- A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety
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A versatile and robust synthetic protocol for the preparation of β-diketones bearing 2-thienyl and perfluorinated alkyl radicals of different length or a methyl group was developed. This protocol is suitable for the preparation of multigram quantities of diketones without cumbersome purification procedures. Moreover, the known method for purification of diketones via copper chelates was improved considerably.
- Taydakov, Ilya V.,Kreshchenova, Yuliya M.,Dolotova, Ekaterina P.
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- Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors
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Based on a new pyrazole sulfonate synthetic method, a novel class of molecules with a basic structure of pyrazole N-aryl sulfonate have been designed and synthesized. The interest in conducting intensive research stems from quite evident anti-inflammatory effects exhibited by the compounds in preliminary animal experiments. A series of compounds were synthesized by different substitutions of the R1, R2, and R3 groups. Within the series, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and phenyl 5-methyl-3-(4-(trifluoromethyl) phenyl)-1H-pyrazole-1-sulfonate exhibited excellent anti-inflammatory activity (% inhibition of auricular edemas = 27.0 and 35.9, respectively); the in vivo analgesic activity of phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate was confirmed to be effective (inhibition ratio of writhing = 50.7% and 48.5% separately), and compounds phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate were identified as selective COX-2 inhibitors (SI = 455, 10,497 and >189 severally). In Acute Oral Toxicity assays conducted in vivo, the lethal dose 50 (LD50) of 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate to mice was >2000 mg/kg BW.
- Yao, Haiyan,Guo, Quanping,Wang, Mengran,Wang, Rui,Xu, Zhaoqing
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- Direct synthesis of 2,3,5-trisubstituted pyrroles: via copper-mediated one-pot multicomponent reaction
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We have developed a copper-mediated one-pot synthesis of 2,3,5-trisubstituted pyrroles from 1,3-dicarbonyl compounds and acrylates using ammonium acetate as a nitrogen source. The reaction achieves C-C and C-N bond formation and provides an efficient approach to access highly functionalized pyrroles without further raw material preparation. This method is operationally simple, compatible with a wide range of functional groups, and provides the target products in moderate to good yields. This journal is
- He, Jian-Ping,Huang, Guo-Sheng,Luo, Nan,Zhan, Zhen-Zhen,Zhang, Ming-Ming
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supporting information
p. 9831 - 9835
(2021/01/05)
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- Direct Access to Functionalized Indoles via Single Electron Oxidation Induced Coupling of Diarylamines with 1,3-Dicarbonyl Compounds
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Under aerobic copper catalysis, an unprecedented direct synthesis of functionalized indoles via single electron oxidation induced coupling of diarylamines with 1,3-dicarbonyl compounds is presented. The protocol proceeds with good functional group and substrate compatibility, the use of readily available feedstocks and naturally abundant catalyst system, high step and atom efficiency, as well as selectivity, which offers a platform for accessing a new class of indoles with the potential for the discovery of functional molecules.
- Liang, Taoyuan,Zhao, He,Gong, Lingzhen,Jiang, Huanfeng,Zhang, Min
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supporting information
p. 6736 - 6740
(2019/09/09)
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- Pyrrolecarboxylic acid derivative synthesis method
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The invention discloses a pyrrolecarboxylic acid derivative synthesis method, which comprises: obtaining a group substituted formylacetone derivative by using a group substituted acetyl derivative andethyl acetate as raw materials; carrying out cyclization with diethyl aminomalonate hydrochloride to generate a pyrrolecarboxylic acid derivative ethyl ester; and carrying out a hydrolysis reaction to obtain the target product pyrrolecarboxylic acid derivative. According to the present invention, the method has characteristics of mild reaction conditions, simple purification, high yield and highproduct purity, and is suitable for process amplification and mass production.
