51980-54-2

Usage

Chemical Properties

Solid

InChI:InChI=1/C11H13NO/c13-9-10-3-5-11(6-4-10)12-7-1-2-8-12/h3-6,9H,1-2,7-8H2

Upstream product

• 4096-21-3 N-phenylpyrrolidine 
• 93-61-8 N-methyl-N-phenylformamide 
• 123-75-1 pyrrolidine 
• 79865-85-3 p-methoxybenzylidenedimethylimmonium iodide 
• 68-12-2 N,N-dimethyl-formamide 
• 459-57-4 4-fluorobenzaldehyde 
• 13114-23-3 4-methoxybenzyl-N-methylimine 
• 123-11-5 4-methoxy-benzaldehyde 
• 62-53-3 aniline 
• 1122-91-4 4-bromo-benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 110-52-1 1,4-dibromo-butane 
• 556-18-3 4-aminobenzaldehyde 

Downstream Products

• 98271-41-1 4,4'-dipyrrolidino-ξ-stilbene 
• 76304-57-9 3-(4-Pyrrolidin-1-yl-phenyl)-1H-pyrrole-2,4-dicarboxylic acid dimethyl ester 
• 139484-21-2 5,5-Dimethyl-2-(4-pyrrolidin-1-yl-benzylidene)-cyclohexane-1,3-dione 
• 139484-12-1 C₂₇H₃₅NO₄ 
• 127868-60-4 2-[4-(Pyrrolidin-1-yl)phenyl]benzothiazole 

Relevant academic research and scientific papers

Anti-androgens with full antagonistic activity toward human prostate tumor LNCaP cells with mutated androgen receptor

Anti-androgens were designed based on the principle of inhibiting the folding of helix 12 of the nuclear androgen receptor. The prepared anti-androgens exhibited full antagonistic activity toward human prostate tumor LNCaP cells with T877A point-mutated nuclear androgen receptor, as far as examined, towards which other known anti-androgens, including hydroxyflutamide, are inactive or act as androgen agonists.

Biocatalytic Cross-Coupling of Aryl Halides with a Genetically Engineered Photosensitizer Artificial Dehalogenase

Devising artificial photoenzymes for abiological bond-forming reactions is of high synthetic value but also a tremendous challenge. Disclosed herein is the first photobiocatalytic cross-coupling of aryl halides enabled by a designer artificial dehalogenase, which features a genetically encoded benzophenone chromophore and site-specifically modified synthetic NiII(bpy) cofactor with tunable proximity to streamline the dual catalysis. Transient absorption studies suggest the likelihood of energy transfer activation in the elementary organometallic event. This design strategy is viable to significantly expand the catalytic repertoire of artificial photoenzymes for useful organic transformations.

Crystal-packing modes determine the solid-state ESIPT fluorescence in highly dipolar 2′-hydroxychalcones

This work describes the systematic study of the structure-luminescence relationship of 15 hydroxy-chalcones directly in the crystal state. Chalcones are easily assembled at the gram scale allowing for efficient variation of their substitution motifs. Our molecule variants combine two modes of fluorescence generation, ESIPT and ICT, both known for their potential to achieve significant quantum yields even with emission in the red to near infrared, a region preferred for technologies as diverse as optoelectronics and chemical sensing. Quantum yields as high as 48% (at 665 nm) and emission wavelengths in the deep red region (710 nm, 5%) were achieved with variants equipped with a strained amino substituent in the donor portion (azetidinyl). Systematic XRD analysis of large monocrystals allowed for the identification of the subtle interplay of several inter- and intra-molecular parameters in achieving such performances, be it intramolecular planarity, non-classical H-bonds, and stacking modes.

Dehydrogenation/(3+2) Cycloaddition of Saturated Aza-Heterocycles via Merging Organic Photoredox and Lewis Acid Catalysis

Herein, we report a photoinduced dehydrogenation/(3+2) cycloaddition reaction by merging organic photoredox and Lewis acid catalysis, providing a straightforward and efficient approach for directly installing a benzofuran skeleton on the saturated aza-heterocycles. In this protocol, we also describe a novel organic photocatalyst (t-Bu-DCQ) with the advantages of a wider redox potential, easy synthesis, and a low price. Furthermore, the stepwise activation mechanism of dual C(sp3)-H bonds was demonstrated by a series of experimental and computational studies.

