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Anticancer Study of Azo-Imine Heterocyclic Compounds

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 Emerging Trends in Chemical ISSN: 2349-4786 (Online)
Engineering Volume 11, Issue 1, 2024
DOI(Journal): 10.37591/ETCE
http://sciencejournals.stmjournals.in/index.php/etce/inde
STM JOURNALS
Research ETCE

Synthesis ,Spectral Investigation, Anticancer Study of Azo-Imine

Heterocyclic Compounds

Marwah Tahseen Neamah1 , Noor Saad Jaafer2

Abstract
Many Schiff base reactions are known within a famous series of addition reactions to the azomethine group, where
reagents are added to the polarized double bond and the nucleophilic (nucleophilic) reagents attack the carbon
atom in the azomethine bond.. An example of this type of reaction is the addition of alkyl halides, which produces
quaternary amine salts, which in turn are converted to the secondary amine. These compounds have an effective
role and great importance in many fields, as they are considered the starting material for the preparation of a large
number of heterocyclic compounds and their coordination complexes, as well as used in the preparation of large
molecular weight polymers. Various studies have also shown that the imine derivatives have biological activities.
In addition to its effectiveness in inhibiting various cancerous tumors and its importance in the medical and
pharmaceutical fields. It has been shown that the azomethine bond is responsible for this biological activity that
appears on Schiff bases.
Keywords: great compound, important, polar, composite..

INTRODUCTION
Schiff's rules are of great importance in many scientific, industrial and agricultural fields . They are of great
importance in life processes, for example in reactions involving the transfer of an imine group by a non-enzymatic
transfer reaction and some reactions accelerated by vitamin B6 [1-3]. Some of them are effective against cancer ,
and they are also effective against bacteria and fungi. They
*Author for Correspondence are considered fever reducers and pain relievers and are
Marwah Tahseen Neamah1 , Noor Saad Jaafer2 used as plant growth regulators. Since Schiff bases are
1,2
Assist. Lecturer., Department of Chemistry, College of sometimes multi-segment ligands, they form colored
Education for Girls, Kufa University, Iraq.
complexes with many metal ions, so they are considered a
Received Date: March 19. 2024 selective and sensitive method [4-6].
Accepted Date: March 27, 2024 To estimate metals , their industrial importance cannot be
Published Date: April 8, 2024 enumerated. The summary is that they are used as
antioxidants and catalysts in the processes of preparing
Citation: Marwah Tahseen Neamah , Noor Saad
Jaafer. Synthesis ,Spectral Investigation, Anticancer epoxy compounds and non-olefins. They are also used as
Study of Azo-Imine Heterocyclic Compounds. plasticizers and stabilizers for polymers and gasoline and as
Emerging Trends in Chemical Engineering. 2024; initiators of the polymerization process [7,8] Schiff's rules
11(01):22-43., were found to have two geometric similarities due to the
https://journals.stmjournals.com/etce/article=2024 spatial distribution around the double bond of the imine
/view=140946 group. If the group substituted on the nitrogen atom was the
syn-like, the stability of one with respect to the other
depends on the groups bonded to both carbon and nitrogen

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Emerging Trends in Chemical Engineering
Volume 11, Issue 1
I SSN: 2349-4786 (Online)

atoms, and any of the two like-types can be converted thermally or optically [9-12]. Since Schiff's bases have a
double chain, this confirms the existence of two geometric similarities [13-16], namely sys and trans. These two
isomers are found in the products of the reactions together. It is difficult to separate them, and this is due to the
rotation around the double bond between carbon and nitrogen [17-25] which arises due to the large difference in
electronegativity between carbon and nitrogen [26-31], which reduces the property of the double bond between the
two atoms due to polarization. [32-40].,Photo (1).

Photo. 1: Structure of Schiff base

Instruments and Experimental Part

The infra-red spectra were recorded in the frequency range (4000-400) cm-1 using KBr disc for ligands and CsI
disc in the frequency range (4000-200) cm-1 for their complexes by using (8400 SFTIR SHIMADZU
spectrophotometer). The spectra of 1 HNMR and 13CNMR were recorded BRUKER AV 400 Avance-III (400
MHz and 100MHz), Iran , using DMSO-d6 as the solvent, and anticancer assay against Breast cancer.

