- Geometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF3for (E)-Vinyl Trifluoromethyl Thioethers
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An efficient copper(II)-promoted denitrative trifluoromethylthiolation under mild reaction conditions has been developed for vinyl trifluoromethyl thioethers to construct Cvinyl-SCF3 bonds with stable AgSCF3 as a source of the trifluoromethylthio. This reaction system tolerates a broad range of functional groups to commendably achieve a high product yield and excellent stereoselectivity of E/Z.
- Fang, Ge,Hong, Jianquan,Huang, Shuai,Jiang, Chao,Liu, Yang,Zhang, Wei,Zheng, Changge
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supporting information
(2020/07/03)
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- Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase
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Fructose-1,6-bisphosphatase (FBPase) is an attractive target for affecting the GNG pathway. In our previous study, the C128 site of FBPase has been identified as a new allosteric site, where several nitrovinyl compounds can bind to inhibit FBPase activity. Herein, a series of nitrostyrene derivatives were further synthesized, and their inhibitory activities against FBPase were investigated in vitro. Most of the prepared nitrostyrene compounds exhibit potent FBPase inhibition (IC50 3, CF3, OH, COOH, or 2-nitrovinyl were installed at the R2 (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5–55 folds compared to those compounds with the same groups at the R1 (para-) position. In addition, the preferred substituents at the R3 position were Cl or Br, thus compound HS36 exhibited the most potent inhibitory activity (IC50 = 0.15 μM). The molecular docking and site-directed mutation suggest that C128 and N125 are essential for the binding of HS36 and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R3 position is Cl > H > CH3. CoMSIA analysis is consistent with our proposed binding mode. The effect of compounds HS12 and HS36 on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100 μM, respectively.
- Chen, Haifeng,Guo, Yanrong,Han, Xinya,Hu, Wei,Huang, Yunyuan,Ren, Yanliang,Tang, Zilong,Wang, Qi,Wei, Lin,Xia, Qinfei,Yan, Jufen
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supporting information
(2020/07/23)
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- A photocatalyst-free photo-induced denitroalkylation of β-nitrostyrenes with 4-alkyl substituted Hantzsch esters at room temperature
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A photocatalyst-free stereoselectively photo-induced strategy for the denitroalkylation of β-nitrostyrenes using 4-alkyl substituted Hantzsch esters as the alkyl source under xenon lamp irradiation is developed. The reaction proceeds at room temperature and affords the corresponding products in moderate to excellent yields. The oxidant di-t-butyl peroxide serves as an efficient radical initiator under irradiation of a Xenon lamp, initiating alkyl radicals from the 4-alkyl substituted Hantzsch esters.
- Duan, Chunying,Hao, Xinyu,Jin, Kun,Li, Yaming,Wang, Jiaao,Zhang, Rong,Zhang, Siyu
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supporting information
(2020/02/18)
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- Novel approach in the synthesis of imidazo [1, 2-a] pyridine from phenyl acrylic acids
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This paper describes highly efficient concise method for the synthesis of imidazo[1,2-a] pyridine. It is a first report employing, amino pyridines, copper nitrate, and phenyl acrylic acids in the synthesis of imidazo[1,2-a] pyridine. The silent features of the devised protocol include the high yield, milder reaction conditions, and shorter reaction time.
- Mutkule, Nilesh,Bugad, Nageshprasad,Mokale, Santosh,Choudhari, Vilas,Ubale, Milind
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supporting information
p. 3186 - 3192
(2020/06/23)
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- Preparation method of beta-trans-nitroolefin
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The invention relates to a preparation method of beta-trans-nitroolefin. The method comprises: sequentially adding an olefin compound, a nitration reagent and a solvent into a reaction container, mixing the substances uniformly, and carrying out constant temperature reaction for 18h under an illumination condition to obtain a reaction solution; and sequentially carrying out drying, concentration and column chromatography treatment on the reaction solution to obtain the beta-trans-nitroolefin compound. The method is simple and practicable, low in cost and high in product yield, can realize large-scale production, and has good industrial application prospects in the aspects of functional organic material, bioactive compound and drug synthesis.
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Paragraph 0060-0062
(2020/06/17)
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- Preparation method of nitroolefin derivative with nitrate as nitro source
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The invention relates to a nitroolefin derivative with nitrate as nitro source and a preparation method thereof. Under the atmosphere of nitrogen, an olefin compound, nitrate, trimethylchlorosilane (TMSC1) and copper salt are stirred in acetonitrile at 0-30 DEG C; in addition, the reaction degree is monitored by using a TLC point plate; after the olefin compound is completely consumed, alkali is added to an obtained mixture to be stirred for 20-30 min; then after a solvent is removed from an obtained mixture by using a rotary evaporator, the nitroolefin derivative can be obtained through silicagel column purification. Compared with the prior art, the nitroolefin derivative with the nitrate as the nitro source, provided by the invention, has the advantages of mild reaction condition, high yield, high E type selectivity and the like.
