1Department of Pharmaceutical Chemistry, Pravara Rural College of Pharmacy, Pravaranagar, Rahata, Ahmednagar, Maharashtra, INDIA
Corresponding author.
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Contents
ABSTRACT
ABSTRACT
Introduction:
This study describes a new route to the synthesis of novel (2-chloro-N- {[(2-chlorophenyl) amino] sulfinyl}-N -phenylbenzamide derivatives. Benzamide-based derivatives were prepared through a reaction of benzoyl chloride with 2-chloroaniline with conventional methods by alkylation with Thionyl chloride and then a reaction with 2-chloroaniline to get target compound i.e., novel 2-chloro-N-{[(2-chlorophenyl)amino]sulfinyl}-N-phenylbenzamide. Benzamides are structural parent of carbonic acid amide of the benzoic acid. Benzamides has the carbon snippet being attached to oxygen and also a nitrogen group attached with hydrogen atom2. In pharmaceutical request; three active medicines have been considerably in used for psychiatry and other affiliated medical fields; i.e., Sulpiride, Amisulpride and Remoxipride.
Objectives:
To synthesize 2-chloro-N-{[(2-chlorophenyl)amino]sulfinyl}-N-phenylbenzamide derivative and with its Characterization and its biological activity.
Materials and Methods:
The structure confirmations were done by FTIR, Magnetic Resonance Spectroscopy (MRS) and MS. The (2-chloro-N-{[(2-chlorophenyl) amino] sulfinyl}-N-phenylbenzamide compounds and its derivatives were investigated for in vitro screening. Structural activity relationship studies reveal that compounds possessing an electron-withdrawing group exhibit better activity than electron-donating groups.
Results:
Based on the results obtained, when compared to common medicines like Ciprofloxacin; the compounds 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl formate (BB8), 2-({[(2-chlorobenzoyl) (phenyl) amino] sulfinyl} amino)phenyl-2-aminophenyl-2-(4-nitrophenoxy) aniline (BB9), 2-({[(2-chlorobenzoyl) (phenyl) amino]sulfinyl}amino)phenyl-2-aminophenyl-2-(3-nitrophenoxy) aniline (BB10) showed good significant activity. Against S. aureus and Pseudomonas aeruginosa.
Conclusion:
The title compounds and its derivatives were investigated for anti-bacterial Activity. Structural activity relationship studies told that electron-withdrawing group exhibit good activity than the electron-donating groups.
INTRODUCTION
Lately, the people use and demand for new anti-bacterial, anti-fungal and new fungicides has been adding with the enhancement of people’s living norms. Numerous scientists work on new kinds of anti-bacterial, anti-fungal and new fungicides with high effectiveness, low toxin and low residue and they developed new derivatives.1 Benzamides base heterocyclic derivations having important attention because of their colorful natural conditioning. Benzamides are structural parent of carbonic acid amide of the benzoic acid. Benzamides has the carbon snippet being attached to oxygen and also a nitrogen group attached with hydrogen atom.2 In pharmaceutical request; three active medicines have been considerably in used for psychiatry and other affiliated medical fields; i.e., Sulpiride, Amisulpride and Remoxipride. Remoxipride medicine was removed from the request due to life hanging side goods in 1993. This group of benzamide pharmocophore gives effective bioactive composites. Benzamide and its derivations have been reported with antimicrobial, analgesic anticancer, carbonic anhydrase inhibitory, cholinesterase inhibitory conditioning and so on. In once exploration, we study about benzamides derivatives.3 It was observed that benzamides derivations have anti-depressant exertion, anti-convulsant exertion, anti-inflammatory exertion, analgesic parcels, serotonin (5-HT) exertion, antitumor exertion, and anti-microbial activity.4,5 Particularly, it