Chem Basis ACEIs and ARBs Structures 2

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    What is this drug?
    Lisinopril
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    This aminobutyl group (creating a lysine) in place of the normal CH3 has what effect on the molecule?
    Enhances oral bioavailability (even without the presence of an ester at the side chain carboxylic group)

    (Lisinopril)
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    What effect does this part of the structure have and what type of bond does it form with the receptor?
    Increase affinity for binding to the enzyme and for better inhibition

    Hydrophobic bond

    (Enalapril analogs)
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    What effect does this part of the structure have and what type of bond does it form with the receptor?
    Increase affinity for binding to the enzyme and for better inhibition

    Hydrogen Bond

    (Enalapril analogs)
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    For phosphorous analogs, hydroxyl group of the phosphinyl group can both be made into _________by substituting __________ for R2 which make them lipophilic and allow for oral activity.
    Ester by substituting an ethyl
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    For enalapril analogs, hydroxyl group of the carboxylic group on the side chain can both be made into _________by substituting __________ for R2 which make them lipophilic and allow for oral activity.
    Ester by substituting an ethyl
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    The Form with an H at R2 is only given  ______________, has good water solubility and does not have good oral bioavailability.
    Intravenously

    (Phosphorous containing analog)
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    The Form with an H at R2 is only given  ______________, has good water solubility and does not have good oral bioavailability.
    Intravenously

    (Enalapril Analog)
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    Is the Imidazole ring required, why or why not?
    Yes, to mimic the His6 side chain of Ag-II BUT can also be other heteroaromatic rings: pyrazole and pyrrole ring

    (ARB pharmacophore)
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    If the Imidazole were an open ring imidazole with a keto group, would this structure have activity?
    Yes, may add an additional H bond to the receptor (as in Valsartan)

    (ARB pharmacophore)
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    What effect do these substitutions at the imidazole ring have on the molecule?
    Can enhance potency (Irbesartan) and are an acceptable substitution (Candesartan Cilexetil)

    (ARBs)
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    Formation of this ester off of the imidazole ring has what effect on the drug?
    Produces a Prodrug
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    What can the acidic group be on an ARB?
    Carboxylic acid, a Phenyl tetrazole or a Phenyl carboxylate
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    A phenyl tetrazole acidic group has what effect on the ARB?
    Increases metabolic stability, lipophilicity and oral bioavailability
  15. Image UploadIf the Acidic group is a phenyl carboxylate or phenyl tetrazole, what position do they need to be in?
    Ortho position

    (ARB)
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    An ARB with a Phenyl tetrazole or Phenyl Carboxylate acidic group will have what oral activity?
    Good
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    If the acidic group of the ARB is a phenyl ring can they be attached by a linker or directly linked in order to have good oral activity?
    • Directly
    • linked
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    The imidazole ring can be changed to a benzimidazole ring?
    Yes
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    R groups including:____________________________________________________ are required to mimic the Phe8  of AgII and enhance binding to the AT1 resulting in enhanced blocking activity.
    • –COOH,
    • methyl alcohol, ether or alkyl
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    The ring structure (5-oxo-1,2,4-oxadiazole ring ) on this drug has what effect on
    the structure’s activity?
    • Enhances oral bioavailability
    • (Alizartan)
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    What is this drug?
    Azilsartan

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Author:
kyleannkelsey
ID:
250092
Filename:
Chem Basis ACEIs and ARBs Structures 2
Updated:
2013-12-02 03:17:24
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Chem Basis ACEIs ARBs Structures
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Chem Basis ACEIs and ARBs Structures 2
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