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Sugar bis-aryl triazole compounds with antimicrobial activity, and synthesis method and medicinal use thereof

A technology of bisaryltriazoles and bisaryltriazoles, which is applied in the field of synthesis of sugar bisaryltriazoles, can solve the problems of low bioavailability and high liver toxicity, and achieve significant antibacterial activity Effect

Inactive Publication Date: 2011-06-08
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the wide application of such drugs, drug-resistant strains continue to emerge, and some drugs still have disadvantages such as high hepatotoxicity and low bioavailability.

Method used

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  • Sugar bis-aryl triazole compounds with antimicrobial activity, and synthesis method and medicinal use thereof
  • Sugar bis-aryl triazole compounds with antimicrobial activity, and synthesis method and medicinal use thereof
  • Sugar bis-aryl triazole compounds with antimicrobial activity, and synthesis method and medicinal use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Methyl 2,3-O-bis{1-[N-(4-methylphenyl)triazolyl]-methylene}-4,6-oxo-benzylidene-α- Preparation of D-glucopyranoside (compound 1 for short):

[0032]

[0033] In a 50mL round-bottomed flask, add 10mL DMSO, 5mL water, sugar diacetylenide (500mg, 1.40mmol), p-tolyl azide (372mg, 2.80mmol), sodium ascorbate (55mg, 0.28mmol), and add it under stirring at room temperature. CuSO 4 ·5H 2 O (35mg, 0.14mmol), the system turned into light yellow, thin-layer chromatography (developing solvent: ethyl acetate / petroleum ether, 5 / 1, V / V) tracked until the end of the reaction, the reaction system was diluted with 20mL of water, ethyl acetate Ester extraction (3×10 mL), combined ethyl acetate layers, washed with saturated brine, dried, concentrated under reduced pressure, silica gel column chromatography (eluent: ethyl acetate / petroleum ether, 5 / 1, V / V), 850 mg of khaki solid was obtained, that is, compound 1, yield: 97.4%, melting point: 106.5-107.2°C. (c 0.5, CHCl 3...

Embodiment 2

[0034] Example 2: Methyl 2,3-O-bis{1-[N-(4-methoxyphenyl)triazolyl]-methylene}-4,6-oxo-benzylidene-α - Preparation of D-glucopyranoside (abbreviated as compound 2):

[0035]

[0036] According to the synthesis method of Example 1, the reaction materials are (500mg, 1.40mmol) sugar diacetylenide, (416mg, 2.80mmol) p-methoxyphenyl azide, (55mg, 0.28mmol) sodium ascorbate, (35mg, 0.14 mmol) copper sulfate pentahydrate to obtain 844 mg of syrupy compound, ie compound 2, yield: 92.1%. (c0.5, CHCl 3 ); 1 H NMR (300MHz, CDCl 3 , J in Hz) δ: 8.26 (s, 1H, triazole H), 8.00 (s, 1H, triazole H), 7.65 (d, 2H, J=8.8, Ar H), w.49 (s, 1H, Ar H ), 7.47(s, 1H, Ar H), 7.4=(s, 1H, Ar H), 7.37(d, 3H, J=2.6, Ph 2-H, 4-H, 6-H), 7.0(d , 2H, J (=2.6, Ph 3-H, 5-H), 6.95 (s, 1H, Ar H), 6.90 (d, 1H, Ar H), 5.57 (s, 1H, Ph-CH), 5.16 ~5.04(m, 2H, OCH 2 ), 4.99 (s, 2H, OCH 2 ), 4.93 (d, 1H, J=3.3, 1-H), 4.10 (dd, 1H, 3 J 6eq，5 = 4.2, 2 J 6eq，6ax =9.7,6-H eq ), 4.05(t, 3 J 4，3 =9.3, 3 J ...

Embodiment 3

[0037] Example 3: Methyl 2,3-O-bis{1-[N-(3-chlorophenyl)triazolyl]-methylene}-4,6-oxo-benzylidene-α-D -Preparation of glucopyranoside (compound 3 for short):

[0038]

[0039] According to the synthesis method of Example 1, the reaction materials are (500mg, 1.40mmol) sugar diykyne compound, (427mg, 2.80mmol) m-chlorophenyl azide, (55mg, 0.28mmol) sodium ascorbate, (35mg, 0.14mmol) Copper sulfate pentahydrate, to obtain 927mg of light yellow solid, that is, compound 3, yield: 86.1%, melting point: 76.5-77.8°C. (c0.5, CHCl 3 ); 1 H NMR (300MHz, CDCl 3 , Jin Hz) δ: 8.38 (s, 1H, triazole H), 8.08 (s, 1H, triazole H), 7.86 (s, 1H, Cl-Ph 2-H), 7.73 (s, 1H, Cl-Ph 2 -H), 7.68(d, 1H, Cl-Ph 4-H), 7.59(t, 3H, 3 J=6.2, Cl-Ph 4-H, 5-H), 7.45~7.37 (m, 7H, Cl-Ph 6-H, Ph 2-H, 3-H, 4-H, 5-H, 6- H), 5.57(s, 1H, Ph-CH), 5.13~5.02(m, 2H, OCH 2 ), 4.98 (s, 2H, OCH 2 ), 4.93(d, 1H, 3 J 1，2 =2.9,1-H), 4.31(dd, 3 J 6eq，5 = 4.3, 2 J 6eq，6ax =9.8,6-H eq ), 4.05(t, 3 J 4，3 =9.2, ...

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Abstract

The invention relates to sugar bis-aryl triazole compounds with antimicrobial activity, and a synthesis method and medicinal use thereof. The invention relates to a synthesis method for the sugar bis-aryl triazole compounds, which comprises the following steps of: performing click reaction of 4,6-O-benzal-2,3-dioxo-propargyl-alpha-D-glucopyranoside serving as a raw material and a series of self-made organic azides to obtain benzylidene protected sugar bis-aryl triazole compounds; and performing deprotection and neutralization by using diluted hydrochloric acid to obtain the sugar bis-aryl triazole compounds and salts thereof. The invention also relates to the medicinal use of the sugar bis-aryl triazole compounds.

Description

technical field [0001] The invention relates to a synthesis method and medical application of sugar bisaryl triazole compounds with antimicrobial activity. Background technique [0002] Triazole compounds have become one of the most widely used antifungal drugs. At present, there are many 1,2,4-triazole antimicrobial drugs used in clinical practice, such as: terconazole (terconazole), itraconazole (itraconazole), fluconazole (fluconazole), fosfluconazole (fosfluconazole), voriconazole (voliconazole) and posaconazole (posaconazole), etc. However, with the widespread use of such drugs, drug-resistant strains have emerged continuously, and some drugs still have disadvantages such as high hepatotoxicity and low bioavailability. Therefore, there is an urgent need to develop antimicrobial drugs with novel structures, better efficacy, lower toxicity, and broad antibacterial spectrum. With the proposal of "click chemistry", 1,2,3-triazole, as the isostere of 1,2,4-triazole, has at...

Claims

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Application Information

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IPC IPC(8): C07H15/26A61K31/7056A61P31/04A61P31/10
Inventor 周成合魏金建
Owner SOUTHWEST UNIVERSITY