Synthesis, Characterization and Studying of Biological Activity of some new Six–membered Compounds derived from Schiff bases
Nadia Sadiq Majeed, Fatima Naeem Abdul-Hussein
Department of Chemistry, College of Education for Girls, University of Kufa, Iraq.
*Corresponding Author E-mail: nadia.albobaid@uokufa.edu.iq
ABSTRACT:
A series of six - membered rings has been synthesized from Dapsone drug. In the first step examination Dapsone has been taken as initial material and treated with different aromatic aldehydes to prepare new Schiff bases compounds. then imine compounds react with (2-aminobenzoic acid and 2-mercaptobenzoic acid) to prepare Hydroqinazoline and Thiazinone derivatives. In the second step all these derivatives were tested against different bacteria (Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus, Bacillus anthracis). The high efficacy results of these derivatives proved significantly greater than the efficacy of the same Dapsone drug. These compounds were identified and confirmed by FT- IR, 1HNMR and 13C-NMR.
KEYWORDS: Dapsone, Schiff bases, Hydroqiazoline, Thiazinone, anti-bacterial activity.
1. INTRODUCTION:
Schiff bases are condensation products of primary (aromatic) amines with aldehydes or ketones carrying the azomethine (imino) moiety (-CR=N-). They are considered versatile pharmacophores for various pharmacological activities where the azomethine group has been demonstrated to be critical to the bioactivity. For example, Schiff bases, whether of natural or non-natural origin, have exhibited promising antibacterial, antitubercular, antifungal, antiparasitic, antiviral, antioxidant, anticancer1,2. diaminodiphenyl sulfone (DDS) or Dapsone a sulfones class antibiotic drug3 reduces swelling (inflammation) and stops the bacteria’s development. Generally, it is administered with rifampicin and clofazimine in the treatment of leprosy, elimination half-life 20–30 hours4. Dapsone is widely employed as effective antibiotic for prophylaxis agent pneumocystis and an opportunistic disease in (HIV).
thiazinone which are heterocyclic compounds having one nitrogen, one sulphur atom and four carbon atoms at various positions in the six member ring and exist as 1,2, 1,3 and 1,4 isomers5,6,7.
However their derivatives having (N-C-S) linkage have been used in the fields of pharmaceutical chemistry and medicinal and reported to exhibit a variety of biological activities such as antitubercular8, antimicrobial9, antitumor10, fungicidal11 and anti-inflammatory activities12. Quinazoline derivatives are an important class of fused heterocycles that display a wide range of pharmacological and medicinal properties involving anti-inflammatory13, antibiotic, antipyretic, antihypertonic and diuretic activities14. All these new compounds were prepared from Schiff bases derivatives with anhydride, 2-mercapto benzoic acid and 2-amino benzoic acid by many different methods.
2. Experimental:
2.1 Materials and Instruments:
Reagents and reactants are used like obtained from commercial providers without further purification. Solvents were purified beforehand. The purity of derivatives and path of reaction were monitored using
Thin layer chromatography on silica gel-G (Merck grade) with ethanol and benzene mixture as mobile phase. The melting points were measured in open capillaries, with the help of (Stuart) melting point (SMP30, England) melting point apparatus are uttered in ï C and are uncorrected.
Infrared spectra (IR) were recorded on Shimadzu Prestige-21 Spectrophotometer by using potassium bromide (KBr pellets) and the values are uttered in cm-1, 1H NMR and 13CNMR spectra of the derivatives were recorded on Bruker (Avance III, Bruker 300MHz NMR
spectrophotometer using TMS as an interior standard and the values are expressed in ppm in University of Tehran-Iran.
2.2 Preparations of Schiff base (F1-F6)15,16
4,4'-(4,4'-sulfonylbis(4,1-phenylene)bis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(N,N-dimethylaniline) F1
4,4'-(4,4'-sulfonylbis(4,1-phenylene)bis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(2-methoxyphenol) F2
4,4'-sulfonylbis(N-(naphthalen-1-ylmethylene)aniline) F3
4,4'-sulfonylbis(N-((4-(methylthio)phenyl)((4-(pyrimidin-2- ylsulfonyl)phenyl) diazenyl)methylene)aniline) F4
4,4'-sulfonylbis(N-(4-nitrobenzylidene)aniline) F5
4,4'-sulfonylbis(N-(4-chlorobenzylidene)aniline) F6
To a stirred solution of aromatic aldehydes substituted by different groups (0.02mol.) in absolute ethanol (20 mL) added (2-3drops) of glacial acetic acid and Dapsone (0.01mol.) in (10mL) of absolute ethanol was slowly added and refluxed in water bath for different period depending on the type of aldehyde. After completion of reaction cooling the mixture and filtering the precipitate. The product was recrystallized from mixture of ethanol as shown in Table-1.
