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Baoan Song - One of the best experts on this subject based on the ideXlab platform.
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design synthesis and anti tocv activity of novel 4 3h quinazolinone derivatives bearing Dithioacetal moiety
Journal of Agricultural and Food Chemistry, 2020Co-Authors: Xiuhai Gan, Dandan Xie, Awei Zhang, Huanyu Yang, Baoan SongAbstract:Tomato chlorosis virus (ToCV) has caused great harm to the production of tomato worldwide. To develop efficient anti-ToCV agents, some novel 4(3H)-quinazolinone derivatives containing Dithioacetal were designed and synthesized, and their anti-ToCV activities were evaluated by microscale thermophoresis (MST) using ToCV coat protein (ToCV-CP) as a new target. The results showed that some compounds had a strong binding capacity to ToCV-CP. In particular, compounds C5 and C22 have an excellent binding capacity to ToCV-CP, with binding constant values of 0.24 and 0.25 μM, respectively. Additionally, reduced ToCV-CP gene expression levels of 81.05 and 87.59% could be achieved when tomato was treated with compounds C5 and C22, respectively, which were obviously higher than the levels after ningnanmycin (NNM) treatment (43.88%) and lead compound Xiangcaoliusuobingmi (XCLSBM) treatment (63.56%). Therefore, this work indicates that 4(3H)-quinazolinone derivatives containing Dithioacetal moiety can be used as novel anti-ToCV agents.
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Design, synthesis and anti-TMV activities of novel chromone derivatives containing Dithioacetal moiety
Bioorganic & medicinal chemistry letters, 2020Co-Authors: Ningning Zan, Maoxi Huang, Donghao Jiang, Baoan SongAbstract:Abstract Thirty-five novel chromone derivatives containing Dithioacetal moiety were designed, synthesized, and their anti-TMV activities were evaluated through half-leaf method. The results showed compound c23 illustrates highly curative, protective and inactivating activities against TMV at 500 mg/L, with the values of 68.8%, 58.8%, 86.0% respectively, which were superior to that of Ribavirin (42.3%, 49.8%, 68.4%, respectively) and similar to that of Ningnanmycin (59.4%, 52.4%, 88.4%, respectively). The EC50 value of inactivating activities of compound c23 is 9.3 mg/L, which was better than that of Ribavirin (135.2 mg/L), and equivalent to that of Ningnanmycin (8.8 mg/L). Furthermore, compound c23 can destroy the integrity of TMV-CP, resulting in reduced infectivity of TMV. Meanwhile, compound c23 can combine with TMV protein coat and hydrolyze TMV protein coat to impact the process of self-assembling of TMV, with the association constant (Kd) 4.5 mg/L. This finding suggests that chromone derivatives containing Dithioacetal moiety can be used as new antiviral agent.
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The spectrogram data of quinazoline derivatives containing a Dithioacetal moiety
Data in brief, 2018Co-Authors: Dandan Xie, Jing Shi, Awei Zhang, Zhiwei Lei, Xiuhai Gan, Limin Yin, Baoan SongAbstract:Abstract The nuclear magnetic resonance, and high-resolution mass spectrometry of quinazoline derivatives containing a Dithioacetal moiety, which was hosted in the research article entitled “Syntheses, antiviral activities and induced resistance mechanisms of novel quinazoline derivatives containing a Dithioacetal moiety”. The data include 1H nuclear magnetic resonance (1H NMR), 13C nuclear magnetic resonance (13C NMR), and high-resolution mass spectrometry. In this article, a more comprehensive data interpretation and analysis is explained.
