BibTex RIS Kaynak Göster

Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-triazole-5- 4-Bromophenoxymethyl -3- 4-substituted Benzyl sulfide

Yıl 2017, Cilt: 45 Sayı: 2, 251 - 255, 01.06.2017

Öz

Aseries 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 1H 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.

Kaynakça

  • 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.
  • 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.
  • R.R. Malii, R.R. Somani, M.P. Toraskar, K.K. Mali, and P.Y. Shirodkar, Synthesis of some antifungal and Anti- tubercular 1,2,4-triazole analoges, Int. J. Chem. Tech. Res., 1 (2009) 168-173.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • B. Tozkoparan, E. Kupeli, E. Yesilada, M. Ertan, Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatory- analgesic activity, Bioorg. Med. Chem., 15 (2007) 1808- 1814.
  • 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.
  • 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.
  • 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.
  • W. Mark, F. Jeremy, Policy: An intergovernmental panel on antimicrobial resistance, Nature, 509 (2014) 555–557.
  • 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. 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.
  • S. Ahmed, M.F. Zayed, S.M. El-Messery, M. Al- Agamy, 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.
  • B. Mounyr, S. Moulay, K.I. Saad, Methods for in vitro evaluating antimicrobial activity, J. Pharm. Anal., 6 (2016) 71-79
  • 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.
  • D. Mengin-Lecreulx, B. Flouret,J. van Heijenoort, Cytoplasmic steps of peptidoglycan synthesis in escherichia coli, J. Bacteriol., 151 (1982) 1109–1117.
  • J. Van Heijenoort, Recent advances in the formation of the bacterial peptidoglycan monomer unit, Nat. Prod. Rep., 18 (2001) 503–519.

4H-1,2,4-triazol-5- 4-Bromofenoksimetil -3- 4-Substitue Benzil Sülfidin Sentezi, Karakterizasyonu ve Antibakteriyel Aktivitesinin Değerlendirilmesi

Yıl 2017, Cilt: 45 Sayı: 2, 251 - 255, 01.06.2017

Öz

H-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 1H 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

Kaynakça

  • 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.
  • 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.
  • R.R. Malii, R.R. Somani, M.P. Toraskar, K.K. Mali, and P.Y. Shirodkar, Synthesis of some antifungal and Anti- tubercular 1,2,4-triazole analoges, Int. J. Chem. Tech. Res., 1 (2009) 168-173.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • B. Tozkoparan, E. Kupeli, E. Yesilada, M. Ertan, Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatory- analgesic activity, Bioorg. Med. Chem., 15 (2007) 1808- 1814.
  • 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.
  • 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.
  • 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.
  • W. Mark, F. Jeremy, Policy: An intergovernmental panel on antimicrobial resistance, Nature, 509 (2014) 555–557.
  • 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. 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.
  • S. Ahmed, M.F. Zayed, S.M. El-Messery, M. Al- Agamy, 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.
  • B. Mounyr, S. Moulay, K.I. Saad, Methods for in vitro evaluating antimicrobial activity, J. Pharm. Anal., 6 (2016) 71-79
  • 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.
  • D. Mengin-Lecreulx, B. Flouret,J. van Heijenoort, Cytoplasmic steps of peptidoglycan synthesis in escherichia coli, J. Bacteriol., 151 (1982) 1109–1117.
  • J. Van Heijenoort, Recent advances in the formation of the bacterial peptidoglycan monomer unit, Nat. Prod. Rep., 18 (2001) 503–519.
Toplam 22 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Research Article
Yazarlar

Mazin N. Mousa Bu kişi benim

Yayımlanma Tarihi 1 Haziran 2017
Yayımlandığı Sayı Yıl 2017 Cilt: 45 Sayı: 2

Kaynak Göster

APA Mousa, M. N. (2017). Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-triazole-5- 4-Bromophenoxymethyl -3- 4-substituted Benzyl sulfide. Hacettepe Journal of Biology and Chemistry, 45(2), 251-255.
AMA Mousa MN. Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-triazole-5- 4-Bromophenoxymethyl -3- 4-substituted Benzyl sulfide. HJBC. Haziran 2017;45(2):251-255.
Chicago Mousa, Mazin N. “Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-Triazole-5- 4-Bromophenoxymethyl -3- 4-Substituted Benzyl Sulfide”. Hacettepe Journal of Biology and Chemistry 45, sy. 2 (Haziran 2017): 251-55.
EndNote Mousa MN (01 Haziran 2017) Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-triazole-5- 4-Bromophenoxymethyl -3- 4-substituted Benzyl sulfide. Hacettepe Journal of Biology and Chemistry 45 2 251–255.
IEEE M. N. Mousa, “Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-triazole-5- 4-Bromophenoxymethyl -3- 4-substituted Benzyl sulfide”, HJBC, c. 45, sy. 2, ss. 251–255, 2017.
ISNAD Mousa, Mazin N. “Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-Triazole-5- 4-Bromophenoxymethyl -3- 4-Substituted Benzyl Sulfide”. Hacettepe Journal of Biology and Chemistry 45/2 (Haziran 2017), 251-255.
JAMA Mousa MN. Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-triazole-5- 4-Bromophenoxymethyl -3- 4-substituted Benzyl sulfide. HJBC. 2017;45:251–255.
MLA Mousa, Mazin N. “Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-Triazole-5- 4-Bromophenoxymethyl -3- 4-Substituted Benzyl Sulfide”. Hacettepe Journal of Biology and Chemistry, c. 45, sy. 2, 2017, ss. 251-5.
Vancouver Mousa MN. Synthesis, Characterization, and Evaluation Of Antibacterial 4H-1,2,4-triazole-5- 4-Bromophenoxymethyl -3- 4-substituted Benzyl sulfide. HJBC. 2017;45(2):251-5.

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