Chapter 1 (E1) Flashcards
Review of key organic principles, brief history of medicines, FDA, case studies.
The notation used to draw organic molecules (also referred to as “line angle” or “zig zag”).
What is bond line?
Any atom in a bond line structure that is not a C or an H.
What is a heteroatom?
What is the typical order for a molecular formula?
CxHy, and then alphabetical order for the rest of the elements
The “R” group in a chemical formula.
What is a generic alkyl?
The “X” group in a chemical formula.
What is a halogen?
The “Ph” group in a chemical formula.
What is phenyl?
The part of a molecule where reactions occur.
What is a functional group?
Electronegativity becomes greater as we move to the { } and { } on the periodic table (HINT: blanks are directions).
1) Right
2) Up
Atomic radius/size becomes greater as we move to the { } and { } on the periodic table (HINT: blanks are directions).
1) Left
2) Down
A ring containing one or more heteroatoms.
What is a heterocycle?
The number of unsaturations in a molecule.
What is the index of hydrogen deficiency (IHD)?
For every 1 unsaturation, how many hydrogens do we lose?
2
Under what 2 molecular conditions do unsaturations occur?
1) Multi-bonds (i.e., double & triple)
2) Rings
The mixing of atomic orbitals to form new hybrid orbitals.
What is hybridization?
When does hybridization typically occur?
In preparation for bonding
How many bonding areas (or areas of electron density) will you see with sp3 hybridization?
4
How many bonding areas (or areas of electron density) will you see with sp2 hybridization?
3
How many bonding areas (or areas of electron density) will you see with sp hybridization?
2
A tetrahedral, sp3-carbon with 4 different groups attached.
What is a stereocenter?
Non-superimposable mirror images.
What are enantiomers?
What are the 4 rules for the Cahn-Ingold-Prelog (CIP) naming convention when assigning stereocenters?
1) Assign priorities from highest to lowest based on atomic number (1=highest priority)
2) If 2 groups have same priority, continue down chain until you see a difference
3) Visualize molecule so that lowest priority group is pointed away from you, then trace in a circle 1->2->3
4) For groups containing multi-bonds (i.e., double or triple bonds), assign priorities as if both atoms were duplicated or triplicated
For Rule 3 of the CIP naming convention, a clockwise circle has an { } configuration.
R
For Rule 3 of the CIP naming convention, a counterclockwise circle has an { } configuration.
S
True or False: Enantiomers have identical physical properties.
True
In what 2 ways do enantiomers differ from one another?
1) They show different interactions with other chiral molecules
2) They rotate plane-polarized light in opposite directions (i.e., optical activity)
Does a negative sign correlate to a molecule being levorotary or dextrorotary?
Levorotary
Does a positive sign correlate to a molecule being levorotary or dextrorotary?
Dextrorotary
An instrument used to measure the optical activity of a chiral compound.
What is a polarimeter?
Non-superimposable, non-mirror images, containing multiple stereocenters in which one or more, but not all, differ.
What are diastereomers?
This plant was used in early China to treat coughs.
What is ma huang?
What is the active ingredient in ma huang?
Ephedrine
This Indian spice treats many ailments and is even used as a dietary supplement today.
What is turmeric?
What is the active ingredient in turmeric?
Curcumin
This Greek seed was a known analgesic.
What is the poppy seed?
What is the active ingredient in poppy seeds?
Morphine
This Peruvian tree bark is used to treat malaria and fever.
What is cinchona bark?
What is the active ingredient in chinchona bark?
Quinine
Are amino acids naturally L- or D-configured?
L
Are sugars naturally L- or D- configured?
D
How do you determine if a Fischer projection is L- or D-configured?
L-configured: chiral center’s OH group on the left (NOTE: this only applies to the chiral center furthest from the C=O bond)
D-configured: chiral center’s OH group on the right (NOTE: this only applies to the chiral center furthest from the C=O bond)
What birth defect did thalidomide cause?
Shortened limbs
Which thalidomide enantiomer treated nausea?
R
Which thalidomide enantiomer caused birth defects?
S
How did S-thalidomide cause birth defects? What was the mechanism of action?
It prevented the growth of new blood vessels, particularly during the critical period of limb development early on in pregnancy
Why did FDA medical officer Frances Kelsey deny thalidomide to be used in the U.S. for pregnant mothers?
There was not enough safety testing
Why was there no point in isolating ONLY the R-thalidomide enantiomer?
It racemized in the body, so you would still end up with the S enantiomer
What disease is thalidomide effective in treating today?
Multiple myeloma
What does NSAID stand for?
Non-steroidal anti-inflammatory drug
What does COX stand for?
Cyclooxygenase
What is the relationship between COX enzymes, prostaglandin, pain, inflammation, and COX inhibitors?
COX enzymes produce prostaglandins, which are chemicals that cause pain and inflammation. COX inhibitors prevent the production of prostaglandins, thus preventing pain and inflammation
Which 2 COX enzymes produce prostaglandins?
1 & 2
Although acetaminophen is a COX-3 inhibitor, why is it not considered an NSAID?
Acetaminophen does not prevent inflammation, only pain and fever
What is the serious side-effect of COX inhibitors?
Tightening of arteries, resulting in heart attacks and strokes
Why was fen-phen removed from the market?
It caused pulmonary hypertension, often associated w/ heart valve problems
What was the intended purpose of fen-phen?
Weight loss via amine-induced appetite suppression
What medications was fen-phen a mixture of?
Either fenfluramine or dexfenfluramine mixed w/ phentermine
