Medicinal Chemistry Flashcards
Hybridization if electronic configurations
SP3 = Alkanes = 107 = Tetrahedral SP2 = Alkenes = 120 = Trigonal SP = Alkynes = 180 = Linear
Primary to tertiary alcohol oxidations
1* oxidation produces an aldehyde.
2* oxidation produce ketone.
3* Does not undergo oxidation.
Water solubility of alcohol, amines
1⬅️3 alcohols, amine= water solubility
3⬅️1 amines⬅️ aromatic = base strength
Amines undergo (phase 2 metabolism) glucuronidation, sulfate conjugation and methylation, state each 1-3
- 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
Acidic funcx grp.
Acid or base sensitive funcx grp and example
Carboxylic acid
Esters, due to Hydrolysis=
acid + alcohol
Pen G and other acid sens. B lac antibiotics undergo hydrolysis
This funcx grp undergo hydrolysis but slower than Esters.
Amides, hydrolysis ➡️ acid + amine
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
- 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
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.
Lead structure- Chem subs w tx use
Analog- Molecule with same skeletal structure with diff funcx grps attached.
PHARMACOPHORE
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.
Homolog- Difference of -CH2- in identical molecules
Phenothiazine and Chlorpromazine
Bioisosters: Phenothiazine and diethyl stilbesterol
Drugs containing Pyridine ring
Nicotinic Acid
Nicotinamide
Nicotine
Isoniazid
What ring molecule is based upon pyridine that have been semi-saturated with two substituent’s replacing one double bond?
Dihydropyridine ring- L-type Ca channel blockers
Amlodipine
Nifedipine
Felodipine
Present in numerous natural alkaloids and is the main active chemical agent in black pepper and relatives, hence the name.
Piperidine ring: Morphine
Codeine Heroin Meperidine Thioridazine Haloperidol Risperidone
Muscarinic blockers: Atropine Ipratropium Bromotropin Scopolamine
Piperidine is also a structural element of many pharmaceutical drugs such as
raloxifene, minoxidil, thioridazine and mesoridazine
Piperidine ring + Pyrrolidine = ________
Quasi ring
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?
Pyrrolidine
leaves of tobacco and carrot
a.a. proline and hydroxyproline
nitrogen containing heterocyclic derived from what? Drug example is Clonidine
Imidazoline from Imidazole
Isoxazole also form the basis for the COX-2 inhibitor, give chem struc. And drug ex.
Isoxazole is an azole with an oxygen atom to the nitrogen.
Sulfonamides
Penicillin nucleus. _____ is the square at the centre and drug ex. And give amino deriv. of this drug examples
β-Lactams: Penicillin’s Cephalosporin
Amino penicillins: Amoxi, Ampi
Pyrazole receptor inhibitor and tx uses
COX II inhibitors
analgesics antiinflamm antipyretic antiarryth tranquilizing musc relaxing psychoanaleptic anticonvulsant MAO inhibiting, antidiabetic and antibacterial activities
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.
Indole ring
Serotonin: Triptans and setrons
It also occurs in coal tar.
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
Quinoline or benzopyridine
Quinolone: Quinine, hydroxyl quinine and quinidine
What ACEi consist of this that gives rash and metallic taste and give what chemical ring.
Captopril— Sulfhydryl group is active group binds with enzyme.
Proline ring in ACEi
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.
GABA derivatives: Gabapentin, Pregabalin, Vigabatrin
Imidazole drug derivatives
Imidazole: Histamine, histidine
and
azole antifungals
