73031-16-0

Upstream product

• 120-72-9 indole 
• 32331-75-2 2-oxo-N-phenylacetamide 
• 52190-18-8 2-(1H-indol-3-yl)-N-phenyl acetamide 
• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 62-53-3 aniline 

Downstream Products

• 108977-92-0 2-(1-methyl-1H-indol-3-yl)-2-oxo-N-phenylacetamide 
• 19611-80-4 [2-(1H-indol-3-yl)ethyl]phenylamine 
• 1489263-00-4 2-(1-benzyl-1H-indole-3-yl)-2-oxo-N-phenylacetamide 

Relevant academic research and scientific papers

Novel positive allosteric modulators of A2B adenosine receptor acting as bone mineralisation promoters

Small-molecules acting as positive allosteric modulators (PAMs) of the A2B adenosine receptor (A2B AR) could potentially represent a novel therapeutic strategy for pathological conditions characterised by altered bone homeostasis, including osteoporosis. We investigated a library of compounds (4-13) exhibiting different degrees of chemical similarity with three indole derivatives (1-3), which have been recently identified by us as PAMs of the A2B AR able to promote mesenchymal stem cell differentiation and bone formation. Evaluation of mineralisation activity of 4-13 in the presence and in the absence of the agonist BAY60-6583 allowed the identification of lead compounds with therapeutic potential as anti-osteoporosis agents. Further biological characterisation of one of the most performing compounds, the benzofurane derivative 9, confirmed that such a molecule behaves as PAM of the A2B AR.

Fe-Catalyzed Pictet-Spengler-Type Cyclization via Selective Four-Electron Reductive Functionalization of CO2

Herein, we describe a novel catalytic Pictet-Spengler-type cyclization using CO2 as a nontoxic and sustainable C1 feedstock with environmentally benign and non-precious-metal iron as catalyst. The reaction is achieved by selective four-electron reduction of CO2 into methylene level intermediate through carefully tuning the reaction parameters. A variety of tetrahydro-β-carbolines and other nitrogen-containing heterocycles can be easily obtained under mild conditions. Mechanistic studies have shown that tetrahydro-β-carbolines are probably obtained via spiroindolenine intermediates.

Synthesis of α-ketoamides using potassium superoxide (KO2) as an oxidizing agent

A simple and convenient method for the synthesis of α-ketoamides by the oxidation of aryl acetamides using potassium superoxide (KO2) as an oxidizing agent is disclosed here. The scope of the developed method is successfully tested with fifteen substrates. In addition, the utility of method has been demonstrated by synthesizing an orexin receptor antagonist, a medicinally interesting compound.

Design, synthesis, biological evaluation and molecular modelling studies of indole glyoxylamides as a new class of potential pancreatic lipase inhibitors

A series of eighteen indole glyoxylamide analogues were synthesized, characterized and evaluated for their pancreatic lipase inhibitory activity. Porcine pancreatic lipase (Type II) was used with 4-nitrophenyl butyrate (as substrate) for the in vitro assay. Compound 8f exhibited competitive inhibition against pancreatic lipase with IC50 value of 4.92 μM, comparable to that of the standard drug, orlistat (IC50 = 0.99 μM). Compounds 7a-i and 8a-i were subjected to molecular docking into the active site of human PL (PDB ID: 1LPB) wherein compound 8f possessed a potential MolDock score of ?153.037 kcal/mol. Molecular dynamics simulation of 8f complexed with pancreatic lipase, confirmed the role of aromatic substitution in stabilizing the ligand through hydrophobic interactions (maximum observed RMSD = 3.5 ?).

Indole amide synthesis of derivatives and their use as plant growth regulators

The invention discloses indole amide derivatives and its synthetic method, is to indole, oxalyl, aromatic amine as the main raw material, by conventional solvent method and ultrasonic radiation method for synthesis of a indolyl for the skeleton to amide derivatives. Because the indole amide in the molecule containing both indole group, but also has the amide structure, under the condition of the best concentration demonstrates the role in promoting the growth of wheat, indole acetic acid than more dominating, and therefore as a plant growth regulator is applied to the agricultural production has very good prospects.

