CENTRAL ASIAN JOURNAL OF MEDICAL AND NATURAL SCIENCES

Volume: 05 Issue: 01 | Jan-Feb 2024 ISSN: 2660-4159

http://cajmns.centralasianstudies.org

SYNTHESIS, CHARACTERIZATION, AND STUDY OF

BIOLOGICAL ACTIVITY OF OXAZEPINE COMPOUNDS
DERIVED FROM 1,3,4-OXADIAZOLE
1. Maha Mahdi Saleh Abstract: This study involves the synthesis of pentagonal
2. Fawzi Hamid Juma rings of oxazepine derivatives through the reaction of one
mole of hydrazide base derivatives with two moles of
malic anhydride. The validity of the compound structures
was confirmed using physical and spectroscopic methods
Received 20th Nov 2023, such as UV-Vis. spectroscopy, infrared spectroscopy,
Accepted 28th Dec 2023,
Online 17th Jan 2024 proton nuclear magnetic resonance spectroscopy.
Additionally, melting points and purity were determined,
and reaction progress was monitored by Thin-Layer
1,2
Department of Chemistry / College of Chromatography (TLC). The impact of some prepared
Education for Women / Tikrit University compounds on the growth of two bacterial isolates, one
Gram-negative (Escherichia coli) and the other Gram-
positive (Staphylococcus aureus), was studied. Antibiotics
amoxicillin, ampicillin, and ciprofloxacin were used as
controls, and some of the prepared compounds showed
good inhibitory effectiveness against the tested bacteria.
Key words: Oxazepine, Schiff base, Hydrazide,
Biological activity, Escherichia coli, Staphylococcus
aureus.

1. Introduction [3]. This unique arrangement sets them apart

Oxazepine compounds have been captivating from other heterocyclic compounds, paving the
the attention of researchers and chemists alike, way for an exploration of their electronic and
as these chemical entities bring a unique blend steric properties [4]. Understanding the
of structure and functionality to the realm of methods of synthesizing oxazepine compounds
organic chemistry [1]. This topic delves into is crucial to unveiling their potential
the fascinating world of oxazepine compounds, applications [5]. Researchers have developed
shedding light on their intricate molecular diverse synthetic routes, ranging from
structure, synthesis methods, and the diverse traditional methods to cutting-edge techniques,
range of applications that make them stand out each presenting its own set of advantages and
in the scientific landscape [2]. At the heart of challenges [6]. Exploring these synthesis
the discussion lies the distinctive molecular pathways provides valuable insights into the
structure of oxazepine compounds, feasibility and efficiency of producing
characterized by a seven-membered ring oxazepine compounds on a laboratory scale [7].
containing one oxygen and two nitrogen atoms The functional diversity of oxazepine

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CAJMNS Volume: 05 Issue: 02 | Jan-Feb 2024
compounds is a key aspect of their allure. 2.3. Preparation of oxazepine derivatives
These compounds exhibit a wide range of (M32-M37) [18, 19]
biological activities, making them of interest in A mixture of 0.2 grams (0.0005 moles) of pre-
medicinal chemistry [8, 9]. From potential dissolved hydrazide bases in 25 mL of dry
pharmaceutical agents to innovative materials, benzene was combined with (0.098 grams,
oxazepine compounds offer a versatile palette 0.001 moles) of malic anhydride dissolved in
for researchers to explore and exploit [10]. This 15 mL of the same solvent. The mixture was
topic explores the biological and medicinal refluxed for a period of (6-10) hours, and the
significance of oxazepine compounds, completion of the reaction was verified using
highlighting their interactions with biological Thin-Layer Chromatography (TLC) technique.
systems and potential therapeutic applications After cooling, the mixture was filtered, washed
[11, 12]. From anticonvulsant properties to with cold water, and the resulting crystals were
anti-inflammatory effects, the pharmacological recrystallized using methanol [30, 31]. Table
potential of oxazepine compounds is a (1) illustrates the physical properties of the
promising avenue for further research and oxazepine derivatives.
development in the field of medicine [13, 14].
In conclusion, oxazepine compounds stand as a 2.4. Biological activity study [20, 21]
captivating subject within the realm of organic Two types of pathogenic bacteria were used in
chemistry, with their unique molecular this study, one of which is Gram-positive,
structure, diverse synthesis methods, and which is Staphylococcus aureus, and one of
potential applications across various domains which is Gram-negative, which is Escherichia
[15, 16]. As researchers continue to unravel the coli. These bacteria were taken from the
mysteries surrounding these compounds, the laboratories of the College of Education for
possibilities for advancements in medicine, Pure Sciences, Department of Life Sciences,
materials science, and beyond appear and the culture medium was used, a type of
boundless, making oxazepines a topic ripe for Multer Hinton Agar [39]. It is used to measure
exploration and discovery [17]. and determine the minimum inhibitory
2. Experimental: concentration (MIC), and chemical solutions of
2.1. Material: All chemicals used in this (M32, M34, M37) were prepared in
work were purchased from Fluka, concentrations (25, 50, 75) mg/ml and using a
Aldrich, and BDH and used without solvent Dimethyl sulfoxide (DMSO). The
further purification. sensitivity test for the bacteria isolates used in
the study was carried out by diffusion method
2.2. Devices used: The melting points were in the nutrient medium Mueller-Hinton agar.
measured using Electrothermal Melting The medium was prepared and sterilized by
Apparatus 9300. Shimadzu FT-IR 8400S autoclave, then distributed in dishes and left to
spectrophotometer with a scale of (400- harden, then small pits were made at a rate of
4000) cm-1 by KBr disc. 1H-NMR and
13 four holes in each plate. Then it was incubated
C-NMR spectra on Bruker instruments
at (37 0C) for a period of (24 hours). The
running at 400 MHZ. Shimadzu UV-1800 results were read on the next day to show the
spectrophotometer with quartz cells and derivatives sensitivity derivatives used, which
in the range of 200-800 nanometers, depends on the diameter of the inhibition
Tikrit University. Thin Layer evident in the dishes around the holes used, as
Chromatography (TLC) was performed the increase in diameter Inhibition means the
using Fluka silica gel plates with 0.2 mm increase in the biological activity of the
thickness, activated with fluorescent prepared compounds and compare that with the
silica gel G, and visualization was diameter of inhibition for antibiotics [22, 23].
achieved using UV light.