having both electron withdrawing and electron giving groups attached with Benzamide-grounded ring showed more inhibitory eventuality against fungal strains and bacterial strains than standard medicine. The microbial bacterial or parasitic bacteria like Staphylococcus aureus, and Escherichia coli having moderate impact on the mucosal health of humans. These microbial growths give destruction of host towel and life-changing conditions. Staphylococcus aureus and Escherichia coli bacterial spongers beget food poisoning, fever and diarrhea. It affects millions of individualities in developing countries also. Further than 60 million people worldwide are infected and over to 1,30,000 of people worldwide die from these infections every time. There are some antibiotics to treat this infection like Amoxicillin, Norfloxacin and Ciprofloxacin.6 They’re the most generally used medicines for this bacterial infection but they give severe side-goods. Thus, significant sweats given by new scientist of whole world and they’ve been made by numerous exploration groups to find out new anti-microbial medicine. On the other hand, pharmacologically, Benzamide-grounded derivations represent one of the most important classes of organic heterocyclic composites with anti-microbial exertion like anti-bacterial, anti-fungal, herbicidal and anti-viral activities.7–9 Grounded on these donation; we will durability of our medicine exploration program concerning conflation of new, safer and further biologically active derivatives,10,11 so that it gives interest to synthesize a new series of Benzamide-grounded derivations so that it gives more active and less- poisonous antimicrobial agents. The first Benzamide was set Wohler and Liebig in 1832.12 2-chloro- N-{((2-chlorophenyl) amino) sulfinyl}-N-phenylbenzamide having sulphur snippet being attached to oxygen and also a carbon snippet group attached with hydrogen snippet (Figure 1). Sulpiride, Amisulpride and Remoxipride are given in Figure 2.
Figure 1:
2-chloro-N-{[(2-chlorophenyl)amino]sulfinyl}-N-phenylbenzamide nucleus.
Figure 2:
Benzamide containing drugs Sulpiride, Amisulpride and Remoxipride.
MATERIALS AND METHODS
Materials
Benzoyl chlorides, 2-Chloro Aniline, Thionyl chloride, Benzoic acid, Para nitro Phenol, Acetic acid, 1-naphthol, 2- naphthol and Meta nitro phenol are used for the synthesis. All chemicals were of logical grade. All chemicals were of bought from Modern Chemicals, Nashik and Some chemicals were available in college.
Methods
We used conventional method for synthesis of these (2-chloro- N-{[(2-chlorophenyl)amino]sulfinyl}-N-phenylbenzamide and its derivatives. The synthetic scheme of these (2-chloro- N-{[(2-chlorophenyl) amino] sulfinyl}-N-phenylbenzamide derivatives are shown in Scheme 1A. (Figure 3).
Figure 3:
Scheme 1A: Synthesis of (2-chloro-N-{[(2-chlorophenyl) amino] sulfinyl}-N-phenylbenzamide and its derivatives (See Table 1).
| Label | Structure |
|---|---|
| BB4 | |
| BB5 | |
| BB6 | |
| BB7 | |
| BB8 | |
| BB9 | |
| BB10 | |
| BB11 |
Experimental Work
(Scheme IA)
Procedure
Synthesis of 2-chloro-N-phenylbenzamide: (BB1)
Place 2.4 g (0.025 mol) of benzoyl chloride, 3.0 mL (0.05 mol) of 2- Chloro Aniline and 75 mL of ethanol in a 100 mL RBF. Set up an influx condenser with the beaker and using an electric heating mantle for at least 3.0 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; it gives 2-chloro-N-phenylbenzamide.
Synthesis of (2-chlorobenzoyl) phenyl sulfuramidous chloride: (BB2)
Place 1.2 g (0.015 mol) of 2-chloro-N-phenylbenzamide and 15 mL of Thionyl chloride in a 100 mL RBF. Set up an influx condenser with the beaker and using an electric heating mantle for at least 2.0 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; it gives (2-chlorobenzoyl) phenyl sulfuramidous chloride.
