Synthesis and characterization of various alkyl, aryl and hetero aryl substituted hydrazines and study of their biological activity

Article abstract of DOI:10.13005/ojc/330262

Due to the presence of N-N linkage hydrazines are well-known for their diverse biological activity.N-N linkage has been used as a key structural motif in various bioactive agents. A series of aryl, alkyl and hetero aryl substituted hydrazine derivatives has been synthesized, for this diazotization of alkyl, aryl amines has been done, followed by reduction with stannous chloride or sodium sulfite. All synthesized compounds were characterized by elemental analysis, IR, 1H-NMR, Mass spectra and their biological activity has been studied.

Full text of DOI:10.13005/ojc/330262

ISSN: 0970-020 X
CODEN: OJCHEG
017, Vol. 33, No. (2):
Pg. 1041-1044
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
2
www.orientjchem.org
Synthesis and Characterization of Various Alkyl, Aryl and
Hetero Aryl Substituted Hydrazines and Study of their
Biological Activity
ANIL GUPTA and POONAM GOKLANI
P.G. Department of Chemistry, Govt. Dungar College, Bikaner, India.
*
Corresponding Author E-mail: anil362@gmail.com
http://dx.doi.org/10.13005/ojc/330262
(Received: January 20, 2017; Accepted: April 06, 2017)
ABSTRACT
Due to the presence of N-N linkage hydrazines are well-known for their diverse biological
activity.N-N linkage has been used as a key structural motif in various bioactive agents. A series of
aryl, alkyl and hetero aryl substituted hydrazine derivatives has been synthesized, for this diazotization
of alkyl, aryl amines has been done, followed by reduction with stannous chloride or sodium sulfite.
All synthesized compounds were characterized by elemental analysis, IR, 1H-NMR, Mass spectra
and their biological activity has been studied.
Keywords: Hydrazine derivatives, N-N linkage,Biological activity, Diazotization.
INTRODUCTION
based peptidomimetics, were found to be potent
7
,8,9
against hepapititas, AIDS & SARS .Hydrazines
derivatives occur naturally in tobacco and
mushrooms,p-tolylhydrazine(bioactive molecule)
isolated as a degradation product from the
mushroom Agaricus bisporus, was found to be
highly active compared to 5-flourouracil in vitro
Among the nitrogen-nitrogen bond
containing chemical the hydrazines are well-known
for their diverse biological activity and as therapeutic
agents in medicines. Many hydrazine derivatives
are known to exhibit significant biological activity
and several compounds with hydrazine moiety were
shown to be effective for treatment of tuberculosis,
10
anticancer studies
.
1
Parkinson’s disease and hypertension .Hydrazines
Diacylhydrazines have been identified
shows neuroprotective, antitumor antidepressant
as one of the most important types of insect
2,3,4,5
11-13
and antimicrobial properties
.
regulators
. Several commercial compounds,
such as tebufenozide, methoxyfenozide,
chromafenozide,and halofenozide, are all classified
as diacylhydrazines, and all of these insecticides
The hydrazine moiety has been used for
modification of peptides .Azapeptides hydrazine
6

