新产品编号:570029
Chemical Name: 2-[3-(4-Chlorophenyl)-2-propenyl]-5,6-bis(4-methoxyphenyl)pyridazin-3(2H)-one
CAS No. 225666-41-1
项目整合开发状态: Preclinical
项目研究机构: Kowa (Originator)
合成路线:Glyoxylic acid (II),generated in situ by oxidative cleavage of tartaric acid (I) with sodium periodate,was condensed with deoxyanisoin (III) to provide the aldol adduct (IV).Cyclization of hydroxyacid (IV) with hydrazine gave rise to the hydroxy dihydropyridazinone (V),which was further dehydrated to (VI) upon treatment with p-toluenesulfonic acid in refluxing benzene.Finally,alkylation of pyridazinone (VI) with 4-chlorocinnamyl chloride (VII) in the presence of potassium carbonate furnished the title compound.
📌 参考资料/链接：
参考文献标题:Novel pyridazine derivs.and drugs containing the same as the active ingredient
文献作者:Yoshizaki,H.; Habata,Y.; Kumai,N.; Kotaki,K.; Ohkuchi,M.; Ohgiya,T.; Yamazaki,Y.; Matsuda,T.; Kitamura,T.; Koshi,T.; Kyotani,Y.; Shigyo,H.(Kowa Co.,Ltd.)
参考来源:EP 1043317; JP 1999152274; JP 2000198776; US 6348468; WO 9925697
📄 详细内容
合成路线:Glyoxylic acid (II),generated in situ by oxidative cleavage of tartaric acid (I) with sodium periodate,was condensed with deoxyanisoin (III) to provide the aldol adduct (IV).Cyclization of hydroxyacid (IV) with hydrazine gave rise to the hydroxy dihydropyridazinone (V),which was further dehydrated to (VI) upon treatment with p-toluenesulfonic acid in refluxing benzene.Finally,alkylation of pyridazinone (VI) with 4-chlorocinnamyl chloride (VII) in the presence of potassium carbonate furnished the title compound.
参考文献标题:Synthesis and bioactivities of novel 5,6-bis(4-methoxyphenyl)-2H-pyridazin-3-one derivatives: Inhibitors of interleukin-1 beta (IL-1beta) production
文献作者:Matsuda,T.; Aoki,T.; Koshi,T.; Ohkuchi,M.; Shigyo,H.
参考来源:Bioorg Med Chem Lett 2001,11(17),2373