4H-1,2,4-triazol-5-(4-Bromofenoksimetil)-3-(4-Substitue Benzil) Sülfidin Sentezi, Karakterizasyonu ve Antibakteriyel Aktivitesinin Değerlendirilmesi
4H-1, 2,4-triazol-5-(4-Bromofenoksimetil)-3-(4-substitue benzil) sülfid türevli serisi (6a-6g) tasarlanmış ve hazırlanmıştır. Yapılar, FT-IR spektroskopisi, elemental analiz ve 1 H NMR kullanılarak doğrulanmıştır. Antibakteriyel çalışmalar, gram+ve (Staphylococcus aureus ve Bacillus cereus) ve gram mikro mikroorganizmalar (Escherichia coli ve Pseudomonas aeruginosa) kullanılmış ve disk difüzyon yöntemi ile antibakteriyel aktivitenin değerlendirilmesiyle gerçekleştirilmiştir. Bileşik 6a en düşük etkiyi gösterirken, bileşik 6d en yüksek etkiyi göstermiştir. Hazırlanan bileşiklerin hepsi antibakteriyel etkiye sahiptir. Fakat bunların hiçbiri standart Sefuroksime göre daha yüksek etkiye sahip değildir.
Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-triazole-5-(4-Bromophenoxymethyl)-3- (4-substituted Benzyl) sulfide
A series of 4H-1,2,4-triazole-5-(4-Bromophenoxymethyl)- 3-(4-substitutedBenzyl) sulfide derivative (6a-6g) were designed and prepared. The structures have been confirmed using FT-IR spectroscopy, elemental analysis and 1 H NMR.Antibacterial study was done using gram+ve (Staphylococcus aureus, and Bacillus cereus) and gram-ve microorganisms (E. coli, and Pseudomonas aeruginosa) and disc diffusion method for evaluation of antibacterial activity. Compound 6d showed the highest effect, while compound 6a showed the lowest. All of the prepared compound has antibacterial activity, but none of them has higher effect than the standard Cefuroxime.
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- S. Ahmed, M.F. Zayed, S.M. El-Messery, M. AlAgamy, and H.M. Abdel-Rahman, Design, synthesis, antimicrobial evaluation and molecular modeling study of 1,2,4-triazole-based 4-thiazolidinones, Molecule, 21 (2016) 568-585.
- J. Van Heijenoort, Recent advances in the formation of the bacterial peptidoglycan monomer unit, Nat. Prod. Rep., 18 (2001) 503–519.
- D. Mengin-Lecreulx, B. Flouret,J. van Heijenoort, Cytoplasmic steps of peptidoglycan synthesis in escherichia coli, J. Bacteriol., 151 (1982) 1109–1117.
- R.G. Dinesh, A.J. Ananad, M.S. Anil, and P.M. Jignasu, Synthesis and biological screening of 1,2,4-triazole derivatives, Ind. J. Chem., 54 (2015) 556-564.
- B. Mounyr, S. Moulay, K.I. Saad, Methods for in vitro evaluating antimicrobial activity, J. Pharm. Anal., 6 (2016) 71-79
- W. Fichtali, E.M. Laaboudi, F. El Hadrami, A. El Aroussi, M. Ben-Tama, S.E. Benlemlih, Synthesis, characterization and antimicrobial activity of novel benzophenone derived 1,2,3-triazoles, J. Mater. Environ. Sci., 7 (2016) 1633-1641.
- E.M. Hussain, Synthesis of 1,2,4-Triazole Derivatives And Their Biological Activity Study, Ibn. Al. Hait. J. Pur. Appl. Sci., 23 (2010) XX-XX.
- W. Mark, F. Jeremy, Policy: An intergovernmental panel on antimicrobial resistance, Nature, 509 (2014) 555–557.
- A. Varvaresou, T.A. Tsotinis, A. Tsantili-Kakoulidou, A. Vamvakides, Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2,4-triazole, Il Farmaco, 53 (1998) 320-326.
- A. Almasirad, S.A. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi, A. Shafiee, Synthesis and anticonvulsant activity of new 2-substituted-5-[2- (2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles, Bioorg. Med. Chem. Lett., 14 (2004) 6057-6059.
- M. Kritsanida, A. Mouroutsou, P. Marakos, N. Pouli, S. Papakonstantinou-Garoufalias, C. Pannecouque, M. Witvrouw,E. De Clercq, Synthesis and antiviral activity evaluation of some new 6-substituted 3-(1-adamantyl)- 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles, Il Farmaco, 57 (2002) 253-257.
- B. Tozkoparan, E. Kupeli, E. Yesilada, M. Ertan, Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatoryanalgesic activity, Bioorg. Med. Chem., 15 (2007) 1808- 1814.
- I. Kucukguzel, S.G. Kucukguzel, S. Rollas, M. Kiraz, Some 3-thioxo/alkylthio-1,2,4-triazoles with a substituted thiourea moiety as possible antimycobacterials, Bioorg. Med. Chem. Lett., 11 (2001) 1703-1707.
- S. Sharma, S. Gangal, A. Rauf, M. Zahin, Synthesis, Antibacterial and Antifungal Activity of Some Novel 3,5-Disubstituted-1H-1,2,4-triazoles, Arch. Pharm. Chem. Life. Sci., 341 (2008) 714-720.
- 8. B.S. Holla, B. Veerendra, M.K. Shivananda, B. Poojary, Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles, Eur. J. Med. Chem., 38 (2003) 759–767.
- G. Turan-Zitouni, Z.A. Kaplacikli, M.T. Yildiz, P. Chevallet, D. Kaya, Synthesis and antimicrobial activity of 4-phenyl/cyclohexyl-5-(1-phenoxyethyl)-3-[N-(2- thiazolyl)acetamido]thio-4H-1,2,4-triazole derivatives Eur. J. Med. Chem., 40 (2005) 607-913.
- G. Nurhan, S. Mevlut, C. Elif, S. Ali, and D. Neslihan, Synthesis and antimicrobial activity of some new 1,2,4-triazole derivatives, Turk. J. Chem., 31 (2007) 335-348.
- J.H. Abeer, Synthesis and antimicrobial evolution of some new bis-1,3,4oxadiazole, bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives, M. Sc. Thesis, College of Education/Ibn Al-Haitham Baghdad University, (2002) 29-34.
- D. Neslihan, Synthesis and characterization of new trihetrocyclic compounds consisting of 1,2,4-triazol-3- one, 1,3,4-thiadiazole and 1,3,4-oxadiazole rings, Turk. J. Chem., 29 (2005) 125-133.
- R.R. Malii, R.R. Somani, M.P. Toraskar, K.K. Mali, and P.Y. Shirodkar, Synthesis of some antifungal and Antitubercular 1,2,4-triazole analoges, Int. J. Chem. Tech. Res., 1 (2009) 168-173.
- T. Anjali, S. Puspraj, P. Kumar Shukla, A. Verma and P. Pathak, 1,2,4-Triazole Scafolds: Recent Advances and Pharmacological Applications, Int. J. Curr. Res. Aca. Rev., 4 (2016) 277-296.
- H. Sabir, S. Gyoti, H. Mohd, Synthesis and antimicrobial activities of 1,2,4-triazole and 1,3,4-thiadiazole derivatives of 5-amino-2-hydroxybenzoic acid, E. J. Chem., 5 (2008) 963-968.