Synthesis of thiazole linked indolyl-3-glyoxylamide derivatives as tubulin polymerization inhibitors

A series of thiazole linked indolyl-3-glyoxylamide derivatives were synthesized and evaluated for their in vitro cytotoxic activity against DU145 (prostate), PC-3 (prostate), A549 (lung) and HCT-15 (colon) cancer cell lines by employing the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized compounds, compound 13d displayed cytotoxicity of IC50 = 93 nM towards DU145 cancer cell line. The most active compound 13d was also tested on RWPE-1 cells and was found to be safe compared to the DU145 cells. The target compounds were also evaluated for their inhibition activity of tubulin polymerization. Further, the treatment of compound 13d on DU145 cells led to the inhibition of cell migration ability. The detailed studies such as acridine orange/ethidium Bromide (AO/EB), DAPI, annexin V-FITC/propidium iodide staining assay suggested that the compound 13d induced apoptosis in DU145 cells. The influence of the cytotoxic compound 13d on the cell cycle distribution was assessed on the DU145 cell line, exhibiting a cell cycle arrest at the G2/M phase. Moreover, the treatment with compound 13d caused collapse of mitochondrial membrane potential and elevated intracellular ROS levels in DU145 cells. The results from molecular modelling studies revealed that these compounds bind at the colchicine binding site of the tubulin. Thus, this new molecular scaffold could be a new lead for the development of anticancer agents that target tubulin.

Fe-catalyzed regioselective Friedel-Crafts hydroxyalkylation of N-substituted glyoxylamide with indoles

An efficient regioselective Friedel-Crafts hydroxyalkylation of N-substituted glyoxylamide with various indoles catalyzed by Lewis acids was developed. The reactions proceeded smoothly at room temperature and the 2-hydroxy-2-(1H-indol-3-yl)-N-substituted acetamide resulted from the reactions catalyzed by FeSO4 were synthesized in excellent yields (up to 93%). While the bisindole compounds were obtained when FeCl3 was used as a catalyst in excellent yields (up to 92%). A possible mechanism was proposed.

One-pot three-component synthesis of indole-3-glyoxyl derivatives and indole-3-glyoxyl triazoles

A general and efficient reaction of indole with oxalyl chloride and nucleophiles providing indole-3-glyoxyl derivatives has been developed in mild conditions. In the same fashion, the other reaction involved the addition of organic azides leading to the synthesis of indole-3-glyoxyl-1,2,3-triazoles, which proceeds smoothly generating the products in moderate to high yields.

Modulation of A2B adenosine receptor by 1-Benzyl-3-ketoindole derivatives

We have disclosed a series of 1-benzyl-3-ketoindole derivatives acting as either positive or negative modulators of the human A2B adenosine receptor (A2B AR) depending on small differences in their side chain. The new compounds were designed taking into account structural similarities between AR antagonists and ligands of the GABAA/benzodiazepine receptor. All compounds resulted totally inactive at A2A and A 3 ARs and showed small (8a,b) or none (7a,b, 8c and 9a,b) affinity for A1 AR. When tested on A2B AR-transfected CHO cells, 7a,b and 8a acted as positive modulators, whereas 8b,c and 9a,b acted as negative modulators, enhancing or weakening the NECA-induced increase of cAMP levels, respectively. Compounds 7-9 might be regarded as useful biological and pharmacological tools to explore the therapeutic potential of A2B AR modulators, while their 3-ketoindole scaffold might be taken as a reference to design new analogs.

Synthetic analogs of indole-containing natural products as inhibitors of sortase A and isocitrate lyase

Guided by the inhibitory activities of indole-containing natural products against isocitrate lyase (ICL) from Candida albicans and sortase A (SrtA) from Staphylococcus aureus, a series of compounds structurally analogous to natural products were synthesized. Eight SrtA inhibitors and an ICL inhibitor having higher activities than the natural products were discovered by screening the enzyme inhibitory activities of synthesized compounds. Among the SrtA inhibitors discovered, six exhibited higher activities than p-hydroxymercuribenzoic acid, which suggests that these compounds have great potential as alternative antibacterial agents.