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Medicinal and Pharmaceutical Chemistry

Fischer esterification Alcohol with Carboxylic acid
single bonds could be shorter than expected Due to resonance
Resonance in amides also reduces Electrophilicity and bond length, and basicity
Electron withdrawing groups decrease ______ of amines basicity
Electron _______ groups increase basicity of amines donating
Imines are Schiff base
Acidic "Positively charged" Glutamate, Aspartate
Basic "Negatively charged" Lysine, Histidine Arginine
Hydrophobic Amino acids Alanine, Phenylalanine, Valine
Hydrophilic Amino Acids Serine, Tyrosine
Amino Acid with sulfur containing side chains Cystine Methionine
- SH is a Thiol Functional Group
Amino Acids With aromatic functional groups Phenylalanine, Tyrosine Tryptophan
All naturally occurring α-amino acids (except Cys) have the (__) configuration S configuration
A deficiency of GABA is associated with _______ Huntington’s chorea
Peptides amino acids linked together by amide/peptide bonds
Disulfide bonds Formed between the side-chains of two cysteines
Vasopressin Antidiuretic Hormone
Oxytocin Uterus-Contracting Hormone
endopeptidase Enzymatic Hydrolysis at internal peptide bond
exopeptidase Enzymatic Hydrolysis at terminals of peptide bond
Glutathione (GSH) Function is ? protects cells from oxidising agents such as peroxides ROOH
Angiotensin II is an octapeptide which constricts blood capillaries and contributes to the regulation of blood pressure
Alpha helix is stabilised by hydrogen bonding between NH to C=O of the main chain but beside it
B- sheers are stabilised by hydrogen bonding between NH C=O of the main chain but at the other side of the turn
myoglobin oxygen binding enzyme in muscle tissue
Monosaccharides Glucose, Fructose
Disaccharides Sucrose Maltose Lactose
Polysaccharides Starch, cellulose
Monosaccharides General Formula Cn(H2O)n
Aldehyde + Alcohol = Hemiacetal Formation
Anomeric Carbon When the Hydroxyl attacks the carbonyl group in Glucose to create the ring, A new Chiral center is created at the hemiacetal carbon number 1 "Carbonyl previously"
Galactosemia A genetic metabolic disease in which there is a defect in the body's ability to use the sugar galactose
Sucrose 1’,2’- α, β Glycosidic link
Can Sucrose undergo Mutarotation? No
Aldehydes react with amines to give imines schiff base
Molecules which can be superimposed upon their mirror images are said to be ‘’ achiral
A pair of molecules that are related as non-superimposable mirror images are called enantiomers
solubility of______ decreases as the carbon chain increase alcohol
BrØnsted-Lowry acids proton donors
BrØnsted-Lowry bases proton acceptor
Substituents increasing electron density on carbon will_______ the alkoxide destabilise
Substituents decreasing electron density on carbon will_____ the alkoxide stabilise
in alcohol : Acidity_______ as number of alkyl group_______ decreases - increases
primary alcohol are______ acidic than tertiary alcohol more
in alcohol , halogens _____ the acidity increase
Alcohols are also Lewis_____ bases
Lewis bases is (electron pair donors)
Lewis acid is (electron pair acceptor)
tertiary alcohol are ______ than primary alcohol more basic
Tertiary carbocation is _______ ____ than Primary carbocation more stable
the more substituted alkene is formed preferentially zaitzev
Names of aldehydes end in al
Names of ketones end in one
AH: strong acid A is ______ in this case nucleophile
aH: weak acid a is ______ in this case is a base
Nucleophile can be an oxygen nucleophile, nitrogen nucleophile, carbon nucleophile (or sulphur nucleophile).
Neutral nucleophiles oxygen and nitrogen nucleophiles
Oxygennucleophile: reactionisslowwithout (acid or basic) catalysis
Nitrogennucleophile reactioncantakeplace without catalyst, but will be much faster with (acid) catalysis.