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Paragraph 0042; 0049-0054; 0097-0099
(2019/08/20)
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- A chiral bicyclic skeleton-tethered bipyridine-Zn(OTf)2 complex as a Lewis acid: Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes
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A conformationally rigid chiral bicyclic skeleton tethered bipyridine-Zn(OTf)2 complex facilitated the enantioselective Friedel-Crafts alkylation of indoles with trans-β-nitroarylalkenes in an enantioselective manner at elevated temperature. Indoles reacted smoothly with β-nitroarylalkenes to generate the corresponding 3-(2-nitroalkyl)indoles in good to excellent yields (up to 94%) with moderate to excellent enantioselectivities (up to 91%). The stereochemical outcome of the product from indole and trans-β-nitrostyrene in the presence of the CRCB tethered bipyridine-Zn(OTf)2 complex and the DFT calculation of the CRCB tethered bipyridine-Zn:trans-β-nitrostyrene complex support the si-face attack of indole on trans-β-nitrostyrene.
- Venkatanna, Kesa,Yeswanth Kumar, Santhakumar,Karthick, Muthupandi,Padmanaban, Ramanathan,Ramaraj Ramanathan, Chinnasamy
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p. 4077 - 4086
(2019/04/30)
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- Visible light-mediated intermolecular [2 + 2] photocycloaddition of 1-aryl-2-nitroethenes and olefins
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Despite the importance of cyclobutanes there are not many direct [2 + 2] photocycloaddition reactions which can be performed with visible light in the absence of a catalyst. A notable exception is the reaction of 1-aryl-2-nitroethenes and olefins which can be performed at a wavelength of λ = 419 nm or λ = 424 nm in CH2Cl2 as the solvent. In the present study, a total of 15 1-aryl-2-nitroethenes were found to undergo a [2 + 2] photocycloaddition with 2,3-dimethyl-2-butene (28-86% yield) and a set of 12 olefins was studied in their photocycloaddition to 1-phenyl-2-nitroethene (37-88% yield). All mechanistic results are in agreement with a triplet reaction pathway and with the intermediacy of a 1,4-diradical.
- Mohr, Lisa-Marie,Bauer, Andreas,Jandl, Christian,Bach, Thorsten
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supporting information
p. 7192 - 7203
(2019/08/07)
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- Catalytic and Mechanistic Developments of the Nickel(II) Pincer Complex-Catalyzed Hydroarsination Reaction
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Synthetic challenges have significantly slowed the development of the catalytic asymmetric hydroarsination reaction despite it being a highly attractive C?As bond formation methodology. In addition, there is a poor understanding of the main reaction steps in such reactions which limit further development in the field. Herein, key intermediates of the hydroarsination reaction catalyzed by a PCP NiII-Cl pincer complex are presented upon investigating the reaction with DFT calculations, conductivity measurements, NMR spectroscopy, and catalytic screening. The novel Ni–Cl–As interaction proposed was then contrasted against known NiII-catalyzed hydrophosphination reactions to highlight dissimilarities between them even though P and As share a close group relationship. Lastly, the asymmetric hydroarsination of nitroolefins was further developed to furnish a library of chiral organoarsines in up to 99 % yield and 80 % ee under mild conditions (?20 °C to RT) between 5 to 210 mins.
- Tay, Wee Shan,Lu, Yunpeng,Yang, Xiang-Yuan,Li, Yongxin,Pullarkat, Sumod A.,Leung, Pak-Hing
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supporting information
p. 11308 - 11317
(2019/08/07)
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- Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations
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Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.
- Betori, Rick C.,May, Catherine M.,Scheidt, Karl A.
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supporting information
p. 16490 - 16494
(2019/11/03)
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- Synthetic Diversity from a Versatile and Radical Nitrating Reagent
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We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C?H diversification of alkenes and alkynes. Beyond furnishing a library of aryl β-nitroalkenes, this reagent provides unparalleled access to β-nitrohydrins and β-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N?N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, electron paramagnetic resonance spectroscopy, we observed direct evidence of a nitryl radical in solution by nitrone spin-trapping. To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C?H partners to prepare isoxazolines and isoxazoles is presented. This approach allows for the formation of an in situ nitrile oxide from a ketone partner, the presence of which is detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeds in a single-operational step using a mild, regioselective, and general protocol with broad chemoselectivity.
