A kind of medicine for treating brain glioma and preparation method thereof

A technology of pharmacy and compound, applied in the field of pharmacy, can solve the problem of small dosage and so on

Active Publication Date: 2021-01-12
JIAMUSI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] On the basis of the above-mentioned drugs, the applicant has designed and synthesized another anti-tumor compound containing benzodioxane through further research, especially the therapeutic effect on glioma is significantly improved, the dosage is small, and it is effective on normal tissues. The cells are non-toxic, and the water solubility is greatly improved compared with the above-mentioned compounds. It has great application prospects for the treatment of tumor diseases, especially glioma. There is no literature report on the above-mentioned research and discovery.

Method used

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  • A kind of medicine for treating brain glioma and preparation method thereof
  • A kind of medicine for treating brain glioma and preparation method thereof
  • A kind of medicine for treating brain glioma and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the preparation of compound I-a

[0033]

[0034] 1,4-benzodioxane-2-chloromethylamine (1.0mmol) and NaCN (1.05mmol) were dissolved in ethanol, and after reacting at room temperature for 5 hours, TLC detection showed that the reactant 1,4-benzo Dioxane-2-chloromethylamine disappeared, stop the reaction, add 20mL deionized water and 20mL dichloromethane, let stand to separate, collect the organic phase, distill off the solvent under reduced pressure, and proceed directly to the next reaction without purification .

[0035] Dissolve the product after cyano substitution in the previous step and 0.6 equivalent of sodium carbonate in acetonitrile solvent, slowly add carbon disulfide (1.1 equivalent) dropwise within half an hour, heat and reflux and stir for Cook-Heilbron reaction for 10 hours, TLC detects raw materials After disappearing, add an appropriate amount of deionized water, filter to remove insoluble matter, collect the filtrate, add dilute hydroc...

Embodiment 2

[0039] Embodiment 2: the preparation of compound I-b

[0040]

[0041] With 1,4-m-chlorobenzodioxane-2-chloromethylamine as the initial reactant, compound I-b was prepared by the same method as in Example 1, wherein in the (3) step, through flash column chromatography (two Chloromethane:methanol=10:3) to obtain 282 mg of white solid I-b (HPLC purity: 99.4%), with a total yield of 82%.

[0042] 1 H NMR (300MHz, CDCl 3 )δ8.57(s, 1H), δ8.32(d, 1H), 7.64(d, 1H), 7.46(t, 1H), 6.41(d, J 7.6Hz, 2H), 6.17(t, 1H) , 6.09(s, 2H), 5.81-5.96(m, 4H);

[0043] ESI MS m / z 345.0[M+Na] + .

Embodiment 3

[0044] Embodiment 3: the preparation of compound I-c

[0045]

[0046] Using 1,4-m-methoxybenzodioxane-2-chloromethylamine as the initial reactant, the same method as in Example 1 was used to prepare compound I-b, wherein in step (3) flash column chromatography (Dichloromethane:methanol=5:1) to obtain 303 mg of white solid I-c (HPLC purity: 99.8%), with a total yield of 89%.

[0047] 1 H NMR (300MHz, CDCl 3 )δ8.36(s, 1H), δ8.12(d, 1H), 7.57(d, 1H), 7.28(t, 1H), 6.37(d, J 7.1Hz, 2H), 6.29(t, 1H) , 6.02(s, 2H), 5.77-5.97(m, 4H), 4.79(s, 3H);

[0048] ESI MS m / z 341.0[M+Na] + .

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PUM

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Abstract

The present invention relates to a compound containing benzodioxane and thiazole and a pharmaceutically acceptable salt, a preparation method and application thereof. The structure of the compound isrepresented by a formula I, wherein R is selected from hydrogen, C1-C5 alkyl, C1-C5 alkoxy, halogen or COORE and RE is selected from C1-C5 alkyl. The compound has the advantages that the treatment effect on the brain glioma is obviously improved, the dosage is small, the toxicity to normal tissue cells is avoided, the water solubility is also greatly improved in comparison with that of the compound and the compound has great application prospects in the treatment of tumor diseases, particularly the brain glioma.

Description

technical field [0001] The invention relates to the field of pharmacy, in particular to a compound containing benzodioxane and thiazole, a preparation method, and an application thereof for preparing a medicine for treating glioma. Background technique [0002] Glioma is the most common intracranial malignant primary brain tumor, which accounts for 80% of brain malignant tumors. Infiltrative growth is the characteristic of glioma, so the tumor tissue is unclear, making it impossible to completely treat it through surgery. It is very difficult to remove the diseased tissue, so glioma is very easy to relapse after resection. The World Health Organization (WHO) classification of tumors of the central nervous system divides brain gliomas into grades I to IV. Gliomas are grade I. For example, pilocytic tumors are very slow-growing tumors. If this type of tumor is completely resected, Patients may be cured. Glioma grade II (common oligoastrocytoma, astrocytoma, etc.), aggressive...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C07D417/14A61K31/427A61K31/4439A61P35/00
CPCA61P35/00C07D417/04C07D417/14
Inventor 李洪滨张世华杨慧
Owner JIAMUSI UNIVERSITY
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