13114-23-3

Usage

InChI:InChI=1/C9H11NO/c1-10-7-8-3-5-9(11-2)6-4-8/h3-7H,1-2H3/b10-7+

Upstream product

• 593-51-1 methylamine hydrochloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 74-89-5 methylamine 
• 702-24-9 4-methoxy-N-methylbenzylamine 
• 75-52-5 nitromethane 
• 96-31-1 N,N'-Dimethylurea 
• 98760-20-4 C₉H₁₂BrNO 
• 70972-89-3 N-Chlor-p-methoxy-benzylmethylamin 

Downstream Products

• 53059-79-3 2-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-N-methyl-2-phenyl-acetamide 
• 55881-68-0 3r-(4-methoxy-phenyl)-2-methyl-4c-phenyl-[1,2]thiazetidine 1,1-dioxide 
• 55881-68-0 3r-(4-methoxy-phenyl)-2-methyl-4t-phenyl-[1,2]thiazetidine 1,1-dioxide 
• 132525-52-1 N-<2-(1,4-dioxacyclohexyl)-p-methoxybenzyl>methylamine 
• 90490-27-0 (2S,3R)-2-(4-Methoxy-phenyl)-1-methyl-3-phenyl-aziridine 
• 86919-73-5 3-methyl-r-2-phenyl-t-4,c-5-di-(p-methoxyphenyl)oxazolidine 
• 86919-73-5 3-methyl-r-2-phenyl-c-4,t-5-di-(p-methoxyphenyl)oxazolidine 
• 116872-28-7 1-methylthio-3-(p-methoxyphenyl)-1,2-cyclopropanedicarboxylic acid diethyl ester 
• 124-40-3 dimethyl amine 
• 84065-86-1 3-tert-Butyl-2-(4-methoxyphenyl)-1-methyl-4-thioxo-3-azetidincarbonitril 
• 91529-76-9 2-Cyan-3,3,N-trimethylbutyrothioamid 
• 91529-54-3 trans-2,2'-(1,2,4-Trithiolan-3,5-diyliden)bis(3-methylbutyronitril) 
• 344869-62-1 2-<5,6-Dihydro-4-(4-methoxyphenyl)-5-methyl-6-oxo-4H-1,3,5-dithiazin-2-yliden>-3-methylbutyronitril 
• 91529-55-4 trans-2,2'-(1,2,4-Trithiolan-3,5-diyliden)bis(3,3-dimethylbutyronitril) 

Relevant academic research and scientific papers

Design, Synthesis, and Biological Evaluation of Novel 3-Aminomethylindole Derivatives as Potential Multifunctional Anti-Inflammatory and Neurotrophic Agents

The development of multifunctional molecules that are able to simultaneously interact with several pathological components has been considered as a solution to treat the complex pathologies of neurodegenerative diseases. Herein, a series of aminomethylindole derivatives were synthesized, and evaluation of their application for antineuroinflammation and promoting neurite outgrowth was disclosed. Our initial screening showed that most of the compounds potently inhibited lipopolysaccharide (LPS)-stimulated production of NO in microglial cells and potentiated the action of NGF to promote neurite outgrowth of PC12 cells. Interestingly, with outstanding NO/TNF-α production inhibition and neurite outgrowth-promoting activities, compounds 8c and 8g were capable of rescuing cells after injury by H2O2. Their antineuroinflammatory effects were associated with the downregulation of the LPS-induced expression of the inflammatory mediators inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Western blotting and immunofluorescence assay results indicated that the mechanism of their antineuroinflammatory actions involved suppression of the MAPK/NF-κB signal pathways. Further studies revealed that another important reason for the high comprehensive antineuroinflammatory activity was the anti-COX-2 capabilities of the compounds. All these results suggest that the potential biochemical multifunctional profiles of the aminomethylindole derivatives provide a new sight for the treatment of neurodegenerative diseases.

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.

Computationally Driven Structure Optimization, Synthesis, and Biological Evaluation of Imidazole-Based Proprotein Convertase Subtilisin/Kexin 9 (PCSK9) Inhibitors

Proprotein convertase subtilisin/kexin 9 (PCSK9) is responsible for the degradation of the hepatic low-density lipoprotein receptor (LDLR), which in turn regulates the circulating low-density lipoprotein cholesterol (LDL-C) level. For this reason, the PCSK9 inhibition, by small molecules or peptides, is a validated therapeutic approach for fighting hypercholesterolemia and cardiovascular diseases. In this field, we have recently reported an imidazole-based peptidomimetic that has shown PCSK9 inhibitory activity in the micromolar range. Here, by applying advanced computational techniques, the binding mechanism of that imidazole peptidomimetic was predicted. Then, among a small set of poly-imidazole analogs, compounds showing the highest theoretical affinity were suitably synthesized, relying on a van Leusen reaction based multicomponent strategy. One compound (named RIm13) displayed a PCSK9 inhibitory activity 10-fold lower than the template compound, and, remarkably, at a concentration of 1 μM, it successfully prevented the LDLR degradation mediated by PCSK9 on HepG2 cells. As well as increasing the LDL uptake at the same concentration, RIm13 represents currently one of the most potent small molecules targeting the PCSK9/LDLR protein-protein interaction.

