4993-87-7

Usage

InChI:InChI=1/C14H10N2O2/c17-16(18)12-6-7-13-11(8-12)9-14(15-13)10-4-2-1-3-5-10/h1-9,15H

Upstream product

• 5667-47-0 phenacyldimethylsulfonium bromide 
• 100-01-6 4-nitro-aniline 
• 500992-02-9 N-[(4'-nitro-2'-phenylethynyl)phenyl]butyramide 
• 215368-61-9 [4-(2-indolyl)phenyl]phenylmethane 
• 812647-00-0 N-[4'-nitro-2'-(((trifluoromethane)sulfonyl)oxy)phenyl]trifluoroacetamide 
• 536-74-3 phenylacetylene 
• 6293-83-0 2-iodo-4-nitrophenylamine 
• 70-11-1 α-bromoacetophenone 
• 6146-52-7 5-nitroindole 
• 1414866-86-6 5‐nitro‐1‐(pyrimidin‐2‐yl)‐1H‐indole 
• 444681-65-6 1,1-dibromo-2-(3-nitrophenyl)ethene 
• 99-61-6 3-nitro-benzaldehyde 
• 98-80-6 phenylboronic acid 
• 98-86-2 acetophenone 

Downstream Products

• 125061-07-6 3,3-Bis-(5-nitro-2-phenyl-1H-indol-3-yl)-3H-isobenzofuran-1-one 
• 125061-08-7 7-Nitro-3,3-bis-(5-nitro-2-phenyl-1H-indol-3-yl)-3H-isobenzofuran-1-one 
• 84197-44-4 3-Hydroximino-5-nitro-2-phenylindole 
• 6855-64-7 2-phenyl-1H-indol-5-amine 
• 1060749-13-4 (5-nitro-2-phenylindol-3-yl)glyoxylyl chloride 
• 1613132-86-7 C₁₇H₁₄N₆O₂S 
• 1613132-92-5 6-(3-allyl-5-nitro-2-phenyl-1H-indol-1-yl)-5-amino-4,5-dihydro-1,2,4-triazine-3(2H)-thione 
• 1613132-98-1 1-(1-(5-amino-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-6-yl)-5-nitro-2-phenyl-1H-indol-3-yl)ethanone 
• 1613133-10-0 1-(5-amino-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-6-yl)-5-nitro-2-phenyl-1H-indole-3-carboxylic acid 
• 1613133-16-6 1-(5-amino-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-6-yl)-5-nitro-2-phenyl-1H-indole-3-carboxamide 
• 1613132-74-3 C₁₆H₁₁ClN₂O₃ 
• 1169433-92-4 2-(5-nitro-2-phenyl-1 H-indol-1-yl)ethanol 
• 1610423-29-4 C₁₆H₁₂N₂O₄ 
• 4809-61-4 2-benzamido-5-nitrobenzoic acid 

Relevant academic research and scientific papers

Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization

Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.

Pd-Catalyzed Indole Synthesis via C-H Activation and Bisamination Sequence with Diaziridinone

This work describes an efficient Pd-catalyzed indole synthesis. A wide variety of indoles can be obtained in good yields from readily available vinyl bromides. The reaction likely proceeds through a sequential aryl C-H activation and bisamination of a resulting pallada(II)cycle with diaziridinone.

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C?H Aminations

While direct nitrene insertions into C?H bonds have become an important tool for building C?N bonds in modern organic chemistry, the generation of nitrene intermediates always requires transition metals, high temperatures, ultraviolet or laser light. We report a mild synthesis of carbazoles and related building blocks through a visible light-induced intramolecular C?H amination reaction. A striking advantage of this new method is the use of more reactive aryl sulfilimines instead of the corresponding hazardous azides. Different catalysts and divergent light sources were tested. The reaction scope is broad and the product yield is generally high. An efficient gram-scale synthesis of Clausine C demonstrates the applicability and scalability of this new method.