- Zhang, Kun,Jelier, Benson,Passera, Alessandro,Jeschke, Gunnar,Katayev, Dmitry
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supporting information
p. 12929 - 12939
(2019/09/17)
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- Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation
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ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.
- Kim, Hun Young,Oh, Kyungsoo,Si, Tengda
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p. 9216 - 9221
(2019/10/08)
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- Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma
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Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.
- Byrne, Andrew J.,Bright, Sandra A.,Fayne, Darren,McKeown, James P.,McCabe, Thomas,Twamley, Brendan,Williams, Clive,Meegan, Mary J.
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p. 181 - 199
(2018/03/13)
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- One-Step, Effective, and Cascade Syntheses of Highly Functionalized Cyclopentenes with High Diastereoselectivity
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Tetrabutylammonium fluoride works as an effective organocatalyst for the cycloaddition between phenacylmalononitriles and electron-deficient olefins (having substituent groups of NO2, CHO, and COR), providing a facile synthetic route to versatile multifunctionalized cyclopentenes having an allylic quaternary carbon center bearing both cyano and carboxamide groups with high yields and high diastereoselectivity. Preliminary studies reveal that these functionalized cyclopentenes are convenient precursors for making α-cyano-functionalized cyclopentadienone oximes.
- Alishetty, Suman,Shih, Hong-Pin,Han, Chien-Chung
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p. 2513 - 2516
(2018/05/17)
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- Highly Enantioselective Michael Addition of Dithiomalonates to Nitroolefins Catalyzed by New Bifunctional Chiral Thioureas
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We report a highly efficient asymmetric Michael addition of dithiomalonates to trans -β-nitroole?ns catalyzed by versatile cinchona-based bifunctional thioureas, which provides the corresponding adducts in high yields (up to 92%) and with excellent enanti
- Yuan, Jia-Ni,Liu, Hui-Xia,Tian, Qin-Qin,Ji, Nan,Shen, Kuo,He, Wei
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supporting information
p. 2577 - 2586
(2018/05/03)
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- Squaramide-Linked Chloramphenicol Base Hybrid Catalysts for the Asymmetric Michael Addition of 2,3-Dihydrobenzofuran-2-carboxylates to Nitroolefins
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An array of hybrid catalysts incorporating a chloramphenicol base moiety linked to another chiral scaffold through a squaramide linker were developed and successfully used in the Michael addition of 2,3-dihydrobenzofuran-2-carboxylates to nitroolefins. Control experiments suggested that the hybrid catalysts were more reactive than nonhybridized bifunctional catalysts, and matching of the chirality between the two scaffolds was crucial for high reactivity and stereoselectivity. These hybrid organocatalysts could be used with a variety of substrates. At a 0.5 mol-% catalyst loading, a range of 2,3-dihydrobenzofuran-2-carboxylates derivatives bearing quaternary and tertiary stereogenic centers were obtained in high yields (up to 98 %) with excellent enantioselectivities (up to 99 % ee) and moderate diastereoselectivities (up to 8:92 dr).
- Yan, Linjie,Huang, Guanxin,Wang, Haifeng,Xiong, Fangjun,Peng, Haihui,Chen, Fener
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supporting information
p. 99 - 103
(2018/01/17)
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- Metal-free radical trifluoromethylation of β-nitroalkenes through visible-light photoredox catalysis
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A catalytic method for functional group interconversion is immensely important in modern sciences. Here, we report an efficient catalytic conversion of nitroalkenes to highly stereoselective 1-trifluoromethylalkenes at room temperature. This unprecedented metal-free photocatalytic strategy is simple and operates under visible-light irradiation using the commercially available CF3 source.
- Midya, Siba P.,Rana, Jagannath,Abraham, Thomas,Aswin, Bhaskaran,Balaraman, Ekambaram
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supporting information
p. 6760 - 6763
(2017/07/10)
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- Cyanide-Free and Broadly Applicable Enantioselective Synthetic Platform for Chiral Nitriles through a Biocatalytic Approach
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A cyanide-free platform technology for the synthesis of chiral nitriles by biocatalytic enantioselective dehydration of a wide range of aldoximes is reported. The nitriles were obtained with high enantiomeric excess of >90 % ee (and up to 99 % ee) in many cases, and a “privileged substrate structure” with respect to high enantioselectivity was identified. Furthermore, a surprising phenomenon was observed for the enantiospecificity that is usually not observed in enzyme catalysis. Depending on whether the E or Z isomer of the racemic aldoxime substrate was employed, one or the other enantiomer of the corresponding nitrile was formed preferentially with the same enzyme.