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Paragraph 0063; 0065-0067
(2019/11/04)
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- Determination of the enol form of asymmetric 1,3-dicarbonyl compounds: 2D HMBC NMR data and DFT calculations
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In this study, a series of asymmetric aryl 1,3-dicarbonyl compounds were synthesized and their enol forms were observed via experimental data and theoretical calculations. According to the 1H-and 13C-NMR results, all the investigated compounds were found
- Tan, Meltem,Bildirici, Ishak,Menges, Nurettin
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p. 953 - 968
(2018/10/02)
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- Discovery and structure-activity relationships study of thieno[2,3-b]pyridine analogues as hepatic gluconeogenesis inhibitors
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Type 2 diabetes mellitus (T2DM) is a chronic, complex and multifactorial metabolic disorder, and targeting gluconeogenesis inhibition is a promising strategy for anti-diabetic drug discovery. This study discovered a new class of thieno[2,3-b]pyridine derivatives as hepatic gluconeogenesis inhibitors. First, a hit compound (DMT: IC50 = 33.8 μM) characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. Structure activity relationships (SARs) study showed that replaced the CF3 in the thienopyridine core could improve the potency and led to the discovery of 8e (IC50 = 16.8 μM) and 9d (IC50 = 12.3 μM) with potent inhibition of hepatic glucose production and good drug-like properties. Furthermore, the mechanism of 8e for the inhibition of hepatic glucose production was also identified, which could be effective through the reductive expression of the mRNA transcription level of gluconeogenic genes, including glucose-6-phosphatase (G6Pase) and hepatic phosphoenolpyruvate carboxykinase (PEPCK). Additionally, 8e could also reduce the fasting blood glucose and improve the oral glucose tolerance and pyruvate tolerance in db/db mice. The optimization of this class of derivatives had provided us a start point to develop new anti-hepatic gluconeogenesis agents.
- Ma, Fei,Liu, Jian,Zhou, Tingting,Lei, Min,Chen, Jing,Wang, Xiachang,Zhang, Yinan,Shen, Xu,Hu, Lihong
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p. 307 - 317
(2018/05/22)
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- Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof
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The invention discloses a pyrazole compound containing N-aryl sulfonate. A structural formula of the pyrazole compound is shown in the description. Proofed by pharmacological study, the pyrazole compound has the advantages that the activity of cyclooxygenase 2 is inhibited; the high-efficiency inhibition function on the generation of cyclooxygenase 2 due to inflammation mediums is realized, so that the pyrazole compound can be used as an active matter, and the prepared anti-inflammation medicine can be used for treating the inflammations, such as rheumatic arthritis and rheumatalgia, and the diseases and symptoms, such as fevers.
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Paragraph 0025
(2018/07/10)
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- Rhodium(ii)-catalysed generation of cycloprop-1-en-1-yl ketones and their rearrangement to 5-aryl-2-siloxyfurans
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Donor-acceptor cyclopropenes formed from enoldiazoketones undergo catalytic rearrangement to 5-aryl-2-siloxyfurans via a novel mechanism that involves a nucleophilic addition of the carbonyl oxygen to the rhodium-activated cyclopropene.
- Marichev, Kostiantyn O.,Wang, Yi,Carranco, Alejandra M.,Garcia, Estevan C.,Yu, Zhi-Xiang,Doyle, Michael P.
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p. 9513 - 9516
(2018/08/28)
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- Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules
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A practical and general iron-catalyzed Wacker-type oxidation of olefins to ketones is presented, and it uses ambient air as the sole oxidant. The mild oxidation conditions enable exceptional functional-group tolerance, which has not been demonstrated for any other Wacker-type reaction to date. The inexpensive and nontoxic reagents [iron(II) chloride, polymethylhydrosiloxane, and air] can, therefore, also be employed to oxidize complex natural-product-derived and polyfunctionalized molecules.
- Liu, Binbin,Jin, Fengli,Wang, Tianjiao,Yuan, Xiaorong,Han, Wei
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supporting information
p. 12712 - 12717
(2017/09/11)
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- Direct synthesis of 1,3-dicarbonyl compounds via radical coupling of aldehydes with ketones under metal-free conditions
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An efficient approach for the synthesis of 1,3-diketones from aldehydes and ketones has been developed using Bu4NI (TBAI) as the catalyst. In the presence of DTBP-TBHP/p-TsOH, aldehydes undergo radical coupling with ketones to provide the desired products in moderate to high yields at 120 °C. Although various substituents on the aromatic ring of aldehydes are well tolerable under the standard reaction conditions, the protocol is limited by the scope of ketones. The method exhibits advantages in terms of the easy access of the starting materials, operational simplicity, functional group tolerance, and the absence of metal catalyst.