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facile synthesis of novel vanillin derivatives incorporating a bis 2 hydroxyethyl dithhioacetal moiety as antiviral agents
Journal of Agricultural and Food Chemistry, 2017Co-Authors: Jian Zhang, Xiuhai Gan, Lei Zhao, Chun Zhu, Guoping Zhang, Dengyue Liu, Jianke Pan, Baoan SongAbstract:A series of vanillin derivatives incorporating a bis(2-hydroxyethyl)Dithioacetal moiety was designed and synthesized via a facile method. A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent activities against potato virus Y (PVY) and cucumber mosaic virus (CMV), of which, compound 6f incorporating a bis(2-hydroxyethyl)Dithioacetal moiety, exhibited the best curative and protection activities against PVY and CMV in vivo, with 50% effective concentration values of 217.6, 205.7 μg/mL and 206.3, 186.2 μg/mL, respectively, better than those of ribavirin (848.0, 808.1 μg/mL and 858.2, 766.5 μg/mL, respectively), dufulin (462.6, 454.8 μg/mL and 471.2, 465.4 μg/mL, respectively), and ningnanmycin (440.5, 425.3 μg/mL and 426.1, 405.3 μg/mL, respectively). Current studies provide support for the application of vanillin derivatives incorporating bis(2-hydroxyethyl)Dithioacetal as new antiviral agents.
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Facile Synthesis of Novel Vanillin Derivatives Incorporating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents
2017Co-Authors: Jian Zhang, Xiuhai Gan, Lei Zhao, Chun Zhu, Guoping Zhang, Dengyue Liu, Jianke Pan, Baoan SongAbstract:A series of vanillin derivatives incorporating a bis(2-hydroxyethyl)Dithioacetal moiety was designed and synthesized via a facile method. A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent activities against potato virus Y (PVY) and cucumber mosaic virus (CMV), of which, compound 6f incorporating a bis(2-hydroxyethyl)Dithioacetal moiety, exhibited the best curative and protection activities against PVY and CMV in vivo, with 50% effective concentration values of 217.6, 205.7 μg/mL and 206.3, 186.2 μg/mL, respectively, better than those of ribavirin (848.0, 808.1 μg/mL and 858.2, 766.5 μg/mL, respectively), dufulin (462.6, 454.8 μg/mL and 471.2, 465.4 μg/mL, respectively), and ningnanmycin (440.5, 425.3 μg/mL and 426.1, 405.3 μg/mL, respectively). Current studies provide support for the application of vanillin derivatives incorporating bis(2-hydroxyethyl)Dithioacetal as new antiviral agents
Ricardo L. E. Furlan - One of the best experts on this subject based on the ideXlab platform.
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Host Amplification in a Dithioacetal-Based Dynamic Covalent Library
Organic letters, 2017Co-Authors: A. Gastón Orrillo, Andrea M. Escalante, Ricardo L. E. FurlanAbstract:Molecular amplification in a Dithioacetal-based dynamic library is described for the first time. The homatropine induced selection, amplification, and isolation of one cyclophane host demonstrates the utility of Dithioacetal exchange for preparing responsive dynamic libraries. Nuclear magnetic resonance and isothermal titration calorimetry analysis suggest that the amplified macrocycle forms a 1:1 complex with the template. This is the first report about a host/guest system involving a Dithioacetal cyclophane.
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Host Amplification in a Dithioacetal-Based Dynamic Covalent Library
2017Co-Authors: Gastón A. Orrillo, Andrea M. Escalante, Ricardo L. E. FurlanAbstract:Molecular amplification in a Dithioacetal-based dynamic library is described for the first time. The homatropine induced selection, amplification, and isolation of one cyclophane host demonstrates the utility of Dithioacetal exchange for preparing responsive dynamic libraries. Nuclear magnetic resonance and isothermal titration calorimetry analysis suggest that the amplified macrocycle forms a 1:1 complex with the template. This is the first report about a host/guest system involving a Dithioacetal cyclophane
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Dithioacetal exchange a new reversible reaction for dynamic combinatorial chemistry
Chemistry: A European Journal, 2016Co-Authors: Gastón A. Orrillo, Andrea M. Escalante, Ricardo L. E. FurlanAbstract:Reversibility of Dithioacetal bond formation is reported under acidic mild conditions. Its utility for dynamic combinatorial chemistry was explored by combining it with orthogonal disulfide exchange. In such a setup, thiols are positioned at the intersection of both chemistries, constituting a connecting node between temporally separated networks.
Qun Liu - One of the best experts on this subject based on the ideXlab platform.
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Recent developments of ketene Dithioacetal chemistry.
Chemical Society reviews, 2013Co-Authors: Ling Pan, Xihe Bi, Qun LiuAbstract:Ketene Dithioacetals are versatile intermediates in organic synthesis. Extensive research, since the last decade, has given rise to new prospects in their chemistry. The objective of this review is twofold: first, to highlight the new prospects in the chemistry of functionalized ketene Dithioacetals, and second, to provide an intrinsic link between ketene Dithioacetal groups and a variety of other functional groups, which has brought out many new facts that will assist in future designs.
