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Secnidazole derivative as well as preparation method and application thereof

A technology of secnidazole and derivatives, which is applied in the field of secnidazole derivatives and can solve problems such as unseen secnidazole and the like

Inactive Publication Date: 2011-09-14
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There is no related structure drug with both the antibacterial activity of secnidazole and the anti-inflammatory activity of salicylic acid drugs

Method used

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  • Secnidazole derivative as well as preparation method and application thereof
  • Secnidazole derivative as well as preparation method and application thereof
  • Secnidazole derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The preparation of embodiment 1 intermediate

[0025] (1) Preparation of methyl salicylate derivative II

[0026] Weigh salicylic acid derivative I (0.20mol) and add 160mL methanol, carefully add 18mL concentrated sulfuric acid dropwise under stirring, and heat to reflux for 15 hours. Stop heating, evaporate most of the methanol, and carefully add 20% Na 2 CO 3 Aqueous solution until no bubbles emerge, separate the organic layer, wash once with 50mL 20% sodium carbonate solution, wash twice with 50mL water, dry the organic layer with anhydrous sodium sulfate, filter, and evaporate the solvent under reduced pressure to obtain oily salicylic acid Methyl Esters Derivatives II.

[0027] (2) Preparation of Intermediate III

[0028] After dissolving methyl salicylate derivative II with 300mL acetone, add 40g (0.289mol) of anhydrous potassium carbonate, add 50mL epichlorohydrin under stirring, heat up, reflux for 30 hours, cool to room temperature, filter, evaporate Remov...

Embodiment 2

[0029] The secnidazole derivative of embodiment 2 general formula 1 and preparation method thereof

[0030] The secnidazole derivatives of the general formula 1 are 4-nitroimidazole analogues, which belong to esters and are called a series compounds. (1) Preparation of Compound 1a

[0031] Referring to Example 1, using salicylic acid as the starting material to prepare the corresponding methyl salicylate derivatives II and intermediate III; weigh 10g (0.079mol) 2-methyl-5-nitroimidazole, dissolve in Add 18g (0.130mol) of anhydrous potassium carbonate to 70mL of DMF, slowly add (0.158mol) intermediate III dropwise, after the addition is complete, heat up to 90°C, react for 7 hours, evaporate most of the DMF, add ethyl acetate to dissolve, wash with water Three times, the ethyl acetate layer was separated and dried overnight with anhydrous sodium sulfate, and the solvent was evaporated to obtain a solid, which was recrystallized with absolute ethanol to obtain 18.5 g of a white...

Embodiment 3

[0042] The secnidazole derivative of embodiment 3 general formula 2 and preparation method thereof

[0043] The secnidazole derivatives of the general formula 2 are hydrolyzed from a series of compounds, which belong to acids and are called b series compounds.

[0044] (1) Preparation of compound 1b

[0045] Take (0.005mol) compound 1a and dissolve it in 25mL ethanol, add 25mL 2mol / L NaOH solution, stir, react at room temperature for 5 hours, adjust the pH to 3 with 10% dilute hydrochloric acid solution, solid precipitates, filter, and crystallize with absolute ethanol to obtain 1.1 g of yellow solid, yield 65%. 1b: MS (ESI) m / Z: 322 (M+1) + , 1 H NMR (DMSO, 600MHz): δ2.39(s, 3H, -2'-CH 3 ), 3.93-4.11 (m, 2H, -NCH 2 -), 4.13-4.16 (m, 2H, -OCH 2 -), 4.33(dd, J=17.8, 6.8Hz, 1H, -CH(OH)-), 5.63(s, 1H, -OH), 7.04(t, J=7.7Hz, 1H, ArH-5), 7.17(d, J=8.2Hz, 1H, ArH-3), 7.51-7.54(m, J=8.2, 1.8Hz, 1H, ArH-4), 7.72(dd, J=7.7, 1.8Hz, 1H, ArH -6), 8.22 (s, 1H, imidazole CH-5'); 13...

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Abstract

The invention discloses a secnidazole derivative which is synthesized and prepared from a salicylic acid derivative I and 2-methyl5-nitroimidazole. The structure of the derivative is as shown in one of general formula 1-general formula 4, wherein R is hydrogen, 4-methoxy, 4-chloride, 5-chloride, 3-methyl, 4-methyl, 5-methyl, 6-methyl or 4-trifluoromethyl. The secnidazole derivative has a secnidazole structure and a salicylic acid medicament structure, and can exert antibiosis activity and anti-inflammatory activity. The invention also discloses a preparation method of the derivative and application of the preparation method in preparing antibiosis and anti-inflammatory medicaments.

Description

technical field [0001] The present invention relates to a secnidazole derivative, and also relates to a preparation method and application of the derivative in pharmacy. Background technique [0002] Nitroimidazole drugs are commonly used antiprotozoal and anaerobic bacteria drugs in clinical practice. They are mainly used to prevent and treat infections caused by protozoa and anaerobic bacteria, and have good curative effects on inflammation caused by various bacteria. Secnidazole is a representative drug of 5-nitroimidazoles developed in recent years. The role of flagellates and so on. Salicylic acid drugs are non-steroidal anti-inflammatory drugs, which can not only relieve fever and analgesia, but also have anti-inflammatory effects, and can reduce the symptoms of redness, swelling, heat and pain during the onset. [0003] There are no drugs with related structures that have both the antibacterial activity of secnidazole and the anti-inflammatory activity of salicylate...

Claims

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Application Information

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IPC IPC(8): C07D233/94A61K31/4164A61P31/04A61P29/00
Inventor 王立升殷勇黄喜寿冉炜李婉媚段曼周永红
Owner GUANGXI UNIV
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