Pyridoxine-resveratrol hybrids as novel inhibitors of MAO-B with antioxidant and neuroprotective activities for the treatment of Parkinson's disease

A series of pyridoxine-resveratrol hybrids were designed and synthesized as monoamine oxidase B inhibitors for the treatment of Parkinson's disease. Most of them exhibited potent inhibitory activities on MAO-B with high selectivity. Specifically, compounds 12a, 12g and 12l showed the most excellent inhibition to hMAO-B with the IC50 values of 0.01 μM, 0.01 μM and 0.02 μM, respectively. Further reversibility study demonstrated that 12a and 12l were reversible and 12g was irreversible MAO-B inhibitors. Molecular docking studies of MAO revealed the binding mode and high selectivity of these compounds with MAO-B. In addition, these three representative compounds also exhibited low cytotoxicity and excellent neuroprotective effect in the test on H2O2-induced PC-12 cell injury. Moreover, 12a, 12g and 12l showed good antioxidant activities and high blood-brain barrier permeability. Overall, all of these results highlighted 12a, 12g and 12l were potential and excellent MAO-B inhibitors for PD treatment.

Design, synthesis, characterization and fluorescence property evaluation of dehydroacetic acid-based chalcones

Abstract: In this study, we decided to synthesize some new chalcone-type dyes derived from dehydroacetic acid (DHA) by the condensation of 4-amino-substituted benzaldehyde with DHA under the base-catalyzed condition and investigate their ability for rearrangement in acidic condition. For this purpose, initially we prepared the 4-aminobenzaldehyde derivatives via nucleophilic aromatic substitution reaction of 4-fluorobenzaldehyde with variety of amines in the presence of K2CO3 as base in DMF. The Knoevenagel condensation of DHA with 4-aminobenzaldehyde derivatives results in the desired compounds. In continuation, Fries rearrangement applied on DHA-chalcone compounds results in characterization of new pyranilidene-type derivatives. The optical responses of new dyes containing UV–Vis absorption and fluorescence spectroscopy were measured in dichloromethane (ET = 40?kcal/mol). Pyranilidene derivatives show low λmax values in comparison with chalcones, and molecule with strong dipole, in polar solvents, shows the bathochromic shift due to more stabilization of excited state in compared with ground state of molecule. Large stocks shifts were obtained for synthesized compounds. Graphic abstract: [Figure not available: see fulltext.].

Multifunctional quinoxaline-hydrazone derivatives with acetylcholinesterase and monoamine oxidases inhibitory activities as potential agents against Alzheimer’s disease

Multitarget molecules are considered as an effective way for the treatment of AD, instead of the classic one-drug-one-target strategy because of the multifactorial nature of AD. A variety of studies indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted quinoxaline-hydrazone derivatives were synthesized, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity and MAOA/B inhibitory activity. Based on the experimental results, compound 5l exhibited good inhibitory potency on both AchE (IC50 = 0.028 ± 0.001 μM) and monoamine oxidase B (IC50 = 0.046 ± 0.002 μM). Molecular modeling studies showed that 5l could bind to the active site of AChE and MAO-B. Taken together, these results suggested that compound 5l might be a potential multifunctional agent for the treatment of AD.

Cu(II)-catalyzed C-N coupling of (hetero)aryl halides and N-Nucleophiles promoted by α-benzoin oxime

We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaαolds found in FDA-approved pharmaceuticals.

Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation

In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

A two-aromatic substituted propylene ketone compound and its preparation method and application (by machine translation)

The present invention discloses a two-aromatic substituted propylene ketone compound and its preparation method and application, its structural formula such as formula (I) as shown: Wherein A is B is hydrogen, methyl or ethyl; C is a substituted benzene ring, pyridine and furan heterocyclic, 2 - pyridyl, 3 - pyridyl, 4 - pyridyl, 5 - 1 H - indolyl, 4 - (N, N - dimethylamino) phenyl, 4 - (N - pyrrolyl) phenyl, 4 - [1 - (N - methyl piperazinyl)] phenyl or 4 - (1 - morpholinyl) phenyl. The compounds of the invention has a novel structure, to inhibit the cells MCL active effect, high safety, the preparation cost is low and the like, can be used as a MCL very promising drug. (by machine translation)