Skip to main content

Conformational Analysis and Molecular Properties of N-(Substituted Phenylcarbonylamino)- 4-(1-Hydroxymethylphenyl)-1,2,3,6-Tetrahydropyridines

Buy Article:

$63.00 plus tax (Refund Policy)


The three-dimensional structures of active derivatives of N-(substitutedphenylcarbonylamino)-4-(1- hydroxymethylphenyl)-1,2,3,6-tetrahydropyri-dines, which have previously been shown to possess antiinflammatory activities, were built using BIOMEDCAche 5.0 software program. In addition, the three dimensional structures of some of the inactive ones were similarly generated. The conformational analysis, molecular and electronic structures were examined by molecular mechanics and quantum mechanics calculations. The primary objective was to clarify the effects of physicochemical properties of substituents on activity, since the exact role of the substitution pattern on the phenyl ring is uncertain. In addition, the experimental log P values did not appear to have any influence on the anti-inflammatory potencies of these compounds, since compounds having differing lipid solubilities are equiactive. We found that strongly electron-donating group, such as the para-substituted methoxy group, detracts from activity. The conformational analysis indicated that the 4-ethyl derivative had the lowest energy conformation. Except for compound 1, which showed the lowest surface volume, compounds 2-9 had nearly similar surface volumes.

Keywords: anti-inflammatory; conformational; eduiactive; electron-donating; log p; mechanics; phenylcarbonylamino; physicochemical; surface volume; tetrahydropyridine

Document Type: Review Article


Publication date: February 1, 2003

More about this publication?
  • Current Medicinal Chemistry covers all the latest and outstanding developments in medicinal chemistry and rational drug design. Each issue contains a series of timely in-depth reviews written by leaders in the field covering a range of the current topics in medicinal chemistry. Current Medicinal Chemistry is an essential journal for every medicinal chemist who wishes to be kept informed and up-to-date with the latest and most important developments.

Access Key

Free Content
Free content
New Content
New content
Open Access Content
Open access content
Partial Open Access Content
Partial Open access content
Subscribed Content
Subscribed content
Free Trial Content
Free trial content
Cookie Policy
Cookie Policy
Ingenta Connect website makes use of cookies so as to keep track of data that you have filled in. I am Happy with this Find out more