17564-64-6Relevant articles and documents
Synthesis, α-glucosidase inhibition and molecular docking studies of novel thiazolidine-2,4-dione or rhodanine derivatives
Wang, Guang-Cheng,Peng, Ya-Ping,Xie, Zhen-Zhen,Wang, Jing,Chen, Ming
, p. 1477 - 1484 (2017/07/25)
A series of novel thiazolidine-2,4-dione or rhodanine derivatives (5a-5k, 6a-6k) were synthesized and evaluated for their α-glucosidase inhibitory activity. The majority of compounds exhibited potent inhibitory activity in the range of 5.44 ± 0.13 to 50.45 ± 0.39 μM, when compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Among the compounds in the series, compounds 5k, 6a, 6b, 6e, 6h and 6k showed potent inhibitory potential with IC50 values of 20.95 ± 0.21, 16.11 ± 0.19, 7.72 ± 0.16, 7.91 ± 0.17, 6.59 ± 0.15 and 5.44 ± 0.13 μM, respectively. Compound 6k (IC50 = 5.44 ± 0.13 μM), containing chloro and rhodanine groups at the 2- and 4-positions of the phenyl ring respectively, was found to be the most active compound that inhibits α-glucosidase activity. Furthermore, molecular docking studies were performed to understand the binding interactions between the molecule and enzyme.
Efficient synthesis of N-protected 1-substituted homotaurines from a xanthate and olefins
Huang, Zhongyan,Xu, Jiaxi
, p. 1050 - 1056 (2013/02/23)
A series of N-protected 1-substituted homotaurines was synthesized efficiently from various olefins with O-ethyl S-2-phthalimidomethylxanthate as a sulfur-aminomethylation reagent via a radical addition and subsequent performic acid oxidation. The current method is a convenient and practical method for the synthesis of 1-substituted homotaurines with high yields and short synthetic route.
Aminomethylation of Michael acceptors: Complementary radical and polar approaches mediated by dialkylzincs
Maury, Julien,Mouysset, Dominique,Feray, Laurence,Marque, Sylvain R. A.,Siri, Didier,Bertrand, Michele P.
supporting information; experimental part, p. 3241 - 3247 (2012/05/20)
Phtalimidomethyl iodide and substituted maleimidomethyl iodide were used as radical precursors in dialkylzinc-mediated radical addition to diethyl fumarate. The reactions led stereoselectively to functionalized pyrrolizidines. The radical mechanism was supported by spin-trapping experiments and rationalized by theoretical calculations. Radical additions, on the one hand, and carbozincation followed by transmetalation with copper(I), on the other, were shown to be complementary methods to achieve the formal aminomethylation of activated unsaturated compounds. Copyright
Silver-catalyzed decarboxylative chlorination of aliphatic carboxylic acids
Wang, Zhentao,Zhu, Lin,Yin, Feng,Su, Zhongquan,Li, Zhaodong,Li, Chaozhong
experimental part, p. 4258 - 4263 (2012/04/10)
Decarboxylative halogenation of carboxylic acids, the Hunsdiecker reaction, is one of the fundamental functional group transformations in organic chemistry. As the initial method requires the preparations of strictly anhydrous silver carboxylates, several modifications have been developed to simplify the procedures. However, these methods suffer from the use of highly toxic reagents, harsh reaction conditions, or limited scope of application. In addition, none is catalytic for aliphatic carboxylic acids. In this Article, we report the first catalytic Hunsdiecker reaction of aliphatic carboxylic acids. Thus, with the catalysis of Ag(Phen)2OTf, the reactions of carboxylic acids with t-butyl hypochlorite afforded the corresponding chlorodecarboxylation products in high yields under mild conditions. This method is not only efficient and general, but also chemoselective. Moreover, it exhibits remarkable functional group compatibility, making it of more practical value in organic synthesis. The mechanism of single electron transfer followed by chlorine atom transfer is proposed for the catalytic chlorodecarboxylation.
NMR study of the tautomeric behavior of N -(α-Aminoalkyl)tetrazoles
Katritzky, Alan R.,El-Gendy, Bahaa El-Dien M.,Draghici, Bogdan,Hall, C. Dennis,Steel, Peter J.
scheme or table, p. 6468 - 6476 (2010/12/24)
N-(α-Aminoalkyl)tetrazoles exist in solution as equilibrium mixtures of N1 and N2 tautomers. The position of equilibrium depends significantly on the polarity of the solvent and the substituents in the tetrazole ring. Interconversion between individual tautomers is shown to proceed via tight ion-pair intermediates in which intramolecular recombination is faster than the intermolecular crossover since the latter probably requires solvent separation of ion-pair intermediates.