2.3 Preparations of Hydroquinazoline derivatives (F7-F12)17
2-(4-(dimethylamino)phenyl)-3-(4-(4-(2-(4-(dimethylamino)phenyl)-4-oxo-1,2,4,4a-tetrahydroquinazolin-3(8aH)-yl)phenylsulfonyl)phenyl)-2,3-dihydroquinazolin-4(1H)-one F7
2-(4-hydroxy-3-methoxyphenyl)-3-(4-(4-(2-(4-hydroxy-3-methoxyphenyl)-4-oxo-1,2,4,4a-tetrahydroquinazolin-3(8aH)-yl)phenylsulfonyl)phenyl)-2,3-dihydroquinazolin-4(1H)-one F8
2-(naphthalen-1-yl)-3-(4-(4-(2-(naphthalen-1-yl)-4-oxo-1,2,4,4a-tetrahydroquinazolin-3(8aH)-yl)phenylsulfonyl)phenyl)-2,3-dihydroquinazolin-4(1H)-one F9
2-(4-(methylthio)phenyl)-3-(4-(4-(2-(4-(methylthio)phenyl)-4-oxo-1,2,4,4a-tetrahydroquinazolin-3(8aH)-yl)phenylsulfonyl)phenyl)-2,3-dihydroquinazolin-4(1H)-one F10
2-(4-nitrophenyl)-3-(4-(4-(2-(4-nitrophenyl)-4-oxo-1,2,4,4a-tetrahydroquinazolin-3(8aH)-yl)phenylsulfonyl)phenyl)-2,3-dihydroquinazolin-4(1H)-one F11
2-(4-chlorophenyl)-3-(4-(4-(2-(4-chlorophenyl)-4-oxo-1,2,4,4a-tetrahydroquinazolin-3(8aH)-yl)phenylsulfonyl)phenyl)-2,3-dihydroquinazolin-4(1H)-one F12
A solution of 2-amino benzoic acid (0.02mol.) in dioxane was added to Schiff bases (0.01mol.) with 3 ml of DMF. This solution was heated under reflux for (30-35 hrs.) in water bath. The solvent was evaporated under reduced pressure and neutralized the remains with 10% sodium bicarbonate then filtered and recrystallized from the mixture of ethanol as shown in Table- 2.
2.4 Preparations of Thiazinone derivatives (F13-F18)18
2-(4-(dimethylamino)phenyl)-3-(4-(4-(2-(4-(dimethylamino)phenyl)-4-oxo-4,4a-dihydro-2H-benzo[e][1,3]thiazin-3(8aH)-yl)phenylsulfonyl)phenyl)-2H-benzo[e][1,3]thiazin-4(3H)-one F13
2-(4-hydroxy-3-methoxyphenyl)-3-(4-(4-(2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4,4a-dihydro-2H-benzo[e][1,3]thiazin-3(8aH)-yl)phenylsulfonyl)phenyl)-2H-benzo[e][1,3]thiazin-4(3H)-one F14
2-(naphthalen-1-yl)-3-(4-(4-(2-(naphthalen-1-yl)-4-oxo-4,4a-dihydro-2H-benzo[e][1,3]thiazin-3(8aH)-yl)phenylsulfonyl)phenyl)-2H-benzo[e][1,3]thiazin-4(3H)-one F15
2-(4-(methylthio)phenyl)-3-(4-(4-(2-(4-(methylthio)phenyl)-4-oxo-4,4a-dihydro-2H-benzo[e][1,3]thiazin-3(8aH)-yl)phenylsulfonyl)phenyl)-2H-benzo[e][1,3]thiazin-4(3H)-one F16
2-(4-nitrophenyl)-3-(4-(4-(2-(4-nitrophenyl)-4-oxo-4,4a-dihydro-2H-benzo[e][1,3]thiazin-3(8aH)-yl)phenylsulfonyl)phenyl)-2H-benzo[e][1,3]thiazin-4(3H)-one F17
2-(4-chlorophenyl)-3-(4-(4-(2-(4-chlorophenyl)-4-oxo-4,4a-dihydro-2H-benzo[e][1,3]thiazin-3(8aH)-yl)phenylsulfonyl)phenyl)-2H-benzo[e][1,3]thiazin-4(3H)-one F18
A mixture of Schiff base (0.01mol.) and 2-mercapto benzoic acid (0.02mol) were dissolved in mixture of (20 mL) dry benzene and (3mL) of DMF. (A few drops) of triethyl amine was added, then the mixture was refluxed for (30-35hrs.), after that the solvent was removed under vacuum. The remains was transferred to separator funnel and extracted by sodium bicarbonate solution (10%), filtered and recrystallized from dioxane, as shown in Table- 3.
