Microwave Assisted Synthesis, Characterization and Antibacterial Study of Some Novel Schiff's Bases and Azetidinone Compounds derived from Ibuprofen

 

Hanan A. Al-Hazam¹, Suha K. Al-Mosawi², Zeki A. Naser Al-Shamkhani¹

¹Department of Chemistry, College of Science, University of Basrah, Basrah-Iraq

²Department of Pharmaceutical Chemistry, College of Pharmacy, University of Basrah, Basrah-Iraq

*Corresponding Author E-mail: alshamkhani.zeki74@gmail.com

 

 

INTRODUCTION:

Ibuprofen was discovered in 1961 by Stewart Adams and initially marketed as Brufen⁽¹⁾ It is available under a number of trade names, including Advil and Motrin^(2-4). It was first marketed in 1969 in the United Kingdom and in the United States in 1974.^(5-7) It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.⁽⁸⁾ It is available as a generic medication.^[6] Ibuprofen is a medication in the nonsteroidal anti-inflammatory drug (NSAID) class that is used for treating pain, fever, and inflammation⁽⁹⁾. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It typically begins working within an hour. Ibuprofen is practically insoluble in water, but very soluble in most organic solvents like ethanol (66.18g/100mL at 40 °C for 90% EtOH), methanol, acetone and dichloromethane.

 

The original synthesis of ibuprofen by the Boots Group started with the compound 2-methylpropylbenzene. The synthesis took six steps. A modern, greener technique for the synthesis involves only three steps .

 

The chemistry of Schiff base plays a vital role in the progress of chemistry science⁽¹¹⁾, synthesis of Schiff base through classical condensation of aldehydes (or ketone) and imines were pursued⁽¹²⁾ Schiff base are characterized by the N=CH- (imine) group which is important in elucidating the mechanism of transformation in biological systems. Due to great flexibility and diverse structural aspects, wide range of Schiff bases have been synthesized and their complexion behavior was studied ⁽¹³⁾. Furthermore, Schiff base are reported to show a variety of interesting biological activities, including antibacterial⁽¹⁴⁾, antifungal⁽¹⁵⁾, anticancer^(16,17) and herbicidal activities⁽¹⁸⁾. The wide range of biological activities exhibited by azetidinone⁽¹⁹⁾ derivatives, the aim of this study is to prepare azetidinone containing mefenamic acid in the molecule and to explore the pharmacological activity of this combination product. Azetidinone is a heterocyclic compound of four-membered unsaturated ring structure composed of three carbon atoms and nitrogen atoms at nonadjacent positions. The chemistry of azetidinone compounds have been of much interest due to the presence of such heterocycles in a large variety of biologically important molecules⁽²⁰⁾.

 

EXPERIMENTAL:

Melting point were determined in Gallen Kamp melting point apparatus and were uncorrected, Elemental analysis (CHN) were recorded in EA300 Euro-Vector in University of Al-albyat in Jordon. FT-IR Spectra were recorded on Shimadzu FT-IR 8400 Fourier Transformer infrared as KBr disk. Ultraviolet spectra were recorded in spectro scan 80 in the wavelength 200-800 nm. ¹HNMR and ¹³CNMR spectra were recorded on Brucker spctro spin ultra shield magnets400MHz instrument using tetramethyl silane (TMS) as an internal standard and DMSO-d6 as a solvent in university of Tabriz-Iran. Thin layer chromatography were performed on pre-coated sheets with 0.25 mm layer of Slica Gel GF254 of the Merck company.

 

Synthesis of Compounds:

1) Preparation of Hydrazide Derivative (I):

An equimolar mixture of ibuprofen (0.01M) and hydrazine hydrate (0.01M, 99%) in 30 ml ethanol was placed in small conical flask at room temperature then the mixture exposed to microwave irradiation at 300w for 3min., the solid separated on cooling was filtered, washed several times with water, dried and recrystallized from alcohol (M.P: 88-90^oC). FT-IR spectra νmax 3222, 3220, 3030, 2988, 1691, 1452, 1202, 712cm^-1.

 

2) Synthesis Schiff Base (II):

A mixture of ibuprofen hydrazide (1mmole) and aldehyde (1mmole) were dissolved in ethanol (40ml). Drops of acetic acid was added and was placed in small conical flask at room temperature then the mixture exposed to microwave irradiation at 270w for 4min, This reaction was monitored by TLC. The resultant solution was cooled and poured in cold water. The separated solid was filtered, crystallized from ethanol to give crystalline yellow.

