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Sulphonylpyrroles as HDAC inhibitors

A kind of technology of alkyl group and phenyl group, applied in the field of N-sulfonylpyrrole derivatives

Active Publication Date: 2012-12-19
4SC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To date, it is unclear whether targeting HDAC class I or II is specific, or superior in therapeutic effect and index for a single defined isoenzyme phase

Method used

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  • Sulphonylpyrroles as HDAC inhibitors
  • Sulphonylpyrroles as HDAC inhibitors
  • Sulphonylpyrroles as HDAC inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0672] final product

[0673] 1. (E)-N-Hydroxy-3-[1-(toluene-4-sulfonyl)-1-H-pyrrol-3-yl]-acrylamide

[0674] 0.231 g of (E)-3-[1-(toluene-4-sulfonyl)-1-H-pyrrol-3-yl]-acrylic acid (compound A1) was dissolved in 8 ml of dichloromethane at room temperature. After adding 50 μl of N,N-dimethylformamide (DMF), 0.275 g of oxalyl chloride dissolved in 2 ml of dichloromethane was added dropwise, and stirred for 1.5 hours. To the solution was added 0.439 g of O-(trimethylsilyl)hydroxylamine and stirred for 15 hours. Then 20 ml of aqueous hydrochloric acid (strength 1M) were added and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate. It was then filtered and evaporated in vacuo. The crude product was purified by silica gel chromatography (gradient: ethyl acetate:methanol 98:2 to 6:4) to afford 0.050 g of the title compound as a white solid.

[0675] MS(TSP): 307.0(MH + , 100%)

[0676] 1 H-NMR (DMSO-d6): 1 H-NMR (DMSO-d6): 2.37(s, 3H); ...

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Abstract

Compounds of a certain formula I, which R1, R2, R3, R4, R5, R6 and R7 have the meanings indicated in the description, are novel effective HDAC inhibitors.

Description

[0001] invention application field [0002] The present invention relates to novel N-sulfonylpyrrole derivatives for use in the pharmaceutical industry for the production of pharmaceutical compositions. current technology [0003] Transcriptional regulation in cells is a complex biological process. A rationale is through post-translational modification of histone proteins, the histones H2A / B, H3 and H4 that form the octameric histone core complex. Modification of the N-terminus of this complex by acetylation or methylation on lysine residues and on serine residues by phosphorylation constitutes the so-called "histone code" (Strahl & Ellis, Nature 403, 41 -45, 2000). In a simple model, acetylation of positively charged lysine residues reduces the affinity for negatively charged DNA such that the negatively charged DNA becomes accessible to transcription factors. [0004] Acetylation and deacetylation of histones are catalyzed by histone acetyltransferases (HATs) and histone ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/48A61K31/40A61K31/4025C07D403/12C07D401/12C07D409/12
CPCC07D401/12C07D403/12C07D409/12C07D207/48C07D409/14C07D413/12A61K31/40A61P1/04A61P11/00A61P11/02A61P11/06A61P13/08A61P15/00A61P17/00A61P17/06A61P19/02A61P19/06A61P25/00A61P25/16A61P25/28A61P29/00A61P31/18A61P35/00A61P35/02A61P35/04A61P37/00A61P37/04A61P37/08A61P43/00A61P9/00A61P9/04A61P9/10A61P9/14A61K31/4025
Inventor T·迈尔T·贝克尔斯T·贝尔P·吉姆尼希F·杜尔韦伯M·文内曼
Owner 4SC