- A Hg(OTf)2-Catalyzed Enolate Umpolung Reaction Enables the Synthesis of Coumaran-3-ones and Indolin-3-ones
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The potential of mercury catalysis has been extended to the arena of enolate umpolung reactions for the first time by the generation of enolonium species via Hg(OTf)2-catalyzed N-oxide addition to alkynes. The enolonium species formed can undergo intramolecular nucleophilic attack by hydroxyl or amino groups, leading to the synthesis of various coumaran-3-ones and indolin-3-ones.
- Dai, Ning,Hu, Weican,Qian, Guoying,Rong, Zhouting
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p. 3286 - 3290
(2020/04/21)
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- Catalytic synthesis method of 3-benzofuranone compound
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The invention discloses a catalytic synthesis method of a 3-benzofuranone compound. The catalytic synthesis method comprises the following steps: dissolving a 2-acetenyl phenol derivative into a solvent dichloromethane at normal temperature and normal pressure according to a molar volume ratio of the 2-acetenyl phenol derivative to the dichloromethane of 1:5mmol/mL, so as to obtain a dichloromethane solution of the 2-acetenyl phenol derivative; then adding mercury trifluoromethanesulfonate and pyridine-N-oxide into a dichloromethane solution of the 2-ethynylphenol derivative, wherein the molaramounts of mercury trifluoromethanesulfonate and pyridine-N-oxide are respectively 5% and 120% of the molar amount of the 2-ethynylphenol derivative; and then performing stirring for 1 hour at room temperature, and performing reacting to generate the 3-benzofuranone compound. The market price of the catalyst mercury trifluoromethanesulfonate used in the catalytic synthesis method is lower than 30yuan/g, the cost is low, the operation is simple, the reaction time is short, the reaction conditions are mild, the reaction yield is high, and the yield can reach 91.0-96.0%.
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Paragraph 0020; 0021
(2020/05/14)
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- Discovery of benzofuran-3(2H)-one derivatives as novel DRAK2 inhibitors that protect islet β-cells from apoptosis
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Death-associated protein kinase-related apoptosis-inducing kinase-2 (DRAK2) is a serine/threonine kinase that plays a key role in a wide variety of cell death signaling pathways. Inhibition of DRAK2 was found to efficiently protect islet β-cells from apoptosis and hence DRAK2 inhibitors represent a promising therapeutic strategy for the treatment of diabetes. Only very few chemical entities targeting DRAK2 are currently known. We carried out a high throughput screening and identified compound 4 as a moderate DRAK2 inhibitor with an IC50value of 3.15?μM. Subsequent SAR studies of hit compound 4 led to the development of novel benzofuran-3(2H)-one series of DRAK2 inhibitors with improved potency and favorable selectivity profiles against 26 selected kinases. Importantly, most potent compounds 40 (IC50?=?0.33?μM) and 41 (IC50?=?0.25?μM) were found to protect islet β-cells from apoptosis in dose-dependent manners. These data support the notion that small molecule inhibitors of DRAK2 represents a promising strategy for the treatment of diabetes.
- Wang, Sheng,Xu, Lei,Lu, Yu-Ting,Liu, Yu-Fei,Han, Bing,Liu, Ting,Tang, Jie,Li, Jia,Wu, Jiangping,Li, Jing-Ya,Yu, Li-Fang,Yang, Fan
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p. 195 - 208
(2017/03/02)
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- Synthesis and structural characterization of 2-benzylidenebenzofuran-3-(2 H)-ones
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Novel aurone derivatives e.g. 2-(2-(3-methylbut-2-enyloxy)benzylidene) benzofuran-3(2H)-one (3a), 2-(2-(allyloxy)benzylidene)-7-methoxybenzofuran-3(2H) -one (3b), and 2-(5-bromo-2-(3-methylbut-2-enyloxy)benzylidene)-6- hydroxybenzofuran-3(2H)-one (3c) were synthesized. All these compounds were characterized by IR, 1H and 13C NMR, and Mass spectroscopy. Finally, the crystal structures were solved by single crystal X-ray diffraction data and the structures were analyzed in terms of supramolecular interactions. [Supplementary materials are available for this article. Go to the publisher's online edition of Molecular Crystals and Liquid Crystals for the following free supplemental resource(s): supplemental figures 1-12; Spectral data (IR, NMR, MS, and HRMS) of the compounds 3a, 3b and 3c are available in the supporting information in.pdf format. Crystallographic information files (.cif) of compounds 3a, 3b, and 3c are available in the electronic format.]
