新产品编号:339057
Chemical Name: 4-[N-(2,2,4,4-Tetramethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)carbamoyl]benzoic acid methyl ester
CAS No. 203855-93-0
项目整合开发状态: Preclinical
项目研究机构: Oklahoma State University (Originator), University of Oklahoma Health Sci. Cent. (Originator)
合成路线:Thiophenol (I) is treated with mesityl oxide (II) in CHCl3 and Et3N to yield derivative (III),which is then converted into alcohol (IV) by means of methylmagnesium iodide in Et2O.Cyclization of (IV) by means of AlCl3 in CS2 affords benzothiopyrane derivative (V) (1),which is nitrated by means of HNO3 and Ac2O or HOAc followed by treatment with Na2CO3 to provide (VI).Nitro derivative (VI) is then reduced with TiCl3 and HOAc or HCl and treated with NaOH to yield (VII).Amine (VII) is finally acylated with acid chloride (VIII) in benzene and pyridine.
📌 参考资料/链接：
参考文献标题:Heteroarotinoids - Anticancer agents with receptor specificity and TGASE activity
文献作者:Nelson,E.C.; Madler,M.M.; Subramanian,S.; Birckbichler,P.J.; Berlin,K.D.; Patterson,M.K.Jr.; Benbrook,D.M.(Oklahoma State University)
参考来源:WO 9807716
📄 详细内容
合成路线:Thiophenol (I) is treated with mesityl oxide (II) in CHCl3 and Et3N to yield derivative (III),which is then converted into alcohol (IV) by means of methylmagnesium iodide in Et2O.Cyclization of (IV) by means of AlCl3 in CS2 affords benzothiopyrane derivative (V) (1),which is nitrated by means of HNO3 and Ac2O or HOAc followed by treatment with Na2CO3 to provide (VI).Nitro derivative (VI) is then reduced with TiCl3 and HOAc or HCl and treated with NaOH to yield (VII).Amine (VII) is finally acylated with acid chloride (VIII) in benzene and pyridine.
参考文献标题:Heteroarotinoids inhibit head and neck cancer cell lines in vitro and in vivo through both RAR and RXR retinoic acid receptors
文献作者:Zacheis,D.; Dhar,A.; Lu,S.; Madler,M.M.; Klucik,J.; Brown,C.W.; Liu,S.; Clement,F.; Subramanian,S.; Weerasekare,G.M.; Berlin,K.D.; Gold,M.A.; Houck,J.R.Jr.; Fountain,K.R.; Benbrook,D.M.
参考来源:J Med Chem 1999,42(21),4434
合成路线:Thiophenol (I) is treated with mesityl oxide (II) in CHCl3 and Et3N to yield derivative (III),which is then converted into alcohol (IV) by means of methylmagnesium iodide in Et2O.Cyclization of (IV) by means of AlCl3 in CS2 affords benzothiopyrane derivative (V) (1),which is nitrated by means of HNO3 and Ac2O or HOAc followed by treatment with Na2CO3 to provide (VI).Nitro derivative (VI) is then reduced with TiCl3 and HOAc or HCl and treated with NaOH to yield (VII).Amine (VII) is finally acylated with acid chloride (VIII) in benzene and pyridine.
参考文献标题:Novel heteroarotinoids: Synthesis and biological activity
文献作者:Spruce,L.W.; Gale,J.B.; Berlin,K.D.; Verma,A.K.; Breitman,T.R.; Ji,X.H.; van der Helm,D.
参考来源:J Med Chem 1991,34(1),430