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α-葡萄糖苷酶抑制剂Radicamine A的合成 被引量:1

Synthesis of Radicamine A as a α-glucosidase inhibitor
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摘要 Radicamine A was prepared via a key intermediate-cycle nitrone 5 by using D-arabinose as the raw material with a total yield of 15.5%.Cycle nitrone 5 was synthesized by protection of hydroxyl group,introduction of nitrogen and intromolecular cyclization.And then it had a high stereoselective addition reaction with aryl Grignard reagents 6 to form compound 7.Finally,the target compound was obtained by catalytic hydrogenation of compound 7.The novel compounds 3 and 4 were confirmed by 1HNMR,IR,MS and elemental analysis. Radicamine A was prepared via a key intermediate-cycle nitrone 5 by using D-arabinose as the raw material with a total yield of 15.5%.Cycle nitrone 5 was synthesized by protection of hydroxyl group,introduction of nitrogen and intromolecular cyclization.And then it had a high stereoselective addition reaction with aryl Grignard reagents 6 to form compound 7.Finally,the target compound was obtained by catalytic hydrogenation of compound 7.The novel compounds 3 and 4 were confirmed by 1HNMR,IR,MS and elemental analysis.
出处 《化学研究与应用》 CAS CSCD 北大核心 2010年第7期911-914,共4页 Chemical Research and Application
基金 河北省自然科学基金(C2010001761)资助项目
关键词 Radicamine A Α-葡萄糖苷酶抑制剂 环状硝酮 合成 Radicamine A α-glucosidase inhibitor cycle nitrone synthesis
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  • 1Shibano M,Tsukamoto D,Masuda A,et al,Two new pyrrolidine alkaloids,Radicamines A and B,as inhibitors of α-glucosidase from lobelia chinensis LOUR[J].Chem.Pharm.Bull.,2001,49(10):1362-1365.
  • 2Liu CY,Gao JC,Yang G,et al,Enantiospecific synthesis of(-)-radicamine B[J].Lett.Org.Chem.,2007,4(12):556-558.
  • 3Yu CY,Huang MH,Radicamines A and B:synthesis and revision of the absolute configuration[J].Org.Lett.,2006,8(14):3021-3024.
  • 4Gurjar MK,Borhade RG,Puranik VG,et al,Total synthesis of(-)-radicamine B[J].Tetrahedron Lett.,2006,47(39):6979-6981.
  • 5Tsou EL,Chen SY,Yang MH,et al,Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library[J].Bioorg.Med.Chem.,2008,16(24):10198-10204.
  • 6Barker R,Fletcher HG,2,3,5-Tri-O-benzyl-D-ribosyl and -L-arabinosyl bromides[J].J Org Chem.,1961,26(11):4605-4609.
  • 7Tejima S,Fletcher HG.Syntheses with partially benzylated sugars.II.The anomeric 1-O-Benzoyl-L-arabinopyranoses and 1-O-Benzoyl-L-arabinofuranoses and Their tendencies to undergo acyl migration[J].J.Org.Chem.,1963,28(11):2999-3004.
  • 8Bernet B,Mangholz SE,Briner K,et al.Glycosylidene diaziridines:stereoselective addition of ammonia and methylamine to lactone oxime Sulfonates[J].Helv.Chim.Acta,2003,86(5):1488-1521.
  • 9Carmona AT,Robina I,Wightman RH,et al,Synthesis and glycosidase inhibitory activity of 7-deoxycasuarine[J].Helv Chim Acta,2003,86(9):3066-3073.
  • 10Merino P,Revuelta J,Tejero T,et al,Fully stereoselective nucleophilic addition to a novel chiral pyrroline N-oxide:total syntheses of(2S,3R)-3-hydroxy-3-methylproline and its(2R)-epimer[J].Eur.J.Org.Chem.,2004,4:776-782.

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