- Protected Derivatives of (R)-Cysteine and (R)-Cysteinol
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The synthesis of N, O, S protected forms of (R)-cysteine and (R)-cysteinol as bicyclic derivatives is described.The reactivity and the preparation of substituted derivatives of these systems is also discussed.
- Gonzalez, Asensio,Lavilla, Rodolfo,Piniella, Juan F.,Alvarez-Larena, Angel
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- A novel thiazolidine compound induces caspase-9 dependent apoptosis in cancer cells
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The forward chemogenomics strategy allowed us to identify a potent cytotoxic thiazolidine compound as an apoptosis-inducing agent. Chemical structures were designed around a thiazolidine ring, a structure already noted for its anticancer properties. Initially, we evaluated these novel compounds on liver, breast, colon and endometrial cancer cell lines. The compound 3 (ALC67) showed the strongest cytotoxic activity (IC50 ~5 μM). Cell cycle analysis with ALC67 on liver cells revealed SubG1/G1 arrest bearing apoptosis. Furthermore we demonstrated that cytotoxicity of this compound was due to the activation of caspase-9 involved apoptotic pathway, which is death receptor independent.
- Onen-Bayram, F. Esra,Durmaz, Irem,Scherman, Daniel,Herscovici, Jean,Cetin-Atalay, Rengul
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p. 5094 - 5102
(2012/10/30)
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- Reversible thiazolidine exchange: A new reaction suitable for dynamic combinatorial chemistry
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New dynamic combinatorial libraries (DCLs) were generated using the reversible aminothiol exchange reaction of thiazolidines and aromatic aldehydes. The reaction proceeded in aqueous buffered media at pH 4 and room temperature to generate thermodynamically controlled mixtures of heterocycles. The synthesis of an enantiomerically pure thiazolidinyloxazolidine is also reported. The oxazolidine moiety could be exchanged in CH2Cl2 in the presence of catalytic p-TsOH.
- Saiz, Cecilia,Wipf, Peter,Manta, Eduardo,Mahler, Graciela
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supporting information; experimental part
p. 3170 - 3173
(2009/12/05)
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- Design, synthesis and evaluation of potent thymidylate synthase X inhibitors
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Three synthesized series of compounds based on a thiazolidine core allowed identification of potent inhibitors of thymidylate synthase X. The evaluation of the catalytic activity of the enzyme in the presence of these molecules revealed two distinct classes of compounds that inhibit ThyX with submicromolar concentrations, which could lead, after optimization, to effective inhibitors with potential biomedical interest.
- Esra Oenen,Boum, Yap,Jacquement, Claire,Spanedda, Maria Vittoria,Jaber, Nada,Scherman, Daniel,Myllykallio, Hannu,Herscovici, Jean
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scheme or table
p. 3628 - 3631
(2009/04/06)
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- A novel synthesis of (+)-biotin from L-cysteine
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(+)-Biotin (1) was synthesized in 25% overall yield over 11 steps from L-cysteine. The contiguous asymmetric centers at C-3a and C-6a were formed through a novel and highly stereoselective Lewis base-catalyzed cyanosilylation of α-amino aldehyde 3 to provide anti- O-TMS-cyanohydrin 4 with high stereoselectivity and in high yield (anti/syn = 92:8, 96%). Treatment of 4 with a di-Grignard reagent, 1,4-bis(bromomagnesio)butane, followed by carbon dioxide, efficiently installed the 4-carboxybutyl chain at C-4 to give keto acid 5. The final cyclization to bicyclic compound 7b, a precursor to 1, was realized by a palladium-catalyzed intramolecular allylic amination of cis-allylic carbonate 6b that was elaborated from 5.
- Seki, Masahiko,Mori, Yoshikazu,Hatsuda, Masanori,Yamada, Shin-ichi
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p. 5527 - 5536
(2007/10/03)
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- Cycloaddition reactions of thiazolidine derivatives. An approach to the synthesis of new functionalized heterocyclic systems
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A one-pot procedure for the synthesis of two functionalized tricyclic systems having structures of benzo[g]isoquinoline-5,10-dione and dihydrothieno[2,3-b]naphto-4,9-dione (DTNQ) is described. These new series were synthesized from cycloaddition reactions
- Gomez-Monterrey, Isabel M.,Campiglia, Pietro,Mazzoni, Orazio,Novellino, Ettore,Diurno, M.Vittoria
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p. 5755 - 5757
(2007/10/03)
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- Synthesis of Oxazolidines, Thiazolidines, and 5,6,7,8-Tetrahydro-1H,3H-pyrrolooxazole (or thiazole)-1,3-diones from β-Hydroxy- or β-Mercapto-α-amino Acid Esters
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2-Aryl-4-(ethoxycarbonyl)oxazolidines and thiazolidines (1) were prepared from the corresponding α-amino acid ethyl esters containing either hydroxyl or mercapto groups in the β position by fusion with some aromatic aldehydes.Dehydrogenation of 1 with N-b
- Badr, Mahmoud Zarif Amin,Aly, Morsy Mohamed,Fahmy, Atiat Mohamed,Mansour, Mansour Esmael Younis
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p. 1844 - 1847
(2007/10/02)
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