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GUPTA et al., Orient. J. Chem., Vol. 33(2), 1041-1044 (2017)
affect the ecdysonereceptor complex, leading to binding propensity towards the
thymidylate
14,15
16
precociouslethalmolting, especiallyincaterpillars
.
synthase .
MATERIALS AND METHODS
All the reactions were carried out with
Diacylhydrazines have attracted significant attention
because of their high insecticidal selectivity,simple
13
structure, and low toxicity to vertebrates
.
Arylhydrazides and hydrazine compounds A.R. grade chemicals. The C.P. grade chemicals,
shows anticancer activity against 5 cancer cell whenever used, were purified by standard methods.
lines namely A-549, SK-N-SH, HEP-2, PC-3 and All m.p. were determined on aYanaco micro-melting
MCF-7. Gallic acid hydrazide found to be most point apparatus and were uncorrected. Elemental
active,having high scores, indicating highest analysis was get done at CDRI Luckhnow. IR
spectra were taken on a Perkin Elmer System
2000 FT-IR Spectrophotometer, in KBr pellets.
EI-mass spectra were recorded on a VG Biotech
Scheme 1: Synthesis of Hydrazine Derivatives
Table 1: physical characteristics and analytical data of the compounds investigated
Compound Colour
Molecular
mass
Elemental Analysis
Melting
Point C
Molecular
formula
o
g/lmole
C%
H%
N%
O%
1
2
Yellow Powder
160
153
60
47.05
5
4.5
35
27.4
172.50
156
C H N
4
C H N O
6 7 3 2
8
8
Orange-red
needle shaped
crystal
20.9
3
Clear Liquid
136
70.5
8.8
20.5
22, B.P.74
C H N
8 12 2
Table 2: IR spectral data of the compounds investigated in cm-1
Compound
VN-H
VN-N
VC-H
VC-C
VC-N
VC=N
1
2
3
3304, 3411 1373
3000, 2976 1540, 1465
3087 1532, 1501
3020, 2850 1610, 1118
1289
1596, 1668
3322,3202
3405
1377
1395
1341, 1315 1600, 1559
1310
Quattro 5022 spectrometer. 1H-NMR spectra
were recorded on a Bruker AMX-500 in CDCl3
and silica gel 60 F-254 for TLC preparation. TLC
optical rotations were measured using a Jasco DIP
and chemical shifts are given in ppm with TMS
-
370 Polarimeter in CHCl3 .
as internal standard .Silica gel was used for CC

GUPTA et al., Orient. J. Chem., Vol. 33(2), 1041-1044 (2017)
1043
Table 3: NMR and Mass spectral data of the compounds investigated
Compound
Mass
Spectra
m/z
NMR Spectra(ppm)
1
2
3
160
153
136
d 9.25(d,J=1.8Hz,1H,),d 8.05(m,J=7.4,1.7Hz,1H,aromatic),d 7.91(m,2H),d
.88(m,2H,aromatic),d 8.32(m,1H,aromatic),d 4.73(2H,d,J=3.1Hz,NH2)
d 4.58(1H,m,NH)
d 8.14(m,J=8.4,1.4Hz,1H,aromatic),d 7.7(m,J=8.4,1.6Hz,1H,aromatic)
d 7. 13(m,J=7.7,1.6Hz,1H,aromatic),d 6.84(m,J=8.4,1.6Hz,1H,aromatic),
d 5.0 9(t,J=3.0Hz,0H,NH),d 2.93(d,J=2.9Hz,1H,NH2)
7
d 2.07(d,J=3.5Hz,2H,NH ),d 2.84(tt,J=3.5,2.7Hz,1H,NH),d 3.07(td,J=5.5,
2
2
.6Hz,2H,CH ),d 2.74(tt,J=5.4,1.0Hz,2H,CH -
2
2
C=C),d 7.24(m,3H,aromatic),d 7.29(m,2H,aromatic)
Synthesis of compounds
hydrazine derivatives were synthesized.
ANALYSIS
Compound3 shows antidepressant activity
Alkyl,aryl and hetero aryl substituted
. It is a non-selective momoamine oxidase (MAO)
inhibitor commonly used to treat depression and
panic disorder.It is checked by the behavioral
despair test (porsolt –forced swimming test).
17-19
BIOLOGICAL ACTIVITY
RESULTS and DISCUSSIONS
All the synthesized compounds have been
tested for their biological activity.
Compounds were synthesized from their
respective amines. Synthesized compounds
shows antihypertensive , antidepressant and
Compound 1 shows antihypertensive
activity. It can be used to treat high blood
pressure, which helps in preventing strokes, heart
attacks and kidney problem. For thisNon-invasive
anticarcinogenic activity.Compound
2 shows
anticancer activity against SK-N-SH cancer cell
line with IC = 29µg/ml.
50
(
Tail cuff method) has been used.
AKNOWLEDGEMENTS
Compound 2 shows anticancer activity
against SK-N-SH (CNS) cancer cells.Thisactivity of
the compounds have been test by MTT essay.
The author is thankful to Dr. Anil Gupta for
their guidance in the research work and grateful to
Govt. Dungar College Bikaner for providing facilities
to carry out the work.
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