Test 3/ Final Functional Groups, Heterocycles, and EWG/EDG

Ethylene Oxide

Tetrahydrofuran

Furan

Tetrahydropyran

Ethylene Imine

Imidazole

Piperidine

Pyridine

Pyramidine

Thiophene

Oxazole

Thiazole

Morpholine

Morpholine

Indole

Benzimidazole

Benzothiazole

Quinoline

Purine

Acid Definitions

Arrhelias: produces H+ in H2O

Bronstead Lowry: donates proton

Lewis: accepts pair of e-

Base Definitions

Arrhelaus: produces OH- in H20

Brønsted-Lowry: accepts proton

Lewis: donates pair of e-

Alkane reactivity

Usually unreactive

If they do→ oxidation

Alkene reactions (4)

1. hydration

2. Epoxidation

3. Peroxidation

4. Reduction

Halogen metabolism (3)

Decrease boiling point

Increase lipophilicity

Decreases metabolic degradation

Epoxidation

Peroxidation

Alcohol reactions (3)

Oxidation to carboxylic acid or ketone

Glucuronidation

Sulfation

Phenol Reactions: (6)

1. Salt formation with strong base

2. Oxidation by O2 → quinone

3. Hydration by CYP450

4. Glucuronidation by UGT

5. Sulfation

6. Methylation

Hemiaceteal

Acetal

Ketal

Thioester Structure and Reactions (2)

Oxidation and dealkylation

R-S-R

Carboxylic Acid reactions

1. Glucuronidation

2. Acetylation

3. Oxidation at Beta Carbon

Anhydride

Sulfone

Acyl Halide

Lactone

Cyclic ester

Sulfoxide

Rank the Reactivity of carbonyl groups in carboxylic acid derivative

Carbonic acid

Carbonate

Carbamate

Urea

Amidine

Guanidine

Sulfonic Acid

Sulfonamide

Nitro group

Oxime

Hydralizine

Hydrazide

Hydrazone

Amide

Lactam

Nitriles

Phase 1 clinical trials

100 or less healthy volunteers to find safety and PK properties

Phase 2 clinical trials

100-500 and the drugs effectiveness is studied

Phase 3 clinical trials

1000s of people, statistically significant data on effectiveness

Phase 4 clinical trials

Monitor side effects, alternate uses, dosage modifications

Strong electron withdrawing groups (4)

1. Nitro group (NO2)

2. Sulfonic acid and sulfonylurea groups (SO3R)

3. Nitrile/ cyano group (CN)

4. Trihalomethyl group (-CF3, CBr3)

Strong electron donating groups: (2)

1. Amino groups (NH2, NHR, NR2R)

2. Hydroxyl (OH) or alkoxyl (OR)

What is the most common type of pi-pi interaction

Aromatic ring stacking