9-fluoro-5,10-dioxo-5,10-dihydrobenzo[g]isoquinolin-6-yl 4-methylbenzenesulfonate -Drug Synthesis Database

【结构式】

【分子编号】41185

【品名】9-fluoro-5,10-dioxo-5,10-dihydrobenzo[g]isoquinolin-6-yl 4-methylbenzenesulfonate

【CA登记号】

【分子式】C₂₀H₁₂FNO₅S

【分子量】397.3834232

【元素组成】C 60.45% H 3.04% F 4.78% N 3.52% O 20.13% S 8.07%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

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.

参考文献中间体

合成目标

【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：(I)

The cyclization of 9-fluoro-6-(tosyloxy)-5,10-dihydrobenzo[g]isoquinoline-5,10-dione (I) with 2-aminoethylhydrazine (II) gives 2-(2-aminoethyl)-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.

参考文献中间体

合成目标

【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	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)	41188	2-hydrazinoethylamine; 2-hydrazino-1-ethanamine	C₂H₉N₃	详情	详情
(III)	41189	2-(2-aminoethyl)-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl 4-methylbenzenesulfonate	C₂₂H₁₈N₄O₄S	详情	详情
(IV)	14481	(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carbothioic S-acid	C₂₁H₂₆F₂O₄S	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

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.

参考文献中间体

合成目标

【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

Extended Information