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Fatty acid synthase inhibitors

A technology of compounds and complexes, which can be used in the fields of active ingredients of heterocyclic compounds, drug combinations, organic chemistry, etc., and can solve the problem of inactivity of new antibiotics

Inactive Publication Date: 2002-09-18
SMITHKLINE BECKMAN CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no antibiotics on the market that target anti-fatty acid biosynthesis, therefore, it is not possible to justify the inactivity of new antibiotics of this type by a known mechanism of antibiotic blockade

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Preparation of E-2'-[4-(2,6-dichlorobenzyloxy)benzyl]-3,4-methylenedioxycinnamic acid a) 4-(2,6-dichlorobenzyloxy) ) Benzaldehyde

[0039] At 0°C, add 60% hydrogenation solution to 4-hydroxybenzaldehyde (3.59g, 24.39mmol) and 2,6-dichlorobenzyl bromide (7.05g, 29.39mmol) in dimethylformamide (20ml). Sodium (1.176 g, 29.39 mmol). After stirring at room temperature for 16 hours, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with aqueous NaCl and dried (MgSO 4 ). Purification by flash column chromatography (silica gel, hexane / ethyl acetate) afforded the title compound as an off-white solid (7.38 g, 89%). b) Diethyl[4-(2,6-dichlorobenzyloxy)benzylidene]malonate

[0040] To a solution of 4-(2,6-dichlorobenzyloxy)benzaldehyde (5.62 g, 20 mmol) and diethyl malonate (3.52 g, 22 mmol) in benzene (75 mL) was added piperidine (90 L) and ice Acetic acid (0.25 mL). After reflux for 24 hours while removing the azeotropic wat...

Embodiment 2

[0046] Preparation of E-2'-[3,5-dichloro-4-(2,6-dichlorobenzyloxy)benzyl]-3,4-methylenedioxycinnamic acid a) Loaded on Wang resin Diethylphosphonoacetate

[0047] To a suspension of Wang resin (10 g, 17 mmol) in dichloromethane (100 mL) was added 4-dimethylaminopropylpyridine (0.25 g, 2.14 mmol) and diethylphosphono under stirring and argon sparging. Acetic acid (16.67 g, 85 mmol). The mixture was cooled to 0 °C, then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (16.29 g, 85 mmol) was added, and the suspension was warmed to room temperature, and Mix under argon sparge for 18 hours. The solution of reactants was drained and washed with dichloromethane (2X), DMF (1X), 1:1 DMF / water (2X), water (1X), 1:1 DMF / water (1X), DMF (2X ) and methanol (3X) to afford the title compound. b) 2′-diethylphosphono-3,4-methylenedioxycinnamate supported on Wang resin

[0048] To a suspension of diethylphosphonoacetate (3.0 g, 3.9 mmol) and piperonal (8.78 g, 58.5 mmol) in benzene (50 mL) on...

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PUM

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Abstract

The present invention relates to the use of compounds as inhibitors of fatty acid synthase FabH.

Description

field of invention [0001] The present invention relates to the use of compounds as inhibitors of fatty acid synthase FabH. Background of the invention [0002] The biosynthetic pathway of saturated fatty acids is particularly similar to that of prokaryotes and eukaryotes. But while the chemical reactions cannot vary, the structures of biosynthesizers can be quite different. Vertebrate and yeast have type I fatty acid synthases (FASs), in which the entire enzymatic activity is encoded on one or two polypeptide chains, respectively. Acyl carrier protein (ACP) is a major part of this complex. In contrast, in most bacterial and plant FSSs (type II), each reaction is catalyzed by distinct monofunctional enzymes, and ACP is an isolated protein. Mycobacteria are unique in that they possess both type I and type II FASs; the former involved in the biosynthesis of essential fatty acids and the latter in the synthesis of complex cell envelope lipids such as my...

Claims

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Application Information

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IPC IPC(8): A61K31/36A61P31/04A61P43/00C07D317/60
CPCA61K31/36C07D317/60A61P31/04A61P43/00
Inventor 迪米特里·盖塔诺波洛斯杰克·D·莱伯李玫约瑟夫·温斯托克
Owner SMITHKLINE BECKMAN CORP
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