- Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
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We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
- Delost, Michael D.,Njardarson, Jon T.
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p. 6121 - 6125
(2021/08/16)
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- Alkylation of Indoles with α,β-Unsaturated Ketones using Alumina in Hexanes
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We evaluated the influence of solvent on the alumina-promoted C3-alkylation of indoles with α,β-unsaturated ketones. We found that lipophilic solvents were generally superior to hydrophilic ones with hexanes offering the 3-alkyl indole products in high yields. Thus, we demonstrate an inexpensive and procedurally simple new process that pairs acidic alumina with hexanes to achieve this important Michael alkylation. The substrate scope includes twenty-four examples with reaction yields ranging from 61 to 96%. (Figure presented.).
- Zhang, Xiong,Jones-Mensah, Ebenezer,Deobald, Jackson,Magolan, Jakob
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supporting information
p. 5548 - 5551
(2019/11/19)
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- Structural Modification of Natural Product Ganomycin i Leading to Discovery of a α-Glucosidase and HMG-CoA Reductase Dual Inhibitor Improving Obesity and Metabolic Dysfunction in Vivo
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It is a great challenge to develop drugs for treatment of metabolic syndrome. With ganomycin I as a leading compound, 14 meroterpene derivatives were synthesized and screened for their α-glucosidase and HMG-CoA reductase inhibitory activities. As a result, a α-glucosidase and HMG-CoA reductase dual inhibitor ((R,E)-5-(4-(tert-butyl)phenyl)-3-(4,8-dimethylnona-3,7-dien-1-yl)furan-2(5H)-one, 7d) with improved chemical stability and long-term safety was obtained. Compound 7d showed multiple and strong in vivo efficacies in reducing weight gain, lowering HbAlc level, and improving insulin resistance and lipid dysfunction in both ob/ob and diet-induced obesity (DIO) mice models. Compound 7d was also found to reduce hepatic steatosis in ob/ob model. 16S rRNA gene sequencing, SCFA, and intestinal mucosal barrier function analysis indicated that gut microbiota plays a central and causative role in mediating the multiple efficacies of 7d. Our results demonstrate that 7d is a promising drug candidate for metabolic syndrome.
- Wang, Kai,Bao, Li,Zhou, Nan,Zhang, Jinjin,Liao, Mingfang,Zheng, Zhongyong,Wang, Yujing,Liu, Chang,Wang, Jun,Wang, Lifeng,Wang, Wenzhao,Liu, Shuangjiang,Liu, Hongwei
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p. 3609 - 3625
(2018/05/01)
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- The Pharmacological Heterogeneity of Nepenthone Analogs in Conferring Highly Selective and Potent κ-Opioid Agonistic Activities
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To develop novel analgesics with no side effects or less side effects than traditional opioids is highly demanded to treat opioid receptor mediated pain and addiction issues. Recently, κ-opioid receptor (KOR) has been established as an attractive target,
- Li, Wei,Long, Jian-Dong,Qian, Yuan-Yuan,Long, Yu,Xu, Xue-Jun,Wang, Yu-Jun,Shen, Qing,Wang, Zuo-Neng,Yang, Xi-Cheng,Xiao, Li,Sun, Hong-Peng,Xu, Yu-Long,Chen, Yi-Yi,Xie, Qiong,Wang, Yong-Hui,Shao, Li-Ming,Liu, Jing-Gen,Qiu, Zhui-Bai,Fu, Wei
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p. 766 - 776
(2017/04/26)
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- Fluorine-containing three-membered ring compound, preparation method of fluorine-containing three-membered ring compound and preparation method of fluoroalkyl sulfonium salt
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The invention discloses a fluorine-containing three-membered ring compound shown in the formula V-a, V-b or V-c and a preparation method thereof. The preparation method comprises that in an organic solvent, fluoroalkyl sulfur ylide shown in the formula II
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Paragraph 0172; 0173; 0174; 0175; 0184; 0185
(2016/10/08)
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- Diastereoselective Johnson-Corey-Chaykovsky trifluoroethylidenation
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(2,2,2-Trifluoroethyl)diphenylsulfonium triflate was found to be an efficient ylide reagent for the Johnson-Corey-Chaykovsky reaction to afford trifluoromethyl epoxides, cyclopropanes and aziridines. Interestingly, excellent but different diastereoselectivity was observed for these transformations. Both trifluoromethyl epoxides and cyclopropanes were obtained with trans-selectivity, whereas aziridines were obtained with cis-selectivity.
- Duan, Yaya,Zhou, Bin,Lin, Jin-Hong,Xiao, Ji-Chang
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supporting information
p. 13127 - 13130
(2015/08/18)
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- Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group
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In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In gener
- Carrión, M. Dora,Chayah, Mariem,Entrena, Antonio,López, Ana,Gallo, Miguel A.,Acu?a-Castroviejo, Darío,Camacho, M. Encarnación
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p. 4132 - 4142
(2013/07/25)
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- (±)-2-Aryl-2,3-dihydro-4(1H)-quinolinones by a tandem reduction-Michael addition reaction
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An efficient synthesis of (±)-2-aryl-2,3-dihydro-4(1H)-quinolinones has been developed from chalcones prepared from 2′-nitroacetophenone and a series of substituted benzaldehydes. The cyclization sequence is initiated by reduction of the nitro group under dissolving metal conditions using iron powder in concentrated hydrochloric acid. Milder conditions, using acetic acid or acetic acid-phosphoric acid as the reaction medium, were less satisfactory. Procedural details as well as a mechanistic discussion and reaction optimization studies are presented.
- Bunce, Richard A.,Nammalwar, Baskar
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experimental part
p. 613 - 619
(2011/07/31)
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- Synthesis of a new mutagenic benzoazepinoquinolinone derivative
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A novel mutagenic compound 1, isolated as a Maillard product from tryptophan and glucose, was synthesized using Larock's quinoline formation, where addition of iodonium cation to an acetylene moiety of N-propargylaniline triggers subsequent intramolecular
- Ozeki, Minoru,Muroyama, Atsushi,Kajimoto, Tetsuya,Watanabe, Tetsushi,Wakabayashi, Keiji,Node, Manabu
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scheme or table
p. 1781 - 1784
(2009/12/09)
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- Total synthesis of luotonin A and 14-substituted analogues
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A new and concise synthesis of luotonin A was achieved from the previously described compounds ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate and 1-(2-nitrophenyl)prop-2-en-1-one. New 14-substituted luotonin A analogues were prepared using 14-chloroluotonin A as the key intermediate. This journal is The Royal Society of Chemistry.
- Mason, Jeffrey J.,Bergman, Jan
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p. 2486 - 2490
(2008/02/14)
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