Synthesis and Antitumor Activity of Phenyl Carbocyclic Oxetanocin and Related Compounds
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- MARUYAMA Tokumi
- Faculty of Pharmaceutical Sciences, Tokushima Bunri University
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- FUKUHARA Mitsutoshi
- Faculty of Pharmaceutical Sciences, Tokushima Bunri University
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抄録
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.
収録刊行物
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- Chemical & pharmaceutical bulletin
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Chemical & pharmaceutical bulletin 44 (7), 1407-1411, 1996-07-15
公益社団法人日本薬学会
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詳細情報
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- CRID
- 1574231877092214144
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- NII論文ID
- 110003632094
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- NII書誌ID
- AA00602100
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- ISSN
- 00092363
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- 本文言語コード
- en
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- データソース種別
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- CiNii Articles