Experimental Procedures:
Preparation of Azo Compound {1}
Benzene-1,4-diamine (0.01 mole) dissolved in (3 ml) of hydrochloric acid (concentrated) with cold solution of
sodium nitrite ,then reacted with (0.02 mole) of acetyl acetone in basic medium to formation compound after
(48 hrs), the product filtered ,dried ,washed by distilled water, recrystallized to yield Compound [1] by following
procedures in literatures [9,11].

Preparation of Azo- Imine Derivative {2}

Azo compound {1} (0.01 mol) refluxed with (0.04 mol) of p-nitro amine for (4 hrs) with (a few drops) of glacial
acetic acid and absolute ethanol (50 ml), the product filtered ,dried ,recrystallized to yield Azo-Imine Derivative
{2} according to procedures [9,11].

Preparation of Azo- Four-Membered Derivative {3}

Azo –Imine compound {2} (0.01 mol) refluxed with (0.04 mol) of chloro acetyl chloride for (7 hrs) with triethyl
amine with chloroform ,then rotation for (3 hrs), the product filtered ,dried ,recrystallized to yield Azo-four
membered Derivative {3} according to procedures [9,11].

Preparation of Azo- Five-Membered Derivative {4}

Azo –Imine compound {2} (0.01 mol) refluxed with (0.04 mol) of mercapto acetic acid for (6 hrs) with ethanol
(40 ml), the product filtered ,dried ,recrystallized to yield Azo-five membered Derivative {4} according to
procedures [9,11].

Preparation of Azo- Five-Membered Derivative {5}

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Synthesis ,Spectral Investigation, Anticancer Study of Azo-Imine Heterocyclic Compounds Marwah and Noor

Azo –Imine compound {2} (0.01 mol) refluxed with (0.04 mol) of mercapto acetic acid for (6 hrs) with ethanol
(40 ml), the product filtered ,dried ,recrystallized to yield Azo-five membered Derivative {5} according to
procedures [9,11]., Scheme (1 ,2).

Scheme.1:Synthesis of Azo- Compounds {1 ,2}

Scheme.2: Synthesis of Azo-heterocyclic Compounds {3 , 4, 5}

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Emerging Trends in Chemical Engineering
Volume 11, Issue 1
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RESULTS AND DISCUSSION:

Spectral Characterization:
FT.IR- Spectra : The first characterization of Derivatives is appearance band of azo group at (1498 ,1588) for (-
N=N-) and carbonyl of ketone (-CO-) at (1710) in compound {1}., but in compound {2} appeared band of
(CH=N-) Imine group at (1620) Cm-1 and azo [23,24] at (1498 , 1589) in compound {2} and bands for nitro
group appeared [32-37] at (1398 ,1500)Cm-1 , all frequencies clarified according to reference [25] as Identification
reference of all Spectra ., and other functional groups in figures (1-5):

Fig(1): FT.IR of Azo- Derivative[1]

Fig(2): FT.IR of Azo-Imine Derivative[2]

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Synthesis ,Spectral Investigation, Anticancer Study of Azo-Imine Heterocyclic Compounds Marwah and Noor

Fig(3): FT.IR of Azo-Cycle Derivative[3]

Fig(4): FT.IR of Azo-cycle Derivative[4]

Fig(5): FT.IR of Azo-cycle Derivative[5]

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1
H.NMR-Spectra : The portrayal of spinoffs via desertion of topmost for Imine assembly (CH=N) in next
compound{2} (aldamine compound) that were at δ (8.50) in Compound {3 ,4, 5} as (a initial composite) owed to
realization combinations [3 ,4, 5] and realization novel four-membered ring ,totally topmost enlightened
bestowing to orientation as Documentation mention [25] of totally Bands (6-10).

Fig(6): H.NMR- Spectrum of Azo Derivative[1]

Fig(7): H.NMR- Spectrum of Azo-Imine Derivative[2]

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Synthesis ,Spectral Investigation, Anticancer Study of Azo-Imine Heterocyclic Compounds Marwah and Noor

Fig(8): H.NMR- Spectrum of cycle Derivative[3]

Fig(9): H.NMR- Spectrum of cycle Derivative[4]

Fig(10): H.NMR- Spectrum of cycle Derivative[5]

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Emerging Trends in Chemical Engineering
Volume 11, Issue 1
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13
C.NMR- spectra: The characterization of Derivatives by appearance peak of carbon atom carbonyl of ketone
(CO-) appeared [226-28] at (173.73) in compound {1} but in compound {2} the carbonyl of ketone disappeared
[29-33] but other peak appeared for Imine group (C=N) [34,35] in compound (Imine compound) that were at δ
(156. 98) by flowing reference [25] as Identification reference of all Spectra in figures (11-15).

