147-93-3Relevant academic research and scientific papers
Intramolecular Electrostatic and General Acid Catalysis in the Hydrolysis of O,S-Thioacetals
Fife, Thomas H.,Przystas, Theodore J.
, p. 292 - 299 (1980)
The pH-independent release of thiophenolate ion from phthalaldehydic acid O-methyl S-phenyl thioacetal in H2O at 50 deg C and at pH values where the carboxyl group is ionized is 22 times faster than the corresponding reaction in hydrolysis of the terephthalaldehydic acid derivative.This rate difference arises becouse of electrostatic stabilization of the developing carbanium ion by the neighboring carboxylate ion.In the view of the large amount of C-S bond breaking in the transition state the rate enhancement due to electrostatic effects must be near maximal in water for reactions in which a methoxybenzyl carbonium ion is produced.The plot of log kobsd vs. pH for release of thiosalicylic acid from phthalaldehydic acid O-methyl S-(o-carboxyphenyl) thioacetal at 50 deg C in 50percent dioxane-H2O shows hydronium ion catalysis at low pH, and from pH 3 to 7 the profile is bell shaped.The value of the rate constant k2 for hydronium ion catalyzed reaction of the dianionic species is 6*106 greater than the second-order rate constant kH for hydronium ion catalyzed hydrolysis of the dimethyl ester and is 360-fold greater than the corresponding rate constant of terephthalaldehydic acid O-methyl S-(o-carboxyphenyl) thioacetal.The hydronium ion catalyzed neutral species reaction of phthaladehydic acid O-methyl S-(o-carboxyphenyl) thioacetal is retarded in 50percent dioxane-H2O as compared with H2O, but k2 is accelerated 50-fold.Both carboxyl groups are participating in hydrolysis of the monoanionic species, i.e., intramolecular general acid catalysis is occurring in conjunction with electrostatic stabilization effects.It is likely that intramolecular general acid catalysis also occurs in hydrolysis of benzaldehyde O-methyl S-(o-carboxyphenyl) thioacetal and terephthalaldehydic acid O-methyl S-(o-carboxyphenyl) thioacetal, but rate enhancements are small in comparison with corresponding O,O-acetals.The significant electrostatic stabilization effects in the general-acid-catalyzed reaction of phthalaldehydic acid O-methyl S-(o-carboxyphenyl) thioacetal in contrast with the absence of such effects in the intramolecular general-acid-catalyzed reaction of phthalaldehydic acid O-methyl O-salicyl acetal shows that much more bond breaking is required in the transition state in reaction of the thioacetal.The factors influencing concerted bifunctional catalysis are discussed.
First electrospun immobilized molybdenum complex on bio iron oxide nanofiber for green oxidation of alcohols
Noghi, Sedighe Abbaspour,Naeimi, Atena,Hamidian, Hooshang
, p. 229 - 237 (2018)
Bio iron oxide was synthesized from natural Sesbania sesban plant and modified by a molybdenum complex (Fe2O3/MoSB). Fe2O3/MoSB was deposited on polyvinyl alcohol (PVA) using a conventional single nozzle electrospinning technique (PVA/Fe2O3/MoSB). TEM, SEM, AFM, FT-IR, TGA, EDAX, and elemental analysis were used to determine fiber compositional information. The catalytic efficiency of electrospun PVA/Fe2O3/MoSB nanofiber in the oxidation of alcohols was exploited. The green reactions were conducted at solvent free conditions as a green media in the presence of H2O2 to have the desired aldehydes and tert-butyl hydrogen peroxide to obtain acid products in high yields and excellent selectivity. The survival of this nanocomposite was investigated and it could be reused and recycled in consecutive runs.
Scaffold Diversity Inspired by the Natural Product Evodiamine: Discovery of Highly Potent and Multitargeting Antitumor Agents
Wang, Shengzheng,Fang, Kun,Dong, Guoqiang,Chen, Shuqiang,Liu, Na,Miao, Zhenyuan,Yao, Jianzhong,Li, Jian,Zhang, Wannian,Sheng, Chunquan
, p. 6678 - 6696 (2015/09/07)
A critical question in natural product-based drug discovery is how to translate the product into drug-like molecules with optimal pharmacological properties. The generation of natural product-inspired scaffold diversity is an effective but challenging strategy to investigate the broader chemical space and identify promising drug leads. Extending our efforts to the natural product evodiamine, a diverse library containing 11 evodiamine-inspired novel scaffolds and their derivatives were designed and synthesized. Most of them showed good to excellent antitumor activity against various human cancer cell lines. In particular, 3-chloro-10-hydroxyl thio-evodiamine (66c) showed excellent in vitro and in vivo antitumor efficacy with good tolerability and low toxicity. Antitumor mechanism and target profiling studies indicate that compound 66c is the first-in-class triple topoisomerase I/topoisomerase II/tubulin inhibitor. Overall, this study provided an effective strategy for natural product-based drug discovery. (Figure Presented).
