CI-201678(HCl), Cpd-201678, 201678-药物合成数据库

【药物名称】CI-201678(HCl), Cpd-201678, 201678

化学结构式(Chemical Structure):

参考文献No.	45892
标题:	Nouveaux d閞iv閟 du dibenz[cd,f]indole, leur pr閜aration et leur application comme m閐icaments
作者:	Giger, R.K.A. (Novartis AG)
来源:	DE 3124086; FR 2485530; FR 2510996; WO 8200143

合成路线图解说明: The acylation of 9-ethylamino-8-bromo-3,4-dimethoxyphenanthrene (I) with butyryl chloride (II) in CH2Cl2 gives 9-(N-ethyl-N-butyrylamino)-8-bromo-3,4-dimethoxyphenanthrene (III), which is cyclized by means of butyllithium in THF yielding 5-ethyl-4,5-dihydro-9,10-dimethoxy-4-n-propyldibenz[cd,f]indole-4-ol (IV). The reduction of (IV) with Zn-HgCl2 in refluxing ethanol water affords 5-ethyl-4,5,5a,6-tetrahydro-9,10-diethoxy-4-n-propyldibenz[cd,f]indole (V), which is finally demethylated by means of refluxing aqueous 47% HBr.

合成路线图解说明: The reaction of 3,4-dimethoxyphenanthrene-9-carboxylic acid (VI) first with trifluoroacetic anhydride and then with sodium azide gives 9-amino-3,4-dimethoxyphenanthrene (VII), which is acetylated with acetyl chloride in CH2Cl2 yielding 9-acetylamino-3,4-dimethoxyphenanthrene (VIII). The reduction of (VIII) with diborane in THF affords 9-ethylamino-3,4-dimethoxyphenanthrene (IX), which is cyclized with CO2 by means of n-butyllithium in THF affording 5-ethyl-4,5-dihydro-9,10-dimethoxy-4-oxodibenz[cd,f]indole (X). Finally, this compound is submitted to a Grignard synthesis with propylmagnesium bromide (A) in THF to give (IV), already obtained.

参考文献No.	49481
标题:	201678
作者:	Casta馿r, J.; Serradell, M.N.
来源:	Drugs Fut 1985,10(2),99

合成路线图解说明: The acylation of 9-ethylamino-8-bromo-3,4-dimethoxyphenanthrene (I) with butyryl chloride (II) in CH2Cl2 gives 9-(N-ethyl-N-butyrylamino)-8-bromo-3,4-dimethoxyphenanthrene (III), which is cyclized by means of butyllithium in THF yielding 5-ethyl-4,5-dihydro-9,10-dimethoxy-4-n-propyldibenz[cd,f]indole-4-ol (IV). The reduction of (IV) with Zn-HgCl2 in refluxing ethanol water affords 5-ethyl-4,5,5a,6-tetrahydro-9,10-diethoxy-4-n-propyldibenz[cd,f]indole (V), which is finally demethylated by means of refluxing aqueous 47% HBr.

合成路线图解说明: The reaction of 3,4-dimethoxyphenanthrene-9-carboxylic acid (VI) first with trifluoroacetic anhydride and then with sodium azide gives 9-amino-3,4-dimethoxyphenanthrene (VII), which is acetylated with acetyl chloride in CH2Cl2 yielding 9-acetylamino-3,4-dimethoxyphenanthrene (VIII). The reduction of (VIII) with diborane in THF affords 9-ethylamino-3,4-dimethoxyphenanthrene (IX), which is cyclized with CO2 by means of n-butyllithium in THF affording 5-ethyl-4,5-dihydro-9,10-dimethoxy-4-oxodibenz[cd,f]indole (X). Finally, this compound is submitted to a Grignard synthesis with propylmagnesium bromide (A) in THF to give (IV), already obtained.