112934-63-1

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 91-56-5 indole-2,3-dione 
• 7681-65-4 copper(I) iodide 
• 23592-51-0 1-<2-<(4-Methoxyphenyl)amino>phenyl>ethanon 
• 19621-24-0 3-(4-fluorophenyl)-3-benzylindolin-2-one 
• 5720-07-0 4-methoxyphenylboronic acid 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 62-53-3 aniline 
• 696-62-8 para-iodoanisole 
• 551-93-9 2-aminoacetophenone 
• 1234956-15-0 C₁₅H₁₄BrNO₂ 

Downstream Products

• 27382-47-4 1-(4-methoxyphenyl)-2H-benzo[d][1,3]oxazine-2,4(1H)-dione 
• 3295-60-1 2-methoxyacridine 
• 1625679-45-9 1-(p-methoxyphenyl)isoindigo 
• 49742-72-5 2-methoxy-9(10H)-acridinone 
• 1373514-03-4 C₃₇H₄₅NO₁₁ 
• 1307863-96-2 C₂₄H₁₉NO₅ 
• 1307863-97-3 C₂₉H₃₀N₂O₅ 
• 1307863-99-5 C₃₄H₄₀N₂O₁₁S₂ 
• 1373514-04-5 C₂₉H₂₉NO₈S 
• 1373514-02-3 C₂₅H₂₁NO₅ 

Relevant academic research and scientific papers

Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones

The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.

SSAO INHIBITOR

The present invention provides an SSAO inhibitor and an application thereof in preparing a drug for treating a disease related to SSAO. In particular, the present invention provides a compound shown in formula (IV) and a pharmaceutically acceptable salt thereof.

Palladium-Catalyzed Cascade Hydrosilylation and Amino-Methylation of Isatin Derivatives

We demonstrate that using palladium acetate as a catalyst for reduction of DMF and isatin derivatives by hydrosilanes, a cascade hydrosilylation and amino-methylation reaction can be realized. With DMF as a reactant and a solvent, the in-situ generated siloxymethylamine intermediate, an adduct of DMF and hydrosilanes, smoothly participates in the successive stages, providing a serials of Si, N-functionalized indolin-2-ones in moderate to good yields. This strategy exhibits high chemoselectivity toward carbonyl moieties reduction among the substrates. (Figure presented.).

2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities

Because N-arylation of isatin only worked with iodoferrocene (and in low yield), we employed N-arylation of 2-aminophenones and subsequent oxidative cyclization to access various N-arylated isatins. In the course of this work, we observed that N-arylation using 2-iodofuran, 2-iodobenzofuran and 2-iodobenzothiophene did not lead to the expected derivatives, but to (benzo)furo- and (benzo)thieno[2,3-b]quinolines. Separate cyclization was also performed under acidic conditions on 2-(arylamino)phenones in order to obtain acridines and related compounds. Most of the synthesized compounds were screened for their antiproliferative activity in A2058 melanoma cells, and against a panel of disease-relevant kinases such as mammalian CDK5/p25, PIM1, CLK1, DYRK1A, GSK3α/β Haspin and leishmanial CK1. The biological results are reported.

NaI-mediated divergent synthesis of isatins and isoindigoes: A new protocol enabled by an oxidation relay strategy

A new approach for the synthesis of isatins and isoindigoes by an inexpensive and environmentally friendly NaI-mediated transformation is disclosed. The selectivity could be switched by simply varying the solvent, and isatins (using THF) and isoindigoes (using DMSO) could be obtained in moderate to excellent yields.