 

H-yield 77%, Melting point 114-116^oC, CHN analysis that formula C₂₀H₂₄N₂O Calculated C, 77.893 H, 7.840N, 6.087; Found C, 77.765 H, 7.462 N, 5.814. Ultraviolet spectra λmax 240, 255, and 330. FT-IR spectraν max 3222, 3050, 2964, 1690 1620, 1454, 1217,752cm^-1.¹HNMR spectra δppm, (11.2, 1H), (8.5, 1H) (7.3, 5H), (7.2, 2H), (7.0, 2H), (2.32,2H), (1.28,3H),(1.0, 1H) and (1.7, 6H).¹³CNMR spectra δppm, 22, 30,54, 67, 113, 113, 114, 115,125, 127, 142, 145, 151, 164, 180.

 

 

NO₂ yield 72%, Melting point 157-159^oC, CHN analysis that formula C₂₀H₂₃N₃O₃Calculated C, 67.697 H, 6.560N, 11.897; Found C, 67.512 H, 6.233 N, 11.565. Ultraviolet spectra λmax 242, 260, and 325. FT-IR spectraν max 3224, 3010, 1693, 1618, 1466, 1210, 790cm^-1.¹HNMR spectra δppm, , (11.0, 1H), (8.3, 1H) (7.7, 4H), (7.4, 2H), (6.9, 2H), (2.30,2H), (1.17,3H),(1.0, 1H) and (1.71, 6H).¹³CNMR spectra δppm, 20, 37,60, 78, 111, 113, 119, 122,125, 129, 141, 145, 165, 179, 181.

 

Cl yield 81%, Melting point 125-127^oC, CHN analysis that formula C₂₀H₂₃ClN₂OCalculated C, 70.063 H,6.762 N, 8.174; Found C, 69.885 H, 6.212 N, 7.994. Ultraviolet spectra λmax 230, 242, and 300. FT-IR spectraν max 3205, 3100. 2988, 1689, 1612, 1375, 1220, 810cm^-1.¹HNMR spectra δppm, (11.0, 1H), (8.0, 1H) (7.9, 4H), (7.2, 2H), (7.0, 2H), (2.22,2H), (1.20,3H),(1.0, 1H) and (1.78, 6H).¹³CNMR spectra δppm, 15, 27,34, 57, 120, 120, 128, 129,133, 137, 147, 149, 157, 174, 185.

 

Br yield 75%, Melting point 185-187^oC, CHN analysis that formula C₂₀H₂₃BrN₂OCalculated C, 62.023 H, 5.998N, 7.234; Found C, 61.885 H, 5.763 N, 7.015. Ultraviolet spectra λmax 230, 250, and 320. FT-IR spectraνmax 3280, 3050, 1690, 1600, 1384, 1200, 851cm^-1.¹HNMR spectra δppm, (11.2, 1H), (8.2, 1H) (7.7, 4H), (7.2, 2H), (7.0, 2H), (2.02,2H), (1.27,3H),(1.0, 1H) and (1.55, 6H).¹³CNMR spectra δppm, 18, 29,39, 56, 122, 123, 128, 129,133, 139, 154, 156, 157, 170, 188.

 

Fyield 77%, Melting point 108-110^oC, CHN analysis that formula C₂₀H₂₃FN₂OCalculated C, 73.593 H, 7.102N, 8.587; Found C, 73.365 H, 6.962 N, 8.214. Ultraviolet spectra λmax 240, 255, and 330. FT-IR spectraνmax 3200, 3050, 2964, 1691 1620, 1454, 1217,752cm^-1.¹HNMR spectra δppm, (11.7, 1H), (8.8, 1H) (8.1, 4H), (7.7, 2H), (7.4, 2H), (2.00,2H), (1.35,3H), (1.0, 1H) and (1.99, 6H).¹³CNMR spectra δppm, 13, 27,33, 60, 120, 120, 128, 129,133, 137, 140, 149, 161, 174, 185.

 

CH₃yield 84%, Melting point 166-168^oC, CHN analysis that formula C₂₁H₂₆N₂OCalculated C, 78.227 H, 8.130N, 8.697; Found C, 77.982 H, 7.993 N, 8.565. Ultraviolet spectra λmax 242, 260, and 325. FT-IR spectraνmax 3250, 3010, 2985, 1694, 1618, 1466, 1210, 790cm^-1.¹HNMR spectra δppm, (11.0, 1H), (8.2, 1H) (7.7, 4H), (7.2, 2H), (7.0, 2H), (2.15,2H), (1.20,3H),(1.62,3H),(1.0, 1H) and (1.78, 6H).¹³CNMR spectra δppm, 15,17, 27,34, 57, 120, 120, 128, 129,133, 137, 147, 149, 157, 174, 185.

