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

【结 构 式】

【分子编号】40890

【品名】methyl (8S)-8-(bromomethyl)-6-[(E)-3-[3-(dimethylamino)-4-methoxyphenyl]-2-propenoyl]-2-methyl-4-[[(4-nitrophenoxy)carbonyl]oxy]-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate

【CA登记号】

【 分 子 式 】C33H31BrN4O9

【 分 子 量 】707.5347

【元素组成】C 56.02% H 4.42% Br 11.29% N 7.92% O 20.35%

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:(VII)

The hydrolysis of DU-86 (I) with NaOMe gives tetracyclic compound (II), which is acylated with the 4-nitrophenyl cinnamate (III) and NaH yielding the adduct (IV). The opening of the cyclopropane ring of (IV) with HBr in acetonitrile affords the aromatic phenol (V), which is activated with 4-nitrophenyl chloroformate (VI) and TEA to provide the activated anhydride (VII). Finally, this compound is condensed with 4-methylpiperazine-1-amine (VIII), and treated with HBr to furnish the target dihydrobromide.

1 Amishiro, N.; Nagamura, S.; Saito, H.; Kobayashi, E.; Okamoto, A.; Gomi, K. (Kyowa Hakko Kogyo Co., Ltd.); DC-89 deriv.. EP 0702014; US 5670492; WO 9526964 .
2 Nagamura, S.; Murakata, C.; Amishiro, N.; et al.; Synthesis and antitumor activity of duocarmycin derivatives: Modification at C-8 position of A-ring pyrrole compounds bearing the simplified DNA-binding groups. Bioorg Med Chem 2000, 8, 2, 381.
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) 40881 methyl (3bR,4aS)-2-methyl-8-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate C26H25N3O7 详情 详情
(II) 38365 methyl (3bR,4aS)-2-methyl-8-oxo-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate C14H14N2O3 详情 详情
(III) 40887 4-nitrophenyl (E)-3-[3-(dimethylamino)-4-methoxyphenyl]-2-propenoate C18H18N2O5 详情 详情
(IV) 40888 methyl (3bR,4aS)-6-[(E)-3-[3-(dimethylamino)-4-methoxyphenyl]-2-propenoyl]-2-methyl-8-oxo-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate C26H27N3O5 详情 详情
(V) 40889 methyl (8S)-8-(bromomethyl)-6-[(E)-3-[3-(dimethylamino)-4-methoxyphenyl]-2-propenoyl]-4-hydroxy-2-methyl-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate C26H28BrN3O5 详情 详情
(VI) 16605 4-Nitrophenyl chloroformate; 1-[(Chlorocarbonyl)oxy]-4-nitrobenzene 7693-46-1 C7H4ClNO4 详情 详情
(VII) 40890 methyl (8S)-8-(bromomethyl)-6-[(E)-3-[3-(dimethylamino)-4-methoxyphenyl]-2-propenoyl]-2-methyl-4-[[(4-nitrophenoxy)carbonyl]oxy]-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate C33H31BrN4O9 详情 详情
(VIII) 40886 4-methyl-1-piperidinamine; 4-methyl-1-piperidinylamine 19107-42-7 C6H14N2 详情 详情
Extended Information