Design, synthesis and evaluation of N-aryl-glyoxamide derivatives as structurally novel bacterial quorum sensing inhibitors

Bacteria cooperatively regulate the expression of many phenotypes through a mechanism called quorum sensing (QS). Many Gram-negative bacteria use an N-acyl homoserine lactone (AHL)-mediated QS system to control biofilm formation and virulence factor production. In recent years, quorum sensing inhibitors (QSIs) have become attractive tools to overcome antimicrobial resistance exhibited by various pathogenic bacteria. In the present study, we report the design and synthesis of novel N-arylisatin-based glyoxamide derivatives via the ring-opening reaction of N-aryl isatins with cyclic and acylic amines, and amino acid esters. The QSI activity of the synthesized compounds was determined in the LasR-expressing Pseudomonas aeruginosa MH602 and LuxR-expressing Escherichia coli MT102 reporter strains. Compounds 31 and 32 exhibited the greatest QSI activity in P. aeruginosa MH602, with 48.7% and 42.7% reduction in QS activity at 250 μM, respectively, while compounds 31 and 34 showed 73.6% and 43.7% QSI activity in E. coli MT102. In addition, the ability of these compounds to inhibit the production of pyocyanin in P. aeruginosa (PA14) was also determined, with compound 28 showing 47% inhibition at 250 μM. Furthermore, computational docking studies were performed on the LasR receptor protein of P. aeruginosa, which showed that formation of a hydrogen bonding network played a major role in influencing the QS inhibitory activity. We envisage that these novel non-AHL glyoxamide derivatives could become a new tool for the study of QS and potentially for the treatment of bacterial infections.

Copper-catalyzed intramolecular oxidative C(sp3)-H amidation of 2-aminoacetophenones: Efficient synthesis of indoline-2,3-diones

An efficient synthesis of diverse indoline-2,3-diones from 2-aminoacetophenones through copper-catalyzed intramolecular C(sp3)-H amidation is developed. The reaction proceeds in DMSO by using O2 as the sole oxidant to provide the desired products in moderate to good yields.

Design, synthesis and biological evaluation of N-alkyl or aryl substituted isoindigo derivatives as potential dual cyclin-dependent kinase 2 (CDK2)/glycogen synthase kinase 3β (GSK-3β) phosphorylation inhibitors

A series of N-alkyl or aryl substituted isoindigo derivatives have been synthesized and their anti-proliferative activity was evaluated by Sulforhodamine B (SRB) assay. Some of the target compounds exhibited significant antitumor activity, including compounds 6h and 6k (against K562 cells), 6i (against HeLa cells) and 6j (against A549 cells). N-(p-methoxy-phenyl)-isoindigo (6k) exhibited a high and selective anti-proliferative activity against K562 cells (IC50 7.8 μM) and induced the apoptosis of K562 cells in a dose-dependent manner. Compound 6k arrested the cell cycle at S phase in K562 cells by decreasing the expression of cyclin A and CDK2, which played critical roles in DNA replication and passage through G2 phase. Moreover, compound 6k down-regulated the expression of p-GSK-3β (Ser9), β-catenin and c-myc proteins, up-regulated the expression of GSK-3β, consequently, suppressed Wnt/β-catenin signaling pathway and induced the apoptosis of K562 cells. The binding mode of compound 6k with GSK-3β was simulated using molecular docking tools. All of these studies gave a better understanding to the molecular mechanisms of this class of agents and clues to develop dual CDK2/GSK-3β (Ser9) phosphorylation inhibitors applied in cancer chemotherapy.

Copper-catalyzed tandem oxidative cyclization of arylacetamides: Efficient access to N-functionalized isatins

An efficient copper-catalyzed synthesis of N-substituted isatins has been developed in good yields from easily accessible arylacetamides. A wide range of electronically and structurally varied nitrogen fragments could be assembled through this tandem C-O/C-N bond-forming process by tuning the reaction conditions.

Selenium-promoted intramolecular oxidative amidation of 2-(arylamino)acetophenones for the synthesis of N-arylisatins

A convenient method for the synthesis of N-arylisatins from 2-(arylamino)acetophenones by using SeO2 as an oxidant is described. Various substituted N-arylisatins were selectively obtained in good to excellent yields. The reaction tolerates a wide range of functionalities. Copyright