PD-168393-药物合成数据库

【药物名称】PD-168393

化学结构式(Chemical Structure):

参考文献No.	538849
标题:	Extension of the polyanionic cosalane pharmacophore as a strategy for increasing anti-HIV potency
作者:	Cushman, M.; Insaf, S.; Paul, G.; Ruell, J.A.; De Clercq, E.; Schols, D.; Pannecouque, C.; Witvrouw, M.; Schaeffer, C.A.; Turpin, J.A.; Williamson, K.; Rice, W.G.
来源:	J Med Chem 1999,42(10),1767

合成路线图解说明: Title compound was obtained by condensation of the 6-aminoquinazoline (I) with acrylic acid in the presence of EDC.

合成路线图解说明: The demethylation of intermediate (XI) with BBr3 and SMe2 in hot 1,2-dichloroethane gives the phenolic intermediate (cosalane, XV), which is simultaneously alkylated and esterified with 4-(bromomethyl)benzoic acid methyl ester (XVI) by means of K2CO3 in DMF yielding the tetrabenzylated intermediate (XVII). The final hydrolysis of the benzyl ester and methyl ester groups with KCN and K2CO3 in hot ethanol/water affords the target compound.

合成路线图解说明: The demethylation of intermediate (XI) with BBr3 and SMe2 in hot 1,2-dichloroethane gives the phenolic intermediate (cosalane, XV), which is simultaneously alkylated and esterified with 4-(bromomethyl)benzoic acid methyl ester (XVI) by means of K2CO3 in DMF yielding the tetrabenzylated intermediate (XVII). The hydrolysis of the benzyl ester and methyl ester groups with KCN and K2CO3 in hot ethanol/water affords the intermediate tetracarboxylic acid (XVIII), which is finally converted into the target sodium salt by reaction with Na2CO3 in methanol or ethanol.