SYNTHESIS, CHARACTERIZATION AND IN VITRO MICROBIAL EVALUATION OF REGIOISOMERS OF ALLYL PHENYL ETHERS DERIVED 1, 2, 4-TRIAZOLES

Authors

  • Kumar Aswamy B. Department of Chemistry, Kakatiya University, Warangal- 506009 India
  • Ranjith Kumar T. Department of Chemistry, Kakatiya University, Warangal- 506009 India
  • Narsimha S. Department of Chemistry, Kakatiya University, Warangal- 506009 India
  • Vasudeva Reddy N. Department of Chemistry, Kakatiya University, Warangal- 506009 India

Keywords:

1, 2, 4-triazole, Antibacterial activity and Antifungal activity

Abstract

Objective: Synthesis and antimicrobial evaluation of regioisomers of allyl phenyl ethers derived 1, 2, 4-triazoles.

Methods: A series of new 1,2,4-triazole derivatives of allyl phenyl ethers were synthesized by reacting a mixture of regio isomers 1-(3-bromo-2-methoxypropoxy)-arene and 1-(2-bromo-3-methoxypropoxy)-arene with 1,2,4-triazole in presence of K2CO3 and DMF at 80oC in good yields. Allyl phenyl ethers 1(a-f) were synthesized by refluxing the substituted phenols with allyl bromide in the presence of K2CO3 and acetone in excellent yields. The newly synthesized compounds were characterized by IR, 1HNMR, Mass spectral studies and elemental analysis. These compounds were also screened for their In-vitro antibacterial and antifungal activities.

Results: Allyl phenyl ethers derived 1,2,4-triazol derivatives were synthesized in good yields.

Conclusion: Preliminary results revealed that some of the synthesized compounds were showed promising antibacterial and antifungal activity.

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References

Patil BS, Krishnamurthy G, Bhojya Naik HS, Latthe PR, Ghate M. Synthesis, characterization and antimicrobial studies of 2-(4-methoxy-phenyl)-5-methyl-4-(2-arylsulfanyl-ethyl)-2,4-dihydro-[1,2,4] triazolo-3-ones and their corresponding sulfones. Eur J Med Chem 2010;45(8):3329-34.

Bayrak H, Demirbas A, Demirbas N, Karaoglu SA. Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities. Eur J Med Chem 2009;44(11):4362-6.

Padmavathi V, Thriveni P, Sudhakar Reddy G, Deepti D. Synthesis and antimicrobial activity of novel sulfone-linked bis heterocycles. Eur J Med Chem 2008;43(5):917-24.

Soni B, Ranawat MS, Sharma R, Bhandari A, Sharma S. Synthesis and evaluation of some new benzothiazole derivatives as potential antimicrobial agents. Eur J Med Chem 2010;45(7):2938-42.

Xu J, Cao Y, Zhang J, Yu S, Zou Y, Chai X, et al. Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives. Eur J Med Chem 2011;46(7):3142-8.

Tozkpran B, Kupeli E. Yesilada E and Ertan M. Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatoryanalgesic activity. Bioorg Med Chem 2007;15:1808-14.

Holla BS, Veerendra B, Shivananda M.K and Poojary B. Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles. Eur J Med Chem 2003;38(7-8):759-67.

Duran A, Dogan HN, Rollas S. Synthesis and preliminary anticancer activity of new 1,4-dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-5H-1,2,4-triazoline-5-thiones. Farmaco (Societa chimica italiana:1989) 2002;57(7):559-64.

Abdel-Aal MT, El-Sayed WA, El-Kosy SM, El-Ashry ESH. Synthesis and antiviral evaluation of novel 5-(N-Aryl-aminomethyl-1,3,4-oxadiazol-2-yl)hydrazines and their sugars, 1,2,4-triazoles, tetrazoles and pyrazolyl derivatives. Arch Pharm 2008;341(5):307-13.

Kucukguzel I, Kucukguzel S. I. Rollas and M. Kiraz Some 3-thioxo alkylthio 1,2,4-triazoles with a substituted thiourea moiety as possible anti mycobacterials. Bioorg Med Chem Lett 2001;11:1703-7.

