- Discovery of dronedarone and its analogues as NLRP3 inflammasome inhibitors with potent anti-inflammation activity
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Inhibiting NLRP3 inflammasome activation is a prospective therapeutic strategy for uncontrolled inflammatory diseases. It is the first time that dronedarone, a multiply ion channel blocker, was identified as a NLRP3-inflammasome inhibitor with an IC50 value of 6.84 μM against IL-1β release. A series of novel 5-amide benzofuran derivatives were designed and synthesized as NLRP3-inflammasome inhibitors. Compound 8c showed slightly increased activity (IC50 = 3.85 μM) against IL-1β release. Notably, treatment with 8c could significantly inhibit NLRP3-mediated IL-1β release and ameliorate peritoneal inflammation in a mouse model of sepsis. Collectively, 8c is a promising lead compound for further chemical development as a NLRP3 inhibitor with anti-inflammation effects.
- Chen, Hao,Chen, Xiuhui,Sun, Ping,Wu, Dan,Yue, Hu,Pan, Jintao,Li, Xinxuan,Zhang, Cheng,Wu, Xinyi,Hua, Lei,Hu, Wenhui,Yang, Zhongjin
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supporting information
(2021/06/18)
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- Benzofuran compound and application thereof
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The invention provides a benzofuran compound as shown in a formula (I) or pharmaceutically acceptable salt thereof, and application thereof. The compound can selectively inhibit activation of NLRP3 inflammasomes and inhibit maturation and secretion of inflammation activation signal molecules Caspase-1 and P20 and inflammatory cytokines IL-1beta, has a good prevention and treatment effect on NLRP3 inflammasome related diseases, and particularly has a remarkable prevention and treatment effect on peritonitis and gouty arthritis. Therefore, the compound can be used for preparing drugs for treating NLRP3 inflammasome-related diseases, such as anti-inflammatory drugs or auxiliary anti-inflammatory drugs.
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Paragraph 0053-0055; 0059-0061
(2021/08/06)
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- Preparation method of key intermediate of dronedarone
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The invention relates to a preparation method of a key intermediate of drug dronedarone for treating atrial fibrillation, and specifically relates to the 2-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran. According to the method provided by the invention, a series of reactions are performed by using inexpensive p-nitrophenol as a starting material to prepare the 2-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran, the process is smooth, the costs are lower, the yield is higher, the controllability is stronger, and the method is suitable for industrial production.
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Paragraph 0021; 0022
(2019/10/02)
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- Microwave-assisted synthesis of (2-butyl-5-nitrobenzo[b]furan-3-yl)-[4-(substituted ethynyl)phenyl]methanones
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We report a new method for the efficient and rapid synthesis of (2-butyl-5-nitrobenzo[b]furan-3-yl)[4- (substituted ethynyl)phenyl]methanones using a Pd-Cu catalyzed microwave-assisted Sonogashira coupling reaction. In comparison to the conventional heating procedure, the time of synthesis and effort are significantly reduced in the present method, without side-product formation. Microwave irradiation considerably accelerated the formation of (2-butyl-5-nitrobenzo[b]furan-3-yl)[4-(substituted ethynyl)phenyl]methanone analogues.
- Parmar, Nilesh D.,Hadiyal, Sanjay D.,Kapupara, Vimal H.,Joshi, Hitendra S.
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p. 143 - 153
(2018/10/26)
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- An alternative approach to synthesis of 2-n-butyl-5-nitrobenzofuran derivative: A key starting material for dronedarone hydrochloride
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A practical synthesis of (2-butyl-5-nitrobenzofuran-3-yl)(4-hydroxyphenyl) methanone, a key intermediate in the preparation of anti arrhythmic drug, is described. The commercially available 4-nitrophenol (3) is converted in five steps to 2-butyl-5-nitrobenzofuran (9) which upon Friedel-Crafts acylation with 4-methoxybenzoyl chloride followed by deprotection of methyl group gives (2). Indian Academy of Sciences.
- Gopal, P. Raja,Chandrashekar,Saravanan,Bhaskar, B. Vijaya,Somaiah, P. Veera
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p. 1077 - 1085
(2013/03/13)
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- METHOD FOR PREPARING 2-(n-BUTYL)-5-NITROBENZOFURAN
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A method for preparing 2-(n-butyl)-5-nitrobenzofuran from 1-halo-4-nitrobenzene, characterized in that 1-hexen-3-ol is reacted, and then the product is subject to a Claisen rearrangement, followed by catalytic intramolecular cyclization.
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Page/Page column 3
(2011/02/15)
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- 5-Nitrobenzofurans
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The present invention relates to 5-nitrobenzofurans, to a process for preparing 5-nitrobenzofurans, and to 5-nitro-2,3-dihydrobenzofuran-3-ols, to a process for the preparation thereof and to intermediates.
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- Synthesis of 2-alkyl-5-nitrobenzofurans via 2-(2-formyl-4-nitrophenoxy) alkanoic acids
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An efficient synthesis of 2-alkyl-5-nitrobenzofurans from 5-nitrosalicylaldehyde and 2-bromoesters via 2-(2-formyl-4-nitrophenoxy)alkanoic acids is described.
- Kwiecien
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p. 1865 - 1869
(2007/10/03)
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- Method of preparing a benzofuran or benzothiophene compound
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The invention concerns a novel method for preparing a benzofuran or benzothiophene compound by cyclizing an aromatic compound bearing a side-chain comprising at least two carbon atoms, one of the carbon atoms being bound to the benzene cycle by an oxygen or sulphur atom, the other carbon atom is in carboxylic form and a formyl radical in ortho position relative to said chain. The inventive method is characterised in that it consists in cyclizing the latter in the presence of an efficient amount of a carbonate base in a medium comprising a carboxylic acid anhydride and optionally an organic solvent.
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- 3-(1-hydroxy-pentylidene)-5-nitro-3H-benzofuran-2-one a process for the preparation thereof and the use thereof
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A product corresponding to formula (I) or its ketonic tautomer form (II) which is 3-(1-hydroxy-pentylidene)-5-nitro-3H-benzofuran-2-one, a process for the preparation and use of the product corresponding to formula (I) or its tautomeric form (II), a proce
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- 3-benzoyl benzofuran derivatives as thyroid hormone antagonists
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The invention provides compounds according to the formula STR1 in which: Ha=I or BrX=CH 2 or C=OR 1 =C 1-4 alkylR 2 =--NHSO 2 R 3 ;--NHCOR 3 ; or--NHCONHR 3where R 3 =--CF 3,C 1-3 alkyl, 4-R 4 C 6 H 4 --;where R 4 =C 1-4 alkoxy-; hydroxy-; fluoro-; or nitro-;or a pharmaceutically acceptable salt thereof.The compounds may particularly be used in the treatment of T3 regulated gene disorders and diseases.
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- Alkylaminoalkyl derivatives of benzofuran, benzothiophene, indole and indolizine, process for their preparation and compositions containing them
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The subject of the invention is benzofuran, benzothiophene, indole or indolizine compounds of general formula: STR1 in which: Het represents one of the groups: STR2 in which T,T' and T"represent particularly a group: STR3 R and Ra, identical or different, represent X represent --O-- or --S-- Y represents a radical STR4 These compounds are useful as medecines particularly for the treatment of pathological syndroms of the cardio-vascular system.
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