Synthesis and Characterization of Sulfamethoxazole Derivatives

Authors

Abstract

Sulfamethoxazole (SMX) belongs to the sulfonamide group of antibiotics. It was chosen to represent this group because it is widely used and detected in aquatic environments. The thiazolidine ring has been incorporated into many well-known biologically active compounds, either as an additional component or by replacing another ring, prompting researchers to develop several compounds with this structure. Furthermore, the chemistry of chalcones has produced serious scientific readings throughout the world. Chiefly, interest has been concentrated on the creation and biodynamic actions of chalcones so that a diversity of novel heterocycles with favorable pharmaceutical shape can be designed. Synthetic procedures have been successfully developed for the generation of the target compounds. Six different aromatic para-benzaldehydes (H, OH, OCH3, NO2, Cl, & N(CH3)2) were used, following a multi-step reaction procedure. The purity of the products was checked by using thin-layer chromatography (TLC). The chemical structure of the intermediate and final compounds was identified and verified by checking their melting points, using FT-IR spectroscopy, performing elemental microanalysis (CHNS), and analyzing the final compounds with 1H NMR. A preliminary study of antimicrobial activity was conducted on three different strains of bacteria, revealing that the final compounds M3(a-f) exhibit significant activity compared to the standard drug sulfamethoxazole, with moderate to favorable activity.

Keywords: Sulfamethoxazole, Synthesis, Sulfamethoxazole Derivative, Antibiotic.

Keywords:

Sulfamethoxazole, Synthesis, Sulfamethoxazole Derivative, Antibiotic

DOI

https://doi.org/10.22270/jddt.v15i8.7302

Author Biographies

Mohd Haseen, Department of Pharmacy, Kanpur Institute of Technology & Pharmacy, Kanpur-208027, Uttar Pradesh, India

Department of Pharmacy, Kanpur Institute of Technology & Pharmacy, Kanpur-208027, Uttar Pradesh, India

Prashant Kumar Katiyar , Department of Pharmacy, Kanpur Institute of Technology & Pharmacy, Kanpur-208027, Uttar Pradesh, India

 

Department of Pharmacy, Kanpur Institute of Technology & Pharmacy, Kanpur-208027, Uttar Pradesh, India

Brijesh Shukla , Department of Pharmacy, Seiko College of Pharmacy, Harauni, Lucknow-226008, Uttar Pradesh, India

Department of Pharmacy, Seiko College of Pharmacy, Harauni, Lucknow-226008, Uttar Pradesh, India

AKASH SHARMA, Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences, Babasaheb Bhimrao Ambedkar University, Lucknow-226025, Uttar Pradesh, India

Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences, Babasaheb Bhimrao Ambedkar University, Lucknow-226025, Uttar Pradesh, India

Prashant Kumar, Department of Pharmacy, Kanpur Institute of Technology & Pharmacy, Kanpur-208027, Uttar Pradesh, India

Department of Pharmacy, Kanpur Institute of Technology & Pharmacy, Kanpur-208027, Uttar Pradesh, India

Nidhi Tyagi, Department of Pharmacy, Kanpur Institute of Technology & Pharmacy, Kanpur-208027, Uttar Pradesh, India

Department of Pharmacy, Kanpur Institute of Technology & Pharmacy, Kanpur-208027, Uttar Pradesh, India

References

1. Mohr KI. History of antibiotics research. In: Sass P, editor. How to Overcome the Antibiotic Crisis: Facts, Challenges, Technologies and Future Perspectives. Springer; 2016. p. 237-272. https://doi.org/10.1007/82_2016_499 PMid:27738915

2. Hutchings MI, Truman AW, Wilkinson B. Antibiotics: past, present and future. Curr Opin Microbiol. 2019; 51:72-80. https://doi.org/10.1016/j.mib.2019.10.008 PMid:31733401

3. Nii-Trebi NI. Emerging and neglected infectious diseases: insights, advances, and challenges. Biomed Res Int. 2017; 2017(1):5245021. https://doi.org/10.1155/2017/5245021 PMid:28286767 PMCid:PMC5327784

4. Davies J, Davies D. Origins and evolution of antibiotic resistance. Microbiol Mol Biol Rev. 2010; 74(3):417-433. https://doi.org/10.1128/MMBR.00016-10 PMid:20805405 PMCid:PMC2937522

5. Breijyeh Z, Jubeh B, Karaman R. Resistance of gram-negative bacteria to current antibacterial agents and approaches to resolve it. Molecules. 2020; 25(6):1340. https://doi.org/10.3390/molecules25061340 PMid:32187986 PMCid:PMC7144564

6. Levy SB. The Antibiotic Paradox: How Miracle Drugs Are Destroying the Miracle. Springer; 2013.

7. Epand RM, Walker C, Epand RF, Magarvey NA. Molecular mechanisms of membrane targeting antibiotics. Biochim Biophys Acta Biomembr. 2016; 1858(5):980-987. https://doi.org/10.1016/j.bbamem.2015.10.018 PMid:26514603

