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Q CITY
INTRODUCTION TO MEDICINAL CHEMISTRY
UNIVERSTY
I. History of Medicinal Chemistry

A. Drugs of Antiquity
- Oldest records of the use of therapeutic plants and minerals are derived from the ancient civilizations of the
Chinese, the Hindus, the Mayans of Central America and Mediterranean peoples of Antiquity.
- Emperor Shen Nung compiled a pharmacopeia including ch’ang shang and ma huang.
- Ipecacuanha root: used in Brazil for the treatment of dysentery and is still used for the treatment of
Amoebiasis
- Coca leaves, mushrooms: South American Indians used these as hallucinogens
- Opium, squill, viper toxin, metallic drugs such as copper and zinc ores, iron sulfate and cadmium oxide:
found in ancient Greek apothecary shops

B. Middle Ages
- Basic studies of chemistry and physics shifted from the Greco- Roman to the Arabian alchemists between
the 13’" and 16’" centuries.
- Paracelsus: glorified Antimony and its salts in elixirs

C. The 19" Century: Age of Innovation and Chemistry

- Antoine Lavoisier: chemists extended the techniques of chemical analysis
- Adolph Kolbe: synthesis of acetic acid
- Pierre Berthelot: synthesis of methane which set the stage for organic chemistry
- Friedrich Sertürner: isolated morphine
-Pierre- Joseph Pelletier: isolation of emetine from ipecacuanha, purification of caffeine, quinine and
colchicine
- William Withering: used digitalis for the treatment of edema
- Albert Niemann: isolated cocaine in 1860. He also isolated physostigmine from Calabar bean

D. The 20"' Century and the Pharmaceutical Industry

- Gerhard Domagk: 2,4- diaminobenzene- 4’- sulfonamide (Prontosil) can cure systemic gram positive
bacterial infections in man and animals.
- Woods and Fildes: observed that the bacteriostatic action of sulfonamide like drugs is antagonized by p-
am inobenzoic acid
- Alexander Fleming: discovered penicillin

II. Review of Functional Groups

A. Saturated Hydrocarbons
1. Alkanes
- Saturated hydrocarbon in which the carbon arrangement is acyclic.
- An alkane is a hydrocarbon that contains only one carbon- carbon single bonds (saturated) and has no rings
of carbon atoms (acyclic).
- General formula: C H2..2 where n is number of carbon atoms present.
- Substituent:
- Alkyl groups: group of atoms that would be obtained by removing a hydrogen atom from an alkane.

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Molecular Formula IUPAC Prefix Condensed Structural r ‹ou

CMH prup- propane CH —CHP—CH,

CMH „ hul- hutane CH H —CH›—CH,
C,H„ g«nt- nianc CH H•—CHF—CH H,
C , H /, hc.s- hexanc CH —CH —CH•—CH H H
C;Hi+ hupt- heplanc CH —CH H•—CH H H H,
C H /x i- oci c CH,—CH,—CH H H H H H
C H non- nunan< CH,—CH. H•—CH H H H H,—EH
C\„H•. dcc- dcc«nc CH,—CHF—CHF—CH H H•—CH H_—CHF—CH,

She m or
Number oT AIkane Croup
Carbons St ruc I ura I Formu Ia la me Na me

MH meth- — y meinyl
C HM H, eth- l eitiyl
—CH›—CH›—CH , prop- — y propyl
—CH —CH›—CHMH but- l butyl
5 MH•MH•MHMH•MH, pcni- — y prntyl
l
—yl
—yl
CH,—CHP—CHMH•—CHP—CH, hex- —yl hexyl

B. Unsaturated Hydrocarbons
1. Alkene
- Ayclic unsaturated hydrocarbon that contains one or more carbon- carbon double bonds.
- The alkene functional group is C= C group.
- General formula: C H2.
- Cycloalkene: cyclic unsaturated hydrocarbon that contains one or more carbon double bonds within the
ring system.
- Alkenyl group: non- cyclic hydrocarbon substituent in which a carbon- carbon double bond is present.
- Example: methylene (methylidene), ethenyl, 2- propenyl group

2. Alkynes
- ayclic unsaturated hydrocarbon that contains one or more carbon- carbon triple bonds.
- Functional group: C-C
- General formula: CMH, 2
- Exampie: ethyne, butyne

3. Aromatic Hydrocarbons
- unsaturated cyclic hydrocarbon that does not readily undergo addition reactions.
- benzene: simplest aromatic hydrocarbon "

- Benzene Derivatives with one Substituent›

L-H —? H '
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- Benzene Derivatives with two substituents:
• Ortho: The substituents are on adjacent carbon atoms
• Meta: The substituents are one carbon removed from each other
• Para: The substituents are 2 carbons removed from each other (opposite sides of the ring)

- Benzene derivatives with 3 or more substituents:

n,

4. Fused ring aromatic hydrocarbons

- aromatic hydrocarbon whose structure contains two or more rings fused together. Two carbon rings that
share a pair of carbon atoms are said to be fused.