3. Biological activity assay19:
Antibacterial activity of the synthesized compounds [F1-F18] have been carried out against four types of bacteria like, (staphylococcusaureus, Bacillus anthracis) gram positive and (E. coli, Klebsiella pneumoniae) gram negative using nutrient agar medium via well diffusion method(20) . All derivatives were suspended in aqueous solutions in dissimilar concentrations ranged from 0.001 g and 0.1g in 10ml of DMSO, the results are voiced on MIC (minimal inhibitory concentration). and exhibited high biological activity of all these synthesized compounds of these microorganisms more than the effectiveness of Dapsone drug. The biological investigation data is given in Table-4
4. RESULTS AND DISCUSSION:
In this study Schiff bases (F1-F6) were prepared by the reaction of Dapsone with variety of substituted aromatic aldehydes in acidic medium (glacial acetic acid) as a catalyst and absolute ethanol as a solvent, as shown in scheme -1
Scheme 1- Preparation of new derivatives of thiazinone and hydroquinazoline from Schiff bases
FTIR spectra showed the disappearing of ν (NH2) group absorption band at (3400) cm-1 and appearance of absorption band of ν (-C=N) in the range (1585-1627) cm-1 with other value of substituted groups. The other values of FTIR spectral data for compounds (F1- F6) in the Table -1
Table 1: The values of FTIR spectral data for compounds (F1- F6)
|
13C-NMR Spectral data ᵟppm |
1H-NMR Spectral data (ᵟppm) |
Compound Structures
|
Comp. No . |
|
22 (CH3) 116-138(m,C=C,Ar-H) 158(S,C,-C=N)Imine |
1.72 (S,6H,2CH3) 7.4-8.1(m,4H,Ar-H) 8.3(S,1HN=C-H) |
|
F1 |
|
56(OCH3) 105-130(m,C=C,Ar-H) 152(S,C,-C=N)Imine 158(C-OH) |
3.4(S,3H,OCH3) 7.4-7.9(m,5H,Ar-H) 8.9(S,1H,N=C-H)
|
|
F 2 |
|
111-132(m,C=C,Ar-H) 157(S,C,-C=N)Imine |
7.0-7.6(m,4H,Ar-H) 8.3(S,1HN=C-H)
|
|
F3 |
|
18 (CH3) 112-130(m,C=C,Ar-H) 156(S,C,-C=N)Imine |
1.4(S,3H, CH3) 7.02-7.3(m,4H,Ar-H) 8.5(S,1HN=C-H)
|
|
F4 |
|
112-138(m,C=C,Ar-H) 158(S,C,-C=N)Imine |
6.9-7.3(m,4H,Ar-H) 8.6(S,1HN=C-H)
|
|
F5 |
|
105-142(m,C=C,Ar-H) 156(S,C,-C=N)Imine |
6.7-7.9(m,4H,Ar-H) 8.8(S,1HN=C-H)
|
|
F6
|
The target product hydroquinazoline derivatives (F7-F12) were synthesized by the reaction of Schiff bases (F1-F6) with 2- amino benzoic acid in dioxane as a solvent for long period of time about (30 hrs). The FTIR spectral data for compounds (F7-F12) show the disappearance of ν(C=N) band and appearance of ν(C=O) band in the values (1658-1685) cm-1 and ν (-NH) absorption band in the range (3360-3383) cm-1.
