52711-30-5Relevant academic research and scientific papers
Phthalide synthesis through dehydrogenated lactonization of the C(sp3)-H bond by photoredox catalysis
Cai, Shunyou,Cai, Zhixiong,Chen, Shanyi,Huang, Mingqiang,Lai, Qihong,Lin, Yulin,Liu, Chao,Liu, Hui
supporting information, p. 8212 - 8216 (2021/10/29)
A practical and efficient method is established for the direct oxidative lactonization of the C(sp3)-H bonds relying on visible-light-induced photoredox catalysis. This protocol expediently allows the delivery of diverse phthalides using oxygen as the sole terminal oxidant under metal-free conditions at room temperature. Notably, the choice of an appropriate hydrogen atom transfer (HAT) cocatalyst is revealed to be critical for the success of this process.
Diselenides and benzisoselenazolones as antiproliferative agents and glutathione-S-transferase inhibitors
Krasowska, Dorota,Iraci, Nunzio,Santi, Claudio,Drabowicz, Józef,Cieslak, Marcin,Ka?mierczak-Barańska, Julia,Palomba, Martina,Królewska-Golińska, Karolina,Magiera, Jakub,Sancineto, Luca
, (2019/08/20)
A series of variously functionalized selenium-containing compounds were purposely synthesized and evaluated against a panel of cancer cell lines. Most of the compounds showed an interesting cytotoxicity profile with compound 5 showing a potent activity on MCF7 cells. The ethyl amino derivative 5 acts synergistically with cis-platin and inhibits the GST enzyme with a potency that well correlates with the cytotoxicity observed in MCF7 cells. A computational analysis suggests a possible binding mode on the GST enzyme. As the main outcome of the present study, the ethyl amino derivative 5 emerged as a valid lead compound for further, future developments.
CERTAIN PLADIENOLIDE COMPOUNDS AND METHODS OF USE
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Page/Page column 268, (2019/11/04)
The present disclosure provides novel pladienolide compounds, pharmaceutical compositions containing such compounds, and methods for using the compounds as therapeutic agents. These compounds may be useful in the treatment of cancers, particularly cancers in which agents that target the spliceosome and mutations therein are known to be useful. Also provided herein are methods of treating cancers by administering at least one compound disclosed herein and at least one additional therapy.
Hypercoordinated organotin(IV) compounds containing C,O- and C,N- chelating ligands: Synthesis, characterisation, DFT studies and polymerization behaviour
Khan, Aman,Pau, Jeffrey,Loungxay, Julie,Magobenny, Timbila,Wylie, R. Stephen,Lough, Alan J.,Foucher, Daniel
supporting information, (2019/09/12)
A series of 2-methoxymethyl tetraorganotins [2-(MeOCH2)C6H4]SnR3 (21: R = Ph; 22: R = n-Bu; 23: R = Me), diorganotin chlorides [2-(MeOCH2)C6H4]R2SnCl (24: R = Ph; 25a, 25b: R = n-Bu), monoorganotin dichlorides [2-(MeOCH2)C6H4]RSnCl2 (26: R = Ph; 27: R = n-Bu; 28: R = Me) and the tin trichloride [2-(MeOCH2)C6H4]SnCl3 (29) were successfully prepared from the reaction of the organolithium, [2-(MeOCH2)C6H4]Li, and the appropriate chlorostannane. Similarly, a series of dimethylamino stannanes including the tetraorganotin [2-(Me2NCH2)C6H4]SnPh3 (30), the diorganotin halides [2-(Me2NCH2)C6H4]Ph2SnX (34: X = Cl; 35: X = Br), dichlorides [2-(Me2NCH2)C6H4]RSnCl2 (38: R = Ph; 39: R = n-Bu; 40: R = Me) and the tribromide [2-(Me2NCH2)C6H4]SnBr3 (37) were prepared by reaction of the appropriate organochlorostannane and the organolithium [2-(Me2NCH2)C6H4]Li followed by selective halogenations in the case of 34–37. 2-Methoxymethyl and dimethylamino diorganotin dichlorides (27, 28 and 39, 40) were hydrogenated with LiAlH4 to produce new 2-methoxymethyl [2-(MeOCH2)C6H4]RSnH2 (41: R = n-Bu; 42: R = Me) and dimethylamino [2-(Me2NCH2)C6H4]RSnH2 (44: R = n-Bu; 45: R = Me) dihydrides. X-ray structure determination of 30 revealed a nearly tetrahedral stannane, while structural analysis of 24, 29 and 40 display distorted trigonal bipyramidal geometry at Sn with Cl trans to the datively coordinated heteroatom. A selection of DFT methods were assessed for accuracy in predicting the solid-state geometries of the hypercoordinate Sn complexes. Catalytic dehydrocoupling of C,O- (41) and C,N- (44) diorganotin dihydrides was explored using Wilkinson's catalyst at RT leading to the recovery of modest molecular weight polymers (52: Mw = 3.03 × 104 Da, PDI = 1.4, 53: Mw = 3.1 × 104 Da, PDI = 1.86). The new rigid polymers were isolated in moderate (52: 65%) and low yields (53: 18%) and were found to be amorphous by DSC.
