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Camptothecin compound, and preparation method and application thereof

A compound, the technology of camptothecin, which is applied in the field of new camptothecin compounds, can solve the problems such as the research report on the pine wood nematode and the cinnabar spider mite test insect that have not been seen, and achieves good poisoning activity, high product purity, and synthetic simple craftsmanship

Active Publication Date: 2015-06-24
甘肃康扬医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] But so far, there are no research reports on this type of compounds and their use in the control of cabbage aphids, pine wood nematodes, and test insects of Tetranychus cinnabarinus

Method used

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  • Camptothecin compound, and preparation method and application thereof
  • Camptothecin compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 7-( N Synthesis of -p-fluorophenyl-)-methylene-camptothecin (1)

[0020] Synthesis of raw material 7-bromomethylcamptothecin : Dissolve 8.6mmol camptothecin in 90mL and 75mL water, add 75mL75% sulfuric acid dropwise, then add 8.6mmol ferrous sulfate heptahydrate. Under the condition of ice bath, 6.6 mmol 30% hydrogen peroxide was added dropwise. After dropping, stir at room temperature for 14 hours, add 40mml of water to dilute, a large amount of yellow solid is produced, filter, wash the solid with 10mml of water to obtain 2.7g of yellow solid (7-hydroxymethylcamptothecin). Dissolve 0.2mmol 7-hydroxymethylcamptothecin in a mixture of 10mL 45% hydrobromic acid and 0.35mL 97% concentrated sulfuric acid, heat to reflux for 6 hours, evaporate the solvent, and perform column chromatography (the elution system is chloroform: Methanol=40:1) Purified to obtain yellow solid 7-bromomethylcamptothecin. Synthetic method see literature method ( ChemMedChem. 2012, 7(12) ...

Embodiment 2

[0024] 7-( N Synthesis of -p-chlorophenyl-)-methylene-camptothecin (2)

[0025] The experimental procedure is the same as in Example 1, only p-chloroaniline is used instead of p-fluoroaniline.

[0026] The product detection data are as follows: Yield: 40%; Melting point: 243 °C (decomposition);1 H NMR (400MHz, DMS0-d 6 ) δ: 0.87-0.92 (t, J =7.2Hz, 3H, 19-H), 1.85-1.92 (m, 2H, 18-H), 5.12 (d, J =4.8Hz, 2H, -CH 2 -), 5.44 (s, 2H, 5-H), 5.52 (s, 2H, 17-H), 5.62 (s, 1H, NH), 6.53 (s, 1H, 20-OH), 7.37 (s, 1H , 14-H), 7.47 (d, J =8.8Hz, 2H, 2', 6'-H), 7.83-7.87 (m, 1H, 11-H), 7.91(d, J =8.8Hz, 2H, 3', 5'-H), 7.92 (t, 1H, J =7.2Hz, 10-H), 8.24 (d, J =8.4Hz, 1H, 12-H), 8.49 (d, J =8.4Hz, 1H, 9-H); MS-ESI m / z : 488.5[M+H] + .

Embodiment 3

[0028] 7-( N Synthesis of -p-bromophenyl-)-methylene-camptothecin (3)

[0029] The experimental procedure is the same as in Example 1, only p-bromoaniline is used instead of p-fluoroaniline.

[0030] The product detection data are as follows: Yield: 42%; Melting point: 257 °C (decomposition); 1 H NMR (400MHz, DMS0-d 6 ) δ: 0.89-0.93 (t, J =6.8Hz, 3H, 19-H), 1.86-1.91 (m, 2H, 18-H), 5.11(d, J =4.8Hz, 2H, -CH 2 -), 5.46 (s, 2H, 5-H), 5.56 (s, 2H, 17-H), 6.52 (s, 1H, 20-OH), 6.57 (s, 1H, NH), 7.42 (s, 1H , 14-H), 7.52 (d, J =8.8Hz, 2H, 2', 6'-H), 7.65 (m, 1H, 11-H), 7.81(d, J =8.8Hz, 2H, 3', 5'-H), 7.86 (t, 1H, J =7.2Hz, 10-H), 8.17 (d, J =8.4Hz, 1H, 12-H), 8.49 (d, J =8.4Hz, 1H, 9-H); MS-ESI m / z : 533.3[M+H] + .

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Abstract

The invention discloses a camptothecin compound as shown in a formula (I) which is described in the specificaiton, a preparation method for the compound and application of the compound in preparation of pesticide. In the formula (I), R is 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 3-chlorophenyl, 2-chlorophenyl, 4-methoxyphenyl, 4-methylphenyl, 2-methoxyphenyl, 1-naphthyl, benzyl or 2-pyridyl.

Description

technical field [0001] The invention relates to a novel camptothecin compound, a preparation method of the compound and its use in the preparation of pesticides. It belongs to the field of pesticides. Background technique [0002] Camptothecin (Camptothecin) is Wall et al. in 1966 first obtained from China's endemic Davidiaceae plant Camptothecin ( camptotheca acuminata ) is a quinoline alkaloid isolated from ), which has various biological activities such as anticancer, antiviral, insecticidal and antibacterial ( J. Nat. Prod. 2004, 67, 129-135) have attracted the attention of researchers at home and abroad. In recent years, the research on camptothecin has mainly focused on anti-tumor aspects, and in-depth research has been carried out on structural modification, anti-cancer structure-activity relationship, and mechanism of action. Among them, many active compounds such as irinotecan, topotecan, 9-aminocamptothecin, 9-nitrocamptothecin and CKD-602 have been approved ...

Claims

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Application Information

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IPC IPC(8): C07D491/22A01N43/90A01P7/02A01P7/04A01P5/00
CPCA01N43/90C07D491/22
Inventor 刘映前赵晓博张绍勇余海涛胡冠芳乌丹杨柳闫莉婷吴小兵
Owner 甘肃康扬医药科技有限公司
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