196597-96-3

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxy-7-nitro-1-indanone is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of novel molecules and potential drug candidates. Its specific chemical properties allow for the creation of new compounds with therapeutic potential.
Used in Agrochemical Industry:
In the agrochemical industry, 6-Methoxy-7-nitro-1-indanone serves as an intermediate in the synthesis of agrochemicals, aiding in the development of new compounds for agricultural applications, such as pesticides and herbicides.
Used in Advanced Materials Development:
6-Methoxy-7-nitro-1-indanone is utilized in the development of advanced materials due to its unique chemical properties, which can contribute to the creation of innovative materials with specific characteristics for various applications.
Used as a Research Tool in Organic Chemistry:
As a research tool in organic chemistry, 6-Methoxy-7-nitro-1-indanone is employed in various organic chemical reactions, enabling the exploration of new synthetic pathways and the discovery of new chemical compounds.
It is crucial to handle 6-Methoxy-7-nitro-1-indanone with care and adhere to proper safety protocols due to its potential health hazards.

InChI:InChI=1/C10H9NO4/c1-15-8-5-3-6-2-4-7(12)9(6)10(8)11(13)14/h3,5H,2,4H2,1H3

Upstream product

• 13623-25-1 6-methoxy-2,3-dihydro-1H-inden-1-one 

Downstream Products

• 1154740-87-0 7-amino-6-methoxy-2,3-dihydro-1H-inden-1-one 

Relevant academic research and scientific papers

Conformationally constrained analogues of N′-(4-tert-butylbenzyl)-N-(4-methylsulfonylaminobenzyl)thiourea as TRPV1 antagonists

A series of bicyclic analogues having indan and tetrahydronaphthalene templates in the A-region were designed as conformationally constrained analogues of our previously reported potent TRPV1 antagonists (1, 3). The activities for rat TRPV1 of the conformationally restricted analogues were moderately or markedly diminished, particularly in the case of the tetrahydronaphthalene analogues. The analysis indicated that steric constraints at the benzylic position in the bicyclic analogues may be an important factor for their unfavorable interaction with the receptor.

Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists

To develop a new therapeutic agent for sleep disorders, we synthesized a novel series of tricyclic indan derivatives and evaluated them for their binding affinity to melatonin receptors. In our previous paper, we proposed a conformation of the methoxy group favorable for the binding of the MT1 receptor. To fix the methoxy group in an active conformation, we decided to synthesize conformationally restricted tricyclic indan analogues with the oxygen atom in the 6-position incorporated into a furan, 1,3-dioxane, oxazole, pyran, morpholine, or 1,4-dioxane ring system. Among these compounds, indeno[5,4-b]furan analogues were found to be the most potent and selective MT1 receptor ligands and to have superior metabolic stability. The optimization of substituents led to (S)-(-)-22b, which showed very strong affinity for human MT1 (Ki = 0.014 nM), but no significant affinity for hamster MT3 (Ki = 2600 nM) or other neurotransmitter receptors. The pharmacological effects of (S)-(-)-22b were studied in experimental animals, and it was found that a dose of 0.1 mg/kg, po promoted a sleep in freely moving cats, as demonstrated by a decrease in wakefulness and increases in slow wave sleep and rapid eye movement sleep, which lasted for 6 h after administration. Melatonin (1 mg/kg, po) also had a sleep-promoting effect, though it lasted only 2 h. A new chiral method for the synthesis of (S)-(-)-22b starting from 60, which was prepared from 59 employing asymmetric hydrogenation with the (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl-Ru complex, was developed. (S)-(-)-22b (TAK-375) is currently under clinical trial for the treatment of insomnia and circadian rhythm disorders.

Bicyclic compounds and pharmaceutical composition containing tricyclic compound for treating or preventing sleep disorders

A compound having the following general fomula: wherein R1 is an optionally substituted hydrocarbon, amino or heterocyclic group; R2 is H or an optionally substituted hydrocarbon group; R3 is H or an optionally substituted hydrocarbon or heterocyclic group; X is CHR4, NR4, O or S in which R4 is H or an optionally substituted hydrocarbon group; R5 is H, a halogen atom, C1-6 alkyl group, a C1-6 alkoxy group, a hydroxy group, a nitro group, a cyano group or an amino group wherein the C1-6 alkyl group, the C1-6 alkoxy group and the amino group may be substituted by 1 to 5 substituents, Y is C or N; ring B is an optionally substituted benzene ring; m = 1 to 4 and n = 0 to 2; L represents a leaving group such as a halogen atom, an alkylsulfonyl group, an alkylsulfonlyoxy group and arylsulfonyloxy group; or a salt thereof.

Tricyclic compounds, their production and use

A compound of the formula: STR1 wherein R1 is an optionally substituted hydrocarbon, amino or heterocyclic group; R2 is H or an optionally substituted hydrocarbon group; R3 is H or an optionally substituted hydrocarbon or heterocyclic group; X is CHR4, NR4, O or S in which R4 is H or an optionally substituted hydrocarbon group; Y is C, CH or N; ring A is optionally substituted 5- to 7-membered ring; ring B is an optionally substituted benzene ring; and m is 1 to 4, or a salt thereof, a process for producing it, an intermediate for the production and a pharmaceutical composition comprising it are provided.