Nitrogen atom is ____ _______ than oxygen atom more nucleophilic
Negatively charged nucleophiles carbon nucleophiles
has 1 ether and 1 alcohol functional groups on same carbon. Hemiacetal
in CONDENSATION REACTION if the R group is alkyl or phenyl the product is an an imine or Schiff Base
in CONDENSATION REACTION if the R group is OH oxime
in CONDENSATION REACTION if the R group is NH2 or NHR’ hydrazone
Carbonyl compounds containing an α CH group undergo an_____ reaction in basic solution Aldol
H more acidic than a H of a saturated hydrocarbon because negative charge formed by deprotonation is stabilised by ____ resonance with the carbonyl group.
reaction involves 2 molecules of aldehyde/ketone aldol reaction/condensation
aldol reaction require - H atoms on alpha carbon - Basic solution
Aldol condensation require 2 H atoms on the a carbon
Intramolecular cross-links are due to aldol condensations.
Level of oxidation ofa carbon count the number of bonds between the carbon and atoms different from H and C
______ ______ oxidises aldehydes but not ketones. Tollens Reagent
what agent stops the process at aldehyde and doesnt complete it to carboxylic acid ? Pyridinium chlorochromate (PCC)
test to distinguish aldehydes from ketones. Fehling’s Solution
Ketones______ electrophilic than aldehydes less , ketones has 2 R, EDG, so its less positive making it less electrophilic
Mythyle is Electron _____ group donating, 6 electrons closer to the carbon
________ nucleophilic enough to attack carbonyl carbon without protonation of carbonyl oxygen by H⊕ catalyst Nitrogen
is called the acid ionization or acid dissociation constant Ka
Why are carboxylic acids so much more acidic than alcohols, even though both contain –OH groups ? The carboxylate conjugate base is stabilised by resonance, the alkoxide conjugate base is not. Hence the carboxylate conjugate base is formed more easily i.e. the carboxylic acid is a stronger acid.
_____ will reduce the negative charge on Coo- and will make the conjugate base more stable EWG
______ makes an acid stronger EWD
An ____ _____ _____ destabilises the conjugate base: acid is a weaker acid. electron donating group
Electron______ methyl groups weaken acidity. donating
Electron______ (strong) nitro group strengthens acidity withdrawing
Potassium permanganate (strong oxidising agent) KMnO4
Grignard Reaction Reaction of Grignard reagent with CO2 to make COOH
Glycerides are _________ and ______ are carboxylic acid derivatives Esters
are named by first identifying the alkyl group attached to oxygen, R’, and then the carboxylic acid: –ic acid is replaced by -ate Esters
states that any change in a system at equilibrium results in a shift of the equilibrium in the direction which minimises the change Le Chateliers principle
Acid + Alcohol = Ester + Water
esters hydrolysis in basic solution is called saponification
In this reaction OH- is consumed and although it speeds up the reaction it is not a real catalyst. The reaction is said to be base promoted
condition associated with elevation of different forms of lipids in the bloodstream Hyperlipidemia
hydrolysis phospholipids will yield " Fatty Acids " An alcohol (glycerol) " One additional compound (phosphate)
All steroids have the same basic structure and contains four rings : 3 cyclohexane and one cyclopentane
very rich in cholesterol & cholesteryl esters LDL
Transports cholesterol to the liver HDL
Contains low level of cholesterol vs protein and phospholipds HDL
Contains high level of cholesterol & esterified cholesterol vs protein and phospholipds LDL
Transports cholesterol to cells and to the liver LDL
cabroxylic acid derivetaves reactivity amide < Ester < acid anhydride < Acid Chloride
Aspirin is synthesised in the laboratory by reacting _________ with acetic_______ salicylic acid - acetic anhydride = aspirin ethanoic acid
aspirin hydrolysis in acidic catalyst will yield salicylic acid + acetic acid
aspirin hydrolysis in acidic catalyst will yield salicylic acid + sodium acetate
Put name of carbon chain in front >> ethanamide Name ends in amide
Least reactive of the carboxylic derivatives Amides
Why is that the N in amide is weak base Due to resonance
Why is teritery amides doesnt have H bonding Because the N in amide doesn't have H atom to contribute to the H bonding
Prepared by reaction of an acid chloride with ammonia Synthesis of Amides from acid chlorides
Because of the lone pair of electrons on the N: amines are_____ basic
Electron donating groups increase______ of amines basicity
Carbonyl compound + RNH2 = Imine (Schiff Base) + H2O
Primary phenylamines react with HNO2, yielding stable diazonium salts
With the exception of____ , all α-amino acids are optically active since the α carbon is a chiral centre. glycine
Formed between the side-chains of two cysteines Disulfide bonds
Created by: Naser