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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.
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.
Radiation-chemical transformation of elemental sulfur in the presence of ionic liquids
Tarasova,Zanin
, p. 46 - 49 (2015)
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Mustafa et al.
, p. 310 (1967)
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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.
Facile Conversions of Aliphatic Sulfonic Acids, Sulfinic Acids, Thiols, Sulfonates, Thiosulfonates, and Disulfides to the Corresponding Alkyl Iodides by Triphenylphosphine/Iodine
Oae, Shigeru,Togo, Hideo
, p. 371 - 373 (1981)
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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.
GAS-PHASE PYROLYSIS OF BIS(PHENYLTHIO)ACETYLENE
Voronkov, M. G.,Deryagina, E. N.,Sukhomazova, E. N.,Mirskova, A. N.,Seredkina, S. G.
, (1983)
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Alane - A chemoselective way to reduce phosphine oxides
Bootle-Wilbraham, Andrew,Head, Steve,Longstaff, James,Wyatt, Paul
, p. 5267 - 5270 (1999)
Phosphine oxides may be chemoselectively reduced to phosphines in excellent yield in the presence of several other functional groups using alane. An aqueous workup is not required.
SYNTHESIS OF 3-METHYL-2-PHENYLTHIOFURAN AND 1-FORMYL-3-METHYL-2,2-DI(PHENYLTHIO)CYCLOPROPANE
Kulikovich, O. G.,Tishchenko, I. G.,Roslik, N. A.
, p. 112 (1984)
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Rates and Equilibria of the Michael-Type Addition of Benzenethiol to 2-Cyclopenten-1-ones
Van Castelli, Valeria Axel,Bernardi, Fernando,Cort, Antonella Dalla,Mandolini, Luigi,Rossi, Ivan,Schiaffino, Luca
, p. 8122 - 8126 (1999)
The triethylamine-catalyzed addition reactions of benzenethiol to 2-cyclopenten-1-one and its 2-and 3-methyl derivatives have been found to be appreciably reversible in chloroform solution. Rates and equilibria have been carefully measured at 25°C in order to assess the negative influence on addition exerted by methyl groups substituted on the carbon-carbon double bond. 2-Methyl-2-cyclopenten-1-one has been found to react with benzenethiol under kinetic control to give the cis adduct as the sole detectable product in a highly stereoselective anti addition process. However, on prolonged reaction times the system slowly evolved toward a new state of equilibrium in which the more stable trans adduct, derived from a syn addition mode, was the predominant isomer.
Efficient Cu-catalyzed one-pot odorless synthesis of sulfides from triphenyltin chloride, aryl halides and S8 in PEG
Rostami, Abed,Rostami, Amin,Iranpoor, Nasser,Zolfigol, Mohammad Ali
, p. 192 - 195 (2016)
A novel method for the Cu(OAc)2 catalyzed synthesis of unsymmetrical sulfides from triphenyltin chloride and aryl halides using S8 as the sulfur source in PEG200 at 60-80°C is reported. Triphenyltin chloride is capable of delivering all of its phenyl groups to the product. Also, the copper catalyzed synthesis of symmetrical diaryl sulfides from aryl halides using S8 is described.
Plasmon-induced decarboxylation of mercaptobenzoic acid on nanoparticle film monitored by surface-enhanced Raman spectroscopy
Zong, Yi,Guo, Qinghua,Xu, Minmin,Yuan, Yaxian,Gu, Renao,Yao, Jianlin
, p. 31810 - 31816 (2014)
Surface plasmon plays an important role in surface catalysis reactions, and thus the tuning of plasmon on metal nanostructures and the extension of plasmon induced surface catalysis reactions have become important issues. Au nanoparticle monolayer film was fabricated by the assembling of Au nanoparticles at the liquid-air interface with numerous hot spots for strong surface plasmon coupling. A facile approach was developed to achieve the decarboxylation reaction driven by appropriate surface plasmon on the Au nanoparticle monolayer film surface, and surface enhanced Raman spectroscopy (SERS) has been developed as a sensitive tool for the in situ monitoring of the plasmon induced surface reaction. The effects of the power and wavelength of the laser and solution pH on the decarboxylation reaction were investigated. With laser illumination, para-mercaptobenzoic acid (PMBA) was transformed to thiophenol (TP), and the decarboxylation was enhanced on increasing the laser power and illumination time. The results revealed that the carboxylate groups of the adsorbed PMBA molecules were removed to produce TP, which were still adsorbed onto Au surfaces. The solution pH values exhibited a significant influence on the decarboxylation reaction. In air and neutral solution, decarboxylation proceeded at a slow rate to transform PMBA to TP, while it was absent in acidic solution. The deprotonated carboxylate group accelerated the decarboxylation for producing TP with a fast rate in alkaline solution. As a comparison, a similar plasmon driven decarboxylation reaction was observed on a Ag nanoparticle monolayer film surface. These results suggested that the transformation from PMBA to TP molecules on an Au nanoparticle film surface under laser illumination was associated with a surface-catalyzed reaction driven by local surface plasmon.