 

 

OCH₃ yield 79%, Melting point 185-187^oC, CHN analysis that formula C₂₁H₂₆N₂O₂Calculated C, 74.533 H,7.742 N, 8.284; Found C, 74.185 H, 7.552 N, 8.004. Ultraviolet spectra λmax 230, 242, and 300. FT-IR spectraνmax 3218, 3105. 2988, 1688, 1612, 1375, 1220, 810cm^-1.¹HNMR spectra δppm(11.4, 1H), (8.1, 1H) (7.8, 4H), (7.2, 2H), (7.0, 2H),(3.89, 3H), (2.02, 2H), (1.27,3H),(1.0, 1H) and (1.55, 6H).¹³CNMR spectra δppm, 17, 29,40, 56, 90, ,122, 125, 128, 130,133, 139, 154, 156, 159, 174, 182.

 

OH yield 83%, Melting point 115-116^oC, CHN analysis that formula C₂₀H₂₄N₂O₂Calculated C, 74.053 H, 7.468N, 8.634; Found C, 73.885 H, 7.263 N, 8.215. Ultraviolet spectra λmax 230, 250, and 320. FT-IR spectraνmax 3300, 3180, 3050, 1691, 1600, 1384, 1200, 851cm^-1.¹HNMR spectra δppm, (11.7, 1H),(10.2, 1H) (8.8, 1H) (8.1, 4H), (7.7, 2H), (7.4, 2H), (2.00,2H), (1.35,3H),(1.0, 1H) and (1.99, 6H).¹³CNMR spectra δppm, 13, 27,37, 62, 120, 125, 128, 130,135, 137, 140, 149, 166, 170, 181.

 

N(CH₃)₂ yield 75%, Melting point 134-136^oC, CHN analysis that formula C₂₂H₂₉N₃OCalculated C, 75.183 H,8.322 N, 11.958; Found C, 74.891 H, 8.255 N, 11.644. Ultraviolet spectra λmax 230, 242, and 300. FT-IR spectraνmax 3214, 3100. 2985, 1688, 1612, 1375, 1220, 810cm^-1.¹HNMR spectra δppm, (11.0, 1H), (8.2, 1H) (7.7, 4H), (7.2, 2H), (7.0, 2H), (2.15,2H), (1.20,3H),(3.62, 6H),(1.0, 1H) and (1.78, 6H).¹³CNMR spectra δppm, 19,27, 37,44, 57, 121, 121, 128, 129,134, 139, 147, 150, 162, 177, 181.

 

Van yield 78%, Melting point 197-199^oC, CHN analysis that formula C₂₁H₂₆N₂O₃Calculated C, 71.163 H, 7.392N, 7.904; Found C, 70.915 H, 7.069 N, 7.715. Ultraviolet spectra λmax 230, 250, and 320. FT-IR spectraνmax 3195, 3050, 1693, 1600, 1384, 1200, 851cm^-1.¹HNMR spectra δppm(11.0, 1H),(10.2, 1H), (8.0, 1H) (7.9, 4H), (7.1, 2H), (7.0, 2H),(3.78, 3H), (2.32, 2H), (1.22,3H),(1.0, 1H) and (1.55, 6H).¹³CNMR spectra δppm, 17,30,41, 57, 92, ,120, 125, 127, 130,135, 139, 155, 157, 159, 179, 180.

 

2) Synthesis Azetidinone (III):

A mixture of ibuprofen hydrazide (1mmole) and aldehyde (1mmole) were dissolved in ethanol (40ml). Drops of acetic acid was added and was placed in small conical flask at room temperature then the mixture exposed to microwave irradiation at 270w for 4min, This reaction was monitored by TLC. The resultant solution was cooled and poured in cold water. The separated solid was filtered, crystallized from ethanol to give crystalline yellow.