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copper ii bromide boron trifluoride etherate cocatalyzed cyclization of ketene Dithioacetals and p quinones a mild and general approach to polyfunctionalized benzofurans
Advanced Synthesis & Catalysis, 2010Co-Authors: Yingjie Liu, Hongjuan Yuan, Mang Wang, Qun LiuAbstract:A new application of copper(II) bromide-activated ketene Dithioacetals as nucleophiles in organic chemistry has been developed. Under the cocatalysis of copper(II) bromide (2.0 mol% ) and boron trifluoride etherate (10 mol%), the conjugate addition and sequential cyclization of α-electron-withdrawing group-substituted ketene Dithioacetals with p-quinones in acetonitrile at room temperature gave a variety of benzofurans. This formal [3 + 2] cycloaddition provides a general method for catalytic synthesis of polyfunctionalized benzofurans with the advantages of readily available starting materials, cheap catalysts, mild reaction conditions, good yields and wide range of synthetic potential for the benzofuran products. Further transformations of the resulting benzofurans to 2-aminobenzofurans and benzofuro[2,3-d]pyrimidine derivatives are also investigated.
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Unexpected hydrobromic acid-catalyzed C-C bond-forming reactions and facile synthesis of coumarins and benzofurans based on ketene Dithioacetals
Chemistry - A European Journal, 2010Co-Authors: Hongjuan Yuan, Yi-qun Liu, Likui Wang, Mang Wang, Jun Liu, Qun LiuAbstract:Hydrobromic acid was found to be a unique catalyst in C-C bond-forming reactions with ketene Dithioacetals. Distinctly different from other acids (including Lewis and Brønsted acids), the remarkable catalytic performance of hydrobromic acid in catalytic amounts was observed in the "acid"-catalyzed reactions of readily available functionalized ketene Dithioacetals 1 with various electrophiles. Under the catalysis of 0.1 equivalents of hydrobromic acid, the reaction of 1 with carbonyl compounds 2a-l gave polyfunctionalized penta-1,4-dienes 3 or conjugated dienes 4 in good to excellent yields. The reaction tolerated a broad range of substituents on both the ketene Dithioacetals 1 and the carbonyl compounds 2. Application of this efficient C-C bond-forming method generated coumarins 5 and benzofurans 7 under mild, metal-free conditions by hydrobromic acid-catalyzed reactions of 1 with salicylaldehydes 2m-o and p-quinones 6a-d, respectively. A new reactive species, a sulfur-stabilized carbonium ylide, formed depending on the nature of the counterion, and this was proposed as the key intermediate in the unique catalysis of hydrobromic acid.
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Vilsmeier-haack reaction of α-oxo ketene Dithioacetals to α-chlorovinyl/ ethynyl ketene Dithioacetals
Synthesis, 2004Co-Authors: Dewen Dong, Yu‐long Zhao, Yingchun Liu, Zhuo Wang, Qun LiuAbstract:A range of α-oxo ketene Dithioacetals 1 reacted with Vilsmeier reagent (POCl 3 /DMF) to afford α-chlorovinyl ketene Dithioacetals 2. With the treatment of NaOH in ethanol or methanol, the compounds 2 were transformed into the corresponding α-ethynyl ketene Dithioacetals 3 in moderate to high yields.
Tien-yau Luh - One of the best experts on this subject based on the ideXlab platform.
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iron promoted elimination of beta thioalkoxy alcohols olefination by coupling of a carbonyl group with a Dithioacetal
Organic Letters, 2007Co-Authors: Lifu Huang, Chihwei Chen, Tien-yau LuhAbstract:Treatment of propargylic dithiolanes with nBuLi followed by a carbonyl electrophile yields the corresponding propargylic Dithioacetals. Upon treatment with 1 equiv of Fe(acac)3 and excess MeMgI, elimination of SR and OH moieties from 8 affords the corresponding olefins in satisfactory yield. Benzylic Dithioacetals behave similarly. The reaction can be considered an alternative of McMurry coupling of two different carbonyl equivalents.
