fragment' preferentially inhibits a set of kinases
which have an aromatic hinge residue. There are slight
differences in the pKa of the nitrogen of the hinge binding fragments
but we also want to known if there are differences in some properties of
the aromatic rings.

Hi,

 

The "TPSA" value may correlate with  the potentially available hydrogen bonding  property of a molecule. The calculated TPSA of two aromatic rings are on the attached figure.

On the other hand the tautomerization usually take place in case a terminal "OH" group attached to a pi -electron defficient hetero aromtic ring-system.  Keto tautomers are attached on the figure.

We don't have  any case study about the parametrization of the "pi interaction strength" of molecules. 

 

Jozsi

Dear Jozsi,

Thank you very much for the analysis and the information. It was useful to me.

Are there examples where chemaxon properties 'polarizability' and 'orbital electronegativity' were used in drug design? Polarization of the aromatic rings correlates with 'pi interaction strength'.

In addition, are there publications chemaxon was used to relate tautomerization and strength of hydrogen bond formation ?

Thank you and with best regards,

Philip

 

Dear Jozsi,

I am sorry if I was not clear with my request.

I am sure you must have seen QSAR papers which use physicochemical descriptors in their models (cr010154c.pdf ) . Are there some papers where ChemAxon computed descriptors were used to explain the SAR or classify actives from inactives ?

It is important to my work and hence I am writing again.

Thank you and with best regards,

Philip

 

 

Hi,

 

Thanks for clarifying  this issue.

I try to look around on this question asking some other people and go back to you soon.

 

Jozsi