C. Alcohols, Phenols and Ethers: oxygen containing functional groups

1. Alcohols
- organic compound in which an —OH group is bonded to a saturated carbon atom. A saturated carbon atom
is a carbon atom that is bonded to 4 other atoms.
- The -OH group is a characteristic of an alcohol is a hydroxyl group,
- Examples:

Formula IUPAC Name Common Name

ONE CARBON ATOM
CH3OH Methanol Methyl alcohol
TWO CARBON ATOMS
CH3CH,OH or C HSOH Ethanol Ethyl alcohol
THREE CARBON ATOMS
CH CHP CHzOH 1- propanol Propyl alcohol
t”H , t H r 'H 2- propanol Isopropyl alcohol

FOUR CARBON ATOMS

CH CH2 CHP CH2OH 1- butanol Butyl alcohol

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2- methyl-1- propanol Isobutyl alcohol

H -—I ”H—‹ iH 2- butanol Sec- butyl alcohol

‹H
2- methyl- 2- propanolTert- butyl alcohol

- Classification of Alcohols:
• Primary Alcohol: alcohol in which the hydroxyl bearing carbon atom is bonded to only one other
carbon atom.
• Secondary Alcohol: alcohol in which the hydroxyl bearing carbon atom is bonded to two other carbon
atoms.
• Tertiary Alcohol: alcohol in which the hydroxyl bearing carbon atom is bonded to three other carbon
atoms.

2. Phenols
- Organic compound in which an —OH group is attached to a carbon atom that is part of an aromatic carbon
ring system.

- General formula:
- Aryl group: aromatic carbon ring system from which one hydrogen atom has been removed.
oH NH OH
vH
wH
‹. H

‹”›ii

3. Ethers
- Organic compound in which an oxygen atom is bonded to two carbon atoms by single bonds. The carbon
atoms that are attached to the oxygen atom can be part of alkyl, cycloalkyl or aryl groups.
- Ether functional group:
- General formula:
- Examples

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D. Aldehydes and Ketones

1.Aldehydes
- Carbonyl- containing organic compound in which the carbonyl carbon atom has at least one hydrogen
atom directly attached to it. The remaining group attached to the carbonyl atom can be hydrogen, an alkyl
group (R), a cycloalkyl group or an aryl group (Ar).
- One of the two additional bonds that the carbonyl carbon atom forms must be to hydrogen atom. The
other may be to a hydrogen atom, an alkyl or clycloalkyl group, or an aromatic ring system.
- Functional group:
- Naming:
- Note:

2. Ketones
- Carbonyl containing organic compound in which the carbonyl carbon atom has two other carbon atoms
directly attached to it. The groups containing these bonded carbon atoms may be alkyl, cycloalkyl or aryl.
- Both of the additional bonds of the carbonyl atom must be to another carbon atom that is part of an alkyl,
cycloalkyl, or aromatic group.
- Naming:

E. Carboxylic acids, Esters and other derivatives

1. Carboxylic acid
- Organic compound whose functional group is the carboxyl group.
- One of the two additional bonds of the carbonyl atom must be to a hydroxyl group, and the other may be
to a hydrogen atom, an alkyl or cycloalkyl group, or an aromatic ring system. The structural parameters for
a carboxylic acid are the same as those for an aldehyde except that the mandatory hydroxyl group replaces
the mandatory hydrogen atom of an aldehyde.
- Functional group:

‹› ‹› ‹› ‹i

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2. Esters
- Carboxylic acid derivative in which the —OH portion of the carboxyl group has been replaced with an —OR
group.
- One of the two additional bonds of the carbonyl atom must be to an oxygen atom, which in turn is bonded
to an alkyl, cycloalkyl or aromatic group. The other bond may be to a hydrogen atom, alkyl or cycloalkyl
group, or an aromatic ring system.
- Naming:
- Functional group:

li — t — i i— ‹ * I '' . ii —r ‹

F. Amines and Amides

1. Amines
- Organic derivative of ammonia (NHS) in which one or more alkyl, cycloalkyl, or aryl groups are attached to
the nitrogen atom.
- Classification of Amines:
Primary Amine
- Amine in which the nitrogen atom is bonded to one hydrocarbon group and two hydrogen atoms.
- Formula: RNH,
•' Secondary Amine
- Amine in which the nitrogen atom is bonded to two hydrocarbon groups and one hydrogen atom.
- Formula: R2NH
Tertiary Amine
- Amine in which the nitrogen atom is bonded to three hydrocarbon groups and no hydrogen atom.
- Formula: R3N
- Functional group:

2. Amides
- Carboxylic acid derivative in which the carboxyl —OH group has been replaced with an amino or substituted
amino group.
- The element nitrogen, in addition to carbon, hydrogen and oxygen is present.

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- Classification of amides:
Primary amide
- Amide in which two hydrogen atoms are bonded to the amide nitrogen atom
•' Secondary amide
- Amide in which an alkyl (or aryl) group and a hydrogen atom are bonded to the amide nitrogen
atom.
Tertiary amide
- Amide in which two alkyl (or aryl) groups and no hydrogen atoms are bonded to the amide nitrogen
atom.
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Reference:
Stoker, H., General, Organic and Biological Chemistry (5’" edition).

Compiled by:
Maricar Grace F. Mararac, RPh
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