18631-22-6

Usage

Uses

Used in Pharmaceutical Industry:
5H-Indeno[1,2-c]pyridin-5-one is used as a potential therapeutic agent for the treatment of cancer and other diseases. Its pharmacological properties make it a promising candidate for drug discovery and development.
Used in Drug Discovery:
5H-Indeno[1,2-c]pyridin-5-one is used as a lead compound in the search for new drugs with potential therapeutic effects. Its unique structure and biological activities provide a foundation for further research and optimization to develop effective pharmaceuticals.
Used in Medicinal Chemistry:
5H-Indeno[1,2-c]pyridin-5-one is used as a starting point for the design and synthesis of new chemical entities with potential medicinal applications. Its interesting pharmacological properties can be further explored and modified to enhance its therapeutic potential.
Used in Cancer Research:
5H-Indeno[1,2-c]pyridin-5-one is used as a research tool to study the molecular mechanisms underlying cancer development and progression. Its potential as an anticancer agent can be investigated through various in vitro and in vivo models to understand its mode of action and efficacy.
Used in Disease Treatment:
5H-Indeno[1,2-c]pyridin-5-one is used as a potential treatment option for various diseases, including but not limited to cancer. Its diverse biological activities and pharmacological properties make it a valuable compound for exploring new therapeutic approaches to combat different health conditions.

InChI:InChI=1/C12H7NO/c14-12-9-4-2-1-3-8(9)11-7-13-6-5-10(11)12/h1-7H

Upstream product

• 91973-39-6 (2-Aminophenyl)-(pyridin-4-yl)methanone 
• 6625-74-7 N-pivaloylaniline 
• 19352-29-5 methyl-4 phenyl-3 pyridine 
• 122-78-1 phenylacetaldehyde 
• 583-55-1 1-Bromo-2-iodobenzene 
• 70201-43-3 3-bromo-pyridine-4-carbaldehyde 
• 59786-31-1 methyl 3-bromoisonicotinate 
• 104096-15-3 3-phenylpyridine-4-carboxylic acid 
• 244-42-8 3-azafluorene 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 3430-22-6 3-Bromo-4-methylpyridin 
• 13959-02-9 3-bromoisonicotinic acid 
• 626-55-1 3-Bromopyridine 
• 308103-40-4 (2-acetylphenyl)boronic acid 

Downstream Products

• 110576-18-6 3-Azafluorene-9-one semicarbazone 
• 850162-90-2 3-aza-9-hydroxy-9-fluorenylcarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide 

Relevant academic research and scientific papers

On the mechanism of the metalation of 2-(pyridin-3-yl)benzoic acid derivatives

The mechanism of the metalation of 2-(pyridin-3-yl)benzoic acid derivatives with strong bases is discussed.

SYNTHESIS OF 3-AZAFLUORENE AND 2H-2-METHYLINDENOPYRIDINE

4-Methyl-3-phenylpyridine was isolated from the mixture of four isomeric methylphenylpyridines formed in the condensation of crotonaldehyde with phenylacetaldehyde (β-phenylethanol or phenylacetylene) with ammonia in the presence of a cadmium-calcium phosphate catalyst. 4-Methyl-3-phenylpyridine was converted to 3-azafluorene by catalytic dehydrocyclization.A representative of a new series of pseudoazulenes, viz., 2H-2-methylindeno-pyridine, was obtained by treatment of 3-azafluorene methiodide with sodium hydroxide solution; the product was a crystalline black substance that remained unchanged during storage in air for 1 month.

Palladium-catalyzed synthesis of fluoreones from bis(2-bromophenyl)methanols

A palladium-catalyzed synthesis method of fluorenones has been developed. A variety of bis(2-bromophenyl)methanols could undergo the reaction smoothly in the presence of Pd(OAc)2, affording a series of fluorenones in moderate to good yields (two steps). Mechanistic studies reveal that the reaction might be triggered by oxidation of alcohol followed by intramolecular reductive coupling.

Nitrogen introduction of spirobifluorene to form α-, β-, γ-, and δ-aza-9,9′-spirobifluorenes: New bipolar system for efficient blue organic light-emitting diodes

Four aza-9,9′-spirobifluorenes (aza-SBFs) with nitrogen atom at different positions of one fluorene moiety were synthesized to study the structure-properties relationships. α-Aza-SBF and β-aza-SBF possessed almost completely separated the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), while γ-aza-SBF and δ-aza-SBF showed overlapped HOMO and LUMO orbitals. The aza-SBFs showed excellent bipolar features and good thermal stabilities than those of SBFs. The maximum current efficiencies (CE) of α-, β-, γ-, and δ-aza-SBF-based OLEDs were 28.8, 24.9, 25.5, and 27.2 cd/A, respectively. Compared to the SBF, all of four aza-SBFs showed better devices performances. The CE and power efficiency (PE) of OLED based on α-aza-SBF was 28.8 cd/A and 22.6 lm/W, while the SBF-based OLED was only 12.3 cd/A and 8.2 lm/W. The maximum external quantum efficiency of α-aza-SBF-based OLED was 15.4%, which was 2.5 times than that of the SBF-based one (6.6%) due to introduction of nitrogen improving electron transporting. Novel materials based on these components and their potential applications in organic electronics were expected due to their excellent bipolar features.

