Term
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Definition
Alkane
solubility: hydrophobic
interactions: only hydrophobic
ionization states: none
biological reactivity: essentially unreactive
uses in drug structure: short chains, very rare/unusual to see long chains
how common: 50-70% of drugs (but only in short chains) |
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Term
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Definition
Alkenes
-double bond prevents rotation so flexibility of backbone is reduced
solubility: hydrophobic
interactions: only interacts with other hydrophobic molecules
ionization states: none
biological reactivity: only really have to worry about auto-oxidation (will affect shelf life)
uses in drug structures: used in natural products and antibiotics
how common: present in 5-10% (not very common), plants can make these more easily than we can |
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Term
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Definition
Alkynes
solubility: hydrophobic
interactions: none
ionization states: none but has hydrophobic pockets
biological reactivity: none
uses in drug structure: very infrequent
how common: really rare
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Term
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Definition
Cycloalkanes, alkenes, alkynes
-rings will be flexible (boat, chair & twist conformations), addition of double bonds to rings will restric the ring
solubility/interactions/ionization states/biological reactivity: will be the same as parent compound
uses in drug structures: frequent in natural products
how common: frequent in natural products |
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Term
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Definition
Aromatic Rings
-inflexible ring with no chiral carbons
solubility: less hydrophobic/more water-soluble than alkane
interactions: hydrophobic
ionization states: none
biological reactivity: none
uses in drug structures: everywhere
how common: ubiquitous
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Term
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Definition
Heterocycles
-introducing another atom other than carbon into a ring
major building block of drugs because the structural element of the ring is present and you also have potential for other kinds of interactions between heterocycle & receptor other than purely hydrophobic interactions |
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Term
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Definition
Halocarbons
-addition of halogens (F, Cl and sometimes Br and I) to structures
solubility: tend to make a bit more hydrophobic
interactions: potential H-bonding can occur
ionization states: none
biological reactivity: potential to happen but we don't want it to
uses in drug structures: common
how common: very common |
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Term
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Definition
Hydroxyl group (alcohols)
-can be primary, secondary tertiary, or phenolic
effect on polarity: increases
acid-base chemistry: none
usual metabolism in vivo: oxidized to carboxyl or aldehyde
pro-druggability: convert to an ester
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Term
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Definition
Carbonyl group
effect on polarity: doesnt increase as well as alcohols
acid-base chemistry: none
usual metabolism in vivo: redox rxns
pro-druggability: n/a |
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Term
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Definition
Carboxylic Acid
effect on polarity: strongly increases
acid-base chemistry: depends on the pH of its environment, can remain ionized or unionized; normal pka = 3-5
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Term
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Definition
Ester
-able to undergo reversible dehydration
effect on polarity: decrease
acid-base chemistry: gets rid of any
usual metabolism in vivo: degraded by enzymes ususally by esterases
pro-druggability: great for pro-drugs |
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Term
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Definition
Ether
effect on polarity: remains hydrophobic
acid-base chemistry: none
usual metabolism in vivo: not much
pro-druggability: not much valence (oxygen) is used up
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