Topic I: Drug FG and Characteristic Properties/Reactions

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mcucullu
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59180
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Topic I: Drug FG and Characteristic Properties/Reactions
Updated:
2011-01-25 13:35:10
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drug functional group characteristic properties reactions principles drug action
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This unit of instruction reviews the topics in chemistry in the context of basic pharmaceutical sciences. Presentation begin with functional group 'FG' (pharmacophore) commonly found in drug molecules, followed by discussions of chemical basis for their acid-base characteristics and their characteristic stability reactions of functional groups applicable to the drug properties. Top 200 drugs are used as examples to demonstrate the application of principles of drug action.
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  1. List three hydrocarbons.
    • 1) Alkanes
    • 2) Alkenes
    • 3) Alkyles
  2. List two halogen-containing functional groups.
    • 1) Alkyl halides
    • 2) Aryl halides
  3. List five oxygen-containing funtional groups.
    • 1) Aliphatic alcohols and ariphatic alcohols
    • 2) Carbonyl compounds: aldehydes and ketones
    • 3) Carboxylic acids
    • 4) Esters
    • 5) Ethers
  4. Name a sulfur-containing group.
    Thioethers
  5. List four nitrogen-containing functional groups.
    • 1) Aliphatic amines and aromatic amines
    • 2) Quaternary ammoniums
    • 3) Imines
    • 4) Guanidines
  6. List five nitrogen and oxygen-containing functional groups.
    • 1) Carbamates
    • 2) Amides
    • 3) Imides
    • 4) Ureas
    • 5) Ureides
  7. List four sulfur and oxygen-containg functional groups.
    • 1) Sulfoxides
    • 2) Sulfones
    • 3) Sulfonic acid
    • 4) Sulfonate esters
  8. Name a phosphate and oxygen-containing functional groups.
    Phosphate ethers
  9. What is the charge on an atom that is bonded by a dative bond?
    No charge.
  10. Define an alkane.
    Alkanes are structures that contain only carbon-carbon and carbon-hydrogen single bonds.
  11. Define saturated hydrocarbons.
    Saturated hydrocarbons are structures that cannot add any more hydrogens.
  12. Define aliphatic.
    Aliphatic structures are cylic or acyclic structures that are not aromatic.
  13. Define aliphatic ‘R’ groups.
    Aliphatic ‘R’ groups are structures considered to be nonpolar and hydrophobic.
  14. Define cycloalkanes.
    Cycloalkanes are cyclic alkanes.
  15. List the properties of alkanes.
    • 1) Neither acidic or basic
    • 2) Does not undergo nucleophilic substitution
    • 3) Does not undergo oxidation
    • 4) Does not undergo salt formation
    • 5) Does not undergo hydrolysis
  16. Define an alkene.
    Alkene structures are hydrocarbon structures containing at least one carbon=carbon double bond. They are always considered unsaturated, since a hydrogen atom can be added to the double bond. They are normally in cis (Z) or trans (E) conformation They will also be considered an aliphatic ‘R’ group.
  17. List the properties of an alkene.
    • 1) Neither acidic or basic
    • 2) Undergoes oxidation
    • 3) Undergoes hydrolysis
    • 4) Undergoes nucleophilic substitution
  18. Define an alkyne.
    An alkyne is a hydrocarbon that contains at least one carbon=carbon triple bond. These structures are considered unsaturated due to its capability to have hydrogen atoms added to its structure. It is considered an aliphatic ‘R’ group.
  19. List the properties of an alkyne.
    • 1) Neither acidic or basic
    • 2) Undergoes oxidation
  20. List the three aliphatic/alkyl hydrocarbons.
    • 1) Alkanes
    • 2) Alkenes
    • 3) Alkynes
  21. Define an aromatic hydrocarbon ring.
    An aromatic hydrocarbon ring ar cyclic hydrocarbon structures that abides by the 4n+2= # of pi electrons rule, where n is the number of rings. These structures are considered to be really stable.
  22. List the properties of aromatic hydrocarbon rings.
    • 1) Neither acidic or basic
    • 2) Unreactive (due to its high stability)
  23. Define a nonbasic heteroaromatic ring.
    In heteroatomatic rings, both pi bonds and nonbonding pairs of electrons are used to satisfy the 4n+2= # of electrons rule. These nonbonding pairs are generally found on an electronegative atom. In the case of a nonbasic heteroatomatic ring, the nitrogen involved in the ring is using its nonbonding pair of electrons as a means to satisfy this rule. Other nonbasic heteroaromatic rings include other electronegative atoms in the place of a nitrogen.
  24. List the properties of nonbasic heteroaromatic rings.
    1) Unreactive with the exception of thiophene, which undergoes oxidation by means of a dative bond.
  25. Define a basic heteroaromatic ring.
    In heteroatomatic rings, both pi bonds and nonbonding pairs of electrons are used to satisfy the 4n+2= # of electrons rule. These nonbonding pairs are generally found on an electronegative atom. In the case of a basic heteroaromatic ring, two electronegative atoms are present, one being a nitrogen with a nonbonding pair of electrons. While the other electronegative atom uses its nonbonding pair of electrons to establish aromaticity, the nitrogen remains with its nonbonding pair of electrons free to undergo protonation, thus making the structure basic. Another situation may be that the ring has already established aromaticity without the use of nonbonding pairs of electrons, in which case the nitrogen uses its nonbonding pair of electrons as a means of protonation.
  26. List the properties of a basic heteroaromatic ring.
    • 1) Basic
    • 2) Undergoes oxidation to form N-oxides
    • 3) Undergoes salt formation in acidic medium
  27. Define an alkyl halide.
    An alkyl halide is also known as halocarbons. They normally have a formula of R-CH2-X, where X is any of the following halogens: F, Br, Cl, or I. They are classified as 10, 20, or 30 halides, where its degree is determined by how many aliphatic carbons is attached to the carbon the halogen is attached to.
  28. List the properties of alkyl halides.
    • 1) Niether acidic or basic
    • 2) Undergoes nucleophilic substitution.
  29. What effect does nucleophilic substitution of alkyl halide may induce?
    In nucleophilic substitution, an alkyl halide may act as a strong electrophile and cause damage to an organism’s DNA.
  30. Define an aryl halide.
    An aryl halide is a structure in which a halogen is attached to an aromatic ring (heteroaromatic rings as well).
  31. List the on shelf and in vivo properties of aryl halides.
    • On shelf:
    • 1) Neither acidic nor basic
    • 2) Generally unreactive

