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108-98-5Relevant articles and documents
The Selective Deprotection of Thioesters Using Titanium(IV) Chloride/Zinc
Jin, Chung Keun,Jeong, Hyung Jae,Kim, Min Kyu,Kim, Ju Young,Yoon, Yong-Jin,Lee, Sang-Gyeong
, p. 1956 - 1958 (2001)
A new method for deprotection of thioesters using TiCl4/Zn at 0-25 deg C is described. The procedure chemoselectively cleaves the S-CO bond in thioesters in the presence of other carbonyl functional groups and other protecting groups to cleanly produce thiols.
Synthesis of 14-aryl-14H-7-thiadibenzo[a,j]anthracene
Khoramabadi-zad, Ahmad,Akbari, Safar-Ali,Shiri, Azam,Veisi, Hojat
, p. 2443 - 2449 (2005)
Preparation methods of dibenzoxanthene derivatives are surveyed alongside the synthesis of some of the titled compounds, which are the sulfur analogues of dibenzoxanthenes. Our new procedure for the conversion of phenols to thiophenols was used to prove the structure of such sulfur analogues. Copyright Taylor & Francis Inc.
Farnesyl Pyrophosphate Synthase as a Target for Drug Development: Discovery of Natural-Product-Derived Inhibitors and Their Activity in Pancreatic Cancer Cells
Han, Shuai,Li, Xin,Xia, Yun,Yu, Zhengsen,Cai, Ningning,Malwal, Satish R.,Han, Xu,Oldfield, Eric,Zhang, Yonghui
, p. 10867 - 10896 (2019)
Human farnesyl pyrophosphate synthase (Homo sapiens FPPS, HsFPPS) is a target for treating bone resorption diseases and some cancers. HsFPPS is potently inhibited by bisphosphonates, but due to poor cell penetration and distribution in soft tissue, there is currently interest in the development of non-bisphosphonate inhibitors as cancer therapeutics. Here, we report the discovery and development of HsFPPS inhibitors based on the phenolic diterpene carnosic acid (CA), an antimicrobial found in rosemary and sage, which showed better cellular anticancer activities than the bisphosphonate drug zoledronate in pancreatic cancer cell lines, as well as an HsFPPS-dependent mechanism of action. Hit-to-lead optimization of CA improved HsFPPS inhibition by >100-fold. A slow dissociation inhibition pattern and a noncompetitive allosteric binding mode were found, and cellular mechanism-of-action studies showed that these inhibitors inhibit tumor cell growth primarily by inhibiting HsFPPS, leading to downregulation of Ras prenylation and cell apoptosis. The discovery of this series of compounds together with proof-of-mechanism in pancreatic cancer cells may pave the way for targeting HsFPPS in soft tissue cancers using natural-product-derived inhibitors.
Palladium-Catalyzed Double Borylation of Diaryl Sulfoxides with Diboron
Saito, Hayate,Nogi, Keisuke,Yorimitsu, Hideki
, p. 4769 - 4774 (2017)
Borylation of the C-S bond of diaryl sulfoxides with bis(pinacolato)diboron (B 2 pin 2) is accomplished by means of a phosphine-ligated palladium catalyst and LiN(SiMe 3) 2 as a base. Both of the aryl rings of the diaryl sulfoxides are converted into borylated products.
A mild and practical deprotection method for benzyl thioethers
Akao, Atsushi,Nonoyama, Nobuaki,Yasuda, Nobuyoshi
, p. 5337 - 5340 (2006)
A highly effective and mild deprotection method was developed for benzyl thioethers using dibutylmagnesium in the presence of a catalytic amount of titanocene dichloride. This methodology is applicable to both aromatic and aliphatic benzyl thioethers.
