Heterocyclic cytotoxic agents
a cytotoxic agent and heterocyclic compound technology, applied in the field of heterocyclic cytotoxic agents, can solve the problems of limiting cellular uptake and most likely impede cellular uptake, and achieve the effect of effective cytotoxic agents
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example 1
2,3-Dimethoxy-dibenzo[c,h]cinnoline (6)
6-(2-Aminophenyl)-2,3-dimethoxynaphthalene (5, 70 mg, 0.25 mmol) was dissolved in 48% hydrobromic acid (4.25 mL), cooled in ice-salt bath, and treated dropwise with stirring with sodium nitrite (0.13 g) in water (2.2 mL). Stirring was continued for 0.5 h., and to the cold solution was then added with stirring freshly precipitated copper (0.5 g). The mixture was allowed to rise slowly to room temperature and left overnight. The solid was filtered off and washed with hot chloroform. The chloroform solution was washed with diluted sodium hydroxide solution, then with water, dried (anhydrous Na2SO4) and rotaevaporated to give the crude product. Chromatography on silica gel using 50:50 hexanes:ethyl acetate afforded the title compound (13 mg) in 18% yield; 1H NMR (CDCl3) d 4.11(3H, s), 4.24(3H, s), 7.37(1H, s), 7.89˜7.94 (2H, m), 8.14(1H, d, J=8.9), 8.41(1H, d, J=8.8), 8.61˜8.66(1H, m), 8.758.80(1H, m), 9.24(1H, s); 13C NMR d 56.1, 56.4, 104.0, 10...
example 2
2,3-Dimethoxy-8,9-methylenedioxy-dibenzo[c,h]cinnoline (14)
6-(2-Amino-4,5-methylenedioxyphenyl)-2,3-dimethoxy-naphthalene (13, 40 mg, 0.13 mmol) in acetic acid (2 mL) and concentrated hydrochloric acid (0.3 mL) was cooled to 0° C. and diazotised with a solution of sodium nitrite (0.09 g in 1.5 mL water). The diazonium solution was allowed to rise slowly to room temperature and left overnight. Water (50 mL) was added to the red solution with some precipitate. The resulting mixture was extracted with ethyl acetate, washed with diluted sodium hydroxide solution, then with water, dried (anhydrous Na2SO4) and rotaevaporated to give the crude product. Chromatography on silica gel using 40:60 hexanes:ethyl acetate afforded the title compound (20 mg) in 50% yield; 11H NMR (CDCl3) d 4.09(3H, s), 4.22(3H, s), 6.24(2H, s), 7.31(1H, s), 7.80(1H, s), 7.95(1H, s), 8.00(1H, d, J=9.2), 8.13(1H, d, J=8.9), 9.14(1H, s); 13C NMR d 56.5, 56.9, 98.1, 102.9, 104.6, 107.5, 107.9, 117.1, 119.6, 120.6, 12...
example 3
2,3,8,9-Tetramethoxy-dibenzo[c,h]cinnoline (19)
6-(2-Amino-4,5-dimethoxyphenyl)-2,3-dimethoxynaphthalene (18) (11 mg, 0.033 mmol) in acetic acid (0.6 mL) and concentrated hydrochloric acid (0.06 mL) was cooled to 0° C. and diazotised with a solution of sodium nitrite (0.026 g in 0.5 mL water). The diazonium solution was allowed to rise slowly to room temperature and left overnight. Water (30 mL) was added to the red solution with some precipitate. The resulting mixture was extracted with ethyl acetate, washed with diluted sodium hydroxide solution, then with water, dried (anhydrous Na2SO4) and rotaevaporated to give the crude product. Chromatography on silica gel using 40:60 chloroform:ethyl acetate afforded the title compound (5 mg) in 44% yield; 1H NMR (CDCl3) d 4.09(3H, s), 4.18(6H, s), 4.23(3H, s), 7.31(1H, s), 7.74(1H, s), 8.00(1H, s), 8.01(1H, d, J=8.5), 8.20(1H, d, J=8.9), 9.15(1H, s); 13C NMR d 56.5, 56.9, 99.9, 104.5, 107.9, 109.5, 116.9, 118.5, 118.9, 127.0, 128.4, 131.6,...
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