Current Trends in Pharmacy and Pharmaceutical Chemistry

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Get Permission Nerkar and Varpe: Synthesis, and in vitro evaluation of benzene sulfonamide derivatives for antimicrobial and disinfectant properties: Part-I

Journal Information

Journal ID (nlm-ta): Innovative Publication

Journal ID (publisher-id): Innovative Publication

Journal ID (journal_submission_guidelines): https://www.ctppc.org/

Title: Current Trends in Pharmacy and Pharmaceutical Chemistry

ISSN: 2582-5062

Article Information

Copyright: 2024

Date received: 15 November 2023

Date accepted: 28 December 2023

Publication date: 16 February 2024

Volume: 6

Issue: 1

Page: 23

DOI: 10.18231/j.ctppc.2024.005

Synthesis, and in vitro evaluation of benzene sulfonamide derivatives for antimicrobial and disinfectant properties: Part-I

[https://orcid.org/0000-0002-1377-8466] Amit G. Nerkar[1]

Email: dragnerkar@gmail.com

Designation:

Professor (UG) and Research Head

[] Abhishek Varpe[1]

Designation:

Student

 

Dept. of Pharmacy, CAYMET’s Siddhant College of Pharmacy Pune, Maharashtra India

Abstract

The synthesis of benzene sulfonamide derivatives has been reported here for the antimicrobial and disinfectant properties. The synthesis was performed by known literature procedure. P-Toulene sulfonyl chloride was reacted with ethylene diamine to yield to the desired compounds. The synthesis of these agents is reported in part -I of the paper. In subsequent parts the antimicrobial activity and disinfectant properties shall be reported.

Introduction

Benzene sulfonamide is a versatile moiety with several properties. Some of them include antimycobacterial. 1 antitubercular,2 antibacterial3 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.

Figure 1
https://s3-us-west-2.amazonaws.com/typeset-prod-media-server/4f806a3f-6f68-4ffe-9a08-9164afc9e7e0image1.png

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

Figure 2
https://s3-us-west-2.amazonaws.com/typeset-prod-media-server/4f806a3f-6f68-4ffe-9a08-9164afc9e7e0image2.png

  1. 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.

  2. 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).

  3. 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. 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.

  5. 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)

  6. 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

1 

R Hussain T Habib R Ikram M Muddassar Studies on the synthesis of benzene sulfonamides, evaluation of their antimicrobial activities, and molecular dockingLatin Am J Pharm20203913846

2 

RM Shingare YS Patil JN Sangshetti RB Patil DP Rajani SD Rajani Benzene sulfonamide pyrazole thio-oxadiazole hybrid as potential antimicrobial and antitubercular agentsRes Chem Intermediates201844443753

3 

AT Ali MN Mosa ZG Alshaheen MA Muhammad-Ali Characterization and Antibacterial Evaluation of Oxoazetidin-Benzene Sulfonamide Derivatives as a Hybrid Antimicrobial AgentsSyst Rev Pharm202011248794

4 

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 Lett20182820918

5 

M Ashfaq SS Shah T Najjam S Shaheen G Rivera Synthetic routes of sulfonamide derivatives: a brief review.Mini-Rev Organic Chem20131016070

Keywords

Categories:

Subject: Original Research Article

Keywords:

Keywords

Benzimidazole

Antimicrobial

Disinfectant

Synthesis

Evaluation

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Article type

Original Article


Article page

23-25


Authors Details

Amit G. Nerkar, Abhishek Varpe


Article History

Received : 15-11-2023

Accepted : 28-12-2023


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