    • In vivo:
    • 1) Neither acidic nor basic
    • 2) Generally unreactive
  32. Define an α, β-unsaturated carbonyl.
    An α, β-unsaturated carbonyl is a structure that contains a double bond C=C at the α carbon and a double bond C=O at the β carbon. Note: This means that the two functional groups are separated by only one single bond.
  33. List both the on shelf and in vivo properties of α, β-unsaturated carbonyl.
    • On shelf:
    • 1) Neither acidic nor basic
    • 2) Reacts with water/humidity

    • In vivo:
    • 1) Neither acidic nor basic
    • 2) Nucleophilic Substitution (in vivo) due to the presence of a strong electrophile. May react with DNA/RNA, proteins, and enzymes.
  34. Define an aliphatic alcohol.
    An aliphatic alcohol is a structure that contains a hydroxyl (OH) group in which its functional group is directly attached to an aliphatic carbon. These groups can be classified as primary (10), secondary (20), or tertiary (30) functional groups by looking at the amount of carbons is attached to the aliphatic carbon the functional group is attached to. Note: An aromatic alcohol will be directly attached to an aromatic ring.
  35. List both the on shelf and in vivo properties of aliphatic alcohol.
    • On shelf:
    • 1) Neither acidic or basic
    • 2) Sensitive to oxidation
    • 3) 10 alcohol is oxidized to aldehyde
    • 4) 20 alcohol is oxidized to ketone
    • 5) 30 alcohol does not undergo oxidation

    • In vivo:
    • 1) Neither acidic or basic
    • 2) Sensitive to oxidation
    • 3) 10 alcohol is oxidized to aldehyde
    • 4) 20 alcohol is oxidized to ketone
    • 5) 30 alcohol does not undergo oxidation
  36. Define oxidation.
    Oxidation is a reaction in which an oxygen is added or two hydrogens are removed.
  37. Define an aromatic alcohol.
    An armoatic alcohol or a phenol is a structure that contains a hydroxyl (OH) group that is directly connected to an aromatic (or heteroaromatic) ring. Primary (10), secondary (20), and tertiary (30) is not applicable to this structure.
  38. List both the on shelf and in vivo properties of aromatic alcohol.
    • On shelf:
    • 1) Weak acid with a pka of 10.
    • 2) Salt formation in an aqueous basic medium.

    • In vivo:
    • 1) Weak acid with a pka of 10.
    • 2) Undergoes conjugation.
  39. Define an ether.
    An ether is a structure that contains an oxygen in its carbon skeleton. It will have a general formula of C-O-C, where the carbon may be aliphatic or aromatic. Aliphatic and aromatic ethers have similar reactivity.
  40. List both on shelf and in vivo properties of an ether.
    • On shelf:
    • 1) Neither acidic or basic.
    • 2) Unreactive

    • In vivo:
    • 1) Neither acidic or basic
    • 2) Undergoes oxidation via CYTP450 enzymes. Applicable to noncyclic ethers only.
  41. Define a nitro functional group.
    A nitro functional group is a structure that contains a nitrogen attached to two oxygens by a double bond or a dative bond. It has a general formula of -NO2.
  42. List both the on shelf and in vivo properties of a nitro functional group.
    • On shelf:
    • 1) Neither acidic or basic
    • 2) Generally unreactive

    • In vivo:
    • 1) Neither acidic or basic
    • 2) Sensitive to reduction/formation of an amine.
  43. Define an aldehyde.
    An aldehyde is a structure that contains a carbonyl group (C=O) at the end of a carbon skeleton. It has a general formula of R-CHO.
  44. List both the on shelf and in vivo properties of an aldehyde.
    • On shelf:
    • 1) Neither acidic or basic
    • 2) Undergoes oxidation to carboxylic acid
    • 3) Undergoes nucleophilic substitution to form acetal with alcohols

    • In vivo:
    • 1) Neither acidic or basic
    • 2) Undergoes oxidation to carboxylic acid
    • 3) Undergoes nucleophilic substitution to form acetal with alcohols

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