T-2585.HCl-药物合成数据库

【药物名称】T-2585.HCl

化学结构式(Chemical Structure):

参考文献No.	31774
标题:	Naphthalene derivs., process for the preparation thereof, and pharmaceutical compsns. comprising them
作者:	Ukita, T.; Ikezawa, K.; Yamagata, S. (Tanabe Seiyaku Co., Ltd.)
来源:	CA 2178974; EP 0748805; JP 1997059255; US 6005106

合成路线图解说明: The reaction of 2-bromo-4,5-diethoxybenzaldehyde dimethylacetal (I) with 2-chloropyridine-4-carbaldehyde (II) by means of BuLi in THF gives the diarylcarbinol (III), which is cyclized with dimethyl fumarate (IV) by means of AcOH in refluxing toluene (or xylene) yielding the naphthalene-2,3-dicabroxylic ester (V). The reduction of (V) with NaBH4 in THF/methanol affords the bis(hydroxymethyl)naphthalene (VI), which is treated with hydrazine in refluxing water to give the 2-pyridylhydrazine derivative (VII). Finally, this compound is cyclized with 2-(3-pyridylcarbonyl)benzoic acid (VIII) by heating at 150 C in ethylene glycol.

参考文献No.	529523
标题:	Novel, potent, and selective phosphodiesterase-4 inhibitors as antiasthmatic agents: Synthesis and biological activities of a series of 1-pyridylnaphthalene derivatives
作者:	Ukita,T.; Sugahara, M.; Terakawa, Y.; Kuroda, T.; Wada, K.; Nakata, A.; Ohmachi, Y.; Kikkawa, H.; Ikezawa, K.; Naito, K.
来源:	J Med Chem 1999,42(6),1088

合成路线图解说明: The reaction of 2-bromo-4,5-diethoxybenzaldehyde dimethylacetal (I) with 2-chloropyridine-4-carbaldehyde (II) by means of BuLi in THF gives the diarylcarbinol (III), which is cyclized with dimethyl fumarate (IV) by means of AcOH in refluxing toluene (or xylene) yielding the naphthalene-2,3-dicabroxylic ester (V). The reduction of (V) with NaBH4 in THF/methanol affords the bis(hydroxymethyl)naphthalene (VI), which is treated with hydrazine in refluxing water to give the 2-pyridylhydrazine derivative (VII). Finally, this compound is cyclized with 2-(3-pyridylcarbonyl)benzoic acid (VIII) by heating at 150 C in ethylene glycol.