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

Synthesis of Some Biologically Effective 5-substituted-2-(p-tert-butylphenyl)BenzoxazolesMeryem Taşcı1, &nbsp;&Ouml;zlem Temiz-Arpacı2, 1 Erciyes University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Kayseri, Turkey2Ankara University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 06100, Tandogan, Ankara, Turkey.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; 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].&nbsp;&nbsp;&nbsp;&nbsp; In this study, firstly, 5-Amino-2-(p-tert-butylphenyl)-benzoxazole (1) was synthesized by heating&nbsp; 2,4-diaminophenol with p-tert-butyl benzoic acid in polyphosphoric acid (PPA). &nbsp;&nbsp;Then&nbsp; compound 2 was obtained by treating a solution of 2-chloroacetylchloride&nbsp; 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.&nbsp;&nbsp;&nbsp;&nbsp; The 1H-NMR, 13C NMR and mass spectra and elemental analysis results agree with those of the proposed structures.&nbsp; &nbsp; &nbsp; REFERENCESTemiz-Arpaci O., Eylem Cifcioglu Goztepe B., Kaynak-Onurdag F., Ozgen S., Senol F.S., and Erdogan Orhan I . (2013), Synthesis and different biological activities of novel benzoxazoles. Acta Biol. Hung. 64, 249 - 261.Arisoy M., Temiz-Arpaci O., Kaynak-Onurdag F., and Ozgen S. (2012), Synthesis and Antimicrobial activity of novel benzoxazoles. Z. Naturforsch. 67c, 466 - 472.&nbsp;Akbay, A.; Oren, I.; Temiz-Arpaci, O.; Aki-Sener, E.; Yalcin, I. Arzneim. Forsch. 2003, 53(4), 266 -271.&nbsp;Temiz-Arpaci, O.; Tekiner-Gulbas, B.; Yildiz, I.; Aki-Sener, E.; Yalcin,I. Bioorg. Med. Chem. 2005, 13, 6354-6359.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.&nbsp;Correspondence:&nbsp;&nbsp;&nbsp; [email protected] &nbsp;&nbsp;&nbsp;/&nbsp;&nbsp;&nbsp; [email protected]</p

Biological evaluation and docking studies of some benzoxazole derivatives as inhibitors of acetylcholinesterase and butyrylcholinesterase

A series of 2,5-disubstituted-benzoxazole derivatives (1-13) were evaluated as possible inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The results demonstrated that the compounds exhibited a broad spectrum of AChE and BChE inhibitory activity ranging between 6.80% and 90.21% except one compound which showed no activity against AChE at the specified molar concentration. Another derivative displayed a similar activity to that of reference drug (galanthamine) for inhibition of AChE and BChE. In addition, molecular docking of the compounds into active site of AChE was performed using recombinant human AChE (PDB ID: 4ey6) in order to understand ligand-protein interactions