2107-85-9

Usage

Uses

Used in Organic Synthesis:
5,6-Dimethoxy-2-nitroso-2,3-dihydro-1H-inden-1-one is used as a key intermediate in organic synthesis for the creation of various complex organic molecules. Its unique structure allows it to participate in a range of chemical reactions, facilitating the synthesis of new compounds with potential applications in different industries.
Used as a Reagent in Chemical Reactions:
In the field of chemistry, 5,6-Dimethoxy-2-nitroso-2,3-dihydro-1H-inden-1-one serves as a reagent that can initiate or catalyze specific chemical reactions. Its presence can enhance the efficiency of certain processes, making it a valuable tool for chemists working on advanced chemical transformations.
Used in Pharmaceutical Research and Development:
5,6-Dimethoxy-2-nitroso-2,3-dihydro-1H-inden-1-one is utilized in pharmaceutical research and development as a compound with potential medicinal properties. Its unique chemical structure may contribute to the development of new drugs, particularly in the areas that require further exploration and understanding of its pharmacological effects.
Used in Chemical Research:
In the realm of chemical research, 5,6-Dimethoxy-2-nitroso-2,3-dihydro-1H-inden-1-one is employed to study its properties and behavior under various conditions. This research can lead to a better understanding of its reactivity, stability, and potential interactions with other compounds, which is essential for its application in different chemical processes.
Further research is essential to fully comprehend the potential uses and properties of 5,6-Dimethoxy-2-nitroso-2,3-dihydro-1H-inden-1-one, ensuring its safe and effective application across various industries.

Upstream product

• 2107-69-9 5,6-dimethoxy-1-indanone 
• 544-16-1 n-Butyl nitrite 
• 2107-70-2 3,4-methoxycinnamic acid 
• 51842-87-6 3-(3,4-dimethoxy-phenyl)-propionyl chloride 
• 110-46-3 isopentyl nitrite 
• 624-91-9 methyl nitrite 

Downstream Products

• 76254-26-7 2-(cyanomethyl)-4,5-dimethoxybenzoic acid 
• 83598-55-4 5,6-Dimethoxy-2-indanylamine 
• 24634-09-1 2-(cyanomethyl)-4,5-dimethoxybenzoyl chloride 
• 577-68-4 m-hemipinic acid 
• 42337-64-4 5,6-dimethoxyindane-1,2-dione 
• 745060-74-6 N-(5,6-dimethoxy-indan-2-yl)-2-phenyl-N-propyl-acetamide 
• 745064-65-7 N-(5,6-dimethoxy-indan-2-yl)-3-phenyl-N-propyl-propionamide 
• 390361-23-6 [2-(4-bromo-phenyl)-ethyl]-(5,6-dimethoxy-indan-2-yl)-propyl-amine 
• 745062-37-7 2-(4-bromo-phenyl)-N-(5,6-dimethoxy-indan-2-yl)-N-propyl-acetamide 
• 745062-86-6 2-(3-amino-phenyl)-N-(5,6-dimethoxy-indan-2-yl)-N-propyl-acetamide 
• 745061-52-3 N-(5,6-dimethoxy-indan-2-yl)-2-(3-fluoro-phenyl)-N-propyl-acetamide 
• 745062-55-9 N-(5,6-dimethoxy-indan-2-yl)-2-(4-methoxy-phenyl)-N-propyl-acetamide 
• 745062-57-1 N-(5,6-dimethoxy-indan-2-yl)-2-(3,4-dimethoxy-phenyl)-N-propyl-acetamide 
• 745062-85-5 N-(5,6-dimethoxy-indan-2-yl)-N-propyl-2-(4-trifluoromethyl-phenyl)-acetamide 

Relevant academic research and scientific papers

Efficient diastereoselective synthesis of cis-2-amino-1-indanol derivatives and cis- and trans-1-amino-2-indanol via Pd-catalyzed hydrogenation

(±)-cis-2-amino-1-indanol was diastereoselectively synthesized from 1,2-indanedion-2-oxime in ethanol at 25 °C under 10% Pd/C-catalyzed hydrogenation conditions. Under the same hydrogenation condition, 1,2-indanedion-2-oxime and their derivatives having one and/or two electron-donating groups in aliphatic or aromatic part of indanyl ring were diastereoselectively reduced to racemic cis-2-amino-1-indanol derivatives. From 1,2-indanedion-1-oxime, (±)-trans-1-amino-2-indanol was obtained in ethanol at 25 °C over a 10% Pd/BaSO4 catalyst. In contrast, the 10% Pd/BaSO4-catalyzed hydrogenation reaction in ethanol at 45 °C afforded cis-1-hydroxyamino-2-indanol from 1,2-indanedion-1-oxime, followed by reduction to form (±)-cis-1-amino-2-indanol. The diastereoselectivity of β-aminoindanols was dependent on the Pd catalyst, reaction temperature, and pH of the reaction medium.

Synthesis of 2-(Cyanomethyl)benzoic Esters via Carbon-Carbon Bond Cleavage of Indanones

A novel synthesis of 2-(cyanomethyl)benzoic esters from indanone derivatives has been established. This reaction proceeds via a deprotonation of alcohols with a chemical base, followed by a nucleophilic addition to indanones and Beckmann fragmentation. In addition, this reaction could also work under electrochemical conditions, and no external chemical bases were needed. This mild method offers a novel strategy for the late-stage functionalization of various natural alcohols.

