Pharmacy Project Report - Synthesis and Characterization of Some New Thiadiazole Derivatives
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REVIEW OF
LITERATURE
1.
Singh A.K., et. al.2009were
synthesized a series of 1,3,4
thiadiazole derivative from the
condensation of thiosemicarbazide and Benzoyl chloride. The derivatives which
they have prepared [N-( 5 (substituted) 1,3,4) thiadiazole-2-yl
benzamide] and found to be have
potential analgesic activity.
.
(I)
2.
Mathew V., et. al.2007 have synthesized several 3,
6-disubstituted-1, 2, 4-triazolo[3,4-
b]-1,3,4 thiadiazole and their
dihydro analogues. They found that anti-inflammatory and analgesic activity
screening of the tested compounds showed
good anti-inflammatory and analgesic activities.
(II)
3. Matysiak J., et. al.2006 have synthesized a
series of new 5-substituted 2(2,4 dihydroxy phenyl)-1,3,4-thiadiazolesand
evaluated for their antiproliferative activity against the cells of human
cancer lines.They found that Derivatives of different structures prove to be
the most active
(III)
4. Stillings M.R., et. al.1986 has described the anticonvulsants
properties of a number of substituted 2-hydrazino-1,3,4-Thiadiazole. Further
they found that, 2-(aminomethyl)-5-(2-biphenylyl)-1,3,4-Thiadiazole possess
potent anticonvulsants properties in rat and mice and compared favorably with
the standard drugs.
(IV)
5.
Shahar Y.M., et. al.2009 were
synthesized a series of five membered heterocyclics by the reaction between
isoniazide and various substituted isothiocyanates gives a new compound 2-(substituted
phenyl)amino-5-(4-pyridyl)-4H-1,3,4-thiadiazoles and were tested on albino
mice for their anticonvulsant which is
induced by electroconvulsometer.
(V)
6.
Foroumadi A., et. al.2007 were
synthesized a new compounds to protect
mice against convulsion induced by a lethal doses of pentylentetrazole (PTZ)
and maximal electroshock (MES).The result of anticonvulsant data shows that
synthesized compound 5-[4-chloro-2(2chlorophenoxy)phenyl]-N-ethyl-1,3,4-thiadiazol-2-amine
was the most active compound in both MES and PTZ.
(VI)
7. Aly A.A., et. al.2006
were synthesized a new compound N-imidazolylthiadiazolylamine
has been evaluated for antimicrobial activity in vitro using hole plate and
filter paper disc method in which different species of gram-positive and
gram-negative bacteria in addition to some fungal plant pathogens.
.
(VII)
8. Mohd.A., et. al.2008 were synthesized the
triazolo- thiadiazole derivatives
having dual functional properties (anti inflammatory-analgesic and
antimicrobial), and represent a promising class of compounds with an
interesting pharmacological profile.
(VIII)
9.
Khazi I.A.M., et .al.2009 were prepared some novel methylene bridged
benzisoxazolyl imidazo [2, 1-b][1,3,4]- thiadiazoles derivative has exhibited highest antibacterial activity.
The high activity is attributed to the presence of electron withdrawing chloro-
and bromo functional groups. Antifungal results indicated that compound showed
very good antifungal activity
comparable
to that of standard.
(IX)
10. Ahmed B.,
et.
al. 2008 have
synthesized a number of new imine derivatives of
5-amino-1,3,4-thiadiazole-2-thiol and their anti-depressant activity was tested
using imipramine as reference drug.
(X)
11. DabholkarV.V.,
et.
al.2011 have attempted1-(substitutedaroyl)-4-furoyl-thio
semicarbazides are synthesized under phase transfer catalysis, which on
cyclisation with perchloric acid in
acetic anhydride furnish perchloric acid salt of 2-(furoylamino)-5-(substituted
aryl)-1,3,4-thiadiazoles. The sulphur and nitrogen containing compounds were
screened for anti- bacteria.
(XI)
12. Gupta S.K., et. al.2011
have
prepared a new series of 5-(o-hydroxy
phenyl)-2-[4’aryl-3’chloro-2’azetidinon-1-yl]-1,3,4-thiadiazole. In vitro antifungal activity
(MIC activity) was evaluated and compared with standard drugs of ketoconazole.
Compounds has shown interesting
antifungal activity against both C. albicans and A. niger fungus.
(XII)
13.
Vasoya
S.L., et. al.2005,were
prepared 1,3,4-Thiadiazole derivatives by the cyclization of
arylthiosemicarbazides with
concentrated sulphuric acid. All the compounds were screened for their
antitubercular activity against Mycobacterium
tuberculosis and
antimicrobial activity against various microorganisms.
(XIII)
14. Solak N., et. al 2006 investigated a series
of new Schiff bases were synthesized through the condensation reaction of
1,3,4-thiadiazoles containing a aromatic primary amine and
3-hydroxybenzaldehyde, salicylaldehyde,5-nitrofurfuraldehyde and
3-nitrobenzaldehyde. The synthesized compounds screened for antituberculosis
activity against Mycobacterium tuberculosis H37 Rv using BACTEC 460
radiometric system. Among the tested compounds, 2-phenylamino-5-[4-(2-
hydroxybenzylideneamino)phenyl]-1,3,4-thiadiazole showed the highest inhibitory activity (51%).
(XIV)
15. Padmavathi., et. al.2008 synthesized a few
2-(aryl-methanesulfonylmethyl)-5-aryl-1,3,4-thiadiazoles and tested for in
vitro antimicrobial activity against Gram positive bacteria S.aureus,
B. subtilis., Gram negative bacteria Klebsiella pneumoniae, Proteus
vulgaris and Fungi Fusarium solania, Aspergillus niger, etc.
The presence of benzylsulfonyl group and chloro substituent enhances the
activity of the compound.
R
= 4-Cl., R' = 2-Cl
(XV)
RESEARCH ENVISAGED
After
the thorough study of the literatures it has seen that the thiadiazole
heterocyclic nucleus have potential to give various biological activities after
preparing its derivatives like antimicrobial, anticonvulsant, antidepressant,
anticancer etc. This study very much of helpful in exploring the structural
activity relationship to synthesize new derivatives of thiadiazole which may
have improved activity than in the literature already described. So after
observing all the literature it has concluded to attempt the synthesis of
thiadiazole containing compounds (3a-c) which
may provide better biological activity in future.
(3a-c)
Derivatives
|
R
|
3a
|
p-Cl
|
3b
|
p-NO2
|
3c
|
p-NH2
|
PLAN OF WORK
1. Review of literature.
2. Synthesis of thiadiazole derivatives (compound 3a-c)
3. Physicochemical characterization of derivatives:
a.
Appearance.
b.
Solubility.
c.
Melting point.
d.
Absorption
maxima by UV spectrometer.
e.
Rf value by TLC.
f.
Chemical test.
4. Structural characterization by :
a.
FTIR
b.
NMR
