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Compounds and their preparation methods and applications

A compound and composition technology, applied in the field of medicine, can solve the problem that the tumor treatment method needs to be improved, etc.

Active Publication Date: 2019-06-25
HUAZHONG NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, existing tumor treatment methods still need to be improved

Method used

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  • Compounds and their preparation methods and applications
  • Compounds and their preparation methods and applications
  • Compounds and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Compound 1

[0036] 1,5-bis(1-benzyl-1H-1,2,3-triazole)-1,4-pentadien-3-one

[0037]

[0038] Add 0.10mol (12.7g 98%) of benzyl chloride into a 250mL three-neck round bottom flask, dissolve in 150ml of DMF, then add 0.11mol of sodium azide, stir and react at 70°C for 3h, cool the reaction solution to room temperature, add 200ml of water to dissolve the insoluble The substance was dissolved, transferred to a separatory funnel, extracted 3 times with ethyl acetate (30ml×3), collected the organic phase, dried over anhydrous sodium sulfate for 2h, filtered under reduced pressure, and precipitated to obtain a light yellow oily product, benzyl azide 10.37 g, the crude yield is 78%, and it is directly used in the next reaction without purification.

[0039] Add 2.67g (0.01mol) of benzyl azide and 1.12g (0.01mol) of propynyl alcohol into a 100mL three-necked flask. Dissolve in 30ml of a mixed solvent of tert-butanol and water, add 8mol% sodium ascorbate and 2mol% copper su...

Embodiment 2

[0077] Compound 5

[0078] 2,6-bis(1-benzyl-1H-1,2,3-triazole-4-methenyl)cyclohexanone

[0079]

[0080] Add 0.10mol (12.7g 98%) of benzyl chloride into a 250mL three-neck round bottom flask, dissolve in 150ml of DMF, then add 0.11mol of sodium azide, stir and react at 70°C for 3h, cool the reaction solution to room temperature, add 200ml of water to dissolve the insoluble The substance was dissolved, transferred to a separatory funnel, extracted 3 times with ethyl acetate (30ml×3), collected the organic phase, dried over anhydrous sodium sulfate for 2h, filtered under reduced pressure, and precipitated to obtain a light yellow oily product, benzyl azide 10.37 g, the crude yield is 78%, and it is directly used in the next reaction without purification.

[0081] Add 2.67g (0.01mol) of benzyl azide and 2.24g (0.02mol) of propynyl alcohol into a 100mL three-necked flask. Dissolve in 30 ml of mixed solvent of tert-butanol and water, add 5 mol% sodium ascorbate and 2 mol% copp...

Embodiment 3

[0116] Compound 9

[0117] 3,5-bis(1-benzyl-1H-1,2,3-triazole-4-methenyl)-1-methylpiperidin-4-one

[0118]

[0119] Add 0.10mol (12.7g 98%) of benzyl chloride into a 250mL three-neck round bottom flask, dissolve in 150ml of DMF, then add 0.11mol of sodium azide, stir and react at 70°C for 3h, cool the reaction solution to room temperature, add 200ml of water to dissolve the insoluble The substance was dissolved, transferred to a separatory funnel, extracted 3 times with ethyl acetate (30ml×3), collected the organic phase, dried over anhydrous sodium sulfate for 2h, filtered under reduced pressure, and precipitated to obtain a light yellow oily product, benzyl azide 10.37 g, the crude yield is 78%, and it is directly used in the next reaction without purification.

[0120] Add 2.67g (0.01mol) of benzyl azide and 3.36g (0.03mol) of propynyl alcohol into a 100mL three-necked flask. Dissolve in 50 ml of a mixed solvent of tert-butanol and water, add 8 mol% sodium ascorbate an...

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Abstract

The invention provides compounds, and a preparation method and application thereof. The compounds are compounds shown as a formula I, and enantiomers, diastereomers, racemers, pharmaceutically-acceptable salts, crystallization hydrates, ketone-enol tautomerism compounds or solvates thereof, and in the formula I, R1, R2 and R3 are independently at least one halogen, hydrogen, optional substituted alkyl or optional substituted alkoxy, m and n are independently an integer selected from 0 to 5, X is O, (CH2)[s1] and (CH2)[s2]N(R3)(CH2)[s3], and s1, s2 and s3 are independently an integer of 1-5. The compounds are applicable to treat cancer related diseases.

Description

technical field [0001] The present invention relates to the field of medicine. Specifically, the present invention relates to compounds and their preparation methods and applications. More specifically, the present invention relates to compounds represented by formula I, derivatives and preparation methods thereof, pharmaceutical compositions, compounds represented by formula I in Use in the preparation of medicines. Background technique [0002] Tumor is an abnormal lesion formed by the body under the action of various carcinogenic factors when a certain cell in a local tissue loses its normal regulation of its growth at the gene level, resulting in its clonal abnormal proliferation. Tumors are generally divided into two categories, benign and malignant. [0003] However, the existing tumor treatment methods still need to be improved. Contents of the invention [0004] The present invention aims to solve one of the technical problems in the related art at least to a cer...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/04C07D401/14A61K31/4192A61K31/454A61P35/00
Inventor 贺红武符立梧宁丽红梁永钜
Owner HUAZHONG NORMAL UNIV