Transition-Metal-Free Approach for the Synthesis of 4-Aryl-quinolines from Alkynes and Anilines
Phanindrudu, Mandalaparthi,Wakade, Sandip Balasaheb,Tiwari, Dipak Kumar,Likhar, Pravin R.,Tiwari, Dharmendra Kumar
, p. 9137 - 9143 (2018)
An efficient and transition-metal-free approach for the synthesis of 4-arylquinolines from readily available anilines and alkynes in the presence of K2S2O8 and DMSO has been developed. A variety of alkynes and anilines having a diverse range of substitution patterns can undergo the one-pot cascade process successfully. Effectively, this method uses DMSO as one carbon source, thus providing a highly atom-economical and environmentally benign approach for the synthesis of 4-arylquinolines.
Ligand-free copper-catalyzed synthesis of diaryl thioethers from aryl halides and thioacetamide
Tao, Chuanzhou,Lv, Aifeng,Zhao, Nan,Yang, Shuai,Liu, Xiaolang,Zhou, Jian,Liu, Weiwei,Zhao, Jing
, p. 134 - 138 (2011)
Diaryl thioethers can be prepared via a copper-catalyzed cross-coupling between aryl halides and thioacetamide using Cs2CO3 as a base and DMSO-H2O as a solvent at 120 °C. Georg Thieme Verlag Stuttgart - New York.
A new procedure for thioester deprotection using thioglycolic acid in both homogeneous and heterogeneous phase
Mahler, Graciela,Saiz, Cecilia,Villamil, Valentina
, (2021/07/20)
Classic acetyl thioester protection/deprotection methodologies are widely used in organic synthesis, but deprotection step usually requires harsh conditions not suitable for labile substrates. In this work, a new method for thioester deprotection using a thiotransesterification approach is described. Firstly, thioglycolic acid (TGA) was identified as a good deprotecting reagent in solution. In order to develop a thiol polymer-supported reagent, TGA was anchored to a PEG-based resin through an amide bond (TG-NCO-SH). Both homogeneous and heterogeneous approaches were conveniently carried out at room temperature, in aqueous buffer at pH 8. The mild conditions were suitable for alkyl and phenyl thioesters. Moreover labile thioesters containing thiazolidine and oxazolidine scaffolds, bearing amine, ester and acetal functionalities were also deprotected. The polymer-supported TGA gave better deprotection yields compared to TGA in solution, yields ranging from 61 to 90%. The feasibility of the recovery and reuse of TG-NCO-SH reagent was explored, showing it can be reused at least five times without lossing the activity.
Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst
Chang, Yalin,Li, Huiyi,Tao, Chaofu,Wang, Aiping,Wei, Yongge,Xie, Ya,Yu, Han,Yu, Shunming
supporting information, p. 6059 - 6064 (2021/08/23)
Organo disulfides represent an abundant class of compounds in chemical biology, pharmaceutical fields, and industry. They are traditionally synthesized by the oxidation of mercaptan in the presence of an organic ligand supported metal catalyst or toxic oxidants under harsh conditions. Here, we disclose a highly-efficient pathway in which disulfide is synthesized by organic boric acid and Na2S2O3 using the catalyst (NH4)3[CrMo6O18(OH)6], demonstrating a high activity and excellent selectivity. Various boric acid derivatives have been successfully transformed into the corresponding disulfides. Mechanistic insights have been furnished based on the observation of intermediate and control experiments.
A Robust Pd-Catalyzed C-S Cross-Coupling Process Enabled by Ball-Milling
Browne, Duncan L.,Jones, Andrew C.,Nicholson, William I.,Smallman, Harry R.
supporting information, p. 7433 - 7438 (2020/10/09)
An operationally simple mechanochemical C-S coupling of aryl halides with thiols has been developed. The reaction process operates under benchtop conditions without the requirement for a (dry) solvent, an inert atmosphere, or catalyst preactivation. The reaction is finished within 3 h. The reaction is demonstrated across a broad range of substrates; the inclusion of zinc metal has been found to be critical in some instances, especially for coupling of alkyl thiols.