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【结 构 式】

【分子编号】63205

【品名】6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanohydrazide

【CA登记号】

【 分 子 式 】C10H15N3O3

【 分 子 量 】225.24752

【元素组成】C 53.32% H 6.71% N 18.66% O 21.31%

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:(VI)

6-Aminocaproic acid (I) is condensed with maleic anhydride (II) in refluxing AcOH to provide maleimidocaproic acid (III). After activation of acid (III) as the corresponding mixed anhydride with isobutyl chloroformate, coupling with tert-butyl carbazate (IV) affords the N-Boc hydrazide (V). Subsequent acidic cleavage of the Boc group of (V) furnishes hydrazide (VI). Finally, hydrazide (VI) is condensed with doxorubicin (VII) to produce the title hydrazone conjugate.

1 Willner, D.; Trail, P.A.; Hofstead, S.J.; King, H.D.; Lasch, S.J.; Braslawsky, G.R.; Greenfield, R.S.; Kaneko, T.; Firestone, R.A.; (6-Maleimidocaproyl)hydrazone of doxorubicin - A new derivative for the preparation of immunoconjugates of doxorubicin. Bioconjugate Chem 1993, 4, 6, 521.
2 Willner, D.; Trail, P.A.; King, D.H.; Hofstead, S.J.; Greenfield, R.S.; Braslawsky, G.R. (Bristol-Myers Squibb Co.); Thioether conjugates. EP 0554708; JP 1994025012; US 5622929 .
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) 41170 6-aminohexanoic acid 60-32-2 C6H13NO2 详情 详情
(II) 11182 2,5-Furandione; Maleic anhydride 108-31-6 C4H2O3 详情 详情
(III) 63203 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid C10H13NO4 详情 详情
(IV) 10893 tert-butyl 1-hydrazinecarboxylate; tert-butyl carbazate 870-46-2 C5H12N2O2 详情 详情
(V) 63204 tert-butyl 2-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-1-hydrazinecarboxylate C15H23N3O5 详情 详情
(VI) 63205 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanohydrazide C10H15N3O3 详情 详情
(VII) 11675 (8S,10S)-10-[[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-8-glycoloyl-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione C27H29NO11 详情 详情
Extended Information