Organic Chemistry part 2

Question 1

What are small molecules (SMs)?

Answer 1

Classic active substances that constitute 90% of drugs on the market.

Question 2

What are large molecules (biologics)?

Answer 2

Made by living cells or organisms and consist of large, highly complex molecular entities.

Question 3

Nucleophiles (definition)

Answer 3

• Nucleophiles are electron donors
• They are attracted to a positive charge or an area of reduced electron
• Common features: lone pair, negative charge, pi-electrons, sigma-electrons

Question 4

Electrophiles (definition)

Answer 4

• Electron acceptors, attracted to a negative charge or an area of increased electron density
• Common features: positive charge, single bond to an electronegative atom, double bond to an electronegative atom

Question 5

Protonation

Answer 5

• Curly arrow goes from lone pair to H+
• Net loss of 1 electron because the electrons are shared

Question 6

Deprotonation

Answer 6

Arrow goes from OH to H, another arrow from the O-H bond to produce a negative ion

Question 7

Prodrugs

Answer 7

Compounds which are inactive in themselves, but which are converted in the body to the active drug

Question 8

Why are esters important in drug synthesis?

Answer 8

• Can act as prodrugs
• Improving drug distribution (are less polar)
• Increasing oral availability (ester can be hydrolysed by esterases in the bloodstream)
• Prolonging drug duration

Question 9

Draw acid-catalysed ester hydrolysis

Answer 9

Be able to draw it (slide 30 of presentation)

Question 10

Base-promoted ester hydrolysis

Answer 10

Be able to draw it (slide 31 of presentation)

Question 11

Nucleophilic acyl substitution reaction (addition-elimination)

Answer 11

Be able to draw it (slide 33 of presentation)