M.R.

College of Pharmaceutical

Sciences and Research

Name - Salman Sk
University Roll – 36301921043
University Registration –213630201910073
Subject – Medicinal Chemistry II
Subject code – PT513
Semester -5th Year -3rd
Course -B. Pharm; Roll -75
Session - 2023-2024
Slot -2nd (CA2)
Topic -SAR of Benzoic acid derivatives.

STUDENTS SIGNATURE TEACHER SIGNATURE

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 Marks Obtained

CONTENTS

Sl.No Topic Page no

1 Abstract 3

2 Introduction 3

3 Local Anaesthesia 4

4 SAR Of Benzoic Acid derivatives 5

5 Drugs under benzoic acid derivatives 6

 ABSTRACT :
Benzoic acid is type of local Anaesthesia. Local anesthesia is a
medical technique used to induce reversible loss of sensation and pain
in a specific area of the body without unconsciousness. It involves the
administration of anesthetic agents, such as lidocaine or bupivacaine,
near peripheral nerves to block nerve impulses. Local anesthesia is
commonly employed in various medical procedures, from minor
surgeries to dental work, to provide pain relief without affecting the
patient's consciousness. Benzoderivatives, also known as benzene

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derivatives, are a class of organic compounds that contain a benzene
ring as a core structure. The modification of the benzene ring's
structure leads to diverse properties and functionalities .

 INTRODUCTION
Local anaesthesia involves numbing an area of the body using a type
of medicine called a local anaesthetic. These medicines can be used to
treat painful conditions, prevent pain during a procedure or operation,
or relieve pain after surgery. Unlike general anaesthetics, local
anaesthetics don't cause you to lose consciousness. Local anaesthetics
are used for pain relief, soreness, itching, and irritation associated
with disturbance of the integrity of the skin and mucous membranes
(cuts, bites, wounds, rashes, allergic conditions, fungal infections,
skin sores, and cracking). Benzoic acid derivatives are a group of
organic compounds that stem from benzoic acid, a simple aromatic
compound with a carboxylic acid functional group. The benzoic acid
structure consists of a benzene ring fused with a carboxyl group
(COOH). Through chemical modifications, various benzoic acid
derivatives are created.

LOCAL ANAESTHESIA:
 Local anesthesia is a medical technique used to block nerve signals in a
specific area of the body, preventing the sensation of pain during medical
procedures or surgeries.
 Unlike general anesthesia, which renders a person unconscious and affects
the entire body, local anesthesia only numbs a localized region without
affecting consciousness or other bodily functions .
 You can also use local anesthesia for relief from pain caused by cancer and
some bone and joint diseases. Local anesthesia drugs help and are safer than
opioids.

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How Does Local Anesthesia Work?
Y
‌ our nerves carry pain signals to your brain. Local anesthetic drugs block your
nerves and prevent them from carrying these signals. This nerve blockage saves
you from feeling pain.
T
‌ his blockage is temporary. Your nerves will start working in a while. Both
movement and feeling will return.
What Are Types of Local Anesthesia?
‌Local anesthetic drugs are used in three different ways:
Local application. You can apply local anesthetic ointment to open sores or
mouth ulcers.
Local injection. Your doctor injects a local anesthetic drug under the skin or
deeper..
Nerve blocks. Local anesthetic drugs are injected near nerves to block the pain
from the area supplied by the nerve.
What Are the Advantages of Local Anesthesia?
 An anesthesiologist is not needed. Your family doctor or surgeon gives
the local anesthesia before starting the procedure.
 Local anesthesia side effects are uncommon and usually mild.
 You can go home sooner.
 Costs are much lower
Two kinds of local anesthetic drugs are used nowadays. The commonly used
drugs are amides like lignocaine, prilocaine, and bupivacaine. The other group
is esters like cocaine, procaine, and amethocaine

SAR OF BENZOIC ACIDS DERIVATIVES:

In Benzoic Acid derivative there are mainly three group is present.

1. Aryl group

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 2. Bridge X
3. Aminoalkyl Group
 Aryl group:
• The clinically useful local anaesthetics of this series possess an aryl radical
attached directly to the carbonyl group.
• Substitution of aryl group with substituents that increase the electron
density of the carbonyl oxygen enhances activity.
• Favourable substituents in aryl ring include (electron-donating groups)
alkoxy (propoxycaine), amino (procaine), and alkylamino (tetracaine) groups
in the para or ortho positions.