Synthesis of 2-chloro-N-{[(2-chlorophenyl) amino] sulfinyl}-N-phenylbenzamide: (BB3)
Place 1.2 g (0.015 mol) of (2-chlorobenzoyl) phenyl sulfuramidous chloride and again 10 mL of 2- Chloro Aniline in a 100 mL RBF. Set up an influx condenser with the beaker and using an electric heating mantle for at least 4.3 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; It gives 2-chloro-N– {[(2-chlorophenyl) amino] sulfinyl}-N-phenylbenzamide.
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl acetate: (BB4)
Place 1.2 g (0.015 mol) of (2-chlorobenzoyl) phenyl sulfuramidous chloride and 10 mL of glacial acetic acid in a 100 mL RBF Set up an influx condenser with the beaker and using an electric heating mantle for at least 2.0 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; it gives 2-({[(2-chlorobenzoyl) (phenyl)amino]sulfinyl}amino)phenyl acetate.
Synthesis of N-({[2-(carbamothioylamino) phenyl]amino}sulfinyl)-2-chloro-N-phenylbenzamide: (BB5)
Place 1.2 g (0.015 mol) of (2-chlorobenzoyl) phenyl sulfuramidous chloride and 2 gm of Thiourea in a 100 mL RBF. Set up an influx condenser with the beaker and using an electric heating mantle for at least 2.0 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; it gives N-({[2-(carbamothioylamino) phenyl]amino}sulfinyl)-2-chloro-N-phenylbenzamide.
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl-2-aminophenyl benzoate: (BB6)
Place 1.2 g (0.015 mol) of (2-chlorobenzoyl) phenyl sulfuramidous chloride and 2 gm of benzoic acid in a 100 mL RBF. Set up an influx condenser with the beaker and using an electric heating mantle for at least 2.0 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; it gives 2-({[(2-chlorobenzoyl) (phenyl)amino]sulfinyl}amino)phenyl-2-aminophenyl benzoate.
Synthesis of N-({[2-(carbamoylamino)phenyl]amino} sulfinyl)-2-chloro-N-phenylbenzamide: (BB7)
Place 1.2 g (0.015 mol) of (2-chlorobenzoyl) phenyl sulfuramidous chloride and 2 gm of urea in a 100 mL RBF. Set up an influx condenser with the beaker and using an electric heating mantle for at least 2.0 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; it gives N-({[2-(carbamoylamino) phenyl]amino}sulfinyl)-2-chloro-N-phenylbenzamide.
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl formate: (BB8)
Place 1.2 g (0.015 mol) of (2-chlorobenzoyl) phenyl sulfuramidous chloride and 10 mL of formic acid in a 100 mL RBF. Set up an influx condenser with the beaker and using an electric heating mantle for at least 2.0 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; it gives 2-({[(2-chlorobenzoyl) (phenyl)amino]sulfinyl}amino)phenyl formate.
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl-2-aminophenyl-2- (4-nitrophenoxy)aniline: (BB9)
Place 1.2 g (0.015 mol) of (2-chlorobenzoyl) phenyl sulfuramidous chloride and 2 gm of 4-nitro phenol in a 100 mL RBF. Set up an influx condenser with the beaker and using an electric heating mantle for at least 4.0 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; it gives 2-({[(2-chlorobenzoyl) (phenyl)amino]sulfinyl}amino)phenyl-2-aminophenyl-2- (4-nitrophenoxy)aniline.
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl-2-aminophenyl-2- (3-nitrophenoxy)aniline: (BB10)
Place 1.2 g (0.015 mol) of (2-chlorobenzoyl) phenyl sulfuramidous chloride and 2 gm of 3-nitro phenol in a 100 mL RBF. Set up an influx condenser with the beaker and using an electric heating mantle for at least 2.0 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; it gives 2-({[(2-chlorobenzoyl) (phenyl)amino]sulfinyl}amino)phenyl-2-aminophenyl-2- (3-nitrophenoxy)aniline.
