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- DOI 10.18231/j.ctppc.2024.005
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CrossMark
Synthesis, and in vitro evaluation of benzene sulfonamide derivatives for antimicrobial and disinfectant properties: Part-I
- Author Details:
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Amit G. Nerkar *
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Abhishek Varpe
Amit G. Nerkar *
Introduction
Benzene sulfonamide is a versatile moiety with several properties. Some of them include antimycobacterial. [1] antitubercular,[2] antibacterial[3] and antiviral,[4] etc properties. The synthesis of Benzene sulfonamide moieties is reported here from p-toulene sulfonyl chloride and ethylene diamine and to variate the reaction, with propylamine to yield compounds 1 and 2 respectively. The structure of these compounds have been reported in the [Figure 1].
Materials and Methods
TLC was performed on 524nm Merk TLC plates. All chemicals were of synthetic grade and 98% purisis grade. TLC was eluted with 3 different solvents to check the purity of the compounds and visualized in Iodine chamber and further in UV chamber. The 1H-NMR was performed on Bruker 400 MHZ NMR before which FT-IR was performed on Perkin Elmer spectrophotometer. The synthetic scheme for the claimed compounds has been shown in [Figure 2]. The compounds were synthesized by sulfonamide formation reaction.[5]
Synthetic scheme
4- methyl-N-(ethanamine)-benzenesulfonamide (AV1): Equimolar quantities of p-toluene sulfonyl chloride and 1-propanamide were stirred at room temperature for 3 hrs vigorously in round bottom flask and magnetic bead on hot plate mantle with magnetic stirrer.
FT-IR (λ, cm-1): 3454.9 (-NH2 str.), 3108.7 (-N-H-H str), 3085.3 (-NH-H bending), 3001.7 (-SO2 str), 2994.3, 2998.6 (-SO2 bending), 1592.5 (CH2-NH2 str.), 1586.8 (CH2-NH2 str), 1256.7, 1182.5, 1155.0, 1121.6, 1099.2, 1078.4, 1002.6, 934.0, 879.0, 798.0, 664.0, 553.0, 362.0, 283.0, 146.0 (-CH-Aromatic).
1H-NMR (δ shift in ppm): 2.32 (3H, s) (-CH3), 2.87 (2H, t, J = 7.0 Hz) (-NH2), 3.52 (2H, t, J = 7.0 Hz) (CH2), 7.31 (2H, ddd, J = 8.0, 1.8, 0.4 Hz) (-CH Ar), 7.70 (2H, ddd, J = 8.0, 1.5, 0.4 Hz) (-CH Ar).
4- methyl-N-propylbenzenesulfonamide (AV2): Equimolar quantities of p-toluene sulfonyl chloride and 1-propanamide were stirred at room temperature for 3 hrs vigorously in round bottom flask and magnetic bead on hot plate mantle with magnetic stirrer.
FT-IR (λ, cm-1): 3047.4 (-NH Str), 3001.7(-SO2NH Str), 2994.3 (-SO2), 2998.6 (-CH Ar), 1592.5 (-NH-CH2), 1586.8 (-CH2), 1296.3, 1268.5, 1256.7, 1182.5, 1155.0, 1121.6, 1099.2, 1078.4, 1002.6, 934.0, 879.0, 798.0, 664.0, 553.0, 362.0, 283.0, 146 (1296-146,-CH Ar)
1H-NMR (δ shift in ppm): 0.96 (3H, t, J = 7.0 Hz) (-CH3), 1.62 (2H, tq, J = 7.5) (-NH2), 3.52 (2H t, J=7.0 Hz) (-CH2), 2.32 (3H, s) (-CH3), 3.28 (2H, t, J = 7.5 Hz) (-CH2), 7.31 (2H, ddd, J = 8.0, 1.8, 0.4 Hz) (-CH Ar), 7.69 (2H, ddd, J = 8.0, 1.5, 0.4 Hz) (-CH Ar).