- Betke, Tobias,Rommelmann, Philipp,Oike, Keiko,Asano, Yasuhisa,Gr?ger, Harald
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supporting information
p. 12361 - 12366
(2017/09/06)
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- Tetraarylphosphonium inner-salts (TAPIS) as both Lewis base catalyst and phase tag
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Tetraarylphosphonium inner-salts (TAPIS) have been designed, synthesized and verified as recyclable and reusable Lewis base catalysts. The resulted TAPIS catalyst has been successfully applied in Michael addition, cyanation and trifluoromethylation reactions.
- Guo, Shuhui,Mi, Xueling
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supporting information
p. 2881 - 2884
(2017/07/11)
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- Catalyst-free sulfa-Michael addition of pyrimidine-2-thiol to nitroolefins
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Catalyst-free sulfa-Michael addition of pyrimidine-2-thiol to nitroolefins is described. A series of 2-((2-nitro-1-arylethyl)thio)pyrimidines were efficiently synthesized. The protocol has advantages of wide range of substituents tolerance, no catalyst, additives and bases, mild condition, and high yield. The method can also extend to gram scale.
- Li, Zheng,Song, Geyang,He, Jiaojiao,Du, Yan,Yang, Jingya
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p. 686 - 698
(2017/09/06)
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- Fe(III)/Pyridine-Mediated Decarboxylative Nitration of α,β-Unsaturated Acids with Iron Nitrate
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A novel and efficient method for the synthesis of (E)-nitroolefins in moderate to excellent yields is developed by Fe(III)/pyridine-mediated decarboxylative nitration of α,β-unsaturated acids with iron nitrate. A series of α,β-unsaturated acids are well tolerated in this procedure.
- Yang, Zan,Li, Jiao,Hua, Jie,Yang, Tao,Yi, Jianmin,Zhou, Congshan
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supporting information
p. 1079 - 1082
(2017/05/19)
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- Dihydrooxazine N-Oxide Intermediates as Resting States in Organocatalytic Kinetic Resolution of Functionalized Nitroallylic Amines with Aldehydes
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Kinetic resolution of nitroallylic amines was established using chiral α,α-l-diphenylprolinol silyl ether auxiliary through isolation of the dihydrooxazine N-oxide intermediates. Further hydrolyzing the resting states provided tetrahydropyridines in high chemical yields and high to excellent stereoselectivities (up to >20:1 dr and 98% ee). A detailed mechanistic explanation for stereoselective protonation in the dihydrooxazine was probed computationally. In addition, the probable intermediates in α-halogenation of aldehydes (masked with enamines) were isolated to provide crystallographic evidence.
- Gurubrahamam, Ramani,Chen, Yan Ming,Huang, Wan-Yun,Chan, Yu-Te,Chang, Hsiang-Kai,Tsai, Ming-Kang,Chen, Kwunmin
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supporting information
p. 3046 - 3049
(2016/07/13)
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- Yolk-shell-structured mesoporous silica: A bifunctional catalyst for nitroaldol-Michael one-pot cascade reaction
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Great interest in heterogeneous asymmetric catalysis has focused on obtaining an enantioselective cascade reaction through a controllable active site-isolated heterogeneous catalyst. Herein, we utilize a yolk-shell-structured mesoporous silica and assemble an active site-isolated bifunctional heterogeneous catalyst, where chiral cinchonine-based squaramide molecules are anchored within a silicate channel as an outer shell while amine-functionalities are entrapped onto a silicate yolk as an inner core. Structural analyses and characterizations of the heterogeneous catalyst reveal its well-defined single-site chiral active species within its silicate network. Electron microscopy confirms the yolk-shell-structured mesoporous material. As presented in this study, as a bifunctional heterogeneous catalyst, it enables an efficiently nitroaldol-Michael cascade reaction to conduct the three-component coupling of nitromethane, aldehyde and acetylacetone into various chiral diones with high yields and up to 99% enantioselectivities in a one-pot process. As expected, this active site-isolated catalyst not only enhances the catalytic selectivity of the first-step nitroaldol condensation, but also keeps the enantioselectivity of the second-step Michael addition. Moreover, the heterogeneous catalyst can be also recovered easily and recycled repeatedly, making it an interesting feature in a three-component organic transformation.
- An, Juzeng,Cheng, Tanyu,Xiong, Xi,Wu, Liang,Han, Bin,Liu, Guohua
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p. 5714 - 5720
(2016/07/21)
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- Palladium(II)-catalyzed C-C and C-O bond formation for the synthesis of C1-benzoyl isoquinolines from isoquinoline: N -oxides and nitroalkenes
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C1-Benzoyl isoquinolines can be generated via a palladium(ii)-catalyzed C-C and C-O coupling of isoquinoline N-oxides with aromatic nitroalkenes. The reaction proceeds through remote C-H bond activation and subsequent intramolecular oxygen atom transfer (OAT). In this reaction, the N-O bond was designed as a directing group in the C-H bond activation as well as the source of an oxygen atom.
