10075-51-1Relevant articles and documents
Boronic Acid Accelerated Three-Component Reaction for the Synthesis of α-Sulfanyl-Substituted Indole-3-acetic Acids
Das, Amrita,Watanabe, Kenji,Morimoto, Hiroyuki,Ohshima, Takashi
, p. 5794 - 5797 (2017)
Boronic acid was used to accelerate a three-component reaction of indoles, thiols, and glyoxylic acids for the synthesis of α-sulfanyl-substituted indole-3-acetic acids. Boronic acid catalysis to activate the α-hydroxy group in α-hydroxycarboxylic acid in
Gramine Derivatives Targeting Ca2+ Channels and Ser/Thr Phosphatases: A New Dual Strategy for the Treatment of Neurodegenerative Diseases
Lajarín-Cuesta, Rocío,Nanclares, Carmen,Arranz-Tagarro, Juan-Alberto,González-Lafuente, Laura,Arribas, Raquel L.,Araujo De Brito, Monique,Gandía, Luis,De Los Ríos, Cristóbal
, p. 6265 - 6280 (2016)
We describe the synthesis of gramine derivatives and their pharmacological evaluation as multipotent drugs for the treatment of Alzheimer's disease. An innovative multitarget approach is presented, targeting both voltage-gated Ca2+ channels, cl
Tiplaxtinin, a novel, orally efficacious inhibitor of plasminogen activator inhibitor-1: Design, synthesis, and preclinical characterization
Elokdah, Hassan,Abou-Gharbia, Magid,Hennan, James K.,McFarlane, Geraldine,Mugford, Cheryl P.,Krishnamurthy, Girija,Crandall, David L.
, p. 3491 - 3494 (2004)
Indole oxoacetic acid derivatives were prepared and evaluated for in vitro binding to and inactivation of human plasminogen activator inhibitor-1 (PAI-1). SAR based on biochemical, physiological, and pharmacokinetic attributes led to identification of tip
Accelerated benzylation reaction utilizing dibenzyl carbonate as an alkylating reagent
Shieh, Wen-Chung,Lozanov, Mario,Repi?, Oljan
, p. 6943 - 6945 (2003)
Ionic liquids can effectively accelerate slow N-benzylation reactions utilizing dibenzyl carbonate as an alkylating reagent. By applying microwave irradiation in the presence of the same ionic liquid, additional rate enhancement was accomplished.
New Inhibitor Targeting Signal Transducer and Activator of Transcription 5 (STAT5) Signaling in Myeloid Leukemias
Juen, Ludovic,Brachet-Botineau, Marie,Parmenon, Cécile,Bourgeais, Jér?me,Hérault, Olivier,Gouilleux, Fabrice,Viaud-Massuard, Marie-Claude,Prié, Gildas
, p. 6119 - 6136 (2017)
Signal transducers and activators of transcription 5 (STAT5s) are crucial effectors of tyrosine kinase oncogenes in myeloid leukemias. Inhibition of STAT5 would contribute to reducing the survival of leukemic cells and also tackling their chemoresistance. In a first screening experiment, we identified hit 13 as able to inhibit STAT5 phosphorylation and leukemic cell growth. The synthesis of 18 analogues of 13 allowed us to identify one compound, 17f, as having the most potent antileukemic effect. 17f inhibited the growth of acute and chronic myeloid leukemia cells and the phosphorylation and transcriptional activity of STAT5. Importantly, 17f had minimal effects on bone marrow stromal cells that play vital functions in the microenvironment of hematopoietic and leukemic cells. We also demonstrated that 17f inhibits STAT5 but not STAT3, AKT, or Erk1/2 phosphorylation. These results suggest that 17f might be a new lead molecule targeting STAT5 signaling in myeloid leukemias.
Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
Abonia, Rodrigo,Gutiérrez, Luisa F.,Insuasty, Braulio,Quiroga, Jairo,Laali, Kenneth K.,Zhao, Chunqing,Borosky, Gabriela L.,Horwitz, Samantha M.,Bunge, Scott D.
, p. 642 - 654 (2019)
A series of giant tris(heteroaryl)methanes are easily assembled by one-pot three-component synthesis by simple reflux in ethanol without catalyst or additives. Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone aldehydes, chromone aldehydes, and fluorene aldehydes (Ar2CHO) and coumarins (Ar3) in 1:1:1 ratio to form the corresponding tris(heteroaryl)methanes (Ar1Ar2Ar3)CH along with (Ar1Ar1Ar2)CH triads. A series of new 2:1 triads were also synthesized by coupling substituted indoles with Ar2CHO. The coupling reactions could also be carried out in water (at circa 80 °C) but with chemoselectivity favoring (Ar1Ar1Ar2)CH(Ar1Ar2Ar3)CH. The molecular structure of a representative (Ar1Ar2Ar3)CH triad was confirmed by X-ray analysis. Model tris(heteroaryl/aryl)methylium salts were generated by reaction with DDQ/HPF6 and studied by NMR and by DFT and GIAO-DFT.
N-Alkylation of 1H-indoles and 9H-carbazoles with alcohols
Bombrun, Agnes,Casi, Giulio
, p. 2187 - 2190 (2002)
A comparative study of N-alkylation of 1H-indole and 9H-carbazole derivatives with alcohol derivatives was performed using classic Mitsunobu reaction conditions, i.e. DEAD/PPh3, azodicarboxamide derivatives such as TMAD in the presence of PBus
Replacement of Stoichiometric DDQ with a Low Potential o-Quinone Catalyst Enabling Aerobic Dehydrogenation of Tertiary Indolines in Pharmaceutical Intermediates
Li, Bao,Wendlandt, Alison E.,Stahl, Shannon S.
supporting information, p. 1176 - 1181 (2019/02/14)
A transition-metal/quinone complex, [Ru(phd)3]2+ (phd = 1,10-phenanthroline-5,6-dione), is shown to be effective for aerobic dehydrogenation of 3° indolines to the corresponding indoles. The results show how low potential quinones may be tailored to provide a catalytic alternative to stoichiometric DDQ, due to their ability to mediate efficient substrate dehydrogenation while also being compatible with facile reoxidation by O2. The utility of the method is demonstrated in the synthesis of key intermediates to pharmaceutically important molecules.
