4-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione → 10-Aminocamptothecin

HRID 2418789

반응식

HRID 2418789 반응식
[CH3:1][CH2:2][C:3]1([OH:29])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24](=[CH:25][C:14]=1[CH2:13]3)[CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=[CH:20]2)=[O:11].[Sn]>[Pt]=O.[Fe].[Zn]>[CH3:1][CH2:2][C@@:3]1([OH:29])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24](=[CH:25][C:14]=1[CH2:13]3)[CH:23]=[C:22]([NH2:26])[CH:21]=[CH:20]2)=[O:11]

참가 물질

6

반응물 2

HCID 655674-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione2회HCID 5352426Tin atom

생성물 1

HCID 10498610-Aminocamptothecin

시약·촉매·용매 3

HCID 23925Iron촉매HCID 23994Zinc촉매HCID 82844Platinum oxide (PtO)용매

실험 절차

In order to obtain the product of the general formula (I') wherein R3' is an amino group, 10-nitrocamptothecin, its tetrahydro derivative or its 1-acyl-tetrahydro derivative is subjected to a conventional reductive reaction contemplated for reducing a nitro group to an amino group. Usually, Clemensen' reduction method (a combination of dilute mineral acid and tin, iron or zinc) or a catalytic reduction method is used for this purpose. Advantageously, 10-nitrocamptothecin is dissolved in a solvent and hydrogenated at room temperature under atmospheric pressure in the presence of a small amount of platinum oxide. In this case, the desired 10-aminocamptothecin can be obtained by removing the catalyst from the reaction mixture by filtration and evaporating the solvent under reduced pressure.

후처리

  1. customIn order to obtain the product of the general formula (I') wherein R3'
  2. customis subjected to a conventional reductive reaction

출처 및 근거

ORD 기록
ord-3c1640547f49477aa5e96b214bd06609
출처 데이터셋
uspto-grants-1984_09
특허 번호
US04473692

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