Results and Discussion
IR data
4- methyl-N-(ethanamine)-benzenesulfonamide (AV1)
FT-IR (λ, cm-1): 3454.9 (-NH2 str.), 3108.7 (-N-H-H str), 3085.3 (-NH-H bending), 3001.7 (-SO2 str), 2994.3, 2998.6 (-SO2 bending), 1592.5 (CH2-NH2 str.), 1586.8 (CH2-NH2 str), 1256.7, 1182.5, 1155.0, 1121.6, 1099.2, 1078.4, 1002.6, 934.0, 879.0, 798.0, 664.0, 553.0, 362.0, 283.0, 146.0 (-CH-Aromatic)
4-methyl-N-propylbenzenesulfonamide (AV2)
FT-IR (λ, cm-1): 3047.4 (-NH Str), 3001.7(-SO2NH Str), 2994.3 (-SO2), 2998.6 (-CH Ar), 1592.5 (-NH-CH2), 1586.8 (-CH2), 1296.3, 1268.5, 1256.7, 1182.5, 1155.0, 1121.6, 1099.2, 1078.4, 1002.6, 934.0, 879.0, 798.0, 664.0, 553.0, 362.0, 283.0, 146 (1296-146 , -CH Ar)
1H-NMR data
4- methyl-N-(ethanamine)-benzenesulfonamide (AV1): 2.32 (3H, s) (-CH3), 2.87 (2H, t, J = 7.0 Hz) (-NH2), 3.52 (2H, t, J = 7.0 Hz) (-CH2), 7.31 (2H, ddd, J = 8.0, 1.8, 0.4 Hz) (-CH Ar), 7.70 (2H, ddd, J = 8.0, 1.5, 0.4 Hz) (-CH Ar).
4-methyl-N-propylbenzenesulfonamide (AV2): 0.96 (3H, t, J = 7.0 Hz) (-CH3), 1.62 (2H, tq, J = 7.5) (-NH2), 3.52 (2H t, J=7.0 Hz) (-CH2), 2.32 (3H, s) (-CH3), 3.28 (2H, t, J = 7.5 Hz) (-CH2), 7.31 (2H, ddd, J = 8.0, 1.8, 0.4 Hz) (-CH Ar), 7.69 (2H, ddd, J = 8.0, 1.5, 0.4 Hz) (-CH Ar).
Conclusion
From the IR and 1H-NMR data of the compounds, it was confirmed that the compounds were synthesized in Part-I of this paper. Further the evaluation of the compounds shall be done in Part-II of the paper.
Source of Funding
None.
Conflict of Interest
None.
References
- R Hussain, T Habib, R Ikram, M Muddassar. Studies on the synthesis of benzene sulfonamides, evaluation of their antimicrobial activities, and molecular docking. Latin Am J Pharm 2020. [Google Scholar]
- RM Shingare, YS Patil, JN Sangshetti, RB Patil, DP Rajani, SD Rajani. Benzene sulfonamide pyrazole thio-oxadiazole hybrid as potential antimicrobial and antitubercular agents. Res Chem Intermediates 2018. [Google Scholar]
- AT Ali, MN Mosa, ZG Alshaheen, MA Muhammad-Ali. Characterization and Antibacterial Evaluation of Oxoazetidin-Benzene Sulfonamide Derivatives as a Hybrid Antimicrobial Agents. Syst Rev Pharm 2020. [Google Scholar]
- D Zhou, D Xie, F He, B Song, D Hu. Antiviral properties and interaction of novel chalcone derivatives containing a purine and benzenesulfonamide moiety.. Bioorganic Med Chem Lett 2018. [Google Scholar]
- M Ashfaq, SS Shah, T Najjam, S Shaheen, G Rivera. Synthetic routes of sulfonamide derivatives: a brief review.. Mini-Rev Organic Chem 2013. [Google Scholar]