Medicinal Chemistry

Question 1

Hybridization if electronic configurations

Answer 1

SP3 = Alkanes = 107 = Tetrahedral 
SP2 = Alkenes = 120 = Trigonal
SP = Alkynes = 180 = Linear

Question 2

Primary to tertiary alcohol oxidations

Answer 2

1* oxidation produces an aldehyde.
2* oxidation produce ketone.
3* Does not undergo oxidation.

Question 3

Water solubility of alcohol, amines

Answer 3

1⬅️3 alcohols, amine= water solubility

3⬅️1 amines⬅️ aromatic = base strength

Question 4

Amines undergo (phase 2 metabolism) glucuronidation, sulfate conjugation and methylation, state each 1-3

Answer 4

• Primary amines also undergo oxidative deamination (MAO enzymes).
• Primary & Secondary undergo acetylation.
• Secondary & tertiary amines undergo N-dealkylation.
• Tertiary undergoes N-oxidation.
• Phenolic amines susceptible to N-oxidation on the shelf

Question 5

Acidic funcx grp.

Acid or base sensitive funcx grp and example

Answer 5

Carboxylic acid
Esters, due to Hydrolysis=
acid + alcohol
Pen G and other acid sens. B lac antibiotics undergo hydrolysis

Question 6

This funcx grp undergo hydrolysis but slower than Esters.

Answer 6

Amides, hydrolysis ➡️ acid + amine

Question 7

Compounds that have the same molecular formula but different chemical structures.
Contain at least one asymmetric or chiral carbon atom.
Define chiral center and Enantiomers, Diastereomers

Answer 7

• Isomerism, isomers or isomeric
• Optical isomers
• also asymmetric center, C atom attached to four different groups
• Enan-mirror image with one asym center and non-superimp
• Dias-Two asym C atom, super imp and are not mirror images

Question 8

Define Leas structure and Analog.
What is that portion of the molecule containing the essential organic functional group that directly interact with receptor active site thereby it shows biological activity of interest.

Answer 8

Lead structure- Chem subs w tx use
Analog- Molecule with same skeletal structure with diff funcx grps attached.
PHARMACOPHORE

Question 9

Homolog, define and drug examples.
This functional groups or atoms that impact similar physical and chemical properties on a molecule.
Example methyl, ethyl, bromine, and chlorine.
Give drug examples.

Answer 9

Homolog- Difference of -CH2- in identical molecules
Phenothiazine and Chlorpromazine
Bioisosters: Phenothiazine and diethyl stilbesterol

Question 10

Drugs containing Pyridine ring

Answer 10

Nicotinic Acid
Nicotinamide
Nicotine
Isoniazid

Question 11

What ring molecule is based upon pyridine that have been semi-saturated with two substituent’s replacing one double bond?

Answer 11

Dihydropyridine ring- L-type Ca channel blockers
Amlodipine
Nifedipine
Felodipine

Question 12

Present in numerous natural alkaloids and is the main active chemical agent in black pepper and relatives, hence the name.

Answer 12

Piperidine ring: Morphine
Codeine Heroin Meperidine Thioridazine Haloperidol Risperidone
Muscarinic blockers: Atropine Ipratropium Bromotropin Scopolamine

Question 13

Piperidine is also a structural element of many pharmaceutical drugs such as

Answer 13

raloxifene, minoxidil, thioridazine and mesoridazine

Question 14

Piperidine ring + Pyrrolidine = ________

Answer 14

Quasi ring

Question 15

is a cyclic amine
Muscarinic blockers Atropine Ipratropium Bromotropin Scopolamine
found naturally in the leaves of _______
is the central structure of the what amino acids?

Answer 15

Pyrrolidine
leaves of tobacco and carrot
a.a. proline and hydroxyproline

Question 16

nitrogen containing heterocyclic derived from what? Drug example is Clonidine

Answer 16

Imidazoline from Imidazole

Question 17

Isoxazole also form the basis for the COX-2 inhibitor, give chem struc. And drug ex.

Answer 17

Isoxazole is an azole with an oxygen atom to the nitrogen.

Sulfonamides

Question 18

Penicillin nucleus. _____ is the square at the centre and drug ex. And give amino deriv. of this drug examples

Answer 18

β-Lactams: Penicillin’s Cephalosporin

Amino penicillins: Amoxi, Ampi

Question 19

Pyrazole receptor inhibitor and tx uses

Answer 19

COX II inhibitors
analgesics antiinflamm antipyretic antiarryth tranquilizing musc relaxing psychoanaleptic anticonvulsant MAO inhibiting, antidiabetic and antibacterial activities

Question 20

This is an aromatic heterocyclic compound, solid at rt. It occurs naturally in human feces and has an intense fecal odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes.

Answer 20

Indole ring
Serotonin: Triptans and setrons
It also occurs in coal tar.

Question 21

heterocyclic aromatic organic compound It is toxic: short-term exposure to the vapour causes irritation of the nose, eyes, and throat as well as dizziness and nausea. Longer-term effects are uncertain, but quinoline has been linked to liver damage

Answer 21

Quinoline or benzopyridine

Quinolone: Quinine, hydroxyl quinine and quinidine

Question 22

What ACEi consist of this that gives rash and metallic taste and give what chemical ring.

Answer 22

Captopril— Sulfhydryl group is active group binds with enzyme.
Proline ring in ACEi

Question 23

This was initially synthesized to mimic the chemical structure of the GABA, but is not believed to act on the same brain receptors, its tx axn on neuropathic pain is thought to involve voltage gated N- type calcium ion channels.

Answer 23

GABA derivatives: Gabapentin, Pregabalin, Vigabatrin

Question 24

Imidazole drug derivatives

Answer 24

Imidazole: Histamine, histidine
and
azole antifungals