新产品编号:954455
Chemical Name: 3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-2-cyclopenten-1-one hydrochloride
CAS No. 471294-85-6
项目整合开发状态: Preclinical
项目研究机构: Chungnam National University (Originator), Korea Res. Inst. Biosci. Biotechnol. (Originator)
合成路线:Condensation of 2-bromo-3'-methoxy-4-nitroacetophenone (I) with diethyl malonate affords the phenacylmalonate derivative (II).This is converted into the corresponding magnesium enolate and then acylated by 3,4,5-trimethoxyphenylacetyl chloride (III) to furnish the disubstituted malonate (IV).Intramolecular aldol condensation of diketone (IV) in the presence of Et3N leads to cyclopentenone (V).Subsequent hydrolysis and decarboxylation of the keto diester (V) under acidic conditions produces (VI).Finally,the nitro group of (VI) is reduced by means of zinc dust in AcOH to yield the title compound.
📌 参考资料/链接：
参考文献标题:Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues
文献作者:Nam,N.-H.; Kim,Y.; You,Y.-J.; Hong,D.-H.; Kim,H.-M.; Ahn,B.-Z.
参考来源:Bioorg Med Chem Lett 2002,12(15),1955
📄 详细内容
合成路线:Condensation of 2-bromo-3'-methoxy-4-nitroacetophenone (I) with diethyl malonate affords the phenacylmalonate derivative (II).This is converted into the corresponding magnesium enolate and then acylated by 3,4,5-trimethoxyphenylacetyl chloride (III) to furnish the disubstituted malonate (IV).Intramolecular aldol condensation of diketone (IV) in the presence of Et3N leads to cyclopentenone (V).Subsequent hydrolysis and decarboxylation of the keto diester (V) under acidic conditions produces (VI).Finally,the nitro group of (VI) is reduced by means of zinc dust in AcOH to yield the title compound.
参考文献标题:Synthesis,cytotoxicity and antitumor activity of 2,3-diarylcyclopent-2-ene-1-ones
文献作者:Nam,N.-H.; Kim,Y.; You,Y.-J.; Hong,D.-H.; Kim,H.-M.; Ahn,B.-Z.
参考来源:Arch Pharmacal Res 2002,25(5),600