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Dithioacetals as zwitterion synthons
European Journal of Organic Chemistry, 2005Co-Authors: Tien-yau Luh, Chinfa LeeAbstract:This microreview highlights recent advances in the synthetic applications of Dithioacetal functionality. Propargylic Dithioacetals and related compounds have been shown to be useful, with the aid of thiophilic organolithium or organocopper reagents, for the synthesis of polysubstituted allenes, trisubstituted furans, and pyrroles. An extension of this annulation reaction to the bidirectional iterative synthesis of furan-containing oligoaryls and to cyclophane synthesis is described. Alternatively, the convergent synthesis of such oligoaryls from propargylic Dithioacetals is briefly discussed. Not only can the carbon–sulfur bonds in Dithioacetals be readily displaced by carbon–carbon and/or carbon–heteroatom bonds, but in addition a range of reactions involving polarity inversion in neighboring carbon atoms can also take place. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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Dithioacetal as a 1,1-zwitterion synthon. Synthesis of functionalized alkenes by the coupling of benzylic Dithioacetals with another 1,1-zwitterion synthon
Tetrahedron Letters, 2005Co-Authors: Yi-hung Liu, Yu Wang, Tien-yau LuhAbstract:Reaction of a Dithioacetal sequentially with BuLi and alkyl bromide having an electron withdrawing substituent at the α-position followed by treatment with neutral alumina gives the corresponding olefination product in moderate to good yields.
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Recent advances on the synthetic applications of the Dithioacetal functionality
Journal of Organometallic Chemistry, 2002Co-Authors: Tien-yau LuhAbstract:Recent advances on the synthetic applications of the Dithioacetal functionality are briefly reviewed. Nickel-catalyzed silylolefination reaction has led to the synthesis of a range of silyl-substituted olefins for optoelectronic interests. The reactions of propargylic Dithioacetals with organocopper or lithium reagent followed by treatment with electrophiles yield the corresponding sulfur-substituted allenes. Further cross coupling with the Grignard reagent in the presence of a nickel catalyst affords highly substituted allenes. Acid-catalyzed cyclization of the sulfur-substituted allenyl alcohols furnishes a useful route for the synthesis of oligoaryls having highly substituted furan or pyrrole moieties.
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Dithioacetals as geminal dication synthons
Pure and Applied Chemistry, 1996Co-Authors: Tien-yau LuhAbstract:The NiCl2(PPh3)2-catalyzed cross coupling reactions of benzylic and allylic Dithioacetals with alkyl Grignard reagents give the corresponding olefination products. The reactions of the Dithioacetal with cyclopropyl Grignard reagent under the same conditions provide a stereoselective synthesis of substituted butadienes. The applications of this methodology lead to a unified synthesis of vinylsilanes and silyl-substituted butadienes. The aliphatic Dithioacetals can undergo.the coupling reaction when there exists a proximal heteroatom which, in combination with the sulfur moeity, can form a chelation complex with the nickel catalyst. Trithioorthoesters and tetrathioorthocarbonate behave similarly to yield the corresponding alkylative olefination products. The nickel catalyst having a bidentate phosphine ligand can promote geminal dimethylation of allylic Dithioacetals under similar conditions. These reactions can be considered as using Dithioacetals as C2+ synthons.
Zhengkun Yu - One of the best experts on this subject based on the ideXlab platform.
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bronsted acid catalyzed phse transfer versus radical aryl transfer linear codimerization of styrenes and internal olefins
Organic Letters, 2015Co-Authors: Ping Wu, Liandi Wang, Kaikai Wu, Zhengkun YuAbstract:Bronsted acid p-TsOH·H2O-catalyzed hydrovinylation of styrenes with internal olefins α-oxo ketene Dithioacetals was efficiently achieved in the presence of N-phenylselenophthalimide (N-PSP), regioselectively affording Markovnikov phenylselenative hydrovinylation products through PhSe transfer of the phenylseleno ketene Dithioacetal intermediates. Radical reduction of the resultant PhSe-alkyl-substituted ketene Dithioacetals with AIBN/n-Bu3SnH gave the corresponding anti-Markovnikov hydrovinylation products formally from the linear codimerization of styrenes and the internal olefins.