Design, synthesis and biological evaluation of 3,5-diaryl isoxazole derivatives as potential anticancer agents

Derya Anıl Aktaş¹, Gökçen Akinalp², Fatma Sanli³, Mehmet Ali Yucel⁴, Nicola Gambacorta⁵, Orazio Nicolotti⁵, Omer Faruk Karatas³, Oztekin Algul⁶, Serdar Burmaoglu⁷

Affiliations

¹ Department of Chemistry and Chemical Process Technologies, Erzurum Vocational High School, Atatürk University, 25240 Erzurum, Turkey.
² Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey.
³ Department of Molecular Biology and Genetics, Erzurum Technical University, 25050 Erzurum, Turkey; Molecular Cancer Biology Laboratory, High Technology Application and Research Center, Erzurum Technical University, Erzurum, Turkey.
⁴ Dipartimento di Farmacia-Scienze del Farmaco, Università Degli Studi di Bari "Aldo Moro", Via E. Orabona, 4, I-70125 Bari, Italy; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin 33169, Turkey.
⁵ Dipartimento di Farmacia-Scienze del Farmaco, Università Degli Studi di Bari "Aldo Moro", Via E. Orabona, 4, I-70125 Bari, Italy.
⁶ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin 33169, Turkey. Electronic address: oztekinalgul@mersin.edu.tr.
⁷ Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey. Electronic address: sboglu@atauni.edu.tr.

PMID: 32750679
DOI: 10.1016/j.bmcl.2020.127427

Design, synthesis and biological evaluation of 3,5-diaryl isoxazole derivatives as potential anticancer agents

Derya Anıl Aktaş et al. Bioorg Med Chem Lett. 2020.

. 2020 Oct 1;30(19):127427.

doi: 10.1016/j.bmcl.2020.127427. Epub 2020 Jul 23.

Authors

Derya Anıl Aktaş¹, Gökçen Akinalp², Fatma Sanli³, Mehmet Ali Yucel⁴, Nicola Gambacorta⁵, Orazio Nicolotti⁵, Omer Faruk Karatas³, Oztekin Algul⁶, Serdar Burmaoglu⁷

Affiliations

¹ Department of Chemistry and Chemical Process Technologies, Erzurum Vocational High School, Atatürk University, 25240 Erzurum, Turkey.
² Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey.
³ Department of Molecular Biology and Genetics, Erzurum Technical University, 25050 Erzurum, Turkey; Molecular Cancer Biology Laboratory, High Technology Application and Research Center, Erzurum Technical University, Erzurum, Turkey.
⁴ Dipartimento di Farmacia-Scienze del Farmaco, Università Degli Studi di Bari "Aldo Moro", Via E. Orabona, 4, I-70125 Bari, Italy; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin 33169, Turkey.
⁵ Dipartimento di Farmacia-Scienze del Farmaco, Università Degli Studi di Bari "Aldo Moro", Via E. Orabona, 4, I-70125 Bari, Italy.
⁶ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin 33169, Turkey. Electronic address: oztekinalgul@mersin.edu.tr.
⁷ Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey. Electronic address: sboglu@atauni.edu.tr.

PMID: 32750679
DOI: 10.1016/j.bmcl.2020.127427

Abstract

The present study was carried out in the attempt to synthesize a new class of potential anticancer agents comprising eleven compounds (24-34) sharing the 3,5-diarylisoxazole as a core. The chemical structure of the new synthesized compounds was established by IR, ¹H NMR, ¹³C NMR and elemental analysis. Their biological potential towards prostate cancer was evaluated by using cancer PC3 cells and non-tumorigenic PNT1a cells. Interestingly, compound 26 distinguished from others with a quite high selectivity value that is comparable to 5-FU. The binding mode of 26 towards Ribosomal protein S6 kinase beta-1 (S6K1) was investigated at a molecular level of detail by employing docking simulations based on GLIDE standard precision as well as MM-GBSA calculations.

Keywords: Anticancer agent; Isoxazole; Molecular modeling; Proliferation; Synthesis.

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Conflict of interest statement

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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Design, synthesis and biological evaluation of 3,5-diaryl isoxazole derivatives as potential anticancer agents

Affiliations

Design, synthesis and biological evaluation of 3,5-diaryl isoxazole derivatives as potential anticancer agents

Authors

Affiliations

Abstract

Conflict of interest statement

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MeSH terms

Substances

LinkOut - more resources

Full Text Sources

Chemical Information