新产品编号:699753
Chemical Name: 6-Fluoro-2-[4-(methylsulfonyl)phenyl]-3-(3-pyridyl)-4H-1-benzopyran-4-one
CAS No. 259680-30-3
项目整合开发状态: Preclinical
项目研究机构: AmorePacific (Originator)
合成路线:Aldol condensation between 5'-fluoro-2'-hydroxyacetophenone (I) and 4-(methylthio)benzaldehyde (II) produces chalcone (III).Oxidative cyclization of (III) in hot DMSO in the presence of iodine leads to the flavone compound (IV).Further oxidation of the methylthio group of (IV) employing oxone furnishes sulfone (V).Conversion of flavone (V) into the 3-iodo derivative (VI) is carried out by treatment with iodine and bis(trifluoroacetoxy)iodobenzene.Finally,Suzuki coupling of the iodoflavone (VI) with lithium trimethoxy-3-pyridylboronate (VII) provides the desired 2,3-diaryl benzopyranone
📌 参考资料/链接：
参考文献标题:Diarylbenzopyran derivs.as cyclooxygenase-2 inhibitors
文献作者:Kim,J.K.; Choi,J.K.; Lee,C.H.; Joo,Y.H.; Noh,M.-S.; Ha,J.-Y.; Lim,K.M.; Kang,S.-H.(Pacific Corp.)
参考来源:EP 1105384; JP 2002523410; US 6340694; WO 0010993
📄 详细内容
合成路线:Aldol condensation between 5'-fluoro-2'-hydroxyacetophenone (I) and 4-(methylthio)benzaldehyde (II) produces chalcone (III).Oxidative cyclization of (III) in hot DMSO in the presence of iodine leads to the flavone compound (IV).Further oxidation of the methylthio group of (IV) employing oxone furnishes sulfone (V).Conversion of flavone (V) into the 3-iodo derivative (VI) is carried out by treatment with iodine and bis(trifluoroacetoxy)iodobenzene.Finally,Suzuki coupling of the iodoflavone (VI) with lithium trimethoxy-3-pyridylboronate (VII) provides the desired 2,3-diaryl benzopyranone
参考文献标题:Diarylbenzopyran derivatives as a selective inhibitor of cyclooxygenase-2
文献作者:Joo,Y.H.; Kim,J.K.; Kang,S-H.; Noh,M-S.; Ha,J-Y.; Choi,J.K.; Lim,K.M.; Lee,C.H.; Chung,S.
参考来源:224th ACS Natl Meet (Aug 18 2002,Boston) 2002,Abst MEDI 313