- Li, Jiu-Ling,Li, Wei-Ze,Wang, Ying-Chun,Ren, Qiu,Wang, Heng-Shan,Pan, Ying-Ming
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supporting information
p. 10028 - 10031
(2016/08/15)
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- Nitration-Oximization of Styrene Derivatives with tert-Butyl Nitrite: Synthesis of α-Nitrooximes
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A highly efficient method for direct nitration-oximization of styrene derivatives using tert-butyl nitrite (t-BuONO) in DMSO was developed. The present method offers a convenient and practical approach for the synthesis of α-nitrooximes in moderate to high yields. The salient features entail mild reaction conditions, metal-free reagent, environmentally benign solvent and simple experimental procedure.
- Chumnanvej, Napasawan,Katrun, Praewpan,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Kuhakarn, Chutima
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p. 830 - 838
(2016/09/03)
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- Cu(NO3)2-catalyzed nitrodecarboxylation of α,β-unsaturated acids: facile synthesis of (E)-nitroolefins under additive-free conditions
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Abstract: An additive-free, facile, efficient, and ecofriendly protocol for synthesis of (E)-nitroolefins via nitrodecarboxylation of α,β-unsaturated acids has been developed. Cu(NO3)2 was used as both nitrating agent and catalyst. Furthermore, the presented methodology offers several advantages such as easily accessible and stable substrates, inexpensive catalyst, high to excellent yield, short reaction time, and simple posttreatment procedure. Graphical Abstract: [Figure not available: see fulltext.]
- Luo, Zai-Gang,Xu, Feng,Fang, Yu-Yu,Liu, Peng,Xu, Xue-Mei,Feng, Cheng-Tao,Li, Zhong,He, Jie
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p. 6079 - 6087
(2016/06/01)
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- An Acid/Base-Regulated Recyclable Strategy for Homogeneous Cinchona Alkaloid-Derived Primary Amine Organocatalysts in Aldol, Vinylogous Michael and Double-Michael Cascade Reactions
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A practical, recyclable strategy for homogeneous cinchona alkaloid-derived primary amine organocatalysts was developed by controlling the solubilities in an aqueous/organic biphasic system through regulating the pH of the aqueous phase, effecting the prot
- Wan, Jingwei,Zhao, Zhiwei,Wang, Falu,Ma, Xuebing
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supporting information
p. 5755 - 5763
(2015/09/15)
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- Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agents
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A new class of highly substituted pyrroles have been synthesized via a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation. N-Methyl-N-[(E)-1-(methylsulfanyl)-2-nitro-1-ethenyl]amine (NMSM) 1 and β-nitrostyrenes 3 underwent cycloaddition to afford the desired products 4 in excellent yields under solvent and metal free conditions. All the pyrrole derivatives were evaluated for their in vitro anti-bacterial activity. Among the synthesized pyrrole derivatives, 4b, 4c, 4e, 4g, 4i, 4j, 4l, 4m and 4n displayed good inhibitory properties against a panel of Gram positive and negative infectious pathogens.
- Balachandra, Biguvu,Shanmugam, Sivakumar,Muneeswaran, Thillaichidambaram,Ramakritinan, Muthiah
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p. 64781 - 64789
(2015/08/18)
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- METHODS AND COMPOSITIONS FOR SELECTIVE AND TARGETED CANCER THERAPY
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Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.
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Page/Page column 227
(2015/03/28)
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- Hyperbranched polyamines: Tunable catalysts for the Henry reaction
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Hyperbranched polyethylenimine derivatives were successfully employed as catalyst in the Henry reaction. The nitroalcohol products were obtained in excellent yields within short reaction times. A one-pot synthesis of β-nitrostyrenes was developed by using ZnCl2 along with hyperbranched polyethylenimine derivatives. Georg Thieme Verlag Stuttgart New York.