 

 

H yield 76%, Melting point 145-146^oC, CHN analysis that formula C₂₂H₂₅ClN₂O₂Calculated C, 68.653 H, 6.550N, 7.287; Found C, 68.465 H, 6.162 N, 7.014. Ultraviolet spectra λmax 240, 255, and 330. FT-IR spectraνmax 3200, 3050, 2964, 1691, 1688, 1454, 1217,752cm^-1.¹HNMR spectra δppm, (11.0, 1H), (7.9, 5H), (7.2, 4H), (4.0, 1H) ,(4.5, 1H) (2.32,2H), (1.28,3H), (1.0, 1H) and (1.7, 6H).¹³CNMR spectra δppm, 22, 30,54, 67, 70, 86, 100, 110,125, 127, 142, 145, 151, 164,170, 175, 180, 185.

 

NO₂ yield 75%, Melting point 170-171^oC, CHN analysis that formula C₂₂H₂₄ClN₃O₄Calculated C, 61.477 H, 5.630N, 9.767; Found C, 61.112 H, 5.233 N, 9.565. Ultraviolet spectra λmax 242, 260, and 325. FT-IR spectraνmax 3250, 3010, 1694, 1688, 1466, 1210, 790cm-1.1HNMR spectra δppm, (11.3, 1H), (7.7, 4H), (7.0, 4H), (4.1, 1H) ,(4.4, 1H) (2.12, 2H), (1.20, 3H), (1.2, 1H) and (1.71, 6H).¹³CNMR spectra δppm, 22, 30,54, 67, 77, 80, 85, 80,120, 127, 144, 149, 154, 166,172, 175, 181, 184.

 

Cl yield 90%, Melting point 145-147^oC, CHN analysis that formula C₂₂H₂₄Cl₂N₂O₂Calculated C, 63.013 H,5.772 N, 6.68; Found C, 62.885 H, 5.212 N, 6.394. Ultraviolet spectra λmax 230, 242, and 300. FT-IR spectraνmax 3210, 3100. 2988, 1691, 1688, 1375, 1220, 810cm-1.¹HNMR spectra δppm, (10.7, 1H), (7.5, 5H), (7.0, 4H), (4.2, 1H) ,(4.5, 1H) (2.18, 2H), (1.24, 3H), (1.2, 1H) and (1.73, 6H).¹³CNMR spectra δppm, 22, 30,54, 67, 76, 80, 95, 112,125, 129, 142, 148, 151, 160,170, 175, 182, 188.

 

Br yield 85%, Melting point 210-212^oC, CHN analysis that formula C₂₂H₂₂BrClN₂O₄Calculated C, 56.973 H, 5.338N, 6.044; Found C, 56.885 H, 5.063 N, 3.915. Ultraviolet spectra λmax 230, 250, and 320. FT-IR spectraνmax 3180, 3050, 1693, 1688, 1384, 1200, 851cm^-1.¹HNMR spectra δppm, (11.1, 1H), (7.0, 5H), (6.8, 4H), (4.0, 1H) ,(4.3, 1H) (2.02, 2H), (1.20, 3H), (1.2, 1H) and (1.71, 6H).¹³CNMR spectra δppm, 20, 33,44, 57, 72, 87, 90, 110,123, 127, 132, 145, 155, 168,175, 177, 181, 185.

 

F yield 85%, Melting point 102-104^oC, CHN analysis that formula C₂₂H₂₂FClN₂O₄Calculated C, 65.593 H, 6.002 N, 6.957; Found C, 65.365 H, 5.862 N, 6.774. Ultraviolet spectra λmax 240, 255, and 330. FT-IR spectraνmax 3200, 3050, 2964, 1691, 1688, 1620, 1454, 1217,752cm-1.¹HNMR spectra δppm, (10.7, 1H), (7.4, 5H), (7.2, 4H), (4.1, 1H) ,(4.5, 1H) (1.96, 2H), (1.38, 3H), (1.1, 1H) and (1.74, 6H).¹³CNMR spectra δppm, 25, 36,57, 68, 79, 80, 92, 111,119, 127.3, 132, 140, 151, 164, 177, 179, 185, 187.

 

 

CH₃ yield 75%, Melting point 170-172^oC, CHN analysis that formula C₂₃H₂₇ClN₂O₄Calculated C, 69.257 H, 6.820N, 7.027; Found C, 69.112 H, 6.233 N, 6.885. Ultraviolet spectra λmax 242, 260, and 325. FT-IR spectraνmax 3250, 3010, 1694, 1688, 1466, 1210, 790cm^-1.¹HNMR spectra δppm, (11.0, 1H), (7.9, 5H), (7.3, 4H), (4.3, 1H) ,(4.5, 1H) (2.32, 2H),(2.28, 3H), (1.28, 3H), (1.2, 1H) and (1.70, 6H).¹³CNMR spectra δppm, 17,20,33, 45, 70, 79, 90, 110,125, 127, 138, 145, 151,164,167, 170, 177, 182.

