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Synthesis, Structure Revision, and Cytotoxicity of Nocarbenzoxazole G

Kim, Taejung, Lee, Sin-Ae, Noh, Taesub, Choi, Pilju, Choi, Seon-Jun, Song, Bong Geun, Kim, Youngseok, Park, Young-Tae, Huh, Gyuwon, Kim, Young-Joo, Ham, Jungyeob
Journal of natural products 2019 v.82 no.5 pp. 1325-1330
Nocardiopsis lucentensis, chemical bonding, cytotoxicity, human cell lines, humans, microwave treatment, moieties, neoplasm cells, nuclear magnetic resonance spectroscopy, organobromine compounds, positional isomers, protons, uterine cervical neoplasms
The total synthesis of nocarbenzoxazoles F (1) and G (2), originally obtained from the marine-derived halophilic bacterial strain Nocardiopsis lucentensis DSM 44048, was achieved via a simple and versatile route involving microwave-assisted construction of a benzoxazole skeleton, followed by carbon–carbon bond formation with the corresponding aryl bromides. Unfortunately, the ¹H and ¹³C NMR spectra of natural nocarbenzoxazole G did not agree with those of the synthesized compound. In particular, the spectra of the isolated and synthesized compounds showed considerable differences in the signals from the protons and carbons in the aryl group. The revised structure was validated by the total synthesis of the actual nocarbenzoxazole G (8c) molecule, which is a regioisomer of the compound that was reported earlier as nocarbenzoxazole G. The synthesized derivatives showed specific cytotoxicity to the human cervical carcinoma cell line, HeLa, but did not have any remarkable effect on the other cell lines.