SYNO PS IS OF T HE TH ES IS TO BE SUBM ITT ED TO

BHA VN AG AR UNI VE RS IT Y FOR Ph .D . DE GR EE IN

CHEMI ST RY

FACULTY : SCIENCE

TITLE : BIO-ACTIVE HETEROCYCLIC COMPOUNDS AS

POTENTIAL ANTIMICROBIAL AGENTS

NAME OF THE CANDIDATE : SHIHORA PRASHANT NANUBHAI

NAME OF THE GUIDE : PROF. NISHEETH C. DESAI

REGISTRATION NUMBER : 963

DATE OF REGISTRATION : 16/04/2005

PLACE OF WORK : DEPARTMENT OF CHEMISTRY,

BHAVNAGAR UNIVERSITY,
BHAVNAGAR-364 002,
(INDIA)
 BIO-ACTIVE HETEROCYCLIC COMPOUNDS AS
POTENTIAL ANTIMICROBIAL AGENTS

Medicinal and bio-organic chemistry is concerned with the design,

synthesis, and analysis of the relationship between molecular structure
and biological activity for compounds that can be used for the cure or
treatment of disease. Heterocyclic chemistry is fundamental to biology
and medicine. It is not farfetched to say that we are living in the age of
Heterocyclic chemistry. The emergence of drug resistant bacteria has
posed a growing challenge to the search for new chemical entities. Yet,
from the viewpoint of drug discovery it is critical to realize that, despite
the importance of drug knowledge, it is not an exclusive tool. Rather, it
is a tool that must be used with the techniques of combinatorial
chemistry, structural biology, high throughput screening, siRNA, in silico
design & related technologies.
The dynamics of drug development is one of the defining
characteristics of pharmaceutical industry. Despite its importance to
industry, there is little information on how long it takes for particular
drugs to go through human clinical trials and the probabilities of
successful completion.
Useful drugs like risperidone, pyrethrin, isoniazide, rotenone, AZT,
strychnine, reserpine, some antihistamines, ergot alkaloids, caffeine,
cocaine and barbiturates are heterocyclic compounds. Recently some
non-nucleoside heterocyclic compounds like nivirapine, TIBO, BHAP, PETT
and HEPT have been used as anti-HIV agents. The latest anticancer drug
is Fludarabine, which contain heterocyclic framework in the structure.
Looking to the importance of heterocyclic compounds in medicinal
chemistry, we have synthesized the following heterocyclic compounds
and screened for their in vitro antimicrobial activity.

Heterocyclic compounds like 4-oxo-quinazoline, 4-oxo-thiazolidin,

5-oxo-imidazole, 1,2,4-triazol and their derivatives have been found to
possess strong hypnotic, anaesthetic, analgesic, sedative, antifungal,
antitubercular, anticonvulsant, CNS-depressant, anti-HIV, anticancer and
antibacterial activities.

Part-I
Section 1: N-{5-[(aryl)methylene]-2-(2-hydroxyphenyl]-4-oxo(1,3-
thiazolidin-3-yl)}{4-[2-(4-methylphenyl)-4-oxo(3-hydro
quinazolin-3-yl)] phenyl}carboxamides.
Section 2: N-{5-[(aryl)methylene]-2-(4-hydroxyphenyl]-4-oxo(1,3-
thiazolidin-3-yl)}{4-[2-(4-methylphenyl)-4-oxo(3-hydro
quinazolin-3-yl)]phenyl}carboxamides.
Section 3: N-{5-[(aryl)methylene]-2-(4-fluorophenyl]-4-oxo(1,3-
thiazolidin-3-yl)}{4-[2-(4-methylphenyl)-4-oxo(3-hydro
quinazolin-3-yl)]phenyl}carboxamides.
Section 4: N-{5-[(aryl)methylene]-2-(4-chlorophenyl]-4-oxo(1,3-
thiazolidin-3-yl)}{4-[2-(4-methylphenyl)-4-oxo(3-hydro
quinazolin-3-yl)]phenyl}carboxamides.
Part-II
Section 5: N-{4-[(aryl)methylene]-5-oxo-2-phenyl(2-imidazolinyl)} {4-[2-
(3-nitrophenyl)-4-oxo(3-hydroquinazolin-3-yl)]phenyl}
carboxamides.
Section 6: N-{4-[(aryl)methylene]-5-oxo-2-phenyl(2-imidazolinyl)} {4-[2-
(4-nitrophenyl)-4-oxo(3-hydroquinazolin-3-yl)]phenyl}
carboxamides.
Section 7: N-{4-[(aryl)methylene]-5-oxo-2-phenyl(2-imidazolinyl)}-2-(1-
phenyl(3H-1,2,4-triazol-3-yloxy))acetamides.
Section 8: {4-[(Diethoxythioxophosphino)amino]phenyl}-n-{4-[(aryl)
methylene]-5-oxo-2-phenyl(2-imidazolinyl)}carboxamides.

Part-III
Section 9: Phenyl-N-{5-naphthal-3-sulfanyl(1,2,4-triazol-4-yl)}
carboxamides.
Section 10: Phenyl-N-{5-[(4-chlorophenoxy)methyl]-3-sulfanyl(1,2,4-
triazol-4-yl)}carboxamides.
Section 11: Phenyl–N–{5–(2–naphthyloxyacetyl)-3–sulfanyl(1,2,4–triazole-
4-yl)}carboxamides.
Section 12: Phenyl–N–{5–[(3-nitrophenyl)methyl]–3–sulfanyl(1,2,4–triazole-
4-yl)}carboxamides.
 Part-I : Structures of the synthesized compounds
OH
O O

O NH O NH
N N
N N
S OH S
O O
N N

CH 3 Ar CH 3 Ar

Section : 1 Section : 2

F Cl
O O

O NH O NH
N N
N N
S S
O O
N N

CH 3 Ar CH 3 Ar

Section : 3 Section : 4

Where Ar = Different aryl group

Part-II : Structures of the synthesized compounds

O
O
O Ar O O
Ar O
N
N

N N NH N N NH
N R N

Where R = 4-Nitrophenyl
NO2
 Section : 5 Section : 6
Ar O O
CH2
Ar O O
N N NH O N NH
OC2H5
N N N NH P
N S OC2H5

Section : 7 Section : 8

Where Ar = Different aryl group

Part-III : Structures of the synthesized compounds

SH O
N Ar
SH O
N N NH
N Ar

Cl N N NH

CH2
O

Section : 9 Section :10

SH O SH O
N Ar N Ar

N N NH N N NH

CH2 CH2
O

NO2

Section : 11 Section : 12
 Where Ar = Different aryl group
Part-IV: Biological evaluation and characterization
The study in part four is divided into following two sections.

Section A: This section deals with the biological evaluation of the

compounds synthesised in part I, II and III.

Section B: In this section we will discuss the spectroscopic analysis of the

compounds reported in part I, II and III.

Signature of the guide Signature of the candidate

Prof. Nisheeth C. Desai Shihora Prashant Nanubhai
Date: 29/06/2007
Place: BHAVNAGAR