 

OCH₃ yield 80%, Melting point 195-197^oC, CHN analysis that formula C₂₂H₂₂ClN₂O₃ Calculated C, 66.583 H, 6.562 N, 6.752; Found C, 66.385 H, 6.212 N, 6.394. Ultraviolet spectra λmax 230, 242, and 300. FT-IR spectraνmax 3210, 3100. 2988, 1691, 1688, 1375, 1220, 810cm^-1.¹HNMR spectra δppm, (11.0, 1H), (7.9, 5H), (7.2, 4H), (4.0, 1H) ,(4.5, 1H), (3.58, 3H) (2.32, 2H), (1.28, 3H), (1.2, 1H) and (1.7, 6H).¹³CNMR spectra δppm, 16,24,35, 55, 67, 82, 102, 110,120, 127, 130, 145, 157, 164,172, 175, 183, 187.

 

OH yield 79%, Melting point 115-117^oC, CHN analysis that formula C₂₂H₂₅ClN₂O₃Calculated C, 65.913 H, 6.298N, 6.994; Found C, 65.885 H, 5.963 N, 6.715. Ultraviolet spectra λmax 230, 250, and 320. FT-IR spectraνmax 3350, 3180, 3050, 1693, 1687, 1384, 1200, 851cm^-1.¹HNMR spectra δppm, (11.3, 1H),(10.6, 1H), (7.0, 5H), (6.8, 4H), (4.0, 1H) ,(4.3, 1H) (2.02, 2H), (1.20, 3H), (1.2, 1H) and (1.71, 6H).¹³CNMR spectra δppm, 20, 33,44, 57, 74, 87, 91, 112,123, 127, 132, 146, 150, 162,175, 177, 180, 181.

 

N(CH₃)₂ yield 81%, Melting point 145-147^oC, CHN analysis that formula C₂₄H₃₀ClN₃O₂Calculated C, 67.363 H, 7.072 N, 9.824; Found C, 67.185 H, 6.882 N, 9.594. Ultraviolet spectra λmax 230, 242, and 300. FT-IR spectraνmax 3210, 3100. 2988, 1690, 1688, 1375, 1220, 810cm-1.¹HNMR spectra δppm, , (11.0, 1H), (7.9, 5H), (7.3, 4H), (4.3, 1H) ,(4.5, 1H) (2.12, 2H),(4.28, 3H), (1.28, 3H), (1.20, 1H) and (1.70, 6H).¹³CNMR spectra δppm, 19, 20,35, 45, 72, 89, 95, 116,125, 127, 138, 144, 155,164 ,167, 173, 177, 180.

 

Van yield 75%, Melting point 200-202^oC, CHN analysis that formula C₂₃H₂₇ClN₂O₄Calculated C, 64.113 H, 6.328N, 6.504; Found C, 64.005 H, 6.263 N, 6.215. Ultraviolet spectra λmax 230, 250, and 320. FT-IR spectraνmax 3180, 3050, 1693, 1688, 1384, 1200, 851cm^-1.¹HNMR spectra δppm, (12.0, 1H),(11.4, 1H), (7.8, 5H), (7.2, 4H), (4.1, 1H) ,(4.5, 1H), (3.88, 3H) (2.02, 2H), (1.26, 3H), (1.2, 1H) and (1.71, 6H).¹³CNMR spectra δppm, 26,34,45, 55, 67, 82, 102, 110,120, 129, 130, 145, 157, 164,172, 179, 183, 188.

 

 

RESULT AND DISCUSSION:

Ibuprofen derivatives form a group of generally less investigated compounds. However, recently growing efforts are made to synthesize and characterized these compounds. Many profen derivatives possess very promising properties regarding biological activities as shown in literature survey. In the present research, project the conventional methods to prepare some profen compounds with expected biological activity.

 

 

 

The objective of this work is the synthesis of new heterocyclic compound by using pericyclic reaction between new imine with chloro acetyl chloride⁽²¹⁾ indioxane; these compounds may have biological effects besides being prepare for this time.

