合成路线:The synthesis of nitidine chloride was first reported in 1973.The procedure was based on the synthesis of dihydronitidine,which involves hydrocyanation of the corresponding chalcone,followed by hydrolysis,reduction and cyclization to the 2-aryl tetralone.Leukart reaction of the tetralone followed by ring closure with phosphorus oxychloride and catalytic dehydrogenation yields the benzo[c]phenanthridine nucleus.Methylation and quarternization with methyl sulfate followed by anion exchange with sodium chloride forms the chloride salt of the desired compound.Several other syntheses of nitidine chloride have also been reported.These include: a) synthesis of the intermediates by a different route; b) photocyclization of bromobenzamide from 5-aminonaphthalene to phenanthridine; and c) condensation of homophthalic anhydride and the Schiff base to form the 3-arylisoquinoline.Many analogues of nitidine chloride,including fagaronine.The tetramethoxy analogue,the indenoisoquinoline derivative,etc.,possess significant antineoplastic activity.
参考文献标题:Synthesis and biological activity of structural analogues of the anticancer benzophenanthridine alkaloid nitidine chloride
文献作者:Cushman,M.; Mohan,P.; Smith,E.C.R.
参考来源:J Med Chem 1984,27(4),544-547
合成路线:The synthesis of nitidine chloride was first reported in 1973.The procedure was based on the synthesis of dihydronitidine,which involves hydrocyanation of the corresponding chalcone,followed by hydrolysis,reduction and cyclization to the 2-aryl tetralone.Leukart reaction of the tetralone followed by ring closure with phosphorus oxychloride and catalytic dehydrogenation yields the benzo[c]phenanthridine nucleus.Methylation and quarternization with methyl sulfate followed by anion exchange with sodium chloride forms the chloride salt of the desired compound.Several other syntheses of nitidine chloride have also been reported.These include: a) synthesis of the intermediates by a different route; b) photocyclization of bromobenzamide from 5-aminonaphthalene to phenanthridine; and c) condensation of homophthalic anhydride and the Schiff base to form the 3-arylisoquinoline.Many analogues of nitidine chloride,including fagaronine.The tetramethoxy analogue,the indenoisoquinoline derivative,etc.,possess significant antineoplastic activity.
参考文献标题:Preparation and antileukemic activity of some alkoxybenzo[c]phenanthridinium salts and corresponding dihydro derivatives
文献作者:Zee-Chenh,R.K.-Y.; Cheng,C.C.
参考来源:J Med Chem 1975,18(1),66-71
合成路线:The synthesis of nitidine chloride was first reported in 1973.The procedure was based on the synthesis of dihydronitidine,which involves hydrocyanation of the corresponding chalcone,followed by hydrolysis,reduction and cyclization to the 2-aryl tetralone.Leukart reaction of the tetralone followed by ring closure with phosphorus oxychloride and catalytic dehydrogenation yields the benzo[c]phenanthridine nucleus.Methylation and quarternization with methyl sulfate followed by anion exchange with sodium chloride forms the chloride salt of the desired compound.Several other syntheses of nitidine chloride have also been reported.These include: a) synthesis of the intermediates by a different route; b) photocyclization of bromobenzamide from 5-aminonaphthalene to phenanthridine; and c) condensation of homophthalic anhydride and the Schiff base to form the 3-arylisoquinoline.Many analogues of nitidine chloride,including fagaronine.The tetramethoxy analogue,the indenoisoquinoline derivative,etc.,possess significant antineoplastic activity.
合成路线:By reaction of 2-aminobenzophenones (I) with bromoacetyl halide (II) or tosyloxyacetyl halide (VI) to give,respectively,2-(bromoacetylamino)benzophenones (III) or 2-(tosyloxyacetylamino)benzophenones (VII),which are treated with ethanolamine (IV) to give the compounds (V),which with acetic acid in ethanol give the desired compounds.These compounds can also be obtained from (III) and (VI) without isolation of (V)
参考文献标题:
文献作者:Miyadera,T.; et al.
参考来源:J Heterocycl Chem 1973,10(6),85-88
合成路线:The synthesis of nitidine chloride was first reported in 1973.The procedure was based on the synthesis of dihydronitidine,which involves hydrocyanation of the corresponding chalcone,followed by hydrolysis,reduction and cyclization to the 2-aryl tetralone.Leukart reaction of the tetralone followed by ring closure with phosphorus oxychloride and catalytic dehydrogenation yields the benzo[c]phenanthridine nucleus.Methylation and quarternization with methyl sulfate followed by anion exchange with sodium chloride forms the chloride salt of the desired compound.Several other syntheses of nitidine chloride have also been reported.These include: a) synthesis of the intermediates by a different route; b) photocyclization of bromobenzamide from 5-aminonaphthalene to phenanthridine; and c) condensation of homophthalic anhydride and the Schiff base to form the 3-arylisoquinoline.Many analogues of nitidine chloride,including fagaronine.The tetramethoxy analogue,the indenoisoquinoline derivative,etc.,possess significant antineoplastic activity.
参考文献标题:
文献作者:May,H.-J.
参考来源:J Chem Soc 1959,30(10),4010-4012
合成路线:The synthesis of nitidine chloride was first reported in 1973.The procedure was based on the synthesis of dihydronitidine,which involves hydrocyanation of the corresponding chalcone,followed by hydrolysis,reduction and cyclization to the 2-aryl tetralone.Leukart reaction of the tetralone followed by ring closure with phosphorus oxychloride and catalytic dehydrogenation yields the benzo[c]phenanthridine nucleus.Methylation and quarternization with methyl sulfate followed by anion exchange with sodium chloride forms the chloride salt of the desired compound.Several other syntheses of nitidine chloride have also been reported.These include: a) synthesis of the intermediates by a different route; b) photocyclization of bromobenzamide from 5-aminonaphthalene to phenanthridine; and c) condensation of homophthalic anhydride and the Schiff base to form the 3-arylisoquinoline.Many analogues of nitidine chloride,including fagaronine.The tetramethoxy analogue,the indenoisoquinoline derivative,etc.,possess significant antineoplastic activity.
参考文献标题:
文献作者:Pabbathi,V.K.; et al.
参考来源:J Heterocycl Chem 1973,10(2),31-33
合成路线:The synthesis of nitidine chloride was first reported in 1973.The procedure was based on the synthesis of dihydronitidine,which involves hydrocyanation of the corresponding chalcone,followed by hydrolysis,reduction and cyclization to the 2-aryl tetralone.Leukart reaction of the tetralone followed by ring closure with phosphorus oxychloride and catalytic dehydrogenation yields the benzo[c]phenanthridine nucleus.Methylation and quarternization with methyl sulfate followed by anion exchange with sodium chloride forms the chloride salt of the desired compound.Several other syntheses of nitidine chloride have also been reported.These include: a) synthesis of the intermediates by a different route; b) photocyclization of bromobenzamide from 5-aminonaphthalene to phenanthridine; and c) condensation of homophthalic anhydride and the Schiff base to form the 3-arylisoquinoline.Many analogues of nitidine chloride,including fagaronine.The tetramethoxy analogue,the indenoisoquinoline derivative,etc.,possess significant antineoplastic activity.
参考文献标题:
文献作者:Okamoto,T.; et al.
参考来源:Tetrahedron Lett 1974,297(2),2269-2270
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