2252-32-6Relevant academic research and scientific papers
Thiourea-Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion
Fessele, Claudia,Wachtler, Stefan,Chandrasekaran, Vijayanand,Stiller, Carina,Lindhorst, Thisbe K.,Krueger, Anke
, p. 5519 - 5525 (2015)
The study of bacterial adhesion is crucial to our understanding of infection processes as well as for the development of antiadhesives. Here we have investigated new nanodiamond glycoconjugates intended to inhibit adhesion of type 1 fimbriated E. coli bacteria. For conjugation of saccharides and nanodiamond, thiourea-bridging was employed, a method that has not been used before in nanodiamond derivatization. Amino-prefunctionalized diamond nanoparticles were prepared employing aromatic diazonium salts and reacted with different isothiocyanato-functionalized mannose derivatives. The resulting glyconanodiamonds were characterized and then tested in bacterial binding assays. They are recognized by the bacterial protein FimH according to the structure-activity relationships known for this lectin. Thus, owing to the particular properties of nanodiamond, a valuable material is introduced with the potential to control bacterial adhesion and colonization in a favorable way.
Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism
Chelagha, Aida,Khrouz, Lhoussain,Louvel, Dan,Monnereau, Cyrille,Payard, Pierre-Adrien,Rouillon, Jean,Tlili, Anis
supporting information, p. 8704 - 8708 (2021/05/17)
The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.
Aryl Diazonium Salts: Powerful Arylating Agents for Catellani-Typeortho-Arylation
Fu, Ying,Guo, Liang-Liang,Zhang, Yu-Xia
supporting information, p. 17437 - 17444 (2021/12/02)
The Catellani reaction provides an efficient synthetic approach to polyfunctionalized arenes. However, the selectiveortho-arylating reagents employed in these reactions have been strictly limited to activated bromoarenes. As demonstrated in this work, aryl diazonium salts bearing both electron-donating and electron-withdrawing substituents, after in situ transformations with KI into the corresponding iodoarenes, were efficient arylating reagents for Catellani typeortho-arylation approaches.
Transition-Metal- A nd Light-Free Directed Amination of Remote Unactivated C(sp3)-H Bonds of Alcohols
Kurandina, Daria,Yadagiri, Dongari,Rivas, Monica,Kavun, Aleksei,Chuentragool, Padon,Hayama, Keiichi,Gevorgyan, Vladimir
supporting information, p. 8104 - 8109 (2019/06/13)
Due to the great value of amino alcohols, new methods for their synthesis are in high demand. Abundant aliphatic alcohols represent the ideal feedstock for the method development toward this important motif. To date, transition-metal-catalyzed approaches for the directed remote amination of alcohols have been well established. Yet, they have certain disadvantages such as the use of expensive catalysts and limited scope. Very recently, transition-metal-free visible-light-induced radical approaches have emerged as new powerful tools for directed remote amination of alcohols. Relying on 1,5-HAT reactivity, these methods are limited to β-or δ- A mination only. Herein, we report a novel transitionmetal- A nd visible-light-free room-temperature radical approach for remote β-, γ-, and δ-C(sp3)-N bond formation in aliphatic alcohols using mild basic conditions and readily available diazonium salt reagents.
Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: Synthesis of: N -arylpyrazoles
Liu, Jidan,Xu, Erjie,Jiang, Jinyuan,Huang, Zeng,Zheng, Liyao,Liu, Zhao-Qing
supporting information, p. 2202 - 2205 (2020/02/26)
A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed. The reaction was conducted at room temperature within minutes with a broad substrate scope and excellent regioselectivity.
Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)
Pan, Shulei,Zhou, Yangli,Wang, Qiusheng,Wang, Yanlin,Tian, Chenyu,Wang, Tianqi,Huang, Luyi,Nan, Jinshan,Li, Linli,Yang, Shengyong
, (2020/09/01)
Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), which mediate kynurenine pathway of tryptophan degradation, have emerged as potential new targets in immunotherapy for treatment of cancer because of their critical role in immunosuppression in the tumor microenvironment. In this investigation, we report the structural optimization and structure-activity relationship studies of 1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as a new class of IDO1/TDO dual inhibitors. Among all the obtained dual inhibitors, 1-(3-chloro-4-fluorophenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione (38) displayed the most potent IDO1 and TDO inhibitory activities with IC50 (half-maximal inhibitory concentration) values of 5 nM for IDO1 and 4 nM for TDO. It turned out that compound 38 was not a PAINS compound. Compound 38 could efficiently inhibit the biofunction of IDO1 and TDO in intact cells. In LL2 (Lewis lung cancer) and Hepa1-6 (hepatic carcinoma) allograft mouse models, this compound also showed considerable in vivo anti-tumor activity and no obvious toxicity was observed. Therefore, 38 could be a good lead compound for cancer immunotherapy and deserving further investigation.
Gold(I)-Catalyzed Cross-Coupling Reactions of Arenediazonium Salts with Alkynoic Acids
Abrams, J. N.,Chi, B. K.
, p. 1236 - 1244 (2020/09/17)
Abstract: The reaction of simple alkynoate salts with isolated arenediazonium tetrafluoroborate salts that had been pre-conditioned with the gold(I) catalyst AuCl(Me2S) led to the formation of cross-coupled products via a decarboxylative Sonogashira reaction process in modest yield and under mild conditions. The major by-product is a defunctionalized aryl moiety stemming from the diazonium salt, which competitively forms via hydrodediazonation. Good functional group tolerance and reaction site selectivity were attained in this limited investigation.
Heterogeneous visible-light-induced Meerwein hydration reaction of alkenes in water using mpg-C3N4 as a recyclable photocatalyst
Wang, Jingjing,Xue, Linshuang,Hong, Mei,Ni, Bangqing,Niu, Tengfei
supporting information, p. 411 - 416 (2020/02/13)
A green and efficient visible light induced Meerwein hydration reaction of alkenes in aqueous medium using mpg-C3N4 as a recyclabe photocatalyst has been disclosed. This protocol provides a direct approach for the preparation of racemic alcohols via a free radical mechanism. Water acted as both a solvent and a reagent without any additives or co-solvents. The metal-free heterogeneous semiconductor is found to be fully recyclable at least 5 times without any significant reduction in activity. The Meerwein hydration reaction has an excellent substrate scope and gave the desired products in moderate to high yields. Furthermore, this reaction could be carried out under solar light irradiation and is applicable for large-scale reactions with satisfactory results.
Rational Design of Azothiophenes—Substitution Effects on the Switching Properties
Heindl, Andreas H.,Wegner, Hermann A.
supporting information, p. 13730 - 13737 (2020/10/02)
A series of substituted azothiophenes was prepared and investigated toward their isomerization behavior. Compared to azobenzene (AB), the presented compounds showed red-shifted absorption and almost quantitative photoisomerization to their (Z) states. Furthermore, it was found that electron-withdrawing substitution on the phenyl moiety increases, while electron-donating substitution decreases the thermal half-lives of the (Z)-isomers due to higher or lower stabilization by a lone pair–π interaction. Additionally, computational analysis of the isomerization revealed that a pure singlet state transition state is unlikely in azothiophenes. A pathway via intersystem crossing to a triplet energy surface of lower energy than the singlet surface provided a better fit with experimental data of the (Z)→(E) isomerization. The insights gained in this study provide the necessary guidelines to design effective thiophenylazo-photoswitches for applications in photopharmacology, material sciences, or solar energy harvesting applications.
Dual palladium-photoredox catalyzed chemoselective C-H arylation of phenylureas
Babu, Sakamuri Sarath,Shahid,Gopinath, Purushothaman
supporting information, p. 5985 - 5988 (2020/06/04)
A highly chemoselective C-H arylation of phenylureas has been accomplished using dual palladium-photoredox catalysis at room temperature without any additives, base or external oxidants. Regioselective C-H arylation ofN,N'-diaryl substituted unsymmetrical phenylureas has also been accomplished by a careful choice of aryl groups.
