Chem Basis ACEIs and ARBs Structures 1

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kyleannkelsey
ID:
250023
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Chem Basis ACEIs and ARBs Structures 1
Updated:
2013-12-01 20:57:34
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Chem Basis ACEIs ARBs Structures
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Chem Basis ACEIs and ARBs Structures 1
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  1. What is this structure?
    2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore

  2. What part of this molecule is the Proline?
    Green section (2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore)

  3. What part of this molecule is the Mercapto?
    Red (2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore)

  4. What part of this molecule is the Propranoyl?
    Black part (2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore)

  5. What is this part of the molecule essential for?
    Binding the cationic site (2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore)

  6. What is this part of the molecule essential for?
    Binding the Zinc site (2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore)

  7. What is this structure?
    Phosphinylacetyl proline

  8. What is this part of the structure essential for?
    Cationic site binding

  9. What is this part of the structure essential for?
    Zinc site binding

  10. What is this structure?
    1-N-benzyl 2-butyl Imidazole, ARB pharmacophore

  11. What is the significance of these two groups?
    Enhance AT1 receptor binding (ARB pharmacophore)

  12. Adding another Methyl to the succinic acid chain of this compound would enhance or diminish activity?
    Diminish

    (2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore)

  13. What effect does this portion of the molecule have on this structures effect?
    Substantially Increases inhibition

    (2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore)

  14. Would replacement of the Mercapto group with a nitrogen containing group (amines, amides) enhance inhibitory activity?
    No

    (2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore)

  15. What part of this molecule is primarily responsible for many of the adverse effects of ACEI Catapril analogs?
    Mercapto group

    (2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore)

  16. The R1  substituent has what effect on this molecules ability to bind?
    Extends the compound to bind to an auxiliary binding site

    (2D-methyl, 3-mercapto propanoyl-L-proline, Catapril ACEI pharmacophore)

  17. What effect on activity would you expect if R1  =  H?
    very weak activity(Enalapril analog)

  18. What effect on activity would you expect if R1  =  CH3?
    Improve activity extensively(Enalapril analog)

  19. What effect on activity would you expect if R1  =  CH3CH2?
    5 x more active than a Methyl(Enalapril analog)

  20. What effect on activity would you expect if R1  =  (CH3)2-CHCH2CH2?
    ~ = 7 x CH3CH2(Enalapril analog)

  21. What effect on activity would you expect if R1  =  Benzyl?
    ~ = 2 x a Methyl(Enalapril analog)

  22. What effect on activity would you expect if R1  =  Phenyl ethyl?
    ~= (CH3)2-CHCH2CH2(Enalapril analog)
  23. What R1 substituent is optimal for activity and in what configuration?
    R1 = phenyl ethyl group in the S-configuration

    (Enalapril analog)

  24. What can the R2 substituent be?
    H or an Ethyl

    (Enalapril analog)

  25. An H at the R2 of this structure would impart what effects?
    Active structure that is water soluble

    (Enalapril analog)

  26. To make this structure available for IV administration, what would you make R2 and why?
    H, because it would be water soluble

    (Enalapril analog)

  27. What effect would it have if the R2 were an ethyl group?
    Prodrug that is more lipophilic with better oral administration

    (Enalapril analog)

  28. Why would making R2 and ethyl group cause this to be a Prodrug?
    Ethyl forms an ester with the carboxylic group

    (Enalapril analog)

  29. Cyclic amino acids confer what activity at the R1 site of the enalapril analog?
    Particularly high activity

    (Enalapril analog)

  30. Why does a Cyclic amino group at R1 increase therapeutic utility?
    Provides steric hindrance to amidase hydrolysis

    (Enalapril analog)

  31. Changing the size and lipophilicity of of the proline group to something like a cyclopentane or cyclohexane would have what effect on activity?
    No major effect

    (Enalapril analog)

  32. What parts of this molecule are responsible for less binding to the kininase enzyme and subsequently no affect on the breakdown of bradykinins/lack of dry cough?
    Keto group and a methyl on the proline

    (Imidapril)

  33. Incorporating the proline into a seven-membered ring structure is unacceptable or acceptable?
    Acceptable

    (Enalapril analog)

  34. What is the NH important for?
    Important for Inhibitory activity and high affinity for ACE, removal will dramatically decrease activity (400X)

    (Enalapril analog)

  35. What type of interaction would you expect between this part of the structure and the ACE binding site?
    H bond (Probably)

    (Enalapril analog)

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