 

The reaction carry out by microwave oven, the first step included replacement hydroxyl group of acid by hydrazine, then the aromatic aldehyde were condensate with the acyl hydrazide compound to give Schiff base according to well-known procedure^(22,23) was reacted with chloro acetyl chloride to produce four membered heterocyclic compound of Azetidinone, it show in scheme (1).

 

The electron withdrawing groups in the aldehyde led to decreasing the electron density at the carbonatom of carbonyl, so the electrophilic properties were enhance, therefore increase positive charge of the carbon of carbonyl and make easy to attack by the nucleophilic, whereas, these factors increased the yields of products. The structures of the synthesized compounds (I-III) were confirmed by their elemental analysis, UV, IR, and NMR. CHN were situated within the range which confirmed the validity of the suggested structure of the prepared compounds. The purification compounds were tested by thin layer chromatography (TLC) using different eluents. The best separation was obtained in mixture of (benzene: methanol) (3:7) respectively as eluent. Then, the compounds were purified by using ethanol. UV spectrum⁽²⁴⁾ for Schiff bases (II) showing the three band at (220-330) nm were due to transition (π-π*) aromatic ring. While the compound Azetidinone (III) which showing four band at (218-340)nm were due to interferences transition (π-π*) aromatic heterocyclic ring with aromatic benzene ring addition to (n-π*) for carbonyl group come back to azetidinone compound (III).

 

The structures of synthesized compounds were determined on the basis of their FTIR⁽²⁶⁾, The intense band at (1600-1620) cm^-1 in compounds (I-III) confirmed to the stretching vibrations for the C=N group. Cyclisation with chloroacetic acid gave compound (III), these were characterized as the carbonyl group vibrations, hence confirming the process of cyclisation. This compound showed the appearance of new vibration mode at (1720-1750) cm^-1, which was characterized as the peak for carbonyl group, and (1118-1190) cm^-1 for C-N. The IR spectra of these compounds showed a strong infrared absorption band in the region between (3224-3430) cm^-1 due to NH stretching and a strong band in the region between (1680-1693) cm^-1 due to carbonyl group of amide.¹ HNMR appears several signal^{(27 )} for compounds (II-III)showed at the region (6.9-8.4)ppm for the aromatic benzene rings addition to signal of proton azomethane, The CH, CH₂ ,CH₃ groups of the aliphatic series in (II-III) appears signal at δ (2.0-2.3)ppm, in addition to signals for theCH₃ at (2.0-2.4)ppm, which exist in skeleton of ibuprofen.¹³CNMR signal^{( 28)} appears 15 line according to 15 carbon atom exist in the structure of Schiff bases except the equivalents, azetidinone compounds were appears 18 line according to 18 carbon atom exist in the structure.

 

Mechanism of the pericyclic reaction between an imine group and chloroacetyl chloride for preparing azetidinonering systematically investigated as (2+2) cycloaddition. The breaking and formation of bonds occur simultaneously and thus the reaction proceeds via a single cyclic as show in scheme (2).

 

 

 

BIOLOGICAL ACTIVITIES:

The antibacterial ^{(29,30 )} activities of the series (I-III) have been carried out against some strain of bacteria. The result (Table 1) showed that prepared compounds are toxic against the bacteria. The compounds (II) were found more active against the above microbes. The comparison of the antibacterial activity of these compounds with Streptomycin shows that these compounds have almost similar activity. The bacterial cultures for S. aurous, and E. coli were obtained from Department of biology University of Basrah. Iraq. The bacterial cultures were incubated at 30^oC for 24 hours by inoculation into nutrient agar.

 

Schiff bases and azetidinone were stored dry at room temperature and dissolved 20mg/ml in dimethyl sulfoxide (DMSO). Antibacterial activities of each compound were evaluated by the agar disc-diffusion method. Mueller Hinton Agar Media (15 cm³) kept at 45^oC was poured in the Petri dishes and allowed to solidify. Poured Petri plates (9cm) were incubated with 50μL of normal saline solution of above culture media [105-106 bacteria perml]. Discs injected with prepared Schiff bases and azetidinone (50μL) were applied on the solid agar medium by pressing tightly. The Petri plates were placed at 37^oC for 24 hours. At the end of period, the inhibition zones formed on media were measured with a zone reader in millimeters.

 

Table (1): Inhibition Zones (mm) of The Synthesis Schiff Bases and Azetidinones

X= zero activity

 

 

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Received on 03.01.2019                    Modified on 05.03.2019

Accepted on 05.04.2019                   ©AJRC All right reserved