Synthesis and Antibacterial Activity of Some Aryloxyacetic Acid Derivatives Containing Aryl Sulfonate Moiety

Yıl 2023, Cilt: 8 Sayı: 2, 260 - 265, 06.06.2023

Sevil Şenkardeş , Tuğçe Koyuncu , Hilal Basak Erol , Banu Kaşkatepe

https://doi.org/10.26453/otjhs.1270936

Öz

Objective: Today, the development of antibiotic resistance is increasing rapidly. This makes it necessary to discover new antibiotics; therefore, this research aims to find new antibacterial agents.
Materials and Methods: Structures of the newly synthesised compounds (4a-d, 5a-d) were elucidated by elemental analyses and spectroscopic data. Their in vitro antibacterial activities were tested using a micro-dilution technique against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Enterococcus faecalis. Ciprofloxacin was used as the control drug in this study, which was carried out in accordance with the guidelines of the European Committee on Antimicrobial Susceptibility Testing.
Results: The antimicrobial activities of the compounds were found in a wide range with minimum inhibitory concentration (MIC) values of 15.62-125 μg/mL. Particularly, 4-((2-(2-(4-chloro-3-methyl)acetyl)hydrazineylidene)methyl)phenyl p-methyl benzenesulfonate (4b) was found to be most effective against Enterococcus faecalis with MIC value of 15.62 µg/mL.
Conclusion: The findings of this study display that the different derivatives of the molecules in this study may be considered important candidates for future research. Considering the results, it is planned to reach more effective new compounds with modifications to be made by changing the substituents on the aromatic rings.

Anahtar Kelimeler

Hydrazone, sulfonate, aldehyde, antimicrobial activity, hydrazide.

Destekleyen Kurum

TÜBİTAK 2209-A University Students Research Projects Support Program.

Proje Numarası

Project application no: 1919B012107103

Aril Sülfonat Parçası İçeren Bazı Ariloksiasetik Asit Türevlerinin Sentezi ve Antibakteriyel Aktivitesi

Öz

Amaç: Günümüzde antibiyotik direnci gelişimi hızla artmaktadır. Bu da yeni antibiyotiklerin keşfedilmesini gerekli kılmaktadır. Dolayısıyla bu araştırmanın amacı yeni antibakteriyel ajanlar bulmaktır.
Materyal ve Metot: Yeni sentezlenen bileşiklerin (4a-d, 5a-d) yapıları elemental analiz ve spektroskopik verilerle aydınlatıldı. Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, metisiline dirençli Staphylococcus aureus and Enterococcus faecalis’e karşı mikrodilüsyon tekniği kullanılarak in vitro antibakteriyel aktiviteleri test edildi. Avrupa Antibiyotik Duyarlılık Komitesi standartlarına uygun olarak yapılan bu çalışmada, kontrol ilaç olarak siprofloksazin kullanıldı.
Bulgular: Bileşiklerin antimikrobiyal aktivite sonuçları minimum inhibitör konsantrasyon (MİK)=15,62-125 μg/mL olarak geniş bir aralıkta bulundu ve özellikle 4-((2-(2-(4-kloro-3-metil)asetil)hidraziniliden)metil)fenil p-metilbenzensülfonat (4b)' nin 15,62 µg/mL MİK değeri ile Enterococcus faecalis'e karşı en etkili olduğu tespit edildi.
Sonuç: Bu çalışmanın bulguları, bu çalışmadaki moleküllerin farklı türevlerinin gelecekteki araştırmalar için önemli adaylar olarak kabul edilebileceğini göstermektedir. Sonuçlar göz önüne alındığında; aromatik halkaların üzerindeki sübstitüentler değiştirilerek yapılacak modifikasyonlarla daha etkin yeni bileşiklere ulaşılması planlanmaktadır.

