Synthesis and biological evaluation of meta-carborane-containing phenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity

Guangzhe Li; Soyoko Azuma; Hidemitsu Minegishi; Hiroyuki Nakamura

doi:10.1016/j.jorganchem.2015.05.029

Synthesis and biological evaluation of meta-carborane-containing phenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity

Guangzhe Li, Soyoko Azuma, Hidemitsu Minegishi, Hiroyuki Nakamura

薬学研究科・分子薬科学専攻

研究成果: Article › 査読

17 被引用数 (Scopus)

抄録

meta-Carboranylphenoxyacetanilides were synthesized by copper catalyzed coupling reaction of meta-carborane and phenyl iodides. The synthesized compounds were evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter gene assay. Among the compounds synthesized, meta-carborane containing phenoxyanilides 2d and 2h, which have an isobutyl group on meta-carborane, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity toward HeLa cell-based reporter gene assay with the IC<inf>50</inf> values of 0.73 and 0.55μM, respectively.

本文言語	English
ジャーナル	Journal of Organometallic Chemistry
DOI	https://doi.org/10.1016/j.jorganchem.2015.05.029
出版ステータス	Accepted/In press - 2015 3月 30

ASJC Scopus subject areas

無機化学
有機化学
物理化学および理論化学
材料化学
生化学

文献へのアクセス

10.1016/j.jorganchem.2015.05.029

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引用スタイル

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title = "Synthesis and biological evaluation of meta-carborane-containing phenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity",

abstract = "meta-Carboranylphenoxyacetanilides were synthesized by copper catalyzed coupling reaction of meta-carborane and phenyl iodides. The synthesized compounds were evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter gene assay. Among the compounds synthesized, meta-carborane containing phenoxyanilides 2d and 2h, which have an isobutyl group on meta-carborane, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity toward HeLa cell-based reporter gene assay with the IC50 values of 0.73 and 0.55μM, respectively.",

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author = "Guangzhe Li and Soyoko Azuma and Hidemitsu Minegishi and Hiroyuki Nakamura",

year = "2015",

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doi = "10.1016/j.jorganchem.2015.05.029",

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T1 - Synthesis and biological evaluation of meta-carborane-containing phenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity

AU - Li, Guangzhe

AU - Azuma, Soyoko

AU - Minegishi, Hidemitsu

AU - Nakamura, Hiroyuki

PY - 2015/3/30

Y1 - 2015/3/30

N2 - meta-Carboranylphenoxyacetanilides were synthesized by copper catalyzed coupling reaction of meta-carborane and phenyl iodides. The synthesized compounds were evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter gene assay. Among the compounds synthesized, meta-carborane containing phenoxyanilides 2d and 2h, which have an isobutyl group on meta-carborane, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity toward HeLa cell-based reporter gene assay with the IC50 values of 0.73 and 0.55μM, respectively.

AB - meta-Carboranylphenoxyacetanilides were synthesized by copper catalyzed coupling reaction of meta-carborane and phenyl iodides. The synthesized compounds were evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter gene assay. Among the compounds synthesized, meta-carborane containing phenoxyanilides 2d and 2h, which have an isobutyl group on meta-carborane, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity toward HeLa cell-based reporter gene assay with the IC50 values of 0.73 and 0.55μM, respectively.

KW - Hypoxia inducible factor

KW - Inhibitor

KW - meta-Carborane

KW - Transcription

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