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl-2-aminophenyl-2- (2-nitrophenoxy)aniline: (BB11)
Place 1.2 g (0.015 mol) of (2-chlorobenzoyl) phenyl sulfuramidous chloride and 2 gm of 2-nitro phenol in a 100 mL RBF. Set up an influx condenser with the beaker and using an electric heating mantle for at least 2.0 hr. Cool to room temperature, pour the response admixture into 125 mL of water, and mix precisely. Allow the response admixture to stand for 10 min and also filter the product under suction pump; it gives 2-({[(2-chlorobenzoyl) (phenyl) amino] sulfinyl} amino) phenyl-2-aminophenyl-2- (2-nitrophenoxy) aniline.
Characterization
Spectral Data
TLC, Rf value, M.P. and % yield of (2-chloro-N-{[(2-chlorophenyl) amino] sulfinyl}-N-phenylbenzamide derivatives are given in Table 2.
| Comp. Name | TLC image | R f value |
M.P (°C) | % Yields | Comp. Name | TLC image | R f value |
M.P (°C) | % Yields |
|---|---|---|---|---|---|---|---|---|---|
| BB4 | 0.93 | 188-192 | 78 | BB8 | 0.73 | 168-172 | 71 | ||
| BB5 | 0.85 | 187-191 | 69 | BB9 | 0.79 | 178-182 | 94 | ||
| BB6 | 0.78 | 183-186 | 81 | BB10 | 0.68 | 176-179 | 86 | ||
| BB7 | 0.81 | 174-178 | 93 | BB11 | 0.87 | 182-186 | 88 |
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl acetate: (BB4)
FTIR (KBr) ν cm-1: 3036.37 (Aromatic C-H stretching), 1625.7 (Aromatic C=C stretching), 1070.03 (Aromatic C-N stretching), 3344.93 (Aromatic N-H stretching), 3639.62 (S-O stretching), 1755.98 C=O (amide stretching), 743.42 (Aromatic C-Cl stretching), 1448.28 (C-O stretching); 1H Magnetic Resonance Spectroscopy (MRS) (500 MHz) CDCl3 δ ppm: 12.961 Ar N-H (s, 1H, J = 11.1 Hz), 7.927 – 7.089Ar C-H, (m, 17H Ar, J = 16.9 Hz), 3.759. C-H (s, 3H CH3, J = 14.7 Hz); Mol.Wt. 118.
Synthesis of N-({[2-(carbamothioylamino) phenyl] amino} sulfinyl)-2-chloro-N-phenylbenzamide: (BB5)
FTIR (KBr) ν cm-1: 3044.09 (Aromatic C-H stretching), 1667.16 (Aromatic C=C stretching), 1285.87 (Aromatic C-N stretching), 3352.64 (Aromatic N-H stretching), 1785.68 C=O (amide stretching), 747.28 (Aromatic C-Cl stretching), 1170.58 (C-O stretching); 1H Magnetic Resonance Spectroscopy (MRS) (500 MHz)CDCl3 δ ppm: 12.972 Ar N-H (s, 1H, J = 11.1 Hz), 7.993 – 7.089Ar C-H, (m, 17H Ar, J = 16.9 Hz); Mol.Wt. 118.
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl-2-aminophenyl benzoate: (BB6)
FTIR (KBr) ν cm-1: 3059.51 (Aromatic C-H stretching), 1655.56 (Aromatic C=C stretching), 1224.86 (Aromatic C-N stretching), 3341.07 (Aromatic N-H stretching), 1745.08 C=O (amide stretching), 747.28 (Aromatic C-Cl stretching), 1078.01 (C-O stretching); 1H Magnetic Resonance Spectroscopy (MRS) (500 MHz) CDCl3 δ ppm: 10.241 Ar N-H (s, 1H, J = 11.1 Hz), 7.991 – 7.090 Ar C-H, (m, 18H Ar, J = 16.9 Hz); Mol.Wt. 118.