Procaine

Propoxycaine
 Aryl aliphatic radicals that contain a methylene group between the aryl
radical and the carbonyl group result in compounds that have not found
clinical use.
 Bridge X
• The bridge X may be carbon, oxygen, nitrogen, or sulphur.
• In an isosteric procaine series, anaesthetic potency decreased in the following
order: sulphur, oxygen, carbon, nitrogen.
• These modifications also affect duration of action and toxicity. In general,
amides (X=N) are more resistant to metabolic hydrolysis than esters (X=O).
Thioesters (X=S) may cause dermatitis.

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 • In procaine-like analogues, branching (especially at the alpha carbon) will
increase duration of action. This effect is not seen in the lidocaine series.
• Increasing the chain length will increase potency but will also increase
toxicity.


 .Aminoalkyl group
• The aminoalkyl group is not necessary for local anaesthetic activity.
• Tertiary amines result in more useful agents. The secondary amines appear to
be of longer activity, but they are more irritating; primary amines are not very
active and cause irritation.
• The tertiary amino group may be diethylamino, piperidine, or pyrrolidine
leading to the products that exhibit essentially the same degree of activity.
• The more hydrophilic morpholino group usually leads to diminished potency.
• Some analogues have no amino group at all, such as benzocaine. They are
active but have poor water solubility.

 DRUGS UNDER BENZOIC ACIDS DERIVATIVE

There are mainly three drugs comes under the benzoic acids
derivatives .
I. Cocaine
II. Meprylcaine
III. Piperocaine

 COCAINE
IUPAC Name : 2-methoxy carbonyl-tropan-3-yl-benzoate .
It is a natural alkaloid, isolated from the leaves of Erythroxylon coca. It is the
first drug to be used as local anaesthetic.

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Molecular Formula : C17H21NO4
USE : Used as anaesthesia for eye, ear, nose & throat .
 MEPRYLCAINE
IUPAC Name : 2-Methyl-2-(propylamino/isobutylamino)-1-propanol
benzoate .
 Meprylcaine also known as Epirocaine and Oracaine .
 Meprylcaine has a relatively potent inhibitory action on the monoamine
transporter and inhibits the reuptake of dopamine, norepinephrine and
serotonin.

Molecular Formula: C14H21NO2

Uses: Meprylcaine is a local anesthetic with stimulant properties that is
structurally related to dimethocaine .

 Piperocaine
IUPAC Name : 3-(2-Methylpiperidino)propyl benzoate .
It is known as a alpha-1-proteinase inhibitor.

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Piperocaine (Metycaine) is a local anesthetic drug. It is an ester and primarily is
a sodium channel blocker. Piperocaine can partially inhibit dopamine.

Molecular Formula : C16H23NO2

Uses : Used in the form of its hydrochloride as a local or spinal
anesthetic and in dental anesthesia.
Can cause also toxic reactions.

 CONCLUSION :
In conclusion, benzoic acid derivatives constitute a significant class of
compounds with diverse applications in various industries and fields,

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driven by their unique chemical properties. The ability to modify both
the benzene ring and the carboxylic acid group provides researchers
and chemists with a versatile toolbox for designing compounds with
tailored properties, making benzoic acid derivatives essential
components of modern chemistry and technology. As research and
innovation continue, we can expect to see further advancements in the
synthesis, applications, and understanding of these compounds.

REFERENCE’S
1. D. Sriram and P. Yogeeswari, Medicinal chemistry ,Eighteenth
Impression, Second Edition , Pearson India Education Services;
2022,Chapter 6,Page 110-120 .

2. Ashutosh Kar, Medicinal Chemistry , Fourth Edition, Daryaganj

New Delhi- 110002,New Age International Publishers;2006 ,
Chapter 5 , Page 128-142.

3. Malleshappa NNoolvi; Anurekha Jain; Harun M Patel; Textbook of

Medicinal Chemistry; CBS Publishers2014; Chapter 15, Page 354-
380.
4. Parang Mehta , Poonam Sachdev; What to Know About Local
Anesthesia ; WebMD , November 09, 2021.