Synthesis of Some Biologically Effective 5-substituted- 2-(p-tert-butylphenyl)Benzoxazoles

TAŞCI M. , TEMİZ ARPACI Ö.

23rd Young Research Fellow Meeting, Lille, France, 15 - 17 February 2016, pp.29

  • Publication Type: Conference Paper / Full Text
  • City: Lille
  • Country: France
  • Page Numbers: pp.29

Abstract

Synthesis of Some Biologically Effective 5-substituted-

2-(p-tert-butylphenyl)Benzoxazoles

Meryem Taşcı1,  Özlem Temiz-Arpacı2,

1 Erciyes University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Kayseri, Turkey

2Ankara University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 06100, Tandogan, Ankara, Turkey.

      Benzoxazoles, structural isosteres of natural nucleotides that can interact with biopolymers, constitute an important class of heterocyclic compounds [1,2]. So that benzoxazoles showed potential antitumor, antiviral and antibiotic activities as the new topoisomerase I poisons, HIV-1 reverse transcriptase inhibitors and/or potent DNA gyrase inhibitors. [3-5].

     In this study, firstly, 5-Amino-2-(p-tert-butylphenyl)-benzoxazole (1) was synthesized by heating  2,4-diaminophenol with p-tert-butyl benzoic acid in polyphosphoric acid (PPA).   Then  compound 2 was obtained by treating a solution of 2-chloroacetylchloride  with 5-amino-2-(p-tert-butylphenyl)-benzoxazole. Finally, compound 2 was treated by some 4-(p-substituted piperazine/ piperidine derivatives and morpholine. All the results compounds (3-12) (Figure) were prepared as original products (except compound 12) with the hope of discovering new effective antimicrobial agents.

     The 1H-NMR, 13C NMR and mass spectra and elemental analysis results agree with those of the proposed structures.

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  2. Arisoy M., Temiz-Arpaci O., Kaynak-Onurdag F., and Ozgen S. (2012), Synthesis and Antimicrobial activity of novel benzoxazoles. Z. Naturforsch. 67c, 466 - 472.
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  5. Pinar, A.; Yurdakul, P.; Yildiz, I.; Temiz-Arpaci, O.; Acan, N.L.; Aki-Sener, E.; Yalcin I. Biochem. Biophy. Res. Comm. 2004, 317, 670-674.

 

Correspondence:    eczacimeryem@gmail.com    /    meryemtasci@erciyes.edu.tr