Synthesis of N-({[2-(carbamoylamino)phenyl]amino} sulfinyl)-2-chloro-N-phenylbenzamide: (BB7)
FTIR (KBr) ν cm-1: 3051.80 (Aromatic C-H stretching), 1664.27 (Ar C=C stretching), 1247.57 (Ar C-N stretching), 3244.93 (Ar N-H stretching), 1735.08 C=O (amide stretching), 747.28 (Ar C-Cl stretching), 1070.30 (C-O stretching); 1H Magnetic Resonance Spectroscopy (MRS) (500 MHz) CDCl3 δ ppm: 10.248 Ar N-H (s, 1H, J = 11.1 Hz), 7.965 – 7.088 Ar C-H, (m, 18H Ar, J = 16.9 Hz); Mol.Wt. 118.
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl formate: (BB8)
FTIR (KBr) ν cm-1: 3074.94 (Aromatic C-H stretching), 1648.84 (Aromatic C=C stretching), 1116.58 (Aromatic C-N stretching), 3344.93 (Aromatic N-H stretching), 1725.98 C=O (amide stretching), 754.99 (Aromatic C-Cl stretching), 1432.85 (C-O stretching); 1H Magnetic Resonance Spectroscopy (MRS) (500 MHz) CDCl3 δ ppm: 11.048 Ar N-H (s, 1H, J = 11.1 Hz), 8.138 – 7.104 Ar C-H, (m, 18H Ar, J = 16.9 Hz); Mol.Wt. 118.
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl-2-aminophenyl-2- (4-nitrophenoxy) aniline: (BB9)
FTIR (KBr) ν cm-1: 3244.65 (Aromatic C-H stretching), 1662.32 (Aromatic C=C stretching), 1152.87 (Aromatic C-N stretching), 3234.34 (Aromatic N-H stretching), 1673.31 C=O (amide stretching), 1376.24 (Aromatic C-H stretching), 770.42 (Aromatic C-Cl stretching),; 1H Magnetic Resonance Spectroscopy (MRS) (500 MHz) CDCl3 δ ppm: 10.248 Ar N-H (s, 1H, J = 11.1 Hz), 7.965 – 7.088Ar C-H, (m, 17H Ar, J = 16.9 Hz); 7Mol.Wt. 118.
Synthesis of 2-({[(2-chlorobenzoyl)(phenyl) amino]sulfinyl}amino)phenyl-2-aminophenyl-2- (3-nitrophenoxy) aniline: (BB10)
FTIR (KBr) ν cm-1: 3100.01 (Aromatic C-H stretching), 3072.05 (Aromatic C-H stretching), 1625.7 (Aromatic C=C stretching), 1278.57 (Aromatic C-N stretching), 3277.83 (Aromatic N-H stretching); 1725.98 C=O (amide stretching), 1136.83 (C-O stretching); 1H Magnetic Resonance Spectroscopy (MRS) (500 MHz) CDCl3 δ ppm: 8.52 Ar N-H (s, 1H, J = 11.1 Hz), 7.267 – 7.160 Ar C-H, (m, 18H Ar, J = 16.9 Hz; Mol.Wt. 118.
Biological evaluation
In vitro Antimicrobial Activity by Agar Well Diffusion Method
The antimicrobial exertion of composites was estimated using the agar well prolixity system. Mueller Hinton Agar (MHA) was prepared according to manufacturer’s instructions, and 100 μL of bacterial or fungal suspense containing roughly 1.5 × 108 CFU/ mL was spread slightly onto the face of the agar plates. Sterile 6-mm wells were made using a sterile cork borer, and each well was filled with 50 μL of the test at different attention (5, 10, and 15 μg/ mL). Ciprofloxacin was used as the standard reference. The plates were incubated at 37°C for 24 hr for bacteria. After incubation, the periphery of the inhibition zone was measured in millimeters, and the results were recorded. Each test was performed in triplet, and the mean value was calculated. The minimal inhibitory attention was determined by the agar dilution system. The test composites were dissolved in DMSO and added to Mueller Hinton agar in 96-well micro plates. Twice periodical dilutions were prepared, and bacterial or fungal dormancies were added to the wells.13 The plates were also incubated at 37°C for 24 hr for bacteria. The MIC was defined as the smallest attention of the test that fully inhibited the visible growth of the micro-organism. All trials were performed under aseptic conditions, and the results were expressed as mean ± Standard Divagation (SD). Statistical analysis was performed using ANOVA, followed by Tukey’s multiple comparison tests, with p<0.05 considered statistically significant.