1HNMR spectrum for compound (F7-F12) showed singlet signal at δ= (6.3) ppm due to (s, 1H, N-CH)proton; signals at δ= (7.0-8.9) ppm due to aromatic rings protons and singlet signal at δ= (9.4-9.6) ppm due to(s, 1H, NH) . 13CNMR spectral data of compound(F7-F12) were listed in Table-2.
Table-2: Details of 13CNMR spectral data of compound(F7-F12)
|
13C-NMR Spectral data ᵟppm |
1H-NMR Spectral data (ᵟppm)
|
Compound Structures
|
Comp. No. |
|
28 (2CH3) 117-131(m,C=C,Ar-H) 158(S,C,-C-N) 173(C=O)Amide |
1.8 (S,6H,2CH3) 6.7-7.8(m,8H,Ar-H) 8.6(S,1H,N-C-H) 9.4(S,1H,NH)
|
|
F7 |
|
58 (OCH3) 117-131(m,C=C,Ar-H) 154(S,C,-C-N) 159(S,C,C-OH) 175(C=O)Amide |
3.5 (S,3H,OCH3) 7.4-7.8(m,4H,Ar-H) 8.9(S,1H,N-C-H) 9.4(S,1H,NH) 11.6(S,1H,OH)
|
|
F8 |
|
112-130(m,C=C,Ar-H) 158(S,C,-C-N) 173(C=O) |
7.1-8.1(m,8H,Ar-H) 8.3(S,1HN-C-H) 9.6(S,1H,NH)
|
|
F9 |
|
|
1.6 (S,3H, CH3) 6.7-8.1(m,4H,Ar-H) 8.7(S,1H,N-C-H) 9.5(S,1H,NH)
|
|
F 10 |
|
|
7.05-7.6(m,4H,Ar-H) 8.8(S,1H,N-C-H) 9.5(S,1H,NH)
|
|
F11 |
|
48 (C-Cl) 121-131(m,C=C,Ar-H) 158(S,C,N-CH) 170(S,C,C=O) |
7.1-7.3(m,8H,Ar-H) 8.8(S,1H,N-C-H) 9.4(S,1H,NH)
|
|
F12 |
On the other hand Thiazinone derivatives (F13-F18) were obtained by the reaction of Schiff bases with ortho-mercapto benzoic acid in the presence of triethyl amine as a catalyst and dry benzene as a solvent. These compounds also are characterized by FTIR spectra which showed disappearance of ν(C=N) band and appearance of ν(C=O) amide bands in the value (1660-1685) cm-1 and ν(C-S) band in (615-663) cm-1. The other values of FTIR spectral data for compounds (F13-F18) were listed in Table-3
1HNMR spectrum for compound (F13-F18) showed singlet signal at δ= (6.2) ppm due to(s, 2H, N-CH-S) protons and signals at δ= (7.04-8.48) ppm due to aromatic rings protons.13CNMR spectrum data of compound (F13-F18) were listed in Table-3
Table-3: Details of 13CNMR spectrum data of compound (F13-F18)
|
13C-NMR Spectral data ᵟppm |
1H-NMR Spectral data (ᵟppm)
|
Compound Structures
|
Comp. No . |
|
|
1.8 (S,6H,2CH3) 6.9-7.5(m,8H,Ar-H) 8.8(S,1H,N-C-H)
|
|
F13 |
|
57 (OCH3) 116-131(m,C=C,Ar-H) 155(S,C,-C-N) 159(S,C,C-S) 173(C=O)Amide |
3.5 (S,3H,OCH3) 7.05-7.7(m,9H,Ar-H) 8.9(S,1H,N-C-H) 11.5(S,1H,OH)
|
|
F14 |
|
|
7.4-7.9(m,6H,Ar-H) 8.7(S,1H,N-C-H)
|
|
F15 |
|
18 (2CH3) 105-130(m,C=C,Ar-H) 157(S,C,-C-N) 172(C=O)Amide |
1.8 (S,3H, CH3) 7.02-7.3(m,8H,Ar-H) 8.7(S,1H,N-C-H)
|
|
F16 |
|
|
6.7-7.8(m,8H,Ar-H) 8.8(S,1H,N-C-H)
|
|
F17 |
|
117-131(m,C=C,Ar-H) 157(S,C,-C-N) 175(C=O)Amide |
7.4-7.9(m,8H,Ar-H) 8.9(S,1H,N-C-H)
|
|
F18
|
Table-4: Features of compounds (F1-F18)
|
% |
Color |
RF |
M.P (C0) |
M.W |
M.F |
Name of compound |
Comp. |
|
65 |
Light brown |
0.73 |
270-273 |
510.6 |
C30H30N4SO2 |
4,4'-(((sulfonylbis(4,1-phenylene))bis(azaneylylidene))bis(methaneylylidene))bis(N,N-dimethylaniline) |
F1 |
|
82 |
Orange |
0.69 |
63-65 |
516.5 |
C28H24N2SO6 |
4,4'-(((sulfonylbis(4,1-phenylene))bis(azaneylylidene))bis(methaneylylidene))bis(2-methoxyphenol) |
F2 |
|
65 |
Light yellow |
0.65 |
244-246 |
524.6 |
C34H24N2SO2 |
N,N'-(sulfonylbis(4,1-phenylene))bis(1-(naphthalen-1-yl)methanimine) |
F3 |
|
84.2 |
yellow |
0.80 |
281-284 |