- Shen, Xuqian,Borah, Arun Jyoti,Cao, Xihan,Pan, Weixiang,Yan, Guobing,Wu, Xiangmei
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supporting information
p. 6484 - 6487
(2015/11/16)
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- Discovery and structure-activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors
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Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[2,3-b]pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 μM, SI >30.3, 12b, EC50 = 3.5 μM, SI >28.6, 10l, EC50 = 3.9 μM, SI >25.6, 12o, EC 50 = 4.5 μM, SI >22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents.
- Wang, Ning-Yu,Zuo, Wei-Qiong,Xu, Ying,Gao, Chao,Zeng, Xiu-Xiu,Zhang, Li-Dan,You, Xin-Yu,Peng, Cui-Ting,Shen, Yang,Yang, Sheng-Yong,Wei, Yu-Quan,Yu, Luo-Ting
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supporting information
p. 1581 - 1588
(2014/03/21)
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- Direct route to 1,3-diketones by palladium-catalyzed carbonylative coupling of aryl halides with acetylacetone
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Man up your magnesium! By employing a MgCl2/Et3N system, aryl diketones can be generated from the Pd-catalyzed carbonylative α-arylation of acetylacetone with aryl bromides (see scheme). The method is ideal for the introduction of carbon isotopes into more complex structures, since only stoichiometric amounts of carbon monoxide are employed. Copyright
- Korsager, Signe,Nielsen, Dennis U.,Taaning, Rolf H.,Lindhardt, Anders T.,Skrydstrup, Troels
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supporting information
p. 17687 - 17691
(2014/01/17)
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- Palladium-catalysed carbonylative α-arylation of acetone and acetophenones to 1,3-diketones
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Three COmponent α-arylation: A carbonylative ketone α-arylation process employing acetone for the first time, as well as acetophenones, is described (see scheme). The reaction tolerates a range of (hetero)aryl iodides and several functionalised aryl ketone coupling partners. Only low pressures of molecular CO are applied and no additional solvent is necessary. Copyright
- Schranck, Johannes,Tlili, Anis,Alsabeh, Pamela G.,Neumann, Helfried,Stradiotto, Mark,Beller, Matthias
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supporting information
p. 12624 - 12628
(2013/10/01)
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- Strategy for the synthesis of pyridazine heterocycles and their derivatives
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The first synthesis of novel fused pyridazines has been realized starting from 1,3-diketones involving a Diaza-Wittig reaction as a key step. A convenient strategy was elaborated to access versatile pyridazine derivatives allowing the variation of substituents at position 6 of the heterocyclic ring. In a first part, pyridazines bearing an ester group were synthesized as a model to evaluate the methodology. In a second part, an improved procedure has been used for the synthesis of pyridazines bearing a ketone group and different methods of cyclization were carried out, leading to several hitherto unknown biheterocyclic compounds. This reaction scheme represents an attractive methodology for the synthesis of novel fused pyridazine derivatives.
- Bel Abed, Hassen,Mammoliti, Oscar,Bande, Omprakash,Van Lommen, Guy,Herdewijn, Piet
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p. 7845 - 7858
(2013/09/12)
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- Enantioselective synthesis of optically pure β-amino ketones and γ-aryl amines by Rh-catalyzed asymmetric hydrogenation
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A series of optically pure β-amino ketones have been synthesized in high enantioselectivities (ee > 99%) by Rh-DuanPhos-catalyzed asymmetric hydrogenation of readily prepared β-keto enamides. Further reduction of these β-amino ketones with hydrogen and Pd/C leads to the formation of a variety of protected enantiomerically pure γ-aryl amines (ee > 99%), which are key building blocks in many bioactive molecules.
