2716-62-3

Upstream product

• 107-87-9 2-Pentanone 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 
• 591-50-4 iodobenzene 
• 625-30-9 2-pentylamine 
• 625-29-6 2-methyl-1-chlorobutane 
• 6032-29-7 (+/-)-2-pentanol 

Relevant academic research and scientific papers

Design, Synthesis, and Structure-Activity Relationship Studies of Novel Indolyalkylpiperazine Derivatives as Selective 5-HT1A Receptor Agonists

5-HT1A receptor (5-HT1AR) agonists have been implicated in the treatment of a variety of central nervous system (CNS) diseases such as depression and anxiety, et al. Based on our previously found compound FW01 (Ki = 51 ± 16 nM) obtained by virtual screening, a series of FW01 derivatives were designed and synthesized by the modification of the amide tail group as well as indole headgroup of FW01. SAR exploration found that amide tail group and indole headgroup play pivotal roles in determining the binding affinity and selectivity on dopamine and serotonin receptor subtypes. Among all tested compounds, 9_24 has a Ki value of 5 ± 0.6 nM with a good selectivity toward 5-HT1AR. The [35S] GTPγS assay showed that 9_24 is a full agonist toward 5-HT1AR with an EC50 value of 0.059 nM, which shows 266.2 and 146.4-fold selectivity to 5-HT2A and D3 respectively. Molecular dynamics simulations and molecular docking studies with 5-HT1AR-9_24 were performed to disclose the mechanism of its high activity and selectivity. Finally, a detailed stepwise 9_24 induced signal transduction mechanism of 5-HT1AR is proposed.

Reductive Amination by Photoredox Catalysis and Polarity-Matched Hydrogen Atom Transfer

The excitation of a RuII photosensitizer in the presence of ascorbic acid leads to the reduction of iminium ions to electron-rich α-aminoalkyl radical intermediates, which are rapidly converted into reductive amination products by thiol-mediated hydrogen atom transfer (HAT). As a result, the reductive amination of carbonyl compounds with amines by photoredox catalysis proceeds in good to excellent yields and with broad substrate scope and good functional group tolerance. The three key features of this work are 1) the rapid interception of electron-rich α-aminoalkyl radical intermediates by polarity-matched HAT in a photoredox reaction, 2) the method of reductive amination by photoredox catalysis itself, and 3) the application of this new method for temporally and spatially controlled reactions on a solid support, as demonstrated by the attachment of a fluorescent dye on an activated cellulose support by photoredox-catalyzed reductive amination.

Direct Catalytic Asymmetric Reductive Amination of Aliphatic Ketones Utilizing Diphenylmethanamine as Coupling Partner

The highly efficient direct catalytic reductive amination of ketones with diphenylmethanamine catalyzed by iridium-phosphoramidite complexes is described. As an effective coupling partner, diphenylmethanamine is suitable for a wide range of ketones to pro

Higher-Affinity Agonists of 5-HT1AR Discovered through Tuning the Binding-Site Flexibility

Discovery of high-affinity and high-selectivity agonists of 5-HT1AR has become very attractive due to their potential therapeutic effects on multiple 5-HT1AR-related psychological and neurological problems. On the basis of our previously designed lead compound FW01 (Ki = 51.9 nM, denoted as 9a in the present study), we performed large-scale molecular dynamics simulations and molecular docking operations on 5-HT1AR-9a binding. We found the flip-packing events for the headgroup of 9a, and we also found that its tail group could bind flexibly at the agonist-binding site of 5-HT1AR. By finely tuning the flip-packing phenomenon of the 9a headgroup and tuning the binding flexibility of 9a tail group, we virtually designed a series of new 9a derivatives through molecular docking operations and first-principles calculations and predicted that these newly designed 9a derivatives should be higher-affinity agonists of 5-HT1AR. The computational predictions on the new 9a derivatives have been confirmed by our wet-experimental studies as chemical synthesis, binding affinity assays, and agonistic-function assays. The consistency between our computational design and wet-experimental measurements has led to our discovery of higher-affinity agonists of 5-HT1AR, with ～50-fold increase in receptor-binding affinity and ～25-fold improvements in agonistic function. In addition, our newly designed 5-HT1AR agonists showed very high selectivity of 5-HT1AR over subtype 5-HT2AR and also over three subtypes of dopamine receptors (D1, D2, and D3). (Graph Presented).

Facile and efficient reductive N-alkylation of nitrobenzenes with alcohols catalyzed by Cu-Cr/γ-Al2O3

A facile and efficient method for reductive N-alkylation of nitrobenzenes with alcohols catalyzed by the bimetallic catalyst Cu30Cr5/γ-Al2O3, in a fixed-bed reactor, was successfully established. X-ray diffraction, temperature-programmed reduction, and X-ray photoelectron spectroscopy were used to characterize the catalyst. Introduction of Cr to Cu30/γ-Al2O3 was found to substantially enhance the dispersion of Cu0 particles, which are believed to be the active sites for the reductive N-alkylation. The reaction conditions were optimized and a series of alcohols and nitrobenzenes were converted into N-alkylated anilines in more than 90 % yield by use of this catalyst.

Selective N-alkylation of arylamines with alkyl chloride in ionic liquids: Scope and applications

An efficient N-selective alkylation of primary aromatic amines in molten quaternary ammonium salts, as the solvent, under relatively mild and base-free conditions is presented. On the basis of the Kamlet-Taft parameters and the nucleophilicity of the IL (ionic liquid) anions, the influence of the ionic liquid was evaluated. This protocol was validated on a larger multigram scale and with the syntheses of bioactive heterocycles (e.g., 1,4-benzothiazine and quinoxalines) and new efficient MALDI matrixes. Copyright

C-N bond formation catalysed by CuI Bonded to polyaniline nanofiber

Polyaniline nanofiber as a macroligand for the supported cuprous iodide catalyst (CuI-PANInf) has been developed for the coupling of aryl halides (including aryl chlorides) with aliphatic, aromatic, and N(H)-heterocyclic amines under ambient conditions (80 °C for aryl chlorides) has been developed. This simple and efficient method for coupling reactions is highly versatile, convenient, and also the catalyst can be used for several cycles with good-to-excellent yields.

Reductive amination with 5-ethyl-2-methylpyridine borane

We report a new amine borane, 5-ethyl-2-methylpyridine borane complex (PEMB) useful for reductive aminations of ketones and aldehydes in methanol or neat. Two of the three hydrides on PEMB are effectively utilized maximizing the economy of the reagent.

The reductive amination of aldehydes and ketones by catalytic use of dibutylchlorotin hydride complex

The reductive amination of aldehydes or ketones using Ph 2SiH2 or PhSiH3 has been effectively promoted by the direct use of Bu2SnClH-pyridine N-oxide as a catalyst; this method has advantages in terms of its mild conditions and wide application to various carbonyls and amines, including aliphatic examples. The Royal Society of Chemistry 2006.

One-pot reductive amination of aldehydes and ketones with α-picoline-borane in methanol, in water, and in neat conditions

A one-pot reductive amination of aldehydes and ketones with amines using α-picoline-borane as a reducing agent is described. The reaction has been carried out in MeOH, in H2O, and in neat conditions in the presence of small amounts of AcOH. This is a highly efficient and mild procedure that is applicable for a wide variety of substrates. In particular, this is the first successful demonstration that this type of reaction can be carried out in water and in neat conditions.