Highly selective and scalable fullerene-cation-mediated synthesis accessing cyclo[60]fullerenes with five-membered carbon ring and their application to perovskite solar cells
Lin, Hao-Sheng,Jeon, Il,Chen, Yingqian,Yang, Xiao-Yu,Nakagawa, Takafumi,Maruyama, Shigeo,Manzhos, Sergei,Matsuo, Yutaka
, p. 8432 - 8439 (2019/10/16)
Cyclo[60]fullerenes are widely used in many applications including photovoltaic devices owing to their high electron affinity and mobility for an organic molecule. However, their synthesis has been limited to certain derivatives with low yields. In this work, a fullerene-cation-mediated synthesis, accessing a new class of five-membered carbon ring cyclo[60]fullerenes with high yields of up to 93% is showcased. This method utilizes aryl[60]fullerene cations, ArC60 +, as intermediates, which are generated in situ by heating the aryl[60]fullerenyl dimers in the presence of CuBr2. In addition, five-membered carbon ring cyclo[60]fullerenes display excellent device applicability when they are used in perovskite solar cells as over-coating layers of electron-transporting layers. A power conversion efficiency of 20.7% is achieved owing to the favorable energy alignment, optimized substrate design, and electrochemical stability of the five-membered carbon ring fullerenes.
Iron(III) Chloride/Dialkyl Diselenides-Promoted Cascade Cyclization of ortho-Diynyl Benzyl Chalcogenides
do Carmo Pinheiro, Roberto,Back, Davi F.,Zeni, Gilson
supporting information, p. 1866 - 1873 (2019/03/08)
Treatment of ortho-diynyl benzyl chalcogenides with a mixture of iron(III) chloride and diorganyl diselenides led to functionalized chalcogen isochromene-fused chalcogenophene derivatives. The reaction parameters were studied and the results indicated tha
Visible light mediated oxidation of benzylic sp3 C-H bonds using catalytic 1,4-hydroquinone, or its biorenewable glucoside, arbutin, as a pre-oxidant
Finney, Laura C.,Mitchell, Lorna J.,Moody, Christopher J.
supporting information, p. 2242 - 2249 (2018/05/28)
Benzylic ethers undergo a visible light induced C-H activation and oxygen insertion to give the corresponding benzoate esters in moderate to good yields. The conditions employ substoichiometric amounts of 1,4-hydroquinone with copper(ii) chloride dihydrate as an electron-transfer mediator, oxygen as the terminal oxidant and dimethyl carbonate as solvent under visible light irradiation. The naturally occurring glucoside, arbutin, which is commercially available or can be accessed via extraction of the leaves of bearberry (Arctostaphylos uva-ursi) or elephant ears (Bergenia crassifolia) can be used as a biorenewable source of 1,4-hydroquinone. The methodology exploits the increase in oxidizing ability of quinones upon irradiation with visible light, and offers a sustainable alternative for the late stage oxidative functionalization of benzylic C-H bonds. It is applicable to a range of cyclic benzylic ethers such as isochromans and phthalans, and simple benzyl alkyl ethers. It can also be applied in the oxidation of benzylic amines into amides, and of diarylmethanes into the corresponding ketones. Mechanistic studies suggest that the reaction proceeds by H-abstraction by the photo-excited triplet benzoquinone to give a benzylic radical that subsequently reacts with molecular oxygen.
Investigation of Chemical Stability of Dihalogenated Organotelluranes in Organic-Aqueous Media: The Protagonism of Water
Teixeira, Mariana L.,Menezes, Leociley R. A.,Barison, Andersson,De Oliveira, Alfredo R. M.,Piovan, Leandro
, p. 7341 - 7346 (2018/07/29)
The biological activity of tellurium compounds is closely related to the tellurium oxidation state or some of their structural features. Hypervalent dihalogenated organotelluranes 1-[butyl(dichloro)-λ4-tellanyl]-2-(methoxymethyl)benzene (1a) an
Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans
Zheng, Hong-Xing,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
supporting information, p. 3310 - 3313 (2018/06/11)
An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.
77Se and 125Te NMR spectroscopy on a selectivity study of organochalcogenanes with L-amino acids
Silva, Marcio S.,Andrade, Leandro H.
, p. 5924 - 5929 (2015/06/02)
The hypervalent selenium- and tellurium-containing compounds (halo-organoselenuranes and halo-organotelluranes) were treated with amino acids to evaluate their reactivity and chemoselectivity by 1H, 13C, 77Se and 125