516.6 |
C28H24N2S3O2 |
N,N'-(sulfonylbis(4,1-phenylene))bis(1-(4-(methylthio)phenyl)methanimine) |
F4 |
|
81.6 |
yellow |
0.64 |
246-248 |
514.5 |
C26H18N4SO6 |
N,N'-(sulfonylbis(4,1-phenylene))bis(1-(4-nitrophenyl)methanimine) |
F5 |
|
76 |
Light yellow |
0.84 |
161-163 |
493.4 |
C26H18N2SO2Cl2 |
N,N'-(sulfonylbis(4,1-phenylene))bis(1-(4-chlorophenyl)methanimine) |
F6 |
|
83 |
Dark brown |
0.62 |
101-103 |
748.8 |
C44H40N6SO4 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(4-(dimethylamino)phenyl)-2,3-dihydroquinazolin-4(1H)-one) |
F7 |
|
78.3 |
Dark brown |
0.74 |
147-149 |
754.8 |
C42H34N4SO8 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one |
F8 |
|
85 |
red |
0.63 |
113-115 |
762.8 |
C84H34N4SO4 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one) |
F9 |
|
84.2 |
Light brown |
0.86 |
116-118 |
754.9 |
C42H34N4S3O4 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(4-(methylthio)phenyl)-2,3-dihydroquinazolin-4(1H)-one) |
F10 |
|
81.6 |
Light brown |
0.84 |
256-258 |
752.7 |
C40H28N6SO8 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(4-nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one) |
F11 |
|
84 |
Dark red |
0.94 |
163-165 |
731.6 |
C40H28N4SO4Cl2 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one) |
F12 |
|
83 |
yellow |
0.52 |
199-201 |
782.9 |
C44H38N4S3O4 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(4-(dimethylamino)phenyl)-2,3-dihydro-4H-benzo[e][1,3]thiazin-4-one) |
F13 |
|
79.3 |
Dark brown |
0.57 |
124-126 |
788.9 |
C28H24N2S3O8 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-4H-benzo[e][1,3]thiazin-4-one) |
F14 |
|
84 |
Orange |
0.59 |
178-180 |
796.9 |
C48H32N2S3O4 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(naphthalen-1-yl)-2,3-dihydro-4H-benzo[e][1,3]thiazin-4-one) |
F15 |
|
79 |
Light yellow |
0.85 |
169-171 |
789 |
C42H32N2S5O4 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(4-(methylthio)phenyl)-2,3-dihydro-4H-benzo[e][1,3]thiazin-4-one) |
F16 |
|
84 |
Dark yellow |
0.78 |
243-245 |
786.8 |
C40H26N4S3O8 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(4-nitrophenyl)-2,3-dihydro-4H-benzo[e][1,3]thiazin-4-one) |
F17 |
|
75 |
red |
0.58 |
150-152 |
765.7 |
C40H26N2S3O4Cl2 |
3,3'-(sulfonylbis(4,1-phenylene))bis(2-(4-chlorophenyl)-2,3-dihydro-4H-benzo[e][1,3]thiazin-4-one) |
F18 |
Antibacterial activity:
The information about antibacterial activity was listed in Table-5. The results indicate that all synthesized compounds having strong effect against certain types of bacteria while it did not possess any effect against others. Compounds (4a, 8b, and 9b) having strong activity against pseudomonas sp. while compounds (11c, 15c and 20d) having specific strong effect against the same bacteria. Compounds (2a and 9b) having moderate activity against E.coli. while compound (8b) possess specific strong effect against the same bacteria. Compounds (2a, 4a, 8b, 9b and 11c) possess strong effect against proteus sp. while compounds (15c and 20d) showed no inhibition against E.coli and proteus sp., at the last compounds (4a, 8b and 20d) possess specific strong activity against staphylococcus aureus.