- Geng, Huiling,Huang, Kexuan,Sun, Tian,Li, Wei,Zhang, Xiaowei,Zhou, Le,Wu, Wenjun,Zhang, Xumu
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supporting information; experimental part
p. 332 - 334
(2011/03/19)
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- OXADIAZOLE-2-OXIDES AS ANTISCHISTOSOMAL AGENTS
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The invention provides 1,2,5-oxadiazole-containing compounds of Formula (I), wherein R1, A, and R2 are as defined herein, that are useful in treating schistosomiasis. The invention also provides a composition comprising a pharmaceuti
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Page/Page column 23
(2010/04/03)
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- Synthesis of oxadiazole-2-oxide analogues as potential antischistosomal agents
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The synthesis of several 1,2,5-oxadiazole-2-oxide (Furoxan) analogues is described herein. These compounds were prepared in an effort to probe the SAR around the phenyl substituent and oxadiazole core for our studies toward thioredoxin-glutathione reductase (TGR) inhibition and antischistosomal activity.
- Rai, Ganesha,Thomas, Craig J.,Leister, William,Maloney, David J.
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supporting information; experimental part
p. 1710 - 1713
(2009/07/05)
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- INHIBITORS OF HIV REPLICATION
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The present invention relates to compounds of formula (I) wherein R1, R2, R3 and R4 are as defined herein, compositions and uses thereof for treating human immunodeficiency virus (HIV) infection. In particular,
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Page/Page column 38
(2008/12/06)
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- NOVEL DUAL ACTION RECEPTORS ANTAGONISTS (DARA) AT THE AT1 AND ETA RECEPTORS
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The present invention relates to new compounds of the formula [Chemical formula should be inserted here. Please see paper copy] wherein R1, R2, R3, and R31 are as specified herein. The invention also relates to a method for preparation thereof, as well as combinations of the new compounds with previously known agents. The invention also relates to the use of the above-mentioned compounds and combinations for the preparation of a medicament for treating hypertension of different kinds, alleviating organ damage of different kinds, treating or preventing diabetic nephropathy, treating endothelin and angiotensin mediated disorders, and treating prostate cancer.
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Page/Page column 159; 227; 232; 256-257
(2010/11/28)
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- Evaluation of TCS/ZnCl2 with acetic anhydride as an acetylating reagent for methylene ketones
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A new route for the preparation of β-diketones which have applications in organic synthesis by the reaction of methylene ketones, acetic anhydride, TCS and ZnCl2 in the solvent methylene chloride at room temperature produces the corresponding β-diketones in excellent yield. Copyright Taylor & Francis Inc.
- Elmorsy, Saad S.,Badawy, Doria S.,Khatab, Tamer K.
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p. 109 - 116
(2007/10/03)
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- Thienyl-pyrazoles and their use for controlling pests
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The present invention relates to compounds of the formulae (Ia) and (Ib) wherein R1represents C1-10alkyl which may be unsubstituted or substituted with halogen, or represents C2-4alkoxyalkyl, C2-4hydroxyalkyl, C3-6cycloalkyl, hydroxy, C1-9alkoxy which may be unsubstituted or substituted with halogen, or represents C3-6cycloalkoxy, C2-4alkoxyalkoxy or C3-4alkynyloxy, and R2represents hydrogen, C1-4alkoxycarbonyl, C1-3alkylcarbonyl or C2-4alkoxyalkyl, to processes for their preparation and to their use for controlling animal pests.
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- A Study of Three Reactions leading to Isomeric 2-(N,N-Disubstituted Amino)thiazol-5-yl Ketones
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N-Imidoyl-N,N-disubstituted thioureas react with α-halogeno ketones in the presence of triethylamine to give the expected 2-(N,N-disubstituted amino)thiazol-5-yl ketones in high yield.The corresponding reactions of N-acyl-N,N-disubstituted thioureas lead
- Funnell, Richard A.,Meakins, G. Denis,Peach, Josephine M.,Price, Susan J.
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p. 2311 - 2316
(2007/10/02)
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