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Application of 4-1H-1,2,3-triazole-beta-lactam derivative

A technology of lactam and derivatives, applied in the field of 4-1H-1

Inactive Publication Date: 2012-07-18
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are not many existing drugs, and more and more effective chemotherapy drugs need to be discovered and studied to meet clinical needs.

Method used

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  • Application of 4-1H-1,2,3-triazole-beta-lactam derivative
  • Application of 4-1H-1,2,3-triazole-beta-lactam derivative
  • Application of 4-1H-1,2,3-triazole-beta-lactam derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 (1'R, 3R, 4R)-4-(4-(2'-bromophenyl)-1 hydrogen-1,2,3-triazol-1-yl)-3-(1'- Preparation of tert-butyldimethylsilyloxy)ethyl-azetidin-2-one (I-1)

[0024]

[0025] This example relates to the general synthesis method of a class of 4-position-1H-1,2,3-triazole-β-lactam derivatives with cytotoxic activity as shown in formula (I), wherein R1 is t-Butyldimethylsilyl (TBDMS). Specifically related to (1'R,3R,4R)-4-(4-(2'-bromophenyl)-1hydro-1,2,3-triazol-1-yl)-3-(1'-tert Preparation of butyldimethylsilyloxy)ethyl-azetidin-2-one (I-1). Add (1'R,3R,4R)-4-acetoxy-3-(1'-tert-butyldimethylsilyloxy)ethyl-azetidin-2-one (0.8610 g, 3mmol), sodium azide (0.2925g, 4.5mmol), CuI (0.0573g, 0.1mmol), o-bromophenylacetylene (0.5973g, 3.3mmol) and 10mL acetonitrile, stirred, heated to 70°C for reaction, reaction After about 12 hours, the heating was stopped, and the reaction solution was cooled to room temperature. The reaction solution was concentrated and filtered, and the ...

Embodiment 2

[0026] Example 2 Preparation of Compound I-2: Using 4-fluorophenylacetylene as a raw material, the reaction operation was the same as in Example 1, and the crude product was purified by column chromatography (petroleum ether: ethyl acetate=2: 1) to obtain a white solid; Mp 147.8 -149.0℃; IR(KBr): 3431, 3208, 2955, 2930, 1770, 1742, 1497, 1232, 839cm -1 ; 1 H NMR (400MHz, CDCl 3 ): δ8.05(1H, s), 7.79-7.75(2H, m), 7.17(1H, br s, -NH), 7.12-7.08(2H, m), 6.32(1H, s, 4-H) , 4.34(1H, m), 3.54(1H, m, 3-H), 1.27(3H, d, J=6.4Hz), 0.89(9H, s), 0.11, 0.10(total 6H, each s); 13 C NMR (100MHz, CDCl 3 ): δ166.5, 164.0, 161.5, 147.7, 127.5, 127.4, 126.1, 126.0, 116.8, 116.0, 115.8, 77.3, 77.0, 76.6, 68.4, 64.0, 63.1, 25.6, 22.1, 17.8, -4.4, -5.2; MS (ESI): 412.9 [M+Na + ], 390.9[M+H + ].

Embodiment 3

[0027] The preparation of embodiment 3 compound I-3: take 4-bromophenylacetylene as raw material, reaction operation is the same as embodiment 1, crude product column chromatography (petroleum ether: ethyl acetate=4: 1) purifies and obtains white solid; Mp 165.5 -166.5℃; IR(KBr): 3211, 2958, 2930, 1773, 1743, 829cm -1 ; 1 H NMR (400MHz, CDCl 3 ): δ8.05(1H, s), 7.74-7.71(2H, m), 7.60-7.57(2H, m), 6.58(1H, br s, -NH), 6.32(1H, d, J=0.8Hz , 4-H), 4.39(1H, m), 3.54(1H, t, J=2.4Hz, 3-H), 1.30(3H, d, J=6.4Hz), 0.92(9H, s), 0.14, 0.13 (total 6H, each s); 13 C NMR (125MHz, CDCl 3 ): δ166.5, 147.9, 132.4, 129.2, 127.5, 122.8, 117.3, 77.5, 77.3, 77.0, 68.9, 64.3, 63.4, 25.9, 22.4, 18.2, -4.0, -4.9; MS (ESI): 452.0 [M +H + ].

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Abstract

The invention discloses the application of a 4-1H-1,2,3-triazole-beta-lactam derivative. The 4-1H-1,2,3-triazole-beta-lactam derivative is used for preparing a medicine for resisting human brain glioma and colon cancer. The 4-1H-1,2,3-triazole-beta-lactam derivative has better biological activity, and is proved to have stronger propagation inhibitory activity for the human brain glioma (U87mG) and colon cancer tumor (LS-174T) cells by in vitro activity test. Therefore, the 4-1H-1,2,3-triazole-beta-lactam derivative is a potential antitumor drug, and has the application of preparing antitumor pharmaceutical preparation.

Description

technical field [0001] The invention relates to the use of a 4-position-1H-1,2,3-triazole-β-lactam derivative, and the effect of the compound on human glioma (U87mG) and colon cancer (LS-174T) tumors Cytotoxic activity of cells. Such compounds are found to have certain biological activity of inhibiting the growth of the tumor cells, and have potential application as antitumor drugs. Background technique [0002] Cancer is a serious threat to human life and health, and is one of the diseases with the highest mortality rate. Anticancer drugs have always been a hot area of ​​drug research and development. Due to the complexity and particularity of the mechanism of cancer, finding anticancer drugs with high selectivity, high efficiency and low side effects is a very challenging topic in life sciences and requires scientific research. The joint exploration and long-term efforts of the authors. [0003] Glioma is the most common primary intracranial tumor. It is an infiltrating...

Claims

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Application Information

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IPC IPC(8): A61K31/695A61K31/4192A61P35/00
Inventor 雷鸣张宏陈小微
Owner ZHEJIANG UNIV
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