6326-49-4Relevant academic research and scientific papers
Synthesis of difluoromethyl and deuterium-labeled difluoromethyl thioethers from aliphatic electrophiles
Ding, Tianqi,Jiang, Lvqi,Yi, Wenbin
, p. 3995 - 3998 (2020/04/17)
A one-pot difluoromethylthiolation of alkyl electrophiles with thiourea and diethyl bromodifluoromethylphosphonate is described. The transition-metal-free approach, readily available reagents, and mild conditions provide a practical way for the synthesis of difluoromethyl thioethers. By changing the "H" source to the most commonly used "D" sources CD3OD and D2O, this strategy enables efficient synthesis of SCF2D-substituted molecules in good yields with high levels of D incorporation.
Convenient and environment-friendly synthesis of sulfonyl chlorides from S -alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation
Yang, Zhanhui,Xu, Jiaxi
, p. 1675 - 1682 (2013/07/27)
A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from 'waste water' can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable. Georg Thieme Verlag Stuttgart, New York.
Simple synthesis of sulfonyl chlorides from thiol precursors and derivatives by NaClO2-mediated oxidative chlorosulfonation
Yang, Zhanhui,Zheng, Yongpeng,Xu, Jiaxi
supporting information, p. 2165 - 2169 (2013/10/22)
A simple method to synthesize diverse sulfonyl chlorides through NaClO 2-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is presented. The approach features safe operation, environmental friendliness, convenient purification procedures, and delivers high yields of up to 96%. The procedure is also applicable to substrates such as thiols, disulfides, thioacetates, and xanthates. It is a versatile and convenient method for the synthesis of various sulfonyl chlorides from different thiol precursors and derivatives. Georg Thieme Verlag Stuttgart, New York.
Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues
Mostert, Samantha,Mentz, Wayne,Petzer, Anél,Bergh, Jacobus J.,Petzer, Jacobus P.
, p. 7040 - 7050 (2013/01/15)
In a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl)sulfanyl]caffeine (IC50 = 0.223 μM) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl]caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[(phenylethyl)sulfanyl]caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 μM. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl)sulfanyl]caffeine analogues.
Synthesis of N-glyoxyl prolyl and pipecolyl amides and thioesters and evaluation of their in vitro and in vivo nerve regenerative effects
Hamilton, Gregory S.,Wu, Yong-Qian,Limburg, David C.,Wilkinson, Douglas E.,Vaal, Mark J.,Li, Jia-He,Thomas, Christine,Huang, Wei,Sauer, Hansjorg,Ross, Douglas T.,Soni, Raj,Chen, Yi,Guo, Hongshi,Howorth, Pamela,Valentine, Heather,Liang, Shi,Spicer, Dawn,Fuller, Mike,Steiner, Joseph P.
, p. 3549 - 3557 (2007/10/03)
The recent discovery that small molecule ligands for the peptidyl-prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure-activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.
EFFECT OF VICINAL SUBSTITUENTS ON THE REACTIVITY IN BIMOLECULAR NUCLEOPHILIC SUBSTITUTION AT A SATURATED CARBON ATOM. TWO TYPES OF SUBSTITUENTS II. KINETICS OF THE REACTION OF THIOUREA WITH β-SUBSTITUTED BROMOETHANES IN ETHANOL
Ryazantsev, G. B.,Shaposhnikov, A. V.,Fedoseev, V. M.
, p. 1777 - 1782 (2007/10/02)
The kinetics of the reaction of thiourea with β-substituted bromoethanes in ethanol were studied by radiochromatography.The rate constants and activation parameters of the reactions were determined.It was shown that an isokinetic relationship is observed for the two types of substituents.The mechanisms of the effect of the vicinal substituents on the reactivity are discussed.
EFFECT OF VICINAL SUBSTITUENTS ON REACTIVITY IN BIMOLECULAR NUCLEOPHILIC SUBSTITUTION AT A SATURATED CARBON ATOM. TWO TYPES OF SUBSTITUENT I. KINETICS OF THE REACTIONS OF THIOUREA WITH β-SUBSTITUTED BROMOETHANES IN DIMETHYLFORMAMIDE
Ryazantsev, G. B.,Lys, Ya. I.,Fedoseev, V. M.
, p. 776 - 779 (2007/10/02)
The kinetics of the reaction of thiourea with β-substituted bromoethanes in DMFA were studied by radiochromatography.It was shown that there is no isokinetic relationship or Taft equation for all the substituents but that there are isokinetic relationships for two separate reaction series, one of which is described satisfactorily by a Taft equation taking account of the inductive and steric effects of the substituents.On the basis of the obtained data it is supposed that there are two types of vicinal substituents, which affect the reactivity of the bromine at the saturated carbon atom by different mechanisms.For the first type of substituent (H, F, Br, CH3, C6H5) the main factors determining the reactivity are the inductive and steric effects of the substituents.Substituents of the second type (COOH, COOC2H5, CN, NH3Br, SC(NH2)2Br) include charged or highly polar substituents, and this makes it possible to expect a field effect, leading to additional stabilization of the transition state.
