Facile synthesis of 2-aryl 5-hydroxy benzo[d]oxazoles and their in vitro anti-proliferative effects on various cancer cell lines

Bioorg Med Chem Lett. 2018 Dec 15;28(23-24):3639-3647. doi: 10.1016/j.bmcl.2018.10.038.

Neelima D Tangellamudi ¹, Suchita B Shinde ², Venkatesh Pooladanda ³, Chandraiah Godugu ³, Sridhar Balasubramanian ⁴

Affiliations

1 Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Hyderabad 500037, India. Electronic address: neelima@niperhyd.ac.in.
2 Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Hyderabad 500037, India.
3 Department of Regulatory Toxicology, National Institute of Pharmaceutical Education and Research, Hyderabad 500037, India.
4 Indian Institute of Chemical Technology, Hyderabad 500607, India.

PMID: 30389295 DOI: 10.1016/j.bmcl.2018.10.038

Abstract

2-Aryl 5-hydroxy benzo[d]oxazoles were designed as potential Anticancer agents. A one-pot synthesis of these compounds dispenses the need for ortho-disubstituted precursor, aminophenol and proceeds via CN formation as a key step followed by CO cyclization to form benzo[d]oxazoles. The single crystal X-ray diffraction study was used to confirm the molecular structure of a representative compound unambiguously. All of these compounds were evaluated for their anti-proliferative properties in vitro against five Cancer cell lines as well as noncancerous cells. Most of these compounds showed selective growth inhibition of Cancer cells and few of them were found to be promising with IC₅₀ values in the range of 0.8-2.8 μM, comparable to the known Anticancer drug doxorubicin.

Keywords

Aza-Michael attack; Benzo[d]oxazoles; CN bond formation; Cytotoxicity; Quinol.

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