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【结 构 式】 
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【分子编号】41187 【品名】2-[2-(dimethylamino)ethyl]-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C24H22N4O4S 【 分 子 量 】462.52924 【元素组成】C 62.32% H 4.79% N 12.11% O 13.84% S 6.93% |
合成路线1
该中间体在本合成路线中的序号：(III)The cyclization of 9-fluoro-6-(tosyloxy)-5,10-dihydrobenzo[g]isoquinoline-5,10-dione (I) with 2-(dimethylamino)ethylhydrazine (II) gives 2-[2-(dimethylamino)ethyl]-5-(tosyloxy)indazolo[4,3-gh]isoquinolin-6(2H)-one (III), which is finally condensed with N,N-dimethylethylene-1,2-diamine (IV) to afford the title compound.
| 【1】 Gallagher, C.E.; Maresch, M.J.; Krapcho, A.P.; et al.; 6,9-Disubstituted benz[g]isoquinoline-5,10-diones, key intermediates for the synthesis of antitumor 2,5-disubstituted-indazolo[4,3-gh]isoquinoline-6(2H)-ones (9-aza-anthrapyrazoles). 25th Natl Med Chem Symp (June 18, Univ. Michigan, Ann Arbor) 1996, Abst. 15. |
| 【2】 Menta, E.; et al.; Synthesis and antitumor evalution of 2, 5-disubstituted-indazolo[4, 3-gh]isoquinoline-6(2H)-ones (9-aza-anthrapyrazoles). 211th ACS Natl Meet (March 24-28, New Orleans) 1996, Abst MEDI 076. |
| 【3】 Krapcho, A.P.; Menta, E.; Antitumor aza-anthrapyrazoles. Drugs Fut 1997, 22, 6, 641. |
| 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) | 41185 | 9-fluoro-5,10-dioxo-5,10-dihydrobenzo[g]isoquinolin-6-yl 4-methylbenzenesulfonate | C20H12FNO5S | 详情 | 详情 | |
| (II) | 41186 | N-(2-hydrazinoethyl)-N,N-dimethylamine; 2-hydrazino-N,N-dimethyl-1-ethanamine | C4H13N3 | 详情 | 详情 | |
| (III) | 41187 | 2-[2-(dimethylamino)ethyl]-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl 4-methylbenzenesulfonate | C24H22N4O4S | 详情 | 详情 | |
| (IV) | 14881 | N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine | 108-00-9 | C4H12N2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)The cyclization of 9-fluoro-6-(tosyloxy)-5,10-dihydrobenzo[g]isoquinoline-5,10-dione (I) with 2-(dimethylamino)ethylhydrazine (II) gives 2-[2-(dimethylamino)ethyl]-5-(tosyloxy)indazolo[4,3-gh]isoquinolin-6(2H)-one (III), which is finally condensed with ethylene-1,2-diamine (IV) to afford the title compound.
| 【1】 Gallagher, C.E.; Maresch, M.J.; Krapcho, A.P.; et al.; 6,9-Disubstituted benz[g]isoquinoline-5,10-diones, key intermediates for the synthesis of antitumor 2,5-disubstituted-indazolo[4,3-gh]isoquinoline-6(2H)-ones (9-aza-anthrapyrazoles). 25th Natl Med Chem Symp (June 18, Univ. Michigan, Ann Arbor) 1996, Abst. 15. |
| 【2】 Krapcho, A.P.; Menta, E.; Antitumor aza-anthrapyrazoles. Drugs Fut 1997, 22, 6, 641. |
| 【3】 Menta, E.; et al.; Synthesis and antitumor evalution of 2, 5-disubstituted-indazolo[4, 3-gh]isoquinoline-6(2H)-ones (9-aza-anthrapyrazoles). 211th ACS Natl Meet (March 24-28, New Orleans) 1996, Abst MEDI 076. |
| 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) | 41185 | 9-fluoro-5,10-dioxo-5,10-dihydrobenzo[g]isoquinolin-6-yl 4-methylbenzenesulfonate | C20H12FNO5S | 详情 | 详情 | |
| (II) | 41186 | N-(2-hydrazinoethyl)-N,N-dimethylamine; 2-hydrazino-N,N-dimethyl-1-ethanamine | C4H13N3 | 详情 | 详情 | |
| (III) | 41187 | 2-[2-(dimethylamino)ethyl]-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl 4-methylbenzenesulfonate | C24H22N4O4S | 详情 | 详情 | |
| (IV) | 14754 | ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine | 107-15-3 | C2H8N2 | 详情 | 详情 |