Table-5: The information about antibacterial activity
|
C2 mm 10-3 |
C1 mm 10-2 |
Klebse |
C2 mm 10-3 |
C1 mm 10-2 |
B.C |
C2 mm 10-3 |
C1 mm 10-2 |
E.Coli |
C2 mm 10-3 |
C1 mm 10-2 |
Staph |
No .compounds |
|
|
|
|
0 |
18 |
- + |
14 |
20 |
++ |
14 |
22 |
++ |
F10 |
|
22 |
24 |
+++ |
16 |
18 |
++ |
14 |
20 |
++ |
13 |
18 |
++ |
F11 |
|
24 |
35 |
+++ |
15 |
28 |
++ |
0 |
22 |
+ - |
12 |
24 |
++ |
F12 |
|
17 |
18 |
++ |
15 |
17 |
++ |
14 |
18 |
++ |
0 |
24 |
+- |
F13 |
|
18 |
28 |
+++ |
0 |
24 |
++ |
14 |
22 |
+ + |
13 |
26 |
++ |
F15 |
|
|
|
|
17 |
18 |
++ |
20 |
22 |
+++ |
20 |
22 |
+++ |
F16 |
|
|
|
|
14 |
22 |
++ |
18 |
22 |
+++ |
14 |
28 |
+++ |
F10A |
|
|
|
|
16 |
17 |
+ |
0 |
13 |
+ - |
13 |
18 |
++ |
F11A |
|
20 |
22 |
+++ |
0 |
20 |
++ |
16 |
17 |
+ + |
15 |
22 |
++ |
F12A |
|
20 |
22 |
+++ |
14 |
16 |
++ |
14 |
17 |
++ |
12 |
20 |
+++ |
F13A |
|
17 |
20 |
++ |
|
|
|
12 |
16 |
++ |
18 |
24 |
++ |
F15A |
|
20 |
30 |
+++ |
16 |
18 |
++ |
0 |
22 |
+ - |
22 |
28 |
+++ |
F16A |
|
13 |
18 |
++ |
|
|
|
13 |
20 |
++ |
0 |
20 |
+ - |
F10B |
|
|
|
|
12 |
17 |
++ |
0 |
11 |
+ - |
12 |
23 |
++ |
F11B |
|
18 |
20 |
++ |
0 |
12 |
+ - |
13 |
20 |
++ |
13 |
24 |
++ |
F12B |
|
17 |
24 |
++ |
13 |
22 |
++ |
0 |
32 |
++ |
0 |
15 |
+- |
F13B |
|
18 |
28 |
+++ |
13 |
20 |
++ |
16 |
24 |
+++ |
13 |
24 |
+++ |
F15B |
|
17 |
20 |
++ |
17 |
20 |
++ |
20 |
23 |
+++ |
16 |
18 |
++ |
F16B |
CONCLUSION:
The synthesis of the designed compounds has been successfully achieved. Characterization and identification of the target compounds were confirmed by determination of the physical properties, FT-IR spectroscopy , 1H-NMR , 13C-NMR spectra . The synthesized compounds were thereafter evaluated for antibacterial activity against some strains of gram positive and gram negative bacteria. Most of the synthesized compounds show very promising antibacterial activity against some of the bacteria strains while some do not show any activity against some of the bacteria strains.
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Received on 20.07.2022 Modified on 23.09.2022
Accepted on 14.11.2022 © RJPT All right reserved
Research J. Pharm. and Tech 2023; 16(5):2280-2286.
DOI: 10.52711/0974-360X.2023.00374