Synthesis and Antitumor Activity of Phenyl Carbocyclic Oxetanocin and Related Compounds

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概要

• 論文の詳細を見る

• Reaction of trans-2,3-bis[(tert-butyldimethylsilyl)oxymethyl]-1-cyclobutanone (4a) with phenylmagnesium bromide or lithiated aromatic compounds gave two adducts, the (1R^*, 2R^*, 3R^*) isomers (5a-c) and the (1R*, 2S^*, 3S^*) isomers (6a-c). The major products (5a, c) were treated with tetrabutylammonium fluoride to give the (1R^*, 2R^*, 3R^*)-1-aryl-2,3-bis(hydroxymethyl)-1-cyclobutanols (1a, c). The 3-(oxazol-2-yl)-phenyl adduct 5b was converted to the benzamide congener 1b in 6 steps. On catalytic reduction of 1a with Raney Ni the stereochemistry at C-1' was mostly retained, but in the case of 10% Pd-C catalyst, steric inversion occurred. Compounds 1a-c displayed no cytotoxicity towards human nasopharyngeal carcinoma KB cell line.

• 公益社団法人日本薬学会の論文
• 1996-07-15

著者

• MARUYAMA Tokumi

  Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University

• Maruyama Tokumi

  Faculty Of Pharmaceutical Sciences At Kagawa Campus Tokushima Bunri University

• Maruyama T

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• FUKUHARA Mitsutoshi

  Faculty of Pharmaceutical Sciences, Tokushima Bunri University

• Fukuhara M

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

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