Synthesis and biological activity of arthrographol and related compounds

Heterocycles

Volumn 43, Issue 3, 1996, Pages 665-674

  Miyake, Muneharu ^a   Hanaoka, Yoshiaki ^a   Fujimoto, Yasuo ^a   Sato, Yoshio ^b   Taketomo, Naoki ^b   Yokota, Itsuro ^b   Yoshiyama, Yoshihiro ^b  

^a NIHON UNIVERSITY   (Japan)

^b MEIJI DAIRIES CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009539326     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-7355     Document Type: Article

References (12)

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2. W. Pfefferle, H. Anke, M. Bross, B. Steffan, R. Vianden, and W. Steglish, J. Antibiotics, 1990, 43, 648.
3. The authors (Meiji Milk Products Co., Ltd.) isolated this compound from the metabolites of Codinaea sp. MM-167 and found inhibitory activity against 5-lipoxygenase. Y. Sato, N. Taketomo, Y. Yoshiyama, K. Ajisaka, and I. Yokota, U. S. Patent 5,244,918 (1993).
4. a) W. A. Ayer and P. A. Craw, Can. J. Chem., 1991, 69, 1909.
5. b) Preliminary communication; M. Miyake and Y. Fujimoto, Chem. Lett., 1993, 1683.
6. H. Sato, T. Dan, E. Onuma, H. Tanaka, B. Aoki, and H. Koga, Chem. Pharm. Bull., 1991, 39, 1760.
7. At first, we prepared methoxymethyl derivative of compound (2 0), however elimination of the methoxymethyl group under various conditions did not give satisfying results (∼30 % yield). Thus we replaced the protecting group by ethoxyethyl group at this stage.
8. The low yield of this reaction might be due to the enolization of 2-formyldihydrobenzofurans (16) and (18) under reaction conditions. W. A. Ayer and P. A. Craw reported that 5,7-dimethoxy-2-formyldihydrobenzofuran was a mixture of the aldehyde form and its enol tautomer, see Ref. 4a.
9. M. A. Ali and Y. Tsuda, Chem. Pharm. Bull., 1992, 40, 2842.
10. L. Pichat and M. Audinot, Bull. Soc. Chim. France, 1961, 2255.
11. M. Wenke, V. Trcka, L. Blaha, J. Hodrova, and J. Weichet, Czech. Patent 131157 (1967) (Chem. Abstr., 1970, 72, 111007p).
12. T. Shimizu, T. Izumi, Y. Seyama, K. Tadokoro, O. Rådmark, and B. Samuelsson, Proc. Natl. Sci. USA, 1986, 83, 4175.