Efficient Cu-catalyzed base-free C-S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides
Soria-Castro, Silvia M.,Penenory, Alicia B.
, p. 467 - 475 (2013/05/08)
S-aryl thioacetates can be prepared by reaction of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as a ligand in toluene at 100°C after 24 h. Under microwave irradiation the time was drastically reduced to 2 h. Both procedures are simple and involve a low-cost catalytic system. This methodology was also applied to the "one-pot" synthesis of target heterocycles, such as 3H-benzo[c][1,2]dithiol-3-one and 2-methylbenzothiazole, alkyl aryl sulfides, diaryl disulfides and asymmetric diaryl sulfides in good yields.
CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides in aqueous solution
Xu, Hua-Jian,Liang, Yu-Feng,Cai, Zhen-Ya,Qi, Hong-Xia,Yang, Chun-Yan,Feng, Yi-Si
experimental part, p. 2296 - 2300 (2011/06/17)
CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides was developed in the absence of both ligands and organic solvents. Anilines were formed selectively with ammonia competing with hydroxylation and thiophenols were generated selectively with sulfur powder after subsequent reduction competing with hydroxylation and amination.
A general and efficient approach to aryl thiols: Cul-catalyzed coupling of aryl iodides with sulfur and subsequent reduction
Jiang, Yongwen,Qin, Yuxia,Xie, Siwei,Zhang, Xiaojing,Dong, Jinhua,Ma, Dawei
supporting information; scheme or table, p. 5250 - 5253 (2009/12/28)
A Cul-catalyzed coupling reaction of aryl iodides and sulfur powder takes place in the presence of K2CO3 at 90 °C. The coupling mixture is directly treated with NaBH4 or triphenylphosphine to afford aryl thiols in good to
Identification of 2-amino-5-(thioaryl)thiazoles as inhibitors of nerve growth factor receptor TrkA
Kim, Soong-Hoon,Tokarski, John S.,Leavitt, Kenneth J.,Fink, Brian E.,Salvati, Mark E.,Moquin, Robert,Obermeier, Mary T.,Trainor, George L.,Vite, Gregory G.,Stadnick, Linda K.,Lippy, Jonathan S.,You, Dan,Lorenzi, Matthew V.,Chen, Ping
, p. 634 - 639 (2008/09/18)
2-Amino-5-(thioaryl)thiazoles are potent inhibitors of TrkA (e.g., 20h, TrkA IC50 = 0.6 nM) that show anti-proliferative effect in cellular assays. A proposed inhibitor binding mode to TrkA active site is consistent with key SAR observations.
METHOD FOR PRODUCING THIOSALICYLIC ACID
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Page 3, (2008/06/13)
The present invention relates to a method for causing sodium sulfide or a mixture of sodium sulfide and sulfur to react with diazonium salt formed by diazotizing anthranilic acid, wherein the Na/S atomic ratio as calculated on the basis of the employed sodium sulfide and sulfur is adjusted to within the range of 1.33 to 2.0 during the reaction. Thus is made practicable the manufacture of thiosalicylic acid in a high yield without going through the individual route of isolating and reducing dithiosalicylic acid.
A general and highly regio and stereoselective method for the synthesis of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones through palladium-copper catalysis
Nandi, Bidisha,Kundu, Nitya G.
, p. 1649 - 1655 (2007/10/03)
A palladium-copper-catalysed procedure for the synthesis of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a-5h is developed. 3-[2-(Methoxycarbonyl)phenylthio]propyne 2 reacts with aryl iodides 3a-3h in the presence of bis(triphenylphosphine)palladium(II) dichloride, copper(I) iodide and triethylamine in acetonitrile to furnish the disubstituted alkynes 4a-4h in good yields (70-84%). These on alkaline hydrolysis and subsequent cyclisation of the carboxylic acids formed with copper(I) iodide (20 mol%) and triethylamine in tetrahydrofuran under reflux afford (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a-5h in 61-70% yield rather than the expected benzoxathiepinones 6. The reactions of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a and 5g with nucleophites and the hydrogenation of compounds 5a, 5b and 5d are also studied.
Novel inhibitors of the prenylated protein methyltransferase reveal distinctive structural requirements
Marciano, Daniele,Aharonson, Ziporet,Varsano, Tal,Haklai, Roni,Kloog, Yoel
, p. 1709 - 1714 (2007/10/03)
Inhibitors of a prenylated protein methyltransferase were synthesized and evaluated. S-farnesyl-5-fluorothiosalicylic acid and the 5-chloro analog (but not the 4-fluoro, 4-chloro or 3-chloro analogs) were potent inhibitors, as was the parent compound S-farnesyl thiosalicylic acid (FTS), whose methyl ester was far less active. S-geranyl and S-geranylgeranyl thiosalicylic acids were more than ten times less potent than FTS.