Fig(11): C.NMR- Spectrum of Azo Derivative[1]

Fig(12): C.NMR- Spectrum of Azo-Anil Derivative[2]

Fig(13): C.NMR- Spectrum of cycle Derivative[3]

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Synthesis ,Spectral Investigation, Anticancer Study of Azo-Imine Heterocyclic Compounds Marwah and Noor

Fig(14): C.NMR- Spectrum of cycle Derivative[4]

Fig(15): C.NMR- Spectrum of cycle Derivative[5]

Anticancer Study
Line processing and implantation of breast cancer cells and live cell line were carried out at Biotechnology Center
– in Tehran University (MCF-7 cell line) and (MCF- 10 A cell line grew in 95% of RPMI–1640) supplemented
with (10% FBS), cell suspension and incubation at (37 °C) in incubator {(CO2) % 5} according to study [9], all
data in Tables(1, 2, 3, 4).

Table. (1): Cytotoxic Activity of Compound{1} on Breast Cancer Cells line (MCF-7) and Healthy Cells
(MCF-10A) at the same concentration using 24 hrs ., MTT test 370c.
Con.( μg.mL−1) Mean Percentage (%) for each cell line
MCF-7 MCF-10A
Cancerous line cells of MCF-7 Normal line cells of MCF-10A
Compound {1}
Cell Viability Cell Inhibition Cell Viability Cell Inhibition
6.25 84.11 20.93 94.83 1.11
12.5 72.12 31.39 94.81 4.2
25 47.54 53.63 925.46 5.56
50 41.33 57.65 90.94 7.06
100 37.22 67.74 70.92 18.03

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Table. (2 ): Cytotoxic Activity of Compound{2} on Breast Cancer Cells line (MCF-7) and Healthy Cells
(MCF-10A) at the same concentration using 24 hrs ., MTT test 370c.

Con.( μg.mL−1) Mean Percentage (%) for each cell line

MCF-7 MCF-10A
Cancerous line cells of MCF-7 Normal line cells of MCF-10A
Compound {2}
Cell Viability Cell Inhibition Cell Viability Cell Inhibition
6.25 60.45 26.25 94.54 4.43
12.5 54.98 38.14 94.41 4.54
25 41.91 51.00 81.63 11.31
50 30.52 58.99 75.83 18.17
100 22.89 70.10 64.01 28.90

Table. (3): Cytotoxic Activity of Compound{3} on Breast Cancer Cells line (MCF-7) and Healthy Cells
(MCF-10A) at the same concentration using 24 hrs ., MTT test 370c.

Con.( μg.mL−1) Mean Percentage (%) for each cell line

MCF-7 MCF-10A
Cancerous line cells of MCF-7 Normal line cells of MCF-10A
Compound {3}
Cell Viability Cell Inhibition Cell Viability Cell Inhibition
6.25 60.23 30.12 90.06 3.74
12.5 52.64 41.02 90.41 4.53
25 40.93 52.18 80.19 9.77
50 26.51 66.43 70.46 13.47
100 16.19 68.11 61.24 22.25

Table. (4 ): Cytotoxic Activity of Compound{4} on Breast Cancer Cells line (MCF-7) and Healthy Cells
(MCF-10A) at the same concentration using 24 hrs ., MTT test 370c.
Con. ( μg.mL−1) Mean Percentage (%) for each cell line
MCF-7 MCF-10A
Cancerous line cells of MCF-7 Normal line cells of MCF-10A
Compound {4}
Cell Viability Cell Inhibition Cell Viability Cell Inhibition
6.25 58.26 32.84 90.33 2.13
12.5 50.55 43.66 88.91 5.53
25 40.13 53.02 82.89 10.92
50 30.17 58.93 70.73 20.17
100 16.81 71.09 62.01 24.00

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Synthesis ,Spectral Investigation, Anticancer Study of Azo-Imine Heterocyclic Compounds Marwah and Noor

Conclusions
From the results ,we noted that all spectral studies gave strong bands for new compounds and all compounds
have anticancer results and good results towards inhibition of cancer cells. The physical and chemical behavior
of these compounds varies depending on the heterogeneous ring, as there is a difference in basic properties,
solubility in polar and non-polar solvents, and the colors of the compounds when they dissolve in the various
solvents. The effectiveness of these compounds also varies depending on the hybrid atom.

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