Foroumadi A, Kiani Z, Soltani F. Antituberculosis agents VIII. Synthesis and in vitro antimycobacterial activity of alkyl alpha-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetates. Farmaco (Societa chimica italiana:1989) 2003;58(11):1073-6.

Labanauskas L, Udrenaite E, Gaidelis P, Brukstus A. Synthesis of 5-(2-,3-and 4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol derivatives exhibiting anti-inflammatory activity. Farmaco (Societa chimica italiana:1989) 2004;59(4):255-9.

Almasirad A,Sayyed A,Tabatabai, Faizi M, Abbas K, Mehrabi N, Dalvandi A and Abbas S . 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 2004;14:6057-9.

Kucukguzel SG, Kucukguzel I. Rollas S. Synthesis of some 3-(aryl alkyl thio)-4-alkyl/aryl-5-(4-amino phenyl)-, 4H-1,2,4-triazole derivatives and their anticonvulsant activity. IFarmaco 2004 ;59:893-901.

Varvaresou A, Siatra-Papastaikoudi T, Dalla Tsotinis A, Tsantili-Kakoulidou A, Vamvakides A. Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2, 4-triazole. Farmaco (Societa chimica italiana:1989) 1998;53(5):320-6.

Modzelewska-Banachiewicz B, Banachiewicz J, Chodkowska A, Jagiełło-Wójtowicz E, Mazur L. Synthesis and biological activity of new derivatives of 3-(3,4-diaryl-1,2,4-triazole-5-yl)propenoic acid. Eur J Med Chem 2004;39(10):873-7.

Yoshida M, Higuchi M, Shishido K. Stereoselective construction of substituted chromans by palladium-catalyzed cyclization of propargylic carbonates with 2-(2-hydroxyphenyl)acetates. Organic letters 2009;11(20):4752-5.

Esko Taskinen. Thermodynamic, spectroscopic and density functional theory studies of allyl aryl and prop 1-enyl aryl ethers Part 1 Thermodynamic data of isomerization J Chem Soc PerkinTrans 2;2001:1824-34.

Satyanarayana V, Prasad Rao Ch, Krupadanam G.L.D and Srimannarayana G. A. new and facile synthesis of choman-3-ols 3,4- dihydro-2H-[1]-benzopyran-3-ols. Synth Commun 1991;21: 1455-64.

Fernando F. Huerta, Ortiz, Rosa, Yus, Miguel, Huerta. Intramolecular carbolithiation promoted by a DTBB-catalysed chlorine-lithium exchange. Tetrahedron 2003;59:8525-42.

Gottardi-Dubosclard, Christine. Selective Side-chain Halogenoalkoxylation of Unsaturated(Meth)acrylic Esters. J Chem Research Miniprint 1997;8:1901-16.

Fort, Yves, Mandelaire and Arnaud. TwoStep Synthesis of New Bifunctional Meth acrylic Monomers. Synth Commun 1998;28:583-92.

Shi Y, Zhou C-H. Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents. Bioorg Med Chem Lett 2011;21(3):956-60.

Damu,Guri L.V ,Jingsong,Wang, Qinqpeng, Zhang et al.A series of napthalimide azoles:Design,synthesis and bioactive evaluation as potential antimicrobial agents. Sci China Chem2013;56:952-69.

Zhang, Yi-Yi;Zhou, Cheng-He;Zhou, Xiang-Dong;Mi, Jia-Li. Synthesis of novel flucona zoliums and their evaluation for antibacterial and antifungal activities. Eur J Med Chem 2011;46:4391-402.

Published

01-07-2014

How to Cite

B., K. A., R. K. T., N. S., and V. R. N. “SYNTHESIS, CHARACTERIZATION AND IN VITRO MICROBIAL EVALUATION OF REGIOISOMERS OF ALLYL PHENYL ETHERS DERIVED 1, 2, 4-TRIAZOLES”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 6, no. 7, July 2014, pp. 572-5, https://www.innovareacademics.in/journals/index.php/ijpps/article/view/1763.

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