Kinetics and Mechanism of the Aminolysis of O-Ethyl S-Aryl Ditihiocarbonates
Cabrera, Mauricio,Castro, Enrique A.,Salas, Mirtha,Santos, Jose G.,Sepulveda, Patricia
, p. 5324 - 5328 (1991)
The reactions of O-ethyl S-phenyl dithiocarbonate (1) and O-ethyl S-(p-nitrophenyl dithiocarbonate (2) with a series of secondary alicyclic amines, namely, piperidine, piperazine, 1-(β-hydroxyethyl)piperazine, morpholine, 1-formylpiperazine, and (with 2 only) piperazinium ion, are subject to a kinetic study at several pH values.The reaction leads to the corresponding thiocarbamates and thiophenols (measured as thiophenoxide ion by UV-vis spectrophotometry).Pseudo-first-order rate coefficients (kobsd) are found throughout (amine excess).The kinetics are first order in amine for the reactions of 2.The plots of kobsd vs for the reaction of 1, except with 1-formylpiperazine, are linear, but near the origin they are curved, showing a more complex rate equation.The reaction of 1 with 1-formylpiperazine shows a second-order dependence on the amine.No dependence on pH of the second-order rate constant values is observed.The findings are well-accommodated by a mechanistic model involving reversible nucleophilic attack on the thiocarbonyl group, two tetrahedral intermediates, 3 and 4, and a deprotonation step.The Bronsted-type plots obtained are linear (β1 = 0.22) for the reaction of 1 and curved for 2 (β1 = 0.2 and β2 = 0.8).The Bronsted-type plot obtained with the rate constants for amine expulsion from 3 is linear with β-1 = -0.67 and -0.54 for the reactions of 1 and 2, respectively.
First synthesis and characterization of vinylselenols and vinyltellurols
Guillemin, Jean-Claude,Bouayad, Asmae,Vijaykumar, Dange
, p. 1163 - 1164 (2000)
Vinylselenols and vinyltellurols have been prepared by slow addition of tributyltin hydride to the corresponding divinyldiselenide or divinylditelluride in tetraglyme.
Visible-Light-Induced Difluoropropargylation Reaction with Benzothiazoline as a Reductant
Chen, Jingzhi,Huang, Wenhao,Li, Ying,Cheng, Xu
, p. 1466 - 1472 (2018)
The difluoropropargyl group is a useful moiety for biological applications such as in vivo click chemistry for molecular imaging techniques. Silyl-protected bromodifluoropropyne is an important difluoropropargylation reagent with previously unexplored radical reactivity. Herein, we report visible-light-induced thiyl-radical-catalyzed hydrodifluoropropargylation reactions between silyl-protected bromodifluoropropyne and alkenes in the presence of benzothiazoline as a critical reductant. (Figure presented.).
Pd-PVP-Fe (palladium-poly(N-vinylpyrrolidone)-iron) catalyzed S-arylation of thiols with aryl halides in aqueous media
Ghaderi-Shekhi Abadi, Parvaneh,Rafiee, Ezzat,Joshaghani, Mohammad
, p. 162 - 170 (2016)
Pd-PVP-Fe (palladium-poly(N-vinylpyrrolidone)-iron) nano catalyst catalyzes selective C–S cross-coupling (S-arylation) reactions of thiols with aryl halides and avoids the formation of S–S (disulfide) homocoupling byproducts. The reactions were carried out in aqueous media using only 0.23?mol% palladium with high selectivity and short reaction time. The effects of the Pd0and Fe0moieties on the C–S cross-coupling reaction mechanism, yield, and selectivity were investigated. The yield and selectivity can be controlled by adjusting the order of adding the reactants and catalyst into the reaction medium. The X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), electron backscatter diffraction (EBSD) microscopy, energy dispersive X-ray (EDX) spectroscopy, and thermal gravimetric analysis (TGA) tools were used to characterize the catalyst. The C–S cross-coupling reaction process could be repeated up to six times without losing effectiveness. The metals leaching of Pd-PVP-Fe nanocatalyst after reusing cycles were investigated by atomic absorption spectroscopic (AAS) and EDX spectroscopy. The nature of Pd metal after the first run of the C–S cross-coupling reaction was studied by UV–vis spectrophotometry. The morphology of bimetallic nanocatalyst after the first run of the C–S cross-coupling reaction was investigated by SEM, EBSD, and EDX microscopy.
Catalytic Function of a 3,3'-Tetramethylene-bridged 4-Methylthiazolium Salt in the Reductive Cleavage of the Sulphur-Sulphur Bond of Disulphides with o-Methylbenzaldehyde and Bases
Inoue, Hiroo,Tamura, Shigeo
, p. 858 - 859 (1986)
A 3,3'-tetramethylene-bridged 4-methylthiazolium salt, in methanol containing o-methylbenzaldehyde and triethylamine or 1,5-diazabicycloundec-5-ene, catalyses the reduction of diphenyl disulphide and lipoamide to the corresponding thiols, with concomitant oxidation of o-methylbenzaldehyde to methyl o-methylbenzoate.