Anahtar Kelimeler

Aldehit, antimikrobiyal aktivite, hidrazit, hidrazon, sülfonat

Proje Numarası

Project application no: 1919B012107103

Kaynakça

• 1. Rollas S, Küçükgüzel ŞG. Biological activities of hydrazone derivatives. Molecules. 2007;12(8):1910-1939. doi:10.3390/12081910
• 2. Gobis K, Szczesio M, Olczak A, et al. Differen-ces in the structure and antimicrobial activity of hydrazones derived from methyl 4-phenylpicolinimidate. Materials (Basel). 2022;15(9):3085. doi:10.3390/ma15093085
• 3. Küçükgüzel ŞG, Oruç EE, Rollas S, Şahin F, Özbek A. Synthesis, characterisation and biologi-cal activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem. 2002;37(3):197-206. doi:10.1016/S0223-5234(01)01326-5
• 4. Mistry S, Singh AK. Synthesis and in vitro anti-microbial activity of new steroidal hydrazone derivatives. Futur J Pharm Sci. 2022;8:7. doi:10.1186/s43094-021-00391-4
• 5. Tatar E, Şenkardeş S, Sellitepe HE, et al. Synthe-sis, and prediction of molecular properties and antimicrobial activity of some acylhydrazones derived from N-(arylsulfonyl)methionine. Tur-kish J Chem. 2016;40(3):510-534. doi:10.3906/kim-1509-21
• 6. Nabizadeh M, Naimi-Jamal MR, Rohani M, Aze-rang P, Tahghighi A. Hydrazone analogues with promising antibacterial profiles: Synthesis, morp-hology, in vitro and in silico approaches. Lett Appl Microbiol. 2022;75(3):667-679. doi:10.1111/lam.13692
• 7. Balasubramaniyan M, Vinayagam V, Kizhake-dathil MPJ, Karuppiah P. In silico, in vitro anti-microbial and antimycobacterial evaluation of newly synthesized 2r, 6c-diaryl-3t-methylpiperidin-4-one arylsulphonylhydrazones. Bioorg Chem. 2022;128:106033. doi:10.1016/j.bioorg.2022.106033
• 8. Mohi El-Deen EM, Nossier ES, Karam EA. New quinazolin-4(3H)-one derivatives incorporating hydrazone and pyrazole scaffolds as antimicro-bial agents targeting DNA gyraze enzyme. Sci Pharm. 2022;90(3):52. doi:10.3390/scipharm90030052
• 9. Tekin Z, Tekeli Y, Küçükbay Z, Lolak N, Yapar G, Akocak S. Antibacterial and antioxidant acti-vity evaluation of bis-substituted isovanillin deri-vatives. JOTCSA. 2023;10(2):435-442. doi:10.18596/jotcsa.1196335
• 10. Şenkardeş S, Kiymaci ME, Kale K, Kozanoğlu İM, Kaşkatepe B, Küçükgüzel G. Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. J Res Pharm. 2021;25(2):135-141. doi:10.29228/jrp.4
• 11. Aneja B, Azam M, Alam S, et al. Natural product-based 1,2,3-triazole/sulfonate analogues as po-tential chemotherapeutic agents for bacterial in-fections. ACS Omega. 2018;3(6):6912-6930. doi:10.1021/acsomega.8b00582
• 12. Su S, Zhou Q, Tang X, et al. Design, synthesis, and antibacterial activity of novel myricetin deri-vatives containing sulfonate. Monatshefte fur Chemie. 2021;152(3):345-356. doi:10.1007/s00706-021-02739-1
• 13. Xie D, Yang Z, Hu X, Wen Y. Synthesis, anti-bacterial and insecticidal activities of novel cap-saicin derivatives containing a sulfonic acid es-ters moiety. Front Chem. 2022;10:929050. doi:10.3389/fchem.2022.929050
• 14. Koçak Aslan E, Han Mİ, Krishna VS, et al. Isoni-azid linked to sulfonate esters via hydrazone functionality: Design, synthesis, and evaluation of antitubercular activity. Pharmaceuticals. 2022;15(10):1301. doi:10.3390/ph15101301
• 15. Kulabaş N, Tatar E, Bingöl Özakpınar Ö, et al. Synthesis and antiproliferative evaluation of no-vel 2-(4H-1,2,4-triazole-3-ylthio)acetamide deri-vatives as inducers of apoptosis in cancer cells. Eur J Med Chem. 2016;121:58-70. doi:10.1016/j.ejmech.2016.05.017
• 16. Nimavat B, Mohan S, Saravanan J, et al. Synthe-ses, characterization and antioxidant activity of some oxadiazoles. Asian J Chem. 2013;25(3):1691-1694. doi:10.14233/ajchem.2013.13825
• 17. Şenkardeş S, Erdoğan Ö, Çevik Ö, Küçükgüzel ŞG. Synthesis and biological evaluation of novel aryloxyacetic acid hydrazide derivatives as anti-cancer agents. Synth Commun. 2021;51(17):2634-2643. doi:10.1080/00397911.2021.1945105
• 18. Şenkardeş S, İhsan Han M, Gürboğa M, Özakpi-nar ÖB, Küçükgüzel ŞG. Synthesis and antican-cer activity of novel hydrazone linkage-based aryl sulfonate derivatives as apoptosis inducers. Med Chem Res. 2022;31(2):368-379. doi:10.1007/s00044-021-02837-z
• 19. Şenkardeş S, Kart D, Bebek B, Gündüz MG, Kü-çükgüzel ŞG. Synthesis, antimicrobial properties and in silico studies of aryloxyacetic acid deriva-tives with hydrazone or thiazolidine-4-one scaf-fold . J Biomol Struct Dyn. 2022;0(0):1-12. doi:10.1080/07391102.2022.2121761
• 20. The European Committee on Antimicrobial Sus-ceptibility Testing. Breakpoint tables for interpre-tation of MICs and zone diameters. Version 1.3, January 5, 2011. https://www.eucast.org/fileadmin/src/media/PDFs/EUCAST_files/Disk_test_documents/EUCAST_breakpoints_v1.3_pdf.pdf. Accessed May 28, 2023.
• 21. Küçükgüzel ŞG, Koç D, Çikla-Süzgün P, et al. Synthesis of tolmetin hydrazide-hydrazones and discovery of a potent apoptosis inducer in colon cancer cells. Arch Pharm (Weinheim). 2015;348(10):730-742. doi:10.1002/ardp.201500178
• 22. Palla G, Predieri G, Domiano P, Vignali C, Tur-ner WV. Conformational behaviour and E/Z iso-merization of N-acyl and N-aroylhydrazones. Tetrahedron. 1986;42:3649-3654.
• 23. Koç HC, Atlihan İ, Mega-Tiber P, Orun O, Kü-çükgüzel ŞG. Synthesis of some novel hydrazide-hydrazones derived from etodolac as potential anti-prostate cancer agents. J Res Pharm. 2022;26(1):1-12. doi:10.29228/jrp.97
• 24. Aydin S, Kaushik-Basu N, Arora P, et al. Mic-rowave assisted synthesis of some novel flurbip-rofen hydrazidehydrazones as anti-HCV NS5B and anticancer agents. Marmara Pharm J. 2013;17(1):26-34. doi:10.12991/201317389
• 25. Han Mİ, Atalay P, Tunç CÜ, et al. Design and synthesis of novel (S)-Naproxen hydrazide-hydrazones as potent VEGFR-2 inhibitors and their evaluation in vitro/in vivo breast cancer models. Bioorganic Med Chem. 2021;37:116097. doi:10.1016/j.bmc.2021.116097