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

Reaktionsgleichung

Reaktionsgleichung von HRID 2418789
[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]

Komponenten

6

Edukt 2

HCID 655674-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione2×HCID 5352426Tin atom

Produkt 1

HCID 10498610-Aminocamptothecin

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 23994ZincKatalysatorHCID 82844Platinum oxide (PtO)Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3c1640547f49477aa5e96b214bd06609
Quelldatensatz
uspto-grants-1984_09
Patentnummer
US04473692

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