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3. Results and discussion
In this study, pentagonal rings of oxazepine derivatives were synthesized by reacting one mole of
Schiff bases derivatives with two moles of malic anhydride, as depicted in Scheme 1.

Scheme (1): Route of prepared compounds (M32-M37)

3.1. Characterization of oxazepine derivatives (M32-M37)
In this study, the Ultraviolet-Visible (UV-Vis) spectra of tetrazole derivative compounds were
examined using ethanol (95%) as a solvent, with concentrations ranging from (10-4-10-5) molar for the
prepared compounds. Short wavelength absorptions (λ1max) were observed at (210-257) nanometers,
attributed to (π→π*) transitions. Additionally, long wavelength absorptions (λ2max) in the range of
(299-386) nanometers were noted, associated with (π→n*) electronic transitions. The absorption
bands closely matched literature values [24, 25], as shown in Table (2), which provides absorption
values for the prepared tetrazole derivatives.
When studying the infrared spectrum of 1,3-oxazpine 7,4-dione derivatives, it was noted that the
azomethine band disappeared and an absorption band appeared in the range (3054-3092) cm-1, which
belongs to the stretching of the aromatic (CH) bond. Also, an absorption band appeared in the range
(2911-2991) cm-1 is due to the stretching of the aliphatic (CH) bond, and an absorption band appeared
in the range (1718-1727) cm-1 is due to the stretching of the carbonyl (C=O) lactone bond, and an
absorption band appeared in the range (1658-1674) cm- 1 It is due to the stretching of the carbonyl
chain (C=O) of the lactam, and an absorption band appeared in the range (1622-1635) cm-1 It is due to
the stretching of the carbonyl chain (C=N) in the oxadiazole ring. It was also observed that two
absorption bands appeared in the range (1575-1599 & 1475-1497) cm-1 is due to the stretching of the
aromatic (C=C) axis, and the appearance of an absorption band in the range (1308-1380) cm-1 is due
to the stretching of the (C-O) axis, and the appearance of an absorption band in the range (1245-1284)
cm-1 is due to Stretching the joint (C-N) [26, 27], as shown in Table (2) and Figures (1, 2).
When studying the 1H-NMR spectrum of the compound [M33] using a solvent (DMSO-d6), it was
observed that a single signal appeared at the chemical shift (8.85) ppm attributed to the protonation of
the two groups (CH) in the oxazan ring (c). A multiple signal in the range (7.99-8.62) ppm is attributed
to the protons of the aromatic rings (a, b, f), and a double signal appears at the chemical shift (7.67 and
7.64) ppm due to the proton of two groups (=CH) in the ring. The oxazan adjacent to the lactam group
(e), and the appearance of a double signal upon chemical displacement (7.09 and 7.08) ppm due to the
protonation of two groups (=CH) in the oxazan ring adjacent to the lactam group (d), and the
appearance of a single signal upon chemical displacement (3.33) Parts per million is attributed to the
protons of water (HDO), and a signal appears at the chemical shift (2.48). Parts per million is
attributed to the protons of the solvent (DMSO-d6) [28, 29], and as in Figure (3).
3.2. Evaluation of the Biological Activity of Prepared Compounds
Compounds with non-homogeneous rings exhibit varied biological activities against Gram-positive
and Gram-negative bacteria. In this dissertation, the biological activity of the prepared compounds was