- Ganesan, Subramaniapillai Selva,Ganesan, Asaithampi,Kothandapani, Jagatheeswaran
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supporting information
p. 1847 - 1850
(2014/08/18)
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- Highly efficient iridium-catalyzed asymmetric hydrogenation of β-acylamino nitroolefins
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The first highly efficient Ir-catalyzed enantioselective hydrogenation of β-acylamino nitroolefins is reported. This reaction provides straightforward access to chiral β-amino nitroalkanes in high yields and excellent enantioselectivities (up to >99.9% ee) catalyzed by an Ir-(R,R)-f-spiroPhos complex. This journal is
- Yan, Qiaozhi,Liu, Man,Kong, Duanyang,Zi, Guofu,Hou, Guohua
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supporting information
p. 12870 - 12872
(2014/12/11)
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- Oxone/KI-Mediated Nitration of Alkenes and Alkynes: Synthesis of Nitro- and β-Iodonitro-Substituted Alkenes
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Oxone (2KHSO5·KHSO4·K2SO4) was used to promote the nitration of alkenes and alkynes with sodium nitrite (NaNO2) and potassium iodide (KI). This stable, easy-to-handle, and environmentally benign oxidant was used under mild conditions (room temperature) and provided short reaction times. Styrene derivatives that did not contain electron-donating groups afforded the corresponding nitro alkenes in moderate to good yields, whereas aliphatic alkenes and electron-deficient alkenes were not good substrates. Under similar reaction conditions, aryl alkynes yielded β-iodonitro alkenes. Oxone (2KHSO5·KHSO4·K2SO4) was used to promote the reactions of alkenes and alkynes with sodium nitrite (NaNO2) and potassium iodide (KI) to afford the corresponding nitro and β-iodonitro-substituted alkenes, respectively, in moderate to good yields.
- Hlekhlai, Sornsiri,Samakkanad, Natthapol,Sawangphon, Tassaporn,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Jaipetch, Thaworn,Kuhakarn, Chutima
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p. 7433 - 7442
(2016/02/19)
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- LORCASERIN HYDROCHLORIDE
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The present invention relates to amorphous lorcaserin hydrochloride; amorphous solid dispersion comprising lorcaserin hydrochloride and one or more pharmaceutically acceptable carries; processes for preparation thereof; pharmaceutical compositions comprising amorphous lorcaserin hydrochloride and one or more pharmaceutically acceptable carries.
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Page/Page column
(2014/07/08)
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- Synthesis and biological evaluation of novel 3,4-diaryl lactam derivatives as triple reuptake inhibitors This article is dedicated to Professor Jahyo Kang for his lifelong commitment to mentoring graduate students
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A series of 3,4-diarylpyrrolidin-2-one was designed, prepared and evaluated as triple reuptake inhibitors for antidepressant. Most compounds exhibited comparable in vitro efficacy as norepinephrine and dopamine transporter reuptake inhibitors. Especially, 2i showed better potency than GBR-12909 (IC 50 = 14 nM) which was used as reference compound for dopamine transporter. In addition, 2a and 2b showed inhibition (5.17 μM-85.6 nM) for three transporters.
- Park, Jung-Eun,Song, Chiman,Choi, Keehyun,Sim, Taebo,Moon, Bongjin,Roh, Eun Joo
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supporting information
p. 5515 - 5518
(2013/10/01)
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- Asymmetric palladium(II)-catalyzed cascade reaction giving quaternary amino succinimides by 1,4-addition and a nef-type reaction
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Simple starting materials, high-value products: A dinuclear ferrocene-based PdII complex transforms mixtures of racemic N-benzoyl α-amino acids, nitroolefins, acetic anhydride, and manganese acetate into biologically interesting quaternary amin
- Weber, Manuel,Frey, Wolfgang,Peters, Rene
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supporting information
p. 13223 - 13227
(2014/01/06)
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- Pd-catalyzed multidehydrogenative cross-coupling between (Hetero)arenes and nitroethane to construct β-aryl nitroethylenes
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The Pd-catalyzed multidehydrogenative cross-coupling reactions of arenes with nitroethane are described. The established methods afford β-aryl nitroethylenes that are an important class of synthetic intermediates and biologically active compounds in an atom- and step-economical fashion. The reactions were applicable to substituted benzenes and a variety of heterocycles such as benzothiophenes, benzofurans, and indoles. Mechanistic experiments indicated that β-nitroethylbenzene might be the intermediate in this transformation.
- Zhang, Min,Hu, Peng,Zhou, Jun,Wu, Ge,Huang, Shijun,Su, Weiping
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supporting information
p. 1718 - 1721
(2013/06/26)
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- Catalyst-free and solvent-free Michael addition of 1,3-dicarbonyl compounds to nitroalkenes by a grinding method
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An environmentally benign, fast and convenient protocol has been developed for the Michael addition of 1,3-dicarbonyl compounds to β-nitroalkenes in good to excellent yields by a grinding method under catalyst- and solvent-free conditions.