Cu-catalyzed coupling of indanone oxime acetates with thiols to 2,3-difunctionalized indenones

A Cu-catalyzed coupling reaction of indanone oxime acetates with thiols has been developed for the synthesis of 2,3-functionalized 1-indenones. This protocol has several features including easy mild reaction conditions, stabilized enamine products, good t

Novel N-benzylpiperidine carboxamide derivatives as potential cholinesterase inhibitors for the treatment of Alzheimer's disease

A series of fifteen acetylcholinesterase inhibitors were designed and synthesised based upon the previously identified lead compound 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl 1-benzylpiperidine-4-carboxylate (5) which showed good inhibitory activity (IC50 0.03 ± 0.07 μM) against acetylcholinesterase. A series of compounds were prepared wherein the ester linker in the original lead compound was exchanged for a more metabolically stable amide linker and the indanone moiety was exchanged for a range of aryl and aromatic heterocycles. The two most active analogues 1-benzyl-N-(5,6-dimethoxy-8H-indeno[1,2-d]thiazol-2-yl)piperidine-4-carboxamide (28) and 1-benzyl-N-(1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) piperidine-4-carboxamide (20) afforded in vitro IC50 values of 0.41 ± 1.25 and 5.94 ± 1.08 μM, respectively. In silico screening predicts that 20 will be a blood brain-barrier permeant, and molecular dynamic simulations are indicative of a close correlation between the binding of 20 and the Food and Drug Administration-approved cholinesterase inhibitor donepezil (1).

Preparation method of 2-aminoindan derivative

The invention discloses a preparation method of a 2-aminoindan derivative. The preparation method comprises the following steps: with a 1-indanone derivative as a starting raw material, carrying out oximation reaction, and synchronously reducing carbonyl and hydroxyl oxime under the catalysis of Lewis acid such as aluminum chloride in the presence of a boron metal reducing agent, so as to obtain the 2-aminoindan derivative. The invention further provides the 2-aminoindan derivative prepared by virtue of a synthetic method and a corresponding intermediate derivative. Compared with a synthetic method of the 2-aminoindan derivative in the prior art, the synthetic method disclosed by the invention has the beneficial effects that (1) only two reaction steps are adopted, and the reaction steps are obviously less than the reaction steps in the prior art; (2) the cost is relatively low, the operation is simple and convenient, and the yield is high; and (3) the preparation method is suitable for large-scale industrial production and has relatively good application prospects.

Catalytic Asymmetric Mannich/Cyclization of 2-Isothiocyanato-1-indanones: An Approach to the Synthesis of Bispirocyclic Indanone-Thioimidazolidine-Oxindoles

This study demonstrates that novel isothiocyanates derived from 1-indanones are useful building blocks in heteroannulation reactions with isatinimines. This convenient Mannich/cyclization cascade reaction serves as a powerful tool for the enantioselective construction of bispirocyclic indanone-thioimidazolidine-oxindoles bearing two adjacent spiro-quaternary stereocenters in good to excellent yields with excellent diastereo- and enantioselectivities. Versatile transformations of the products into other potential bioactive bispirocyclic heterocycles have also been demonstrated.

Histone lysine methyltransferase structure activity relationships that allow for segregation of G9a inhibition and anti-Plasmodium activity

Plasmodium falciparum HKMTs (PfHKMTs) play a key role in controlling Plasmodium gene expression and represent exciting new anti-malarial epigenetic targets. Using an inhibitor series derived from the diaminoquinazoline HKMT inhibitory chemotype, we have previously identified compounds with highly promising antimalarial activity, including irreversible asexual cycle blood stage-independent cytotoxic activity at nM concentrations, oral efficacy in in vivo models of disease, and the unprecedented ability to reactivate dormant liver stage parasites (hypnozoites). However, future development of this series will need to address host versus parasite selectivity, where inhibitory activity against human G9a is removed from the lead compounds, while maintaining potent anti-Plasmodium activity. Herein, we report an extensive study of the SAR of this series against both G9a and P. falciparum. We have identified key SAR features which demonstrate that high parasite vs. G9a selectivity can be achieved by selecting appropriate substituents at position 2, 4 and 7 of the quinazoline ring. We have also, in turn, discovered that potent G9a inhibitors can be identified by employing a 6-carbon 'Nle mimic' at position 7. Together, this data suggests that while broadly similar, the G9a and potential PfHKMT target(s) binding pockets and/or binding modes of the diaminoquinazoline analogues exhibit clear and exploitable differences. Based on this, we believe this scaffold to have clear potential for development into a novel anti-malarial therapeutic.

SMALL MOLECULE AGONISTS OF NEUROTENSIN RECEPTOR 1

Provided herein are small molecule neurotensin receptor agonists, compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

ANTIMICROBIAL AGENTS

The invention provides a compound of formula (I): or a salt or prodrug thereof, wherein R1, R4-R8, R10, R2'-R6', W, and A have any of the values described in the specification, as well as compositions comprising a compound of formula (I). The compounds are useful as antibacterial agents.

The identification of indacaterol as an ultralong-acting inhaled β2-adrenoceptor agonist

Following a lipophilicity-based hypothesis, an 8-hydroxyquinolinone 2-aminoindan derived series of β2-adrenoceptor agonists have been prepared and evaluated for their potential as inhaled ultralong-acting bronchodilators. Determination of their activities at the human β2-adrenoceptor receptor showed symmetrical substitution of the 2-aminoindan moiety at the 5- and 6-positions delivered the targeted intermediate potency and intrinsic-efficacy profiles relative to a series of clinical reference β2-adrenoceptor agonists. Further assessment with an in vitro superfused electrically stimulated guinea-pig tracheal-strip assay established the onset and duration of action time courses, which could be rationalized by considering the lipophilicity, potency, and intrinsic efficacy of the compounds. From these studies the 5,6-diethylindan analogue indacaterol 1c was shown to possess a unique profile of combining a rapid onset of action with a long duration of action. Further in vivo profiling of 1c supported the long duration of action and a wide therapeutic index following administration to the lung, which led to the compound being selected as a development candidate.