1-substituted benzoyl-4-fatty acyl semicarbazide derivative, preparation method and application thereof as antibacterial agent

A technology of aliphatic acylsemicarbazides and propionyl thiosemicarbazides, which is applied in the field of preparation of 1-substituted benzoyl-4-fatty acylsemicarbazide derivatives, and can solve the problem of 1-aroyl-4-fatty acylaminosulfurides Urea derivatives have little research, weak activity, no antibacterial activity, etc.

Active Publication Date: 2018-08-28
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Judging from the literature, the derivatives with anti-drug-resistant bacteria activity in this type are limited to 1-fatty acyl-4-aroyl thiosemicarbazides and 1,4-diaroyl thiosemicarbazides, and their activity is relatively low. Weak, MIC value is higher than 10μg / ml, it is difficult to develop into a clinical drug with practical value
It is worth noting that there are few studies on 1-aroyl-4-fatty acylthiosemicarbazide derivatives, and there is no report of relevant antibacterial activity

Method used

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  • 1-substituted benzoyl-4-fatty acyl semicarbazide derivative, preparation method and application thereof as antibacterial agent
  • 1-substituted benzoyl-4-fatty acyl semicarbazide derivative, preparation method and application thereof as antibacterial agent
  • 1-substituted benzoyl-4-fatty acyl semicarbazide derivative, preparation method and application thereof as antibacterial agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] Embodiment 1: Preparation and detection of compound LP-1

[0109]

[0110]1.0g (6.5mmol) methyl 4-hydroxybenzoate and 2.7g (19.7mmol) potassium carbonate and 60mL acetone were added to a 100mL three-necked flask, heated to reflux at 60°C, and 1.3ml (9.8mmol) was added thereto After the reaction was completed, the reaction solution was removed under reduced pressure, and 300 mL of water was added to dissolve the product, extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried to obtain 1.4 g of methyl 4-pentyloxybenzoate (yield: 99%).

[0111] Add 0.7g (3.1mmol) of methyl 4-pentyloxybenzoate, 5mL of hydrazine hydrate (80%) and 30mL of methanol into a 100mL three-necked flask, heat to reflux at 70°C, and spin the reaction solution to obtain The white solid was washed with water three times and filtered to obtain 0.65 g of 4-pentyloxybenzoic hydrazide (yield: 93%).

[0112] ...

Embodiment 2

[0114] Embodiment 2: Preparation and detection of compound LP-2

[0115]

[0116] 1.0g (5.9mmol) methyl 2,4-dihydroxybenzoate, 2.7g (19.7mmol) potassium carbonate and 60mL acetone were added to a 100mL three-necked flask, heated to reflux at 60°C, and 1.8ml ( 14.5mmol) of 1-bromopentane, after the reaction was completed, the reaction solution was removed under reduced pressure, 300mL of water was added to dissolve the product, extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and spin-dried From the filtrate, 0.7 g of methyl 2-hydroxy-4-pentyloxybenzoate was obtained (yield: 49%).

[0117] Add 0.7g (2.9mmol) methyl 2-hydroxy-4-pentyloxybenzoate, 5mL hydrazine hydrate (80%) and 30mL methanol into a 100mL three-necked flask, heat to reflux at 70°C, spin dry after the reaction is complete In the reaction solution, a white solid was obtained. The white solid was washed three times with water and filtered to f...

Embodiment 3

[0120] Embodiment 3: Preparation and detection of compound LP-3

[0121]

[0122] 1.0g (5.9mmol) methyl 3,4-dihydroxybenzoate, 2.7g (19.7mmol) potassium carbonate and 60mL acetone were added to a 100mL three-necked flask, heated to reflux at 60°C, and 1.8ml ( 14.5mmol) of 1-bromopentane, after the reaction was completed, the reaction solution was removed under reduced pressure, 300mL of water was added to dissolve the product, extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and spin-dried From the filtrate, 0.7 g of methyl 3-hydroxy-4-pentyloxybenzoate was obtained (yield: 49%).

[0123] Add 0.7g (2.9mmol) methyl 3-hydroxy-4-pentyloxybenzoate, 5mL hydrazine hydrate (80%) and 30mL methanol into a 100mL three-necked flask, heat to reflux at 70°C, spin dry after the reaction is complete In the reaction solution, a white solid was obtained, which was washed three times with water and filtered to finally obt...

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PUM

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Abstract

The invention belongs to the technical field of antibacterial agents, and relates to a 1-substituted benzoyl-4-fatty acyl semicarbazide derivative, a preparation method and application thereof as an antibacterial agent. The compound is shown in a formula (I), wherein R1 is selected from hydrogen, hydroxyl, C1-C3 alkyls, C1-C8 alkoxyls, C3-C6 cycloalkyl oxyls, non-substitute or halogenated phenylsC1-C3 alkoxyls, phenyls, C1-C3 alkylbenzene, halogeno benzene, and the substitution site of R1 is selected from ortho-position or meta-position or para-position; R2 is selected from non-substitute orhalogenated C1-C8 alkyls, non-substitute or halogenated C3-C6 naphthenic bases and non-substitute or halogenated phenyl C1-C3 alkyls; X is selected from sulfur or oxygen. The 1-substituted benzoyl-4-fatty acyl semicarbazide derivative has the high inhibiting effect on drug-resistance bacteria including gram-positive bacteria, in particular to methicillin-resistant staphylococcus aureus (MRSA), methicillin-resistant staphylococcus epidermidis (MRSE) and vancomycin resistant enterococcus (VRE), and can be used for preparing novel drug resistance bacterium drugs. The formula is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of antibacterial drugs, and specifically relates to 1-substituted benzoyl-4-fatty acyl semicarbazide derivatives, a preparation method and their use as antibacterial drugs. Background technique [0002] Bacterial infection is an infection caused by pathogenic bacteria or conditional pathogenic bacteria invading the body to grow and reproduce, producing toxins and other metabolites. Bacterial infection is one of the main factors that endanger human health, and the emergence of bacterial drug resistance in recent years has made the challenge of global public health more severe. Among resistant Gram-positive bacteria, methicillin-resistant Staphylococcus aureus (MRSA), methicillin-resistant surface Staphylococcus (MRSE), and vancomycin-resistant enterococci (VRE) were the most common. The discovery of antibiotics with new structures and / or new mechanisms of action has important clinical significance for the pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C337/06A61K31/175A61P31/04
CPCA61P31/04C07C337/06C07C2601/02C07C2601/04C07C2601/08C07C2601/14
Inventor 吴松夏杰闻刚冯波贾雨晴张文轩杨庆云张驰戚燕
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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