- Xie, Zong-Bo,Wang, Na,Wu, Ming-Yu,He, Ting,Le, Zhang-Gao,Yu, Xiao-Qi
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supporting information; experimental part
p. 534 - 538
(2012/06/29)
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- One-pot synthesis of nitroalkenes via the Henry reaction over amino-functionalized MIL-101 catalysts
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Ethylenediamine moieties with different amounts were incorporated into the metal-organic framework MIL-101 to prepare the amino-functionalized MIL-101 materials, which were used as heterogeneous catalysts in the one-pot synthesis of nitroalkenes via the Henry reaction. Various reaction conditions were optimized. Under the optimized conditions, the selectivity towards nitroalkenes is extremely high in combination with nearly complete conversion of the reactant nitroalkanes. The amino-functionalized MIL-101 behaves as a true heterogeneous catalyst, can be easily recovered by filtration, and can be reused at least twice without significant loss of its catalytic performance.
- Yu, Huixian,Xie, Jianwu,Zhong, Yijun,Zhang, Fumin,Zhu, Weidong
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p. 101 - 104
(2013/01/15)
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- Synthesis of vinylphosphonates and its first exploration of bioactivity
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Phosphonation of β-nitro-alkene with triethyl phosphite was achieved under microwave irradiation using CH2Cl2 as the solvent in the absence of catalyst with moderate to high yields (up to 90%). This method of formation of carbonphosphor bonds is simple, mild, convenient and effective. Synchronously, a number of vinylphosphonates derivatives were synthesized and evaluated biologically preliminary.
- Li, Sheng-Nan,Xu, Lan-Ting,Chenb, Yue,Lia, Ju-Lian,He, Ling
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experimental part
p. 416 - 422
(2012/05/04)
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- An efficient, transition-metal-free process for the synthesis of substituted dihydrofurans via a Michael/cyclization tandem reaction
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An efficient green route for the synthesis of substituted dihydrofurans was developed through a simple base-catalyzed, tandem reaction of nitrostyrene with 1,3-dicarbonyl compounds. The desired products were prepared with a large substrate scope and in excellent yields (up to 95%).
- Wu, Ming-Yu,Wang, Ming-Qi,Li, Kun,Feng, Xing-Wen,He, Ting,Wang, Na,Yu, Xiao-Qi
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supporting information; experimental part
p. 679 - 683
(2011/03/21)
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- A novel enzymatic tandem process: Utilization of biocatalytic promiscuity for high stereoselective synthesis of 5-hydroxyimino-4,5-dihydrofurans
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A lipase-catalyzed protocol for the synthesis of 5-hydroxyimino-4,5- dihydrofurans via tandem coupling between β-nitrostyrenes and 1,3-dicarbonyl compounds was developed in a 'one-pot' strategy. A series of β-nitrostyrenes were employed to expand the scope of this new biocatalytic promiscuity with high stereoselectivity (Z/E up to 99:1) and moderate to good yields. The reaction activity of 1,3-cyclohexanedione was found to be better than linear 2,4-pentanedione, while ethyl acetoacetate and diethylmalonate were not suitable for this reaction under the same conditions. Single-crystal X-ray diffraction analysis indicated that the reaction was stereoselective and Z-stereomer was found to be the major product. A reaction mechanism was supposed to elucidate the biocatalytic process.
- Wu, Ming-Yu,Li, Kun,He, Ting,Feng, Xing-Wen,Wang, Na,Wang, Xiao-Yan,Yu, Xiao-Qi
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experimental part
p. 2681 - 2688
(2011/04/23)
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- A novel catalyst-free tandem reaction for the synthesis of 5-hydroxy-1,5-dihydro-2 h -pyrrol-2-ones in water medium
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A novel catalyst-free, water-medium, tandem reaction for the synthesis of 5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones was developed through a one-pot strategy from nitroethylenes and 1,3-dicarbonyl compounds. A series of 1-aryl-2-nitroethenes and 1-nitroalk-1-enes were surveyed to determine the scope of this tandem reaction with moderate to good yield. Georg Thieme Verlag Stuttgart - New York.
- Wu, Ming-Yu,Li, Kun,Wang, Na,He, Ting,Yu, Xiao-Qi
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experimental part
p. 1831 - 1839
(2011/07/31)
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- Versatile synthesis of α-substituted taurines from nitroolefins
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A series of 1-substituted and 1,1-disubstituted taurines were synthesized from nitroolefins via the Michael addition with sodium ethylxanthate, oxidation with performic acid, and reduction with hydrogen in the presence of palladium on carbon powder. The current route is a versatile and salt-free method for synthesis of both aliphatic and aromatic 1-substituted and 1,1-disubstituted taurines. Springer-Verlag 2010.
