- Exploring hydrogen peroxide responsive thiazolidinone-based prodrugs
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A novel approach for developing prodrugs based on masked carboxylic acids is described. Rather than using conventional esterase-based activation, thiazolidinone protecting groups have been identified that can reveal carboxylic acid groups upon activation by hydrogen peroxide. This may prove valuable in the continuing development of prodrug strategies that rely on reactive oxygen species (ROS) as a trigger. This journal is
- Perez, Christian,Monserrat, Jean-Philippe,Chen, Yao,Cohen, Seth M.
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supporting information
p. 7116 - 7119
(2015/04/27)
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- Ni(II) Tol-BINAP-catalyzed enantioselective orthoester alkylations of N-acylthiazolidinethiones
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The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to
- Evans, David A.,Thomson, Began J.
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p. 10506 - 10507
(2007/10/03)
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- DCC/DMAP-Mediated Coupling of Carboxylic Acids with Oxazolidinones and Thiazolidinethiones
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Dicyclohexylcarbodiimide and catalytic dimethylaminopyridine were successfully used in the coupling of carboxylic acids with oxazolidinones and thiazolidinethiones. The acylated products were obtained in good yields.
- Andrade, Carlos Kleber Z.,Rocha, Rafael O.,Vercillo, Otilie E.,Silva, Wender A.,Matos, Ricardo Alexandre F.
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p. 2351 - 2352
(2007/10/03)
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- Beziehung zwischen C(O)-N-Verdrillungswinkel und chemischer Verschiebung der 17O-NMR-Signale bei verdrillten Amiden
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Stichworte: Amide/ NMR-Spektroskopie/ Strukturaufklaerung/ Thione
- Yamada, Shinji
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p. 1224 - 1226
(2007/10/02)
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- Monitored Aminolysis of 3-Acyl-1,3-thiazolidine-2-thiones: Synthesis of Amides and Amide Alkaloids
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A functional heterocycle, 3-acyl-1,3-thiazolidine-2-thione has been shown to be effective as an acylating reagent for the amino group.ATT (1) was readily prepared by several methods, and reacted with various amino compounds in CHCl3, CH2Cl2, THF, EtOH, THF-H2O, or sulfolane to afford the corresponding amides, 2a-w and 3-10 in very high yields within a short time.This reagent exhibits high chemo-selectivity.Its reaction with the diamines 13 and 15 and the triamine 29, which include a primary amino group(s) and a secondary amino group, gave the products acylated only at the primary amino group(s), 14, 16, and 30, respectively, in high yields.Aminoalcohols and aminophenols were chemoselectively converted into acylaminoalcohols and acylaminophenols, respectively, by ATT (1).By utilizing this method, several amide alkaloids (26, 28, 30, and 34) were efficiently synthesized.This new aminolysis can be monitored by the disappearance of the yellow color of the starting materials, ATT (1); it is remarkably characteristic of this reaction. Keywords - monitored aminolysis; 3-acyl-1,3-thiazolidine-2-thione; high chemo-selectivity; amide synthesis; fagaramide; dolicotheline; spermidine; maytenine; N-ferulyltryptamine
- Nagao, Yoshimitsu,Seno, Kaoru,Kawabata, Kohji,Miyasaka, Tadao,Takao, Sachiko,Fujita, Eiichi
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p. 2687 - 2699
(2007/10/02)
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- MONITORED AMINOLYSIS OF 3-ACYLTHIAZOLIDINE-2-THIONE : A NEW CONVENIENT SYNTHESIS OF AMIDE
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3-Acylthiazolidine-2-thiones (1) were easily prepared and they were treated with several amines in dichloromethane to give amides 4 in very high yields within a short time.Aminoalcohols and aminophenols were selectively converted into acylaminoalcohols and acylaminophenols, respectively, by this reaction.One can monitor the reaction by disappearance of the yellow color of the starting material 1.Some amide alkaloids (15-18) have effectively been synthesized.
- Nagao, Yoshimitsu,Seno, Kaoru,Kawabata, Kohji,Miyasaka, Tadayo,Takao, Sachiko,Fujita, Eiichi
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p. 841 - 844
(2007/10/02)
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- PHOTOCHEMICAL ACTIVATION OF THE CARBOXYL GROUP VIA N-ACYL-2-THIONOTHIAZOLIDINES
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Photolysis of N-acyl derivatives of 2-thionothiazolidine in the presence of ethanol affords ethyl esters; a mechanism involving γ-hydrogen abstraction by sulfur is postulated.
- Burton, Lester P.J.,White, James D.
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p. 3147 - 3150
(2007/10/02)
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