- Rambabu,Srinivas,Manjulatha, Khanapur,Basavoju, Srinivas,Basaveswara Rao,Pal, Manojit
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- Ethylenediamine diacetate (EDDA) mediated synthesis of aurones under ultrasound: Their evaluation as inhibitors of SIRT1
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An improved synthesis of functionalized aurones has been accomplished via the reaction of benzofuran-3(2H)-one with a range of benzaldehydes in the presence of a mild base EDDA under ultrasound. A number of aurones were synthesized (within 5-30 min) and the molecular structure of a representative compound determined by single crystal X-ray diffraction study confirmed Z-geometry of the C-C double bond present within the molecule. Some of the compounds synthesized have shown SIRT1 inhibiting as well as anti proliferative properties against two cancer cell lines in vitro. Compound 3a [(Z)-2-(5-bromo-2-hydroxybenzylidene) benzofuran-3(2H)-one] was identified as a potent inhibitor of SIRT1 (IC50 = 1 μM) which showed a dose dependent increase in the acetylation of p53 resulting in induction of apoptosis.
- Manjulatha, Khanapur,Srinivas,Mulakayala, Naveen,Rambabu,Prabhakar,Arunasree, Kalle M.,Alvala, Mallika,Basaveswara Rao,Pal, Manojit
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p. 6160 - 6165
(2012/10/30)
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- Structure-based design leads to the identification of lithium mimetics that block mania-like effects in rodents. Possible new GSK-3β therapies for bipolar disorders
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More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3β (GSK-3β) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3β inhibitors. The best ligand in this series (having a Ki value of 4.6 nM against GSK-3β) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3β inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.
- Kozikowski, Alan P.,Gaisina, Irina N.,Yuan, Hongbin,Petukhov, Pavel A.,Blond, Sylvie Y.,Fedolak, Allison,Caldarone, Barbara,McGonigle, Paul
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p. 8328 - 8332
(2008/02/09)
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- Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2 H)-benzofuranone derivatives
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A new series of (Z)-2-(1-methyl-5-nitroimidazole-2-ylmethylene)-3(2 H)-benzofuranones (11a-p) and (Z)-2-(1-methyl-4-nitroimidazole-5-ylmethylene)-3(2 H)-benzofuranones (12a-m) were synthesized and assayed for their antibacterial activity against Gram-positive and Gram-negative bacteria. Most of the 5-nitroimidazole analogues (11a-p) showed a remarkable inhibition of a wide spectrum of Gram-positive bacteria (Staphylococcus aureus, Streptococcus epidermidis, MRSA, and Bacillus subtilis) and Gram-negative Klebsiella pneumoniae, whereas 4-nitroimidazole analogues (12a-m) were not effective against selected bacteria. The quantitative structure-activity relationship investigations were applied to find out the correlation between the experimentally evaluated activities with various parameters of the compounds studied. The QSAR models built in this work had reasonable predictive power and could be explained by the observed trends in activities.
- Hadj-esfandiari, Narges,Navidpour, Latifeh,Shadnia, Hooman,Amini, Mohsen,Samadi, Nasrin,Faramarzi, Mohammad Ali,Shafiee, Abbas
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p. 6354 - 6363
(2008/09/21)
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- Palladium assisted substitution of 3-benzo[b]furan triflates
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Triflates of 3-coumaranones were prepared, and experimented as coupling partners in palladium catalyzed Stille, Heck, Suzuki, and Sonogashira coupling reactions. The corresponding 3-substituted benzo[b]furans were obtained in excellent yields.
- Morice, Christophe,Garrido, Fabrice,Mann, André,Suffert, Jean
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p. 501 - 503
(2007/10/03)
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- A practical preparation of 7-methoxy-3(2H)-benzofuranone
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A practical new synthesis suitable for large-scale production of 7-methoxy-3(2H)-benzofuranone by conversion of commercially available 2-hydroxy-3-methoxybenzoic acid to 7-methoxy-3-acetoxybenzofuran followed by hydrolysis is described.
- Bryant III,Huhn
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p. 915 - 920
(2007/10/02)
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