Mechanosynthesis of N-methyl imines using recyclable imidazole-based acid-scavenger: In situ formed ionic liquid as catalyst and dehydrating agent

1,1′-(1,4-Butanediyl)bis(imidazole) was prepared by a modified method and its application as an efficient promoter was demonstrated for the mechanosynthesis of N-methyl imines using ball milling as a non-conventional process under solvent-free conditions. In this new protocol design, the bis-imidazole acted as a recyclable acid-scavenging agent. This efficient approach to the N-methyl imines displays a combination of the synthetic virtues of a non-conventional condensation reaction with ecological benefits and convenience of a facile mechanosynthetic process. The current method has advantages such as reduced waste by avoiding solvent, exclusion of hazardous materials during the reaction, elimination of handling an anhydrous gas in an evacuated container or a solution of methylamine in ethanol, good yields for relatively unreactive benzaldehydes containing electron-donating substituents, short reaction times, and metal- and acid-free conditions. Furthermore, the promoter was easily regenerated and reused several times with no significant loss of activity.

Method for synthesizing imine by catalytic oxidation of asymmetric secondary amine in presence of visible light

The invention belongs to the technical field of chemical engineering and pharmaceutical industry, and particularly relates to a method for synthesizing imine by catalytic oxidation of asymmetric secondary amine in the presence of visible light. With aza-metalloporphyrin containing sulfur as a visible light catalyst, 1,8-diazabicycloundecene-7-alkene as an auxiliary agent, and oxygen as an oxidant,asymmetric secondary amine is subjected to catalytic oxidation under irradiation of visible light of lambda being larger than or equal to 420nm, so as to obtain the oxidation product imine. A new andefficient imine production way is provided.

HALOALLYLAMINE PYRAZOLE DERIVATIVE INHIBITORS OF LYSYL OXIDASES AND USES THEREOF

The present invention relates to novel compounds which are capable of inhibiting certain amine oxidase enzymes. These compounds are useful for treatment of a variety of indications, e.g., fibrosis, cancer and/or angiogenesis in human subjects as well as i

A General Way to Construct Arene-Fused Seven-Membered Nitrogen Heterocycles

Imines react with seven-membered cyclic anhydrides (prepared from the corresponding dicarboxylic acids by a recently discovered in-situ cyclodehydration protocol) by the Castagnoli–Cushman reaction pathway to give privileged seven-membered arene-fused nitrogen-heterocyclic compounds with reagent-controlled diversity of the skeleton and peripheral groups.

A Next Generation Synthesis of BACE1 Inhibitor Verubecestat (MK-8931)

The development of a commercial manufacturing route to verubecestat (MK-8931) is described, highlights of which include the application of a continuous processing step to outcompete fast proton transfer in a Mannich-type ketimine addition, a copper-cataly

Mixed carboxylic-sulfonic anhydride in reaction with imines: A straightforward route to water-soluble β-lactams via a Staudinger-type reaction

The first example of employing a mixed carboxylic-sulfonic anhydride in reaction with imines is reported. Unlike its well-studied isostere homophthalic anhydride, benzo[c][1,2]oxathiin-3(4H)-one 1,1-dioxide gave no product of a formal [4 + 2] cycloaddition and only followed an alternative reaction pathway toward β-lactams, presumably, via a formal [2 + 2] cycloaddition (a Staudinger-type reaction). Optimized reaction conditions involve the use of triethylamine as a base promoter, which also allows isolating the product β-lactam benzene sulfonic acids as respective triethylammonium salts by conventional column chromatography. The reaction shows some preference to trans-isomer formation; pure diastereomers can be isolated in some cases.

Alkyl-guanidine Compounds as Potent Broad-Spectrum Antibacterial Agents: Chemical Library Extension and Biological Characterization

Nowadays, the increasing of multidrug-resistant pathogenic bacteria represents a serious threat to public health, and the lack of new antibiotics is becoming a global emergency. Therefore, research in antibacterial fields is urgently needed to expand the currently available arsenal of drugs. We have recently reported an alkyl-guanidine derivative (2), characterized by a symmetrical dimeric structure, as a good candidate for further developments, with a high antibacterial activity against both Gram-positive and Gram-negative strains. In this study, starting from its chemical scaffold, we synthesized a small library of analogues. Moreover, biological and in vitro pharmacokinetic characterizations were conducted on some selected derivatives, revealing notable properties: broad-spectrum profile, activity against resistant clinical isolates, and appreciable aqueous solubility. Interestingly, 2 seems neither to select for resistant strains nor to macroscopically alter the membranes, but further studies are required to determine the mode of action.