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Methylacryloyl-benzimidazole (sulfur) ketone derivative and application of serving as antibacterial agent thereof

A technology of methacryloyl benzimidazole and benzoyl, which is applied in the field of antibacterial drugs and new methacryloyl benzimidazolone derivatives, which can solve the antibacterial activity of benzimidazolone derivatives. There are few reports And other issues

Inactive Publication Date: 2012-06-20
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] But it is worth noting that there are few reports on the antibacterial activity of benzimidazolone derivatives

Method used

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  • Methylacryloyl-benzimidazole (sulfur) ketone derivative and application of serving as antibacterial agent thereof
  • Methylacryloyl-benzimidazole (sulfur) ketone derivative and application of serving as antibacterial agent thereof
  • Methylacryloyl-benzimidazole (sulfur) ketone derivative and application of serving as antibacterial agent thereof

Examples

Experimental program
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preparation example Construction

[0152] The following specific preparation examples and biological examples help to understand the present invention, but do not limit the content of the present invention.

[0153] The following preparation examples 1-18 further illustrate the preparation method of the compound of general formula (I) and the preparation of the present application, but are not limited thereto.

Embodiment 1

[0155] Synthesis of 3-methacryloyl-1H-benzimidazol-2(3H)-one (compound number: IA-01)

[0156]

[0157] Add 1.08g (10mmol) of intermediate I-1, 0.72g (12mmol) of urea, and 10mL of xylene into a 50mL pear-shaped flask, heat to reflux for 4h, cool to room temperature, add ethyl acetate / water (volume ratio 2 / 1) 30 mL, stirred for 10 min, transferred to a separatory funnel for standing and layered, the aqueous phase was extracted once with 10 mL of ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 1.86 g of intermediate 1-II, Yield 92.1%;

[0158] Weigh 1.62g (8mmol) of dry intermediate 1-II, put 10mL of anhydrous pyridine in a 100mL pear-shaped flask, add 1.04g of methacryloyl chloride (10mmol, dissolved in 5mL of dichloromethane) dropwise under ice-cooling, add After completion, slowly rise to room temperature, continue to stir for 15 minutes, raise the temperature to 60° C. and continue the...

Embodiment 2

[0161] Synthesis of 3-methacryloyl-1H-benzimidazole-2(3H)-thione (compound number: Ia-01)

[0162]

[0163] Except that urea was replaced by thiourea, the rest of the reagents and synthesis steps were exactly the same as in Example 1 to obtain the title compound Ia-01 with a total yield of 52.6%.

[0164] Compound Ia-01: light yellow powder, melting point 163.5-165.2°C. Mass spectrometry (electrospray, negative ion mode) m / z217 (M-H) - . 1 H NMR (CDCl 3 , 500MHz, δ, ppm): 2.16(s, 3H, CH 3 ), 5.60 (s, 1H, C=CH 2 ), 5.63 (s, 1H, C=CH 2 ), 6.85(t, J=8.0Hz, 1H), 6.98(t, J=8.0Hz, 1H), 7.15(d, J=8.0Hz, 1H), 7.66(d, J=8.0Hz, 1H), 5.82(s, 1H, NH). 13 C NMR (CDCl 3 , 125MHz, δ, ppm): 19.6, 109.5, 111.6, 114.7, 122.8, 124.9, 125.7, 131.7, 140.4, 165.9, 172.3.

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Abstract

The invention discloses a novel methylacryloyl-benzimidazole (sulfur) ketone derivative, a preparation method for the compound and an application of the compound serving as an antibacterial agent. The compound has the structure shown in the following general formula (I) in the specification, wherein R and Y in the general formula (I) have meanings as shown in the specification.

Description

technical field [0001] The present invention relates to a new class of methacryloylbenzimidazole (thio) ketone derivatives, the preparation method of the compound, and the use of the compound as an antibacterial drug; especially, the use of the compound as an antibacterial and antifungal drug In particular, the bacteria are bacteria that cause human and animal infection, and the fungi are fungi that cause human and animal infection, or plant pathogenic fungi, and the present invention belongs to the field of medical technology and agricultural technology. Background technique [0002] Benzimidazolone is an oxidized derivative of the carbon atom at the 2-position of the imidazole ring, and is widely used as an intermediate in the dye industry (Jolanta S. et al. Dyes and pigments. 2001, 15-27). In addition, benzimidazolone derivatives also have obvious pharmacological activity, and are generally used as clinical drugs, such as the second-generation antihistamine Oxamide belong...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/26C07D235/28C07D403/04A61K31/4184A61P31/04A61P31/10A61P17/00
CPCY02A50/30
Inventor 姬志勤魏少鹏吴文君
Owner NORTHWEST A & F UNIV
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