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Galactosyl thiourea heterocyclic compounds, synthetic method thereof and antineoplastic applications

A technology of heterocyclic compounds, galactose, applied in the field of galactosylthiourea heterocyclic compounds

Inactive Publication Date: 2008-11-19
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Galactosyl thiosemicarbazide adenine, galactosyl thiosemicarbazide benzimidazole, galactosyl thiosemicarbazide methoxybenzamide benzimidazole provided by the present invention have not been reported so far. new compound

Method used

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  • Galactosyl thiourea heterocyclic compounds, synthetic method thereof and antineoplastic applications
  • Galactosyl thiourea heterocyclic compounds, synthetic method thereof and antineoplastic applications
  • Galactosyl thiourea heterocyclic compounds, synthetic method thereof and antineoplastic applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 : Synthesis of 1-adeninyl-acetyl-4-(1'-N-β-D-galactosyl)-thiosemicarbazide (compound number is a)

[0053] (1) Synthesis of 1-bromo-2,3,4,6-tetra-O-acetyl-α-D-galactose

[0054]Add red phosphorus (4.5g, 3.63mmol) and 60mL glacial acetic acid into a 250mL three-necked flask, add bromine water (12mL, 234.10mmol) with a dropping funnel while stirring, and stir the mixed reaction solution at room temperature for half an hour, filter Discard red phosphorus. Add fully acetylated D-galactose (39g, 100mmol) and react at the same temperature until all the fully acetylated D-galactose of the reactant as detected by thin layer chromatography disappears. The glacial acetic acid was removed under reduced pressure, the residue was extracted three times with saturated sodium carbonate and chloroform, the organic extract was washed three times with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was removed under reduced pressure to obtain 1-br...

Embodiment 2

[0065] Example 2 : Synthesis of 1-benzimidazolyl-acetyl-4-(1'-N-β-D-galactosyl)-thiosemicarbazide (compound number b)

[0066] (1) Synthesis of 1-bromo-2,3,4,6-tetra-O-acetyl-α-D-galactose

[0067] The method and conditions of (1) in Example 1 are adopted for synthesis.

[0068] (2) Synthesis of 2,3,4,6-tetra-O-acetyl-α-D-galactosyl isothiocyanate

[0069] Synthesize using the method and conditions of (2) in Example 1.

[0070] (3) Synthesis of ethyl benzimidazolyl acetate

[0071] The method and conditions of (3) in Example 1 were used for synthesis, only adenine was changed to benzimidazole.

[0072] (4) Synthesis of benzimidazolyl acetylhydrazide

[0073] The method and conditions of (4) in Example 1 were used for synthesis, only ethyl adenyl acetate was changed to ethyl benzimidazolyl acetate.

[0074] (5) 1-Benzimidazolyl-acetyl-4-(1'-N-2',3',4',6'-tetra-O-acetyl-β-D-galactosyl)-amino Synthesis of Thiourea

[0075] Synthesize using the method and conditions of (5...

Embodiment 3

[0079] Example 3 : Determination of inhibitory activity against human lung cancer cell line (PG)

[0080] Using the MTT method, human lung cancer cell line (PG) was used as the target cell, and the cell culture medium was 1640 medium containing 10% BCS. After the logarithmic growth phase cells were digested with trypsin, the cell density was adjusted to 3-5×10 3 per well, seeded in a 96-well culture plate, 100 μl per well, placed in a temperature of 37 ° C, CO 2 Incubate for 24 hours in an incubator with a content of 0.5%. Add 50 μl / well of the prepared samples with different concentrations to the 96-well culture plate. The positive control drug Zidovudine (AZT) with different dilution concentrations is used as the positive control, and the temperature is 37 ° C, CO 2 Continue culturing for 48 hours in an incubator with a content of 0.5%. Take out the 96-well culture plate, add 20 μl of 5 mg / mL MTT to each well, and continue culturing for 4 hours. Take out the culture plate...

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Abstract

The invention discloses a group of galactosyl thioureas heterocyclic compounds, a preparation method and biological activity thereof. The compounds are indicated by the following general formula. A B in the general formula is defined by an instruction book. The invention introduces a method for synthesizing the galactosyl thioureas heterocyclic compounds through six steps, which takes full acetic acid esterified galactosyl, bromine water, lead rhodanide, heterocyclic base, ethyl chloroacetate and hydrazine hydrate as raw materials, takes glacial acetic acid, trifluoroacetic acid, xylene, toluene, ethyl benzene, N,N- dimethyl formamide, dimethyl sulfoxide, dioxane, pyridine, methanol, ethanol, isopropyl alcohol, absolute methanol and absolute ethyl alcohol as solvents, and takes sodium hydride, anhydrous potassium carbonate and sodium methoxide as basic catalysts. The compounds have inhibiting effects on human body lung cancer cell strains and liver cancer cell strains.

Description

Technical field: [0001] The present invention relates to a group of galactosylthiourea heterocyclic compounds; the present invention also relates to the synthesis method of all the compounds and their application in antitumor. Background technique: [0002] Sugar compounds have long been known as energy storage carriers in organisms. With the in-depth development of molecular biology and cell biology, other biological functions of sugar have gradually been revealed. As an information molecule, it recognizes many plays an important role in processes such as bacterial and viral infection of organisms, signal transduction, etc. [Cleophax, J.; Olesker.A.; Rolland, A.; Gero, S.D. Tetrahedron 1977, 33, 1303.], the study of sugars has become a hot area [(a) Spedaliere, C.J.; Ginter, J.M.; Johnston, M.V.; Mueller, E.G.Am.Chem.Soc. 2004, 126, 12758. (b) Chayajarus, K.; Chambers, D.J.; Chughtai, M.J.; Fairbanks, A.J.Org.Lett.2004, 3797. (c) Xu, R.; Hanson.S.R.; Zhang, Z.W.; 15654.(d...

Claims

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Application Information

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IPC IPC(8): C07H13/12A61K31/7052A61P35/00
Inventor 张书圣詹天荣杨波程坤夏有凤
Owner QINGDAO UNIV OF SCI & TECH
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