Scope of regioselective Suzuki reactions in the synthesis of arylpyridines and benzylpyridines and subsequent intramolecular cyclizations to azafluorenes and azafluorenones

The current investigation on regioselective Suzuki reactions of 2,3-dihalopyridines and 2-halo-3-halomethylpyridines yielded the unexplored synthesis of arylpyridines and benzylpyridines bearing synthetic handles for further functionalization. Indeed, the scope of intramolecular cyclizations of arylpyridines and benzylpyridines prepared in this study for the synthesis of azafluorenes and azafluorenones has been investigated.

Aza-spirobifluorene derivative and preparation method thereof

The invention discloses an aza-spirobifluorene derivative. The aza-spirobifluorene derivative is characterized by having a structural formula as shown in the specification, wherein only one of X1, X2, X3 and X4 is a nitrogen atom, and the other three are carbon atoms; and R is an aromatic or heterocyclic aromatic ring containing 6-60 carbon atoms. The aza-spirobifluorene derivative disclosed by the invention can be used as an illuminant material; the aza-spirobifluorene derivative can be independently used as an illuminating layer or doped dye for illuminating or can be formed into an exciplex with the other materials for illuminating; the aza-spirobifluorene derivative also has a carrier transporting capacity; and a group has a hole transmitting capacity and an electron transmitting capacity. The aza-spirobifluorene derivative provided by the invention can be prepared into an excellent amorphous film according to vacuum evaporation or solution methods (spin coating, printing, and the like). The aza-spirobifluorene derivative also has higher thermal stability and photo-stability.

Intramolecular Minisci acylation under silver-free neutral conditions for the synthesis of azafluorenones and fluorenones

Despite its synthetic potential, intramolecular acylation by the Minisci reaction remains unexplored. The development of a new intramolecular Minisci acylation under silver-free neutral conditions providing access to azafluorenones and fluorenones is described. Distinct from the current literature known approaches for Minisci acylation, the report described herein features a method that: (a) avoids the use of silver that is invariably used in Minisci acylation, (b) does not require any acidic conditions for the activation of pyridines, and (c) shows tolerance to functional groups under neutral conditions.

9-Hydroxyazafluorenes and their use in thrombin inhibitors

Optimization of a previously reported thrombin inhibitor, 9-hydroxy-9-fluorenylcarbonyl-L-prolyl-trans-4-aminocyclohexylmethylamide (1), by replacing the aminocyclohexyl P1 group provided a new lead structure, 9-hydroxy-9-fluorenylcarbonyl-L-prolyl-2-aminomethyl-5-chlorobenzylamide (2), with improved potency (Ki = 0.49 nM for human thrombin, 2× APTT = 0.37 μM in human plasma) and pharmacokinetic properties (F = 39%, iv T1/2 = 13 h in dogs). An effective strategy for reducing plasma protein binding of 2 and improving efficacy in an in vivo thrombosis model in rats was to replace the lipophilic fluorenyl group in P3 with an azafluorenyl group. Systematic investigation of all possible azafluorenyl P3 isomers and azafluorenyl-N-oxide analogues of 2 led to the identification of an optimal compound, 3-aza-9-hydroxyfluoren-9(R)-ylcarbonyl-L-prolyl-2-aminomethyl-5- chlorobenzylamide (19b), with high potency (Ki = 0.40 nM, 2× APTT = 0.18 μM), excellent pharmacokinetic properties (F = 55%, T 1/2 = 14 h in dogs), and complete efficacy in the in vivo thrombosis model in rats (inhibition of FeCl3-induced vessel occlusions in six of six rats receiving an intravenous infusion of 10 μg/kg/min of 19b). The stereochemistry of the azafluorenyl group in 19b was determined by X-ray crystallographic analysis of its N-oxide derivative (23b) bound in the active site of human thrombin.

A General Synthesis of Substituted Fluorenones and Azafluorenones

Twenty-one variously substituted fluorenones and azafluorenones have been synthesized via photochemical Pschorr cyclizations of 2-diazoniodiaryl ketones as the key ring-forming step.Direct, (bipy)3RuII-, or (bipy)3RuII/CuII-photosensitized conditions were used, depending on the system to be cyclized.Where selectivities were possible in the ring closure, the isomer ratios obtained were in accord with an aryl radical as the reactive intermediate.The precursor aminodiaryl ketones were obtained from the sequence ortho lithiation of an arylpivalamide, reaction withan aryl aldehyde to give a 2-pivalamidodiarylcarbinol, oxidation to give a 2-pivalamidodiaryl ketone, and hydrolysis to give the 2-aminodiaryl ketone.