Convenient routes to trifluoromethyl-substituted pyridyl-isothiocyanates and isocyanates starting from 2,3-dichloro-5-trifluoromethyl pyridine
Fodor, Elena,Maftei, Catalin-Vasile,Mangalagiu, Ionel,Jones, Peter G.,Daniliuc, Constantin-Gabriel,Franz, M. Heiko,Neda, Ion
scheme or table, p. 559 - 564 (2011/08/22)
A convenient preparative route for the synthesis of 3-chloro-2- (isothiocyanatoethyl)-5-(trifluoromethyl)pyridine (1) and 3-chloro-2- (isocyanatoethyl)-5-(trifluoromethyl)pyridine (2) has been developed, involving 5 steps starting from 2, 3-dichloro-5-(trifluoromethyl)pyridine (3). All intermediates and final products were obtained in good yields and purity. The structure of one intermediate, 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl) malonate, was confirmed by X-ray crystallography.
Reaction of γ-dicarboxylic acids amides and imides with trifluoromethanesulfonamide and formaldehyde
Moskalik,Meshcheryakov,Shainyan
experimental part, p. 1644 - 1650 (2010/04/27)
Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and succinamide depending on the reaction conditions led alongside bis(trifluoromethanesulfonamido)methane to the formation of a substitution product, bis[(trifluoromethylsulfonyl)aminomethyl]succinamide, or to a cyclization product, N-[trifluoromethylsulfonyl)aminomethyl]succinimide. The attempt to obtain the latter by the reaction of the trifluoromethanesulfonamide sodium salt CF3SO2NHNa with N-chloromethylsuccinimide unexpectedly resulted in N,N-bis(succinimidomethyl)-trifluoromethanesulfonamide. Analogously the reaction of CF3SO2NHNa with N-chloromethyl-phthalimide gave N,N-bis(phthalimidomethyl)trifluoromethanesulfonamide. The reaction of CF3SO2NHNa with succinimide and phthalimide in water and alcohol solution resulted in the ring opening and further transformation of the formed monosubstituted N-(trifluoromethylsulfonyl)amides of succinic and phthalic acids.
Synthesis and photophysical properties of N-styrylazinones
Cho, Su-Dong,Hwang, Jaeyoung,Kim, Ho-Kyun,Yim, Heung-Sup,Kim, Jeum-Jong,Lee, Sang-Gyeong,Yoon, Yong-Jin
, p. 951 - 960 (2008/03/29)
(Chemical Equation Presented) N-Styrylazinones and 1-styrylbenzotriazine were synthesized, and their photophysical properties were investigated. (Z)- and/or (E)-N-Styrylazinones (or azine) 4 were prepared from the corresponding heterocycles 1 and benzaldehyde (3) by four methods. The absorption maxima of (Z)- and/or (E)-4a - 4j were measured in four solvents. Their absorption maxima showed a moderate dependence upon solvents. The absorption maxima of (Z)-isomers were blue-shifted as compared the corresponding (E)-isomers. Emission maxima, fluorescence band half-widths, 0,0 transition energies, Stokes shifts, and quantum yields of (Z)- and/or (E)-4a, 4b, 4d, 4e and 4j were measured in organic solvents. The fluorescence spectra show moderate solvatochroism. The fluorescence properties of N-styrylheterocycles vary with every heterocycles.
Stereoselective Amidoalkylation Reactions via N,O-Acetals
Arenz, Thomas,Frauenrath, Herbert,Raabe, Gerhard,Zorn, Martin
, p. 931 - 942 (2007/10/02)
The isomerization of N,O-acetals 1 yields N-acyl-O-vinyl acetals 2 or 2-aminomethyl-1,3-butadienes 10, depending on the nature of the nitrogen substituents.In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) the N,O-acetals 2h-u are converted stereoselectively into β-(N-acylamino)aldehydes 3.The relative configurations of the products 3 have been determined by X-ray analysis and 1H-NMR experiments.The mechanism of the reaction is discussed.Crossover experiments indicate an intermolecular course of the rearrangement. - Key Words: N,O-Acetals / Isomerization / Amidoalkylation, stereoselective / β-(N-Acylamino)aldehydes / 2-Aminomethyl-1,3-butadienes
Mechanism of Hydrolysis of O-Imidomethyl Derivatives of Phenols
Getz, John J.,Prankerd, Richard J.,Sloan, Kenneth B.
, p. 4913 - 4918 (2007/10/02)
Three series of O-imidomethyl derivatives of para-substituted phenolic compounds were synthesized and their rates of hydrolysis were studied.Saccharin, phthalimide, and succinimide served as the imide portions of the derivatives.Their rates of hydrolysis were found to be first order with respect to hydroxide from pH 7.0 to 10 or 11 and dependent on the acidity (leaving group potential) of both the imide and the phenol portions.The more acidic the imide or the phenol, the faster the rate of hydrolysis.However, the rates of hydrolysis were more sensitive to the acidity of the phenol.Trapping experiments with cyanide also suggested that the phenol anion was functioning as the leaving group in what is apparently an SN2 reaction.An amide derivative was found to hydrolyze more slowly than predicted from the analogous series and the pKa of the amide.This result is apparently due partially stereoelectronic constraints in the imide series that cause the CH2-O bond to be oriented more nearly perpendicular to the plane of the C(=O)N group and hence more accessible to nucleophilic attack.
