• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】28960

【品名】2,3-dimethoxy-4b,5,6,11b-tetrahydro[1,3]benzodioxolo[5,6-c]phenanthridine

【CA登记号】

【 分 子 式 】C20H19NO4

【 分 子 量 】337.3752

【元素组成】C 71.2% H 5.68% N 4.15% O 18.97%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IX)

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.

1 Miyadera, T.; et al.; J Heterocycl Chem 1973, 10, 6, 85-88.
2 Pabbathi, V.K.; et al.; J Heterocycl Chem 1973, 10, 2, 31-33.
3 Okamoto, T.; et al.; Tetrahedron Lett 1974, 297, 2, 2269-2270.
4 Muramatsu, I.; Ahmed, M.; Ohnuki, T.; Nagatomo, T.; Futabayashi, Y.; Ishiguro, M.; J Heterocycl Chem 1981, 18, 21, 223-232.
5 Gupta, Y.K.; Sharma, M.; J Org Chem 1978, 43, 21, 286-288.
6 May, H.-J.; J Chem Soc 1959, 30, 10, 4010-4012.
7 Caldwell, J.; Glowka, F.K.; J Chem Soc - Perkins Trans I 1977, 14, 9, 2324-2328.
8 Cheng, C.C.; Zee-Chenh, R.K.-Y.; Preparation and antileukemic activity of some alkoxybenzo[c]phenanthridinium salts and corresponding dihydro derivatives. J Med Chem 1975, 18, 1, 66-71.
9 Cushman, M.; Mohan, P.; Smith, E.C.R.; Synthesis and biological activity of structural analogues of the anticancer benzophenanthridine alkaloid nitidine chloride. J Med Chem 1984, 27, 4, 544-547.
10 Zee-Cheng, R.K.-Y.; Cheng, C.C.; Nitidine Chloride. Drugs Fut 1985, 10, 2, 124.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 28953 1-(1,3-benzodioxol-5-yl)-1-ethanone 3162-29-6 C9H8O3 详情 详情
(III) 28954 (E)-1-(1,3-benzodioxol-5-yl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one C18H16O5 详情 详情
(IV) 28955 4-(1,3-benzodioxol-5-yl)-2-(3,4-dimethoxyphenyl)-4-oxobutanenitrile C19H17NO5 详情 详情
(V) 28956 4-(1,3-benzodioxol-5-yl)-2-(3,4-dimethoxyphenyl)-4-oxobutyric acid C19H18O7 详情 详情
(VI) 28957 4-(1,3-benzodioxol-5-yl)-2-(3,4-dimethoxyphenyl)butyric acid C19H20O6 详情 详情
(VII) 28958 6-(3,4-dimethoxyphenyl)-7,8-dihydronaphtho[2,3-d][1,3]dioxol-5(6H)-one C19H18O5 详情 详情
(VIII) 28959 6-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxol-5-ylformamide C20H21NO5 详情 详情
(IX) 28960 2,3-dimethoxy-4b,5,6,11b-tetrahydro[1,3]benzodioxolo[5,6-c]phenanthridine C20H19NO4 详情 详情
(X) 28961 2,3-dimethoxy[1,3]benzodioxolo[5,6-c]phenanthridine C20H15NO4 详情 详情
(XI) 28962 2,3-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium (sulfonatooxy)methane C22H21NO8S 详情 详情
Extended Information