RESULTS AND DISCUSSION
NMR spectroscopy or Magnetic Resonance Spectroscopy (MRS), and MS mass spectrometry were executed in SPPU College Pune. The effects revealed that utmost of the synthesized composites confirmed varying levels of inhibition in opposition to the examined micro-organisms. In trendy, the inhibitory exertion against the examined a few gram-effective micro-organisms deliver advanced inhibition than a few gram-negative bacteria. Additionally, the composites law name like 2-(((2- chlorobenzoyl) (phenyl) amino) sulfinyl amino) phenyl acetate (BB4), N-((2- (carbamothioylamino) phenyl) amino sulfinyl)-2-chlor o-N-phenylbenzamide (BB5), 2-(((2-chlorobenzoyl)(phenyl) amino) sulfinyl amino) phenyl-2-aminophenyl benzoate (BB6), N-((2-(carbamoyl amino) phenyl) amino sulfinyl)-2-chlor o-N-phenylbenzamide (BB7) against S. aureus and Pseudomonas aeruginosa. The relaxation of oxygen snippet to nitrogen snippet redounded in a barely accelerated antimicrobial exertion. Our observe found out that each one the composites had stronger antibacterial exertion towards Gram-nice micro-organism whilst as compared to Gram-terrible micro-organism. Antimicrobial exertion revealed that these days synthesized compounds 2-(((2-chloro benzoyl)(phenyl) amino) sulfinyl amino) phenyl formate (BB8); 2-(((2-chloro benzoyl)(phenyl) amino) sulfinyl amino) phenyl-2-aminophenyl-2-(2-nitro phenoxy) aniline (BB9); 2-(((2-chloro benzoyl)(phenyl) amino) sulfinyl amino) phenyl-2-aminophenyl-2-(3- nitro phenoxy) aniline (BB10) confirmed excellent large exertion. The effects of the number one antimicrobial testing of the set composites, the typical huge antibacterial medicinal drug like Ciprofloxacin changed into proven in Table 3. The MIC values of those composites had been decided through the agar well prolixity system. BB7 and BB8 confirmed varying degrees of antimicrobial exertion towards the examined microorganisms.
| Compounds | Concentration (μg/mL) | E. coli |
S. aureus |
P. aeruginosa |
|---|---|---|---|---|
| BB4 | 5 | 9.3±0.5 | 8.4±0.3 | 10.2±0.4 |
| 10 | 12.4±0.8 | 14.7±0.6 | 16.9±0.7 | |
| 15 | 19.6±1.2 | 19.8±1.1 | 21.4±1.3 | |
| BB5 | 5 | 9.1±0.4 | 10.9±0.5 | 10.8±0.6 |
| 10 | 13.4±0.9 | 16.8±0.7 | 17.2±1.1 | |
| 15 | 19.7±1.1 | 21.4±1.0 | 21.4±1.2 | |
| BB6 | 5 | 9.4±0.5 | 8.7±0.3 | 10.1±0.4 |
| 10 | 12.5±0.8 | 14.7±0.6 | 16.9±0.7 | |
| 15 | 19.8±1.2 | 19.1±1.1 | 21.4±1.3 | |
| BB7 | 5 | 9.1±0.4 | 10.9±0.5 | 10.8±0.6 |
| 10 | 13.4±0.9 | 16.8±0.7 | 17.4±1.1 | |
| 15 | 19.7±1.1 | 21.4±1.0 | 21.9±1.2 | |
| BB8 | 5 | 9.9±0.5 | 8.8±0.3 | 10.1±0.4 |
| 10 | 12.4±0.8 | 14.7±0.6 | 16.9±0.7 | |
| 15 | 19.8±1.2 | 19.2±1.1 | 21.9±1.3 | |
| BB9 | 5 | 9.1±0.4 | 10.9±0.5 | 10.8±0.6 |
