64984-60-7Relevant academic research and scientific papers
Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: Application to the synthesis of vernakalant
Garad, Dnyaneshwar N.,Tanpure, Subhash D.,Mhaske, Santosh B.
supporting information, p. 1008 - 1016 (2015/08/18)
Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.
Palladium-catalyzed C - O hydrogenolysis in γ-hydroxy γ-lactams as an efficient approach to 5-alkyl(aryl)pyrrolidin-2-ones
Turova,Berezhnaya,Starodubtseva,Ferapontov,Vinogradov
, p. 859 - 863 (2015/12/24)
5-R-Pyrrolidin-2-ones were synthesized by Pd/Sibunit-catalyzed C - O hydrogenolysis of 5-R-5-hydroxypyrrolidin-2-ones with molecular hydrogen.
High affinity ligands and potent antagonists for the α1D- adrenergic receptor. Novel 3,8-disubstituted [1]benzothieno[3,2-d]pyrimidine derivatives
Romeo, Giuseppe,Salerno, Loredana,Pittalà, Valeria,Modica, Maria N.,Siracusa, Maria A.,Materia, Luisa,Buccioni, Michela,Marucci, Gabriella,Minneman, Kenneth P.
, p. 419 - 432 (2014/07/21)
A new series of high affinity ligands and antagonists for the α1D-adrenergic receptor (AR) has been discovered. New molecules present a [1]benzothieno[3,2-d]pyrimidin-2,4(1H,3H)-dione or a [1]benzothieno[3,2-d]pyrimidin-4(3H)-one scaffold and bear a 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl moiety in the 3-position and various amide substituents in the 8-position. In binding assays at the three human cloned α1A-, α1B-, and α1D-AR subtypes, they showed high affinity values, particularly for the α1D-AR subtype. Compound 22 (RX18), N1-methyl-N 5-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxo-1,2,3, 4-tetrahydro[1]benzothieno[3,2-d]pyrimidin-8-yl]-N1-(phenylmethyl) pentanediamide, was the most interesting in the series displaying very high affinity (pKi = 10.25) and potent antagonism (pKb = 9.15) when tested in a functional assay at the α1D-AR.
A convenient one-pot synthesis of polysubstituted pyrroles from N-protected succinimides
Kobeissi, Marwan,Yazbeck, Ogaritte,Chreim, Yamama
supporting information, p. 2523 - 2526 (2014/05/06)
The dienamine products formed by the reaction between polysubstituted succinimides and the Petasis reagent were subjected to isomerization under mild acidic conditions to give polysubstituted pyrroles in excellent yields (85-95%). The scope and limitations of this methodology are explored.
Regioselective synthesis of 1-alkyl-5-(indol-3-yl- and -2-yl)pyrrolidin-2- ones from available reagents
Sadovoy,Kovrov,Golubeva,Sviridova
experimental part, p. 1215 - 1223 (2011/10/09)
The reaction under mild conditions of 1-alkyl-5-hydroxypyrrolidin-2-ones with different indoles having a free 3 position leads exclusively to 1-alkyl-5-(indol-3-yl)pyrrolidin-2-ones but if position 3 is occupied to 1-alkyl-5-(indol-2-yl)pyrrolidin-2-ones.
Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds
Sortino,Garibotto,Cechinel Filho,Gupta,Enriz,Zacchino
experimental part, p. 2823 - 2834 (2011/06/21)
The synthesis, in vitro evaluation and SAR studies of 67 maleimides and derivatives acting as antifungal agents are reported. A detailed SAR study supported by theoretical calculations led us to determine that: an intact maleimido ring appears to be necessary for a strong antifungal activity, dissimilarly affected by the substituents in positions 2 and 3. The best activities were shown by 2,3-nonsubstituted followed by 2,3 dichloro- and 2-methyl-substituted maleimides. They all were fungicide rather than fungistatic enhancing the importance of their antifungal activity. 2,3-Dimethyl and 2,3-diphenyl-maleimides possessed marginal or null activity. The presence of a flexible connecting chain in N-phenylalkyl maleimides appears not to be essential for antifungal activity, although its length shows a correlation with the antifungal behavior, displaying maleimides with alkyl chains of n = 3 and n = 4 the best antifungal activities in most fungi. Different substituents on the benzene ring did not have a clear influence on the activity. Values of chemical potential properties as well as of energy do not sufficiently discriminate between active and inactive compounds. Nevertheless, it was found that, although log P alone is not strong enough to properly predict the antifungal activity, the comparison of its values for compounds within the same sub-type, showed an enhancement of antifungal activity along with an increment of lipophilicity. In addition, the LUMO's electronic clouds of the highly active compounds showed to be concentrated on the imido ring, indicating that their carbon atoms are potential sites for nucleophilic attack. Same results were obtained from MEPs. Most of the active compounds did not show cytotoxic activity against human cancer cell lines and no one possessed hemolytic activity, indicating that their activity is selective to pathogenic fungi and that they are not toxic at MIC concentrations.
Ligand-based modelling followed by synthetic exploration unveil novel glycogen phosphorylase inhibitory leads
Habash, Maha,Taha, Mutasem O.
experimental part, p. 4746 - 4771 (2011/09/20)
Glycogen phosphorylase (GP) is a valid anti-diabetic target. Accordingly, we applied a drug discovery workflow to unveil novel inhibitory GP leads via combining pharmacophore modeling, QSAR analysis and in silico screening, followed by synthetic exploration of active hits. Virtual screening identified six low micromolar inhibitory leads from the National Cancer Institute (NCI) list of compounds. The most potent hits exhibited anti-GP IC50 values of 3.2 and 4.1 μM. Synthetic exploration of hit 59 (IC50 = 4.1 μM) yielded 25 lead inhibitors with the best illustrating IC50 of 3.0 μM. Interestingly, we prepared several novel mixed oxalyl amide anti-GP leads employing new chemical reaction involving succinic acid-based adducts.
The synthesis and characterization of solvatochromic maleimide-fused N-allyl- and N-alkyl-substituted 1,4-dithiines and diels-alder reactions with anthracene
Guelten, Sirin
experimental part, p. 188 - 193 (2010/04/24)
(Chemical Equation Presented) A simple and facile access to new solvatochromic maleimide-fused N-allyl- and N-alkyl-substituted 1,4-dithiines from the corresponding N-substituted succinamic acid derivatives in one-pot with oxidation by thionyl chloride is described. The Diels-Alder reaction of these 1,4-dithiines with anthracene has been investigated. The 1,4-dithiine derivatives react smoothly with anthracene via charge-transfer complexes to form the Diels-Alder adducts in excellent yields.
Atypical oxidation reaction by thionyl chloride: Easy two-step synthesis of N-alkyl-1,4-dithiines
Valla, Alain,Cartier, Dominique,Zentz, Frederic,Labia, Roger
, p. 3591 - 3597 (2007/10/03)
Easy two-step synthesis of a series of dithiines was performed from succinic anhydride via cyclization of the corresponding 4-(alkylamino)-4- oxobutanoic acids (succinamic acids). The reaction, carried out in polar aprotic solvents, gave 4,8-dithiine-indacene-1,3,5,7-tetraones (diimides 3) via 3,7-bis-4,8-dithia-indacene-1,5-diones (diisoimides 2), which could be isolated. Surprisingly, in this reaction, thionyl chloride appeared as an oxidant, and this process seemed to be useful for the syntheses of S-containing heterocyclic compounds such as 1,4-dithiins. A mechanistic pathway was considered. Copyright Taylor & Francis Group, LLC.
