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image of 4-methyl-N-[5-[Phenylamino]Acetyl]-2-yl]Benzenesulfonamides: Synthesis, Characterization, and Preliminary Biological Evaluation

Abstract

Introduction

Oxazole and the compounds containing sulphonamides are utilized for various treatments of microbial disease as well as for diabetic patients. In the current study, the above moiety synthesizes the new molecule for the treatment of diabetes and microbial infection. The present work involved oxazole-based sulphonamide derivatives by the N-acylation and N-sulphonation. The synthesis was carried out by treating substituted anilines with chloroacetic chloride. The cycloaddition reaction was carried out using triethyl amine as a base catalyst. In the final steps, toluene sulphonyl chloride was used for sulphonation. The synthesized substance was confirmed , 1, ESI, Mass spectroscopy, and elemental investigation technique.

Material and Methods

Every reagent and starting material used in the synthesis was pure enough to be used as a reagent. To provide an inert environment, the solvents were purified in accordance with conventional laboratory protocols under a nitrogen atmosphere. Melting points are expressed in degrees Celsius and are uncorrected. They were determined by the open capillary technique. KBr pellets and a Shimadzu 8201 PC FTIR spectrophotometer were used to obtain FTIR spectra. Using JEOL and Bruker 500 MHz NMR spectrometers, ~1H and ~13C NMR spectra were obtained in CDCl and DMSO-d6, with TMS serving as the internal reference. A Thermo-Finnigan mass spectrophotometer was used to determine the masses of the chemical using the ESI technique.

Result

The present work involved oxazole-based sulphonamides derivatives by the N-acylation and N-sulphonation. The synthesis was carried out by treating substituted anilines with chloroacetic chloride. The cycloaddition reaction was carried out using triethyl amine as a base catalyst. In the final steps, toluene sulphonyl chloride was used for sulphonation. IR, 1HNMR, ESI, Mass spectroscopy and elemental analysis technique confirmed the synthesized compound.

Discussion

Oxazoles are also related to compounds called 1,3-azoles[nitrogen and oxygen heteroatoms in a 5-membered ring]. Oxazole demonstrates aromaticity since Huckel's rule requires 6π electrons, which are provided by the delocalization of a single pair of electrons from the oxygen atom. It has a wide range of pharmacological aspects like anti-allergic, hypertension, inflammation, schizophrenia, and inflammation. Similarly, sulphonamides are also used as preventive and chemotherapeutic agents against various diseases such as antibacterial, antiprotozoal, antifungal, and translation initiation inhibitors.

Conclusion

The preliminary biological activity was performed on a preliminary level for the antimicrobial and antidiabetic profile. The disc diffusion approach was utilized to achieve the antibacterial activity; similarly diabetic activity was carried out by the induced method. Out of all the synthesized compounds N-[5-[2-[4-bromophenyl amino]acetyloxazole2 yl]-4methylo benzene sulphonamide [4a], N-[5-2[2-FLoro-5nitrophenyl amino]acetyloxazole2yl]-4methylo benzene sulfonamide [4b] show significant effect compared to standard drugs.

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2025-01-18

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4-methyl-N-[5-[Phenylamino]Acetyl]-2-yl]Benzenesulfonamides: Synthesis, Characterization, and Preliminary Biological Evaluation
Bentham Science Publishers ; https://doi.org/10.2174/0115734072329263241009051355
/content/journals/cbc/10.2174/0115734072329263241009051355
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  • Article Type:     Research Article
Keywords: antibacterial ; Oxazole ; sulphonamides ; STZ ; spectroscopy

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