OC144-093, ONT-093, OC-144-093-药物合成数据库

【药物名称】OC144-093, ONT-093, OC-144-093

化学结构式(Chemical Structure):

参考文献No.	37761
标题:	Imidazole derivs. as MDR modulators
作者:	Zhang, C.; Mjalli, A.M.M. (Ontogen Corp.)
来源:	EP 0999835; US 5840721; WO 9902155

合成路线图解说明: Palladium-catalyzed coupling of 4-bromobenzaldehyde (I) with methyl acrylate (II) furnished methyl 4-formylcinnamate (III). After aldehyde protection as the ethylene acetal (IV), ester group reduction using DIBAL in cold CH2Cl2 gave rise to the cinnamyl alcohol (V). O-Alkylation of (V) with ethyl iodide in the presence of NaH produced the corresponding ethyl ether (VI). The acetal protecting group of (VI) was then hydrolyzed with HCl to yield aldehyde (VII).

合成路线图解说明: Treatment of 4,4'-difluorobenzyl (VIII) with isopropylamine and K2CO3 in hot DMSO produced 4,4'-bis(isopropylamino)benzyl (IX). This was then condensed with the intermediate aldehyde (VII) in the presence of ammonium acetate in HOAc to produce the target triaryl imidazole.

参考文献No.	603412
标题:	2,4,5-Trisubstituted imidazoles: Novel nontoxic modulators of P-glycoprotein mediated multidrug resistance. Part 2
作者:	Zhang, C.; Sarshar, S.; Moran, E.J.; Krane, S.; Rodarte, J.C.; Benbatoul, K.D.; Dixon, R.; Mjalli, A.M.M.
来源:	Bioorg Med Chem Lett 2000,10(23),2603

合成路线图解说明: Palladium-catalyzed coupling of 4-bromobenzaldehyde (I) with methyl acrylate (II) furnished methyl 4-formylcinnamate (III). After aldehyde protection as the ethylene acetal (IV), ester group reduction using DIBAL in cold CH2Cl2 gave rise to the cinnamyl alcohol (V). O-Alkylation of (V) with ethyl iodide in the presence of NaH produced the corresponding ethyl ether (VI). The acetal protecting group of (VI) was then hydrolyzed with HCl to yield aldehyde (VII).

合成路线图解说明: Treatment of 4,4'-difluorobenzyl (VIII) with isopropylamine and K2CO3 in hot DMSO produced 4,4'-bis(isopropylamino)benzyl (IX). This was then condensed with the intermediate aldehyde (VII) in the presence of ammonium acetate in HOAc to produce the target triaryl imidazole.