FUSED RING COMPOUND HAVING UREA STRUCTURE

The present invention relates to a novel fused ring compound having urea structure that exhibits excellent NAMPT activating effect, and a method using the same for treating / preventing metabolic disorder, cardiovascular and kidney disease, mitochondrial disease, neurodegenerative disease, ocular disease, and muscle wasting disorder. The present invention provides a compound represented by following formula (I) or a pharmacologically acceptable salt: Formula (I) wherein A, B, R, R2 and R3 represent the same meanings as in the claims.

Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.

The Trifluoromethyl Group as a Bioisosteric Replacement of the Aliphatic Nitro Group in CB1 Receptor Positive Allosteric Modulators

The first generation of CB1 positive allosteric modulators (e.g., ZCZ011) featured a 3-nitroalkyl-2-phenyl-indole structure. Although a small number of drugs include the nitro group, it is generally not regarded as being "drug-like", and this is particularly true for aliphatic nitro groups. There are very few case studies where an appropriate bioisostere replaced a nitro group that had a direct role in binding. This may be indicative of the difficulty of replicating its binding interactions. Herein, we report the design and synthesis of ligands targeting the allosteric binding site on the CB1 cannabinoid receptor, in which a CF3 group successfully replaced the aliphatic NO2. In general, the CF3-bearing compounds were more potent than their NO2 equivalents and also showed improved in vitro metabolic stability. The CF3 analogue (1) with the best balance of properties was selected for further pharmacological evaluation. Pilot in vivo studies showed that (±)-1 has similar activity to (±)-ZCZ011, with both showing promising efficacy in a mouse model of neuropathic pain.

NaNO2/K2S2O8-mediated Selective Radical Nitration/Nitrosation of Indoles: Efficient Approach to 3-Nitro- and 3-Nitrosoindoles

JPZ acknowledges financial support from the National Natural Science Foundation of China (No. 21172163, 21472133), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and Key Laboratory of Organic Synthesis of Jiangsu Province (KJS1749). (Figure presented.).

Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1

In our ongoing effort of discovering anticancer and chemopreventive agents, a series of 2-arylindole derivatives were synthesized and evaluated toward aromatase and quinone reductase 1 (QR1). Biological evaluation revealed that several compounds (e.g., 2d, IC50 = 1.61 μM; 21, IC50 = 3.05 μM; and 27, IC50 = 3.34 μM) showed aromatase inhibitory activity with half maximal inhibitory concentration (IC50) values in the low micromolar concentrations. With regard to the QR1 induction activity, 11 exhibited the highest QR1 induction ratio (IR) with a low concentration to double activity (CD) value (IR = 8.34, CD = 2.75 μM), while 7 showed the most potent CD value of 1.12 μM. A dual acting compound 24 showed aromatase inhibition (IC50 = 9.00 μM) as well as QR1 induction (CD = 5.76 μM) activities. Computational docking studies using CDOCKER (Discovery Studio 3.5) provided insight in regard to the potential binding modes of 2-arylindoles within the aromatase active site. Predominantly, the 2-arylindoles preferred binding with the 2-aryl group toward a small hydrophobic pocket within the active site. The C-5 electron withdrawing group on indole was predicted to have an important role and formed a hydrogen bond with Ser478 (OH). Alternatively, meta-pyridyl analogs may orient with the pyridyl 3′-nitrogen coordinating with the heme group.

Pd-PEPPSI-IPentCl: A new highly efficient ligand-free and recyclable catalyst system for the synthesis of 2-substituted indoles: Via domino copper-free Sonogashira coupling/cyclization

A pyridine-containing decidedly resourceful Pd-N-heterocyclic carbene complex, Pd-PEPPSI-IPentCl (PEPPSI = pyridine enhanced precatalyst preparation, stabilization, and initiation), is used as a first class recyclable catalytic system for the synthesis of 2-substituted indoles via domino copper-free Sonogashira coupling/cyclization. The catalyst showed a greater performance in the cascade reaction of various 2-bromo anilines with different terminal acetylenes under mild (60 °C) and green conditions (ethanol:water) even in the absence of a copper catalyst and an inert atmosphere. The catalyst is used for the first time in these reactions. The findings suggest that 0.1 mol% of the catalyst is sufficient, and that the catalyst is recyclable and can be reused for up to six cycles.