| 10 | 13.4±0.9 | 16.8±0.7 | 17.2±1.1 | |
| 15 | 19.7±1.1 | 21.4±1.0 | 21.4±1.2 | |
| 15 | 19.7±1.1 | 21.4±1.0 | 21.9±1.2 | |
| Control (Ciprofloxacin) | 5 | 11.2±0.6 | 12.4±0.5 | 11.2±0.6 |
| 10 | 17.2±1.1 | 18.2±0.9 | 17.8±1.2 | |
| 15 | 22.3±1.3 | 22.8±1.2 | 21.8±1.4 |
CONCLUSION
Ciprofloxacin used as the standard reference for this exploration, it showed the loftiest biological activity against all tested microorganisms at all tested attention. At an attention of 5 μg/ mL, 10 μg/mL, and 15 μg/mL ciprofloxacin showed moderate to high exertion against all three microorganisms, with inhibition zones ranging from 11.2 ±0.6 mm to12.6 ±0.5 mm. At an attention of 15 μg/mL, ciprofloxacin showed the loftiest exertion against all three microorganisms, with inhibition zones ranging from 21.8 ± 1.4 mm to 22.8 ± 1.2 mm. Overall, the results suggest that BB7 and BB8 have moderate to high antimicrobial exertion against E. coli, S. aureus, and P. aeruginosa. Still, the biological activity of these composites is lower than that of the standard reference, ciprofloxacin. Farther studies are demanded to determine the medium of action and implicit clinical operations of these composites. also, the composites law name like 2-({((2- chloro benzoyl)(phenyl) amino) sulfinyl} amino) phenyl acetate (BB4), N-({(2-(carbamothioylamino) phenyl) amino} sulfinyl)-2-chloro-N- phenylbenzamide (BB5), 2-({((2- chloro benzoyl)(phenyl) amino) sulfinyl} amino) phenyl-2-aminophenyl benzoate (BB6), N-({(2-(carbamoyl amino) phenyl) amino} sulfinyl)-2-chloro-N-phenylbenzamide (BB7) against S. aureus and Pseudomonas aeruginosa. The relief of oxygen snippet to nitrogen snippet redounded in a slightly increased antimicrobial exertion. Our study revealed that all the composites had stronger antibacterial exertion against Gram-positive bacteria when compared to Gram-negative bacteria. Antimicrobial exertion revealed that recently synthesized 2-({((2-chloro benzoyl)(phenyl) amino) sulfinyl} amino) phenyl formate (BB8), 2-({((2-chloro benzoyl)(phenyl) amino) sulfinyl} amino) phenyl-2- aminophenyl-2-(4-nitro phenoxy) aniline (BB9), 2-({((2-chloro benzoyl)(phenyl) amino) sulfinyl} amino) phenyl-2-aminophenyl-2-(3-nitro phenoxy) aniline (BB10) showed good significant exertion against S. aureus and Pseudomonas aeruginosa.
Cite this article: Bhor RJ, Bangar S, Bhagat DB. Synthesis, Characterization and in vitro Antibacterial Activity of “2-chloro-N-{[(2-chlorophenyl) amino] sulfinyl}-N -phenylbenzamide Nucleus and its Derivatives”. Int. J. Pharm. Investigation. 2023;13(4):837-44.
ACKNOWLEDGEMENT
The authors are thankful to Dr. S.B. Bhawar, Pravara Rural College of Pharmacy, Pravaranagar.
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