8. Lade H, Kim JS. Bacterial targets of antibiotics in methicillin-resistant Staphylococcus aureus. Antibiotics. 2021; 10(4):398. https://doi.org/10.3390/antibiotics10040398 PMid:33917043 PMCid:PMC8067735

9. Wright GD. Bacterial resistance to antibiotics: enzymatic degradation and modification. Adv Drug Deliv Rev. 2005; 57(10):1451-1470. https://doi.org/10.1016/j.addr.2005.04.002 PMid:15950313

10. Prescott JF. Sulfonamides, diaminopyrimidines, and their combinations. In: Giguère S, Prescott JF, Dowling PM, editors. Antimicrobial Therapy in Veterinary Medicine. Wiley-Blackwell; 2013. p. 279-294. https://doi.org/10.1002/9781118675014.ch17

11. Henry RJ. The mode of action of sulfonamides. Bacteriol Rev. 1943; 7(4):175-262. https://doi.org/10.1128/br.7.4.175-262.1943 PMid:16350088 PMCid:PMC440870

12. Smilack JD. Trimethoprim-sulfamethoxazole. In: Mayo Clin Proc. Elsevier; 1999. https://doi.org/10.4065/74.7.730 PMid:10405706

13. La Farre M, Pérez S, Kantiani L, Barceló D. Fate and toxicity of emerging pollutants, their metabolites and transformation products in the aquatic environment. TrAC Trends Anal Chem. 2008; 27(11):991-1007. https://doi.org/10.1016/j.trac.2008.09.010

14. Mohammed Abd Al-Khaliq Z. Synthesis, characterization and antibacterial activity of new series of sulfamethoxazole derivatives. Ministry of Higher Education; 2015.

15. Ashraf MA, Maah MJ, Yusoff I, Wajid A. Synthesis, characterization and biological activity of Schiff bases. IPCBEE. 2011; 10(1):185.

16. Lemire JA, Harrison JJ, Turner RJ. Antimicrobial activity of metals: mechanisms, molecular targets and applications. Nat Rev Microbiol. 2013; 11(6):371-384. https://doi.org/10.1038/nrmicro3028 PMid:23669886

17. Krátký M, Vinšová J, Stolaříková J, et al. Sulfadiazine salicylaldehyde-based Schiff bases: Synthesis, antimicrobial activity and cytotoxicity. Molecules. 2017; 22(9):1573. https://doi.org/10.3390/molecules22091573 PMid:28925956 PMCid:PMC6151383

18. Dua R, Shrivastava S, Sonwane SK, Srivastava S. Pharmacological significance of synthetic heterocycles scaffold: a review. Adv Biol Res. 2011; 5(3):120-144.

19. Jain AK, Vaidya A, Ravichandran V, Kashaw SK, Agrawal RK. Recent developments and biological activities of thiazolidinone derivatives: A review. Bioorg Med Chem. 2012; 20(11):3378-3395. https://doi.org/10.1016/j.bmc.2012.03.069 PMid:22546204

20. Zayed MF. Medicinal chemistry of quinazolines as analgesic and anti-inflammatory agents. ChemEngineering. 2022; 6(6):94. https://doi.org/10.3390/chemengineering6060094

21. Bukhari NA, Jasamai M, Jantan I. Synthesis and biological evaluation of chalcone derivatives (mini review). Mini Rev Med Chem. 2012; 12(13):1394-1403. https://doi.org/10.2174/13895575112091394 PMid:22876958

22. Nowakowska Z. A review of anti-infective and anti-inflammatory chalcones. Eur J Med Chem. 2007; 42(2):125-137. https://doi.org/10.1016/j.ejmech.2006.09.019 PMid:17112640

23. Rajamanickam G, Suresh V, Jayakumar R, et al. In vitro anthelmintic and antimicrobial activity of novel series of quinoxaline-2,3-dione-6-sulphonyl benzimidazoles. J Chem Pharm Sci. 2015; 8:656-660.

24. Rao P, Knaus EE. Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition and beyond. J Pharm Pharm Sci. 2008; 11(2):81s-110s. https://doi.org/10.18433/J3T886 PMid:19203472

Published

2025-08-15
Statistics
Abstract Display: 618
PDF Downloads: 742
PDF Downloads: 98

How to Cite

1.
Haseen M, Katiyar PK, Shukla B, SHARMA A, Kumar P, Tyagi N. Synthesis and Characterization of Sulfamethoxazole Derivatives. J. Drug Delivery Ther. [Internet]. 2025 Aug. 15 [cited 2026 Jan. 17];15(8):60-8. Available from: https://www.jddtonline.info/index.php/jddt/article/view/7302

How to Cite

1.
Haseen M, Katiyar PK, Shukla B, SHARMA A, Kumar P, Tyagi N. Synthesis and Characterization of Sulfamethoxazole Derivatives. J. Drug Delivery Ther. [Internet]. 2025 Aug. 15 [cited 2026 Jan. 17];15(8):60-8. Available from: https://www.jddtonline.info/index.php/jddt/article/view/7302