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Benzofuran- and furan-2-yl-(phenyl)-3-pyridylmethanols: Synthesis and inhibition of P450 aromatase

Saberi, Mohammed Reza, Shah, Kajal and Simons, Claire 2005. Benzofuran- and furan-2-yl-(phenyl)-3-pyridylmethanols: Synthesis and inhibition of P450 aromatase. Journal of Enzyme Inhibition and Medicinal Chemistry 20 (2) , pp. 135-141. 10.1080/14756360400015256

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A series of benzofuran-2-yl-(phenyl)-3-pyridylmethanol derivatives were prepared using an efficient 1-step procedure in good yields. In addition furan-2-yl-(phenyl)-3-pyridylmethanol derivatives were also prepared to determine the effect of the benzene ring in benzofuran with respect to inhibitory activity. The pyridylmethanol derivatives were all evaluated in vitro for inhibitory activity against aromatase (P450AROM, CYP19), using human placental microsomes. The benzofuran-2-yl-(phenyl)-3-pyridylmethanol derivatives showed good to moderate activity (IC50=1.3–25.1 μM), which was either better than or comparable with aminoglutethimide (IC50=18.5 μM) but lower than arimidex (IC50=0.6 μM), with the 4-methoxyphenyl substituted derivative displaying optimum activity. Molecular modelling of the benzofuran-2-yl-(4-fluorophenyl)-3-pyridylmethanol derivative suggested activity to reside with the (S)-enantiomer. The furan-2-yl-(phenyl)-3-pyridylmethanol derivatives were devoid of activity indicating the essential role of the benzene ring of the benzofuran component for enzyme binding.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Subjects: R Medicine > RS Pharmacy and materia medica
Uncontrolled Keywords: Benzofuran-2-yl-(phenyl)-3-pyridylmethanols furan-2-yl-(phenyl)-3-pyridylmethanol derivatives, P450 aromatase, inhibitors, molecular modelling, proton affinity
Publisher: Informa Healthcare
ISSN: 1475-6374
Last Modified: 04 Jun 2017 02:56

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