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

反応式

HRID 2418789 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

HCID 10498610-Aminocamptothecin

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 23994Zinc触媒HCID 82844Platinum oxide (PtO)溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-3c1640547f49477aa5e96b214bd06609
出典データセット
uspto-grants-1984_09
特許番号
US04473692

関連ノート

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