LGD-1550, ALRT-550, ALRT-1550, LG-1550-药物合成数据库

【药物名称】LGD-1550, ALRT-550, ALRT-1550, LG-1550

化学结构式(Chemical Structure):

参考文献No.	30509
标题:	Novel trienoic retinoid cpds. and methods
作者:	Boehm, M.F.; Zhang, L.; Bennani, Y.L.; Nadzan, A.M. (Ligand Pharmaceuticals, Inc.)
来源:	JP 1998511948; US 5721103; US 6083977; WO 9620913

合成路线图解说明: Addition of methyllithium to 3,5-di-tert-butylbenzoic acid (I) at -78 C gave acetophenone (II). The Horner-Emmons condensation of acetophenone (II) with diethyl (cyanomethyl)phosphonate (III) resulted in a mixture of isomeric alpha,beta-unsaturated nitriles (IV). After isolation of the major E-isomer by preparative TLC, cyano group reduction employing DIBAL in CH2Cl2 at -78 C provided aldehyde (V). This was subjected to a new Horner-Emmons condensation with phosphonate (VI) to provide the octatrienoate ester (VII). The target carboxylic acid was then prepared by saponification of ester (VII) with methanolic KOH.

参考文献No.	394945
标题:	Discovery of novel retinoic acid receptor agonists having potent antiproliferative activity in cervical cancer cells
作者:	Zhang, L.; Nadzan, A.M.; Heyman, R.A.; Love, D.L.; Mais, D.E.; Croston, G.E.; Lamph, W.W.; Boehm, M.F.
来源:	J Med Chem 1996,39(14),2659

合成路线图解说明: Addition of methyllithium to 3,5-di-tert-butylbenzoic acid (I) at -78 C gave acetophenone (II). The Horner-Emmons condensation of acetophenone (II) with diethyl (cyanomethyl)phosphonate (III) resulted in a mixture of isomeric alpha,beta-unsaturated nitriles (IV). After isolation of the major E-isomer by preparative TLC, cyano group reduction employing DIBAL in CH2Cl2 at -78 C provided aldehyde (V). This was subjected to a new Horner-Emmons condensation with phosphonate (VI) to provide the octatrienoate ester (VII). The target carboxylic acid was then prepared by saponification of ester (VII) with methanolic KOH.