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CAJMNS Volume: 05 Issue: 02 | Jan-Feb 2024
evaluated against two types of bacteria[30].: Escherichia coli and Staphylococcus aureus, selected due
to their medical significance as they cause various diseases. Additionally, these bacteria differ in their
antibiotic resistance profiles [31, 32]. The biological activity of prepared compounds was assessed
using the agar well diffusion method, measuring the inhibition zone diameter [33, 34]. The results
indicate that the prepared compounds possess the ability to inhibit the growth of both Gram-positive
and Gram-negative bacteria to varying degrees. The compounds exhibited significant inhibitory
activity against Escherichia coli and showed excellent inhibitory effects against Staphylococcus aureus
[35,36]. The relationship between concentration and inhibition was dose-dependent, with higher
inhibition percentages observed at a concentration of 75 milligrams per milliliter, as presented in Table
(3)
Table (1): Some physical properties of tetrazole derivatives.
Molecular Formula/ Time
Comp. R Color M.P (0C) Rf Y. %
M.Wt g/mol (h)
M32 Br C32H18N6O8Br2 / 774.34 Light brown 6 151-153 0.92 81
M33 Cl C32H18N6O8Cl2 / 685.43 Yellow 8 307-309 0.25 84
M34 NO2 C32H18N8O12 / 706.54 Yellow 10 288-289 0.48 76
M35 OH C32H20N6O10 / 648.54 Dark brown 7 239-240 0.38 62
M36 N(CH3)2 C36H30N8O8 / 702.68 Dark yellow 9 216-218 0.81 80
M37 CH3 C34H24N6O8 / 644.60 Orange 9 202-203 0.86 77
Table (2): Uv-Viv and FT-IR absorption results for oxazepine derivatives (M32-M37)
IR (KBr) cm-1
λ1,λ2
Comp. C=O
R max C-O, C-
No. C-H Lactone, C=N C=C Others
(nm) N
Lactam
M8 Br 235, 370 3054, 2913 1718, 1670 1631 1599, 1475 1308, 1246  (C-Br) 592
M9 Cl 210, 386 3091, 2943 1724, 1664 1622 1575, 1479 1371, 1284  (C-Cl) 729
(NO2) 1536,
M10 NO2 228, 302 3092, 2911 1727, 1671 1624 1599, 1496 1376, 1280
1321
M11 OH 256, 337 3087, 2965 1719, 1658 1626 1598, 1477 1345, 1243  (OH) 3400
(CH3) 2948,
M12 N(CH3)2 257, 299 3068, 2948 1724, 1674 1635 1593, 1492 1344, 1282
2844
(CH3) 2991,
M13 CH3 233, 321 3066, 2991 1725, 1666 1630 1589, 1497 1380, 1249
2875
Table (7): Biological effectiveness of prepared compounds and control treatments (inhibition in
mm).
Comp. No. Escherichia coil Staphylococcus aureus
Conc. mg/ml 25 50 75 25 50 75
M32 16 19 20 14 17 19
M34 15 16 21 15 19 22
M37 14 17 22 18 19 20
Amoxicillin 14 17 24 10 14 22
Ampicillin 10 16 22 14 20 24
Ciprofloxacin 12 17 21 15 18 21
Blank disk 0 0 0 0 0 0

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CAJMNS Volume: 05 Issue: 02 | Jan-Feb 2024

90

%T

75

993.27

906.48
1253.64
2837.09

729.04

497.60
1051.13

694.33
831.26

580.53
2943.17

1527.52
60

1107.06
1724.24
3091.68

1371.29

1166.85
1622.02

1479.30

1284.50
1575.73
1664.45
45

3000 2000 1500 1000 500

M33 1/cm

Figure (1): FT-IR spectrum of the compound (M33).

100

%T

90

567.03
80

680.83
815.83

513.03
2948.96

734.83
979.77
1085.85
1521.73

1166.85
1593.09
2844.81
3068.53

1635.52

70
1413.72

1282.57
1724.24

1492.80

1344.29
1674.10

60

3000 2000 1500 1000 500

M36 1/cm

Figure (2): FT-IR spectrum of the compound (M36).

Figure (3): 1H-NMR spectrum of the compound (M33).

4. Conclusions prepared compounds exhibit antibacterial
activity and have the ability to inhibit bacterial
The reaction of hydrazide derivatives with
growth. Some of these compounds even
compounds containing appropriate functional
displayed higher biological efficacy than the
groups often yields heterogeneous Heptagonal
antibiotics used as control samples. Physical
rings. Bioassay results indicate that most of the

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CAJMNS Volume: 05 Issue: 02 | Jan-Feb 2024
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