- Xu, Chuanxiang,Xu, Jiaxi
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scheme or table
p. 195 - 203
(2012/04/10)
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- Platinum-catalyzed michael addition and cyclization of tertiary amines with nitroolefins by dehydrogenation of α,β-sp3 C-H bonds
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A mild platinum-catalyzed oxidative dehydrogenation of α,β- C(sp3)-H bonds of tertiary amines in the presence of ambient oxygen is revealed, and the in situ formed enamines subsequently reacting with various nitroolefins resulted in the development of two one-pot synthetic protocols involving Michael addition-elimination and Michael addition-cyclization. By using different functionalized nitroolefins compatible with the current oxidative conditions, two types of structurally divergent products, trisubstituted enamines and chromano[2,3-b]piperidines, could be expediently accessed, respectively.
- Xia, Xiao-Feng,Shu, Xing-Zhong,Ji, Ke-Gong,Yang, Yan-Fang,Shaukat, Ali,Liu, Xue-Yuan,Liang, Yong-Min
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supporting information; experimental part
p. 2893 - 2902
(2010/07/09)
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- Synthesis and biological evaluation of N-acetyl-β-aryl-1,2-didehydroethylamines as new HIV-1 RT inhibitors in vitro
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A variety of N-acetyl-β-aryl-1,2-didehydroethylamines were synthesized by direct reduction-acetylation of β-aryl-nitroolefins and assayed as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) for the first time. Compound 7a exhibited a TI value of >13.2 with CC50 value of >0.787 mM in C8166 cells. This structure-activity relationship (SAR) study provided a new lead for design and discovery of more potent and selective analogues act as NNRTIs.
- Cheng, Pi,Jiang, Zhi-Yong,Wang, Rui-Rui,Zhang, Xue-Mei,Wang, Qian,Zheng, Yong-Tang,Zhou, Jun,Chen, Ji-Jun
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p. 4476 - 4480
(2008/02/09)
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- A New and Efficient Synthesis of Pyrrolo[2,3-d]pyrimidine Anticancer Agents: Alimta (LY231514, MTA), Homo-Alimta, TNP-351, and Some Aryl 5-Substituted Pyrrolo[2,3-d]pyrimidines
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Alimta, as well as homo-Alimta, a nonbridged analogue of Alimta, and TNP-351 have been prepared by a new method that involves Michael addition of the appropriate 1-nitroalkene with 2,6-diamino-3H-pyrimidin-4-one or 2,4,6-triaminopyrimidine, followed by a Nef reaction of the resulting primary nitro Michael adduct. Spontaneous intramolecular cyclization of the resulting aldehyde with the pyrimidine 6-amino group yields the corresponding pyrrolo[2,3-d]pyrimidine. A series of previously unknown 5-arylpyrrolo[2,3-d]pyrimidines was prepared by the same methodology from the above pyrimidines and nitrostyrenes. It has been found that the intermediate primary nitro Michael adduct can be prepared in a single step by sonication of a mixture of an arylaldehyde, nitromethane, and the 6-aminopyrimidine in acetic acid containing ammonium acetate.
- Taylor, Edward C.,Liu, Bin
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p. 9938 - 9947
(2007/10/03)
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- The influence of substitution at aromatic part of 1,2,3,4-tetrahydroisoquinoline on in vitro and in vivo 5-HT1A/5-HT2A receptor activities of its 1-adamantoyloaminoalkyl derivatives
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Further structure-activity relationship (SAR) studies with the 1,2,3,4-tetrahydroisoquinoline (THIQ) class of 5-HT1A ligands led to the synthesis of new 1-adamantoyloaminoalkyl derivatives. The impact of substituent variations in the aromatic part of THIQ moiety on 5-HT1A and 5-HT2A receptor affinities, as well as in vivo functional properties of the investigated compounds were discussed. It was found that modification reduced the binding affinity for 5-HT1A receptors (in comparison with unsubstituted THIQ derivatives); however, the majority of new compounds still remained potent 5-HT1A ligands (Ki = 4.9-46 nM) and most of them showed features of partial agonists of postsynaptic 5-HT1A receptors. At the same time, their 5-HT2A receptor affinity was slightly increased (Ki = 40-1475 nM), which resulted in a loss of 5-HT2A/5-HT1A selectivity. 5-Br,8-OCH3 derivative - the most potent, mixed 5-HT1A/5-HT2A ligand - produced activation of presynaptic 5-HT1A receptors and showed properties of a 5-HT2A receptor antagonist. Copyright
- Bojarski, Andrzej J,Mokrosz, Maria J,Minol, Sijka Charakchieva,Koziol, Aneta,Wesolowska, Anna,Tatarczynska, Ewa,Klodzinska, Aleksandra,Chojnacka-Wojcik, Ewa
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