The Role of Aromatic Substitution on 1,4-Dihydropyridine Binding

Question 1

Desnitro-nifedipine has no substitutions on the aromatic ring and is thus conformationally flexible about the C[23]-C[24] bond.  To view this:

  • click on the “Select” function, and then “click on the C[23]-C[24] bond.  Both atoms, as well as the bond between them should turn yellow.
  • click on the “Rotation” control and rotate the molecule to view it from the back (i.e., rotate approximately 90 degrees around the Y-axis)
  • change the model display to "Space Filling"
  • to rotate about the C[23]-C[24] bond, simultaneously hold down the “Shift” + “B” keys, and move your mouse close to the molecule.  When you see the icon (a diagonal axis with an arrow wrapped around it), move your mouse cursor either up or down to rotate about the bond. You should notice that this rotation is not very hindered (i.e., you can rotate the bond approximately 40 to 45 degrees before there is any interference between H[41] and the O[11] carbonyl or the O[14] carboxyl atoms).
  • you may also wish to make additional rotations about the x- and y-axes

Is the ability to be able to rotate this upper ring with little to no hindrance a beneficial feature to the compound or does it detract from its potency?  You should be able to provide a brief explanation for your choice. 

 

 


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This site was developed and is maintained by Dr. Marc W. Harrold (harrold@duq.edu)
Copyright, September 2001; Revised 9/18/07.