13623-25-1

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxy-1H-indanone is used as an α1-adrenoceptor antagonist for its potential application in the development of medications targeting various conditions related to the adrenergic system. Its antagonistic properties can be beneficial in treating ailments such as hypertension and benign prostatic hyperplasia.
Used in Chemical Synthesis:
6-Methoxy-1H-indanone is utilized as a key intermediate in the synthesis of various organic compounds. Specifically, it was used in the synthesis of 5-methoxyninhydrin (2,2-dihydroxy-5-methoxy-1,3-indanedione), which can be further employed in the preparation of pharmaceuticals and other specialty chemicals.
These applications highlight the versatility of 6-Methoxy-1H-indanone in both the pharmaceutical and chemical synthesis industries, making it a valuable compound for researchers and manufacturers alike.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 1092, 1949 DOI: 10.1021/ja01171a092

Purification Methods

Crystallise it from MeOH, then sublime it at high vacuum. [Beilstein 8 IV 894.]

InChI:InChI=1/C10H10O2/c1-12-8-4-2-7-3-5-10(11)9(7)6-8/h2,4,6H,3,5H2,1H3

Upstream product

• 54125-02-9 danishefsky's diene 
• 77970-18-4 3-nitro-2-cyclopentenone 
• 201230-82-2 carbon monoxide 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 5111-69-3 5-methoxyindane 
• 15893-42-2 3-(4-methoxyphenyl)propionyl chloride 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 62803-47-8 6-hydroxy-1-indanone 
• 74-88-4 methyl iodide 
• 101596-87-6 2-phenyl-7-methoxytetralone 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 101466-49-3 2-ethenyl-5-methoxybenzaldehyde 

Downstream Products

• 62803-47-8 6-hydroxy-1-indanone 
• 16307-08-7 2-benzylidene-6-methoxy-indan-1-one 
• 137813-03-7 5-methoxy-3-oxo-2,3-dihydro-1H-indene-1-carboxylic acid 
• 66892-37-3 2',3'-dihydro-6'-methoxyspiro-2,5-dione 
• 62015-79-6 2-bromo-6-methoxy-2,3-dihydro-1H-inden-1-one 
• 3469-09-8 6-methoxyindan-1-ol 
• 24077-98-3 (Z)-2-(hydroxyimino)-6-methoxy-2,3-dihydro-1H-inden-1-one 
• 124688-07-9 6-methoxy-2,2-dimethyl-1-indanone 
• 62841-74-1 3-(2'-Benzyloxyethyl)-6-methoxy-indanon 
• 62841-75-2 1-(2'-Benzyloxyethyl)-6-methoxy-1-indenol 
• 24077-98-3 2-(hydroxyimino)-6-methoxy-2,3-dihydro-1H-inden-1-one 
• 1885-13-8 4-methoxyphthalic acid 
• 103028-81-5 6-methoxyindan-1-ylamine 
• 62-53-3 aniline 

Relevant academic research and scientific papers

Enantioselective bioreduction of benzo-fused cyclic ketones with engineered: Candida glabrata ketoreductase 1-a promising synthetic route to ladostigil (TV3326)

Biocatalysis has been recently emerging as a promising alternative to traditional chemical synthesis because of its "green" characteristics and comparable selectivities, which accord with the concept of sustainable development and demand for asymmetric synthesis. In this study, whole-cell biocatalysts containing glucose dehydrogenase (GDH) and Candida glabrata ketoreductase 1 (CgKR1) variants were constructed. These biocatalysts were applied to the reduction of benzo-fused cyclic ketones and showed good to high activities and enantioselectivities. Particularly, CgKR1 variants displayed high activities (90.6%-98.4% conversions) and enantioselectivities (>99.9% ee) towards 5a, a key intermediate of ladostigil (TV3326). Based on these results, a chemoenzymatic synthesis of (S)-5b was developed by using biocatalytic asymmetric reduction as a key step, giving the product with a total yield of 34.0% and 99.9% ee.

Three-chain truxene discotic liquid crystal showing high charged carrier mobility

A new truxene discotic liquid crystal possessing only three octyloxy chains (3C8OTRX) was studied on the mesomorphic and semiconducting properties to reveal that it exhibits a high drift mobility of positive carriers in the order of 10-2 cm2 V-1 s-1 in the hexagonal ordered columnar (Colho) mesophase.

Design, Synthesis, and Evaluation of Donepezil-Like Compounds as AChE and BACE-1 Inhibitors

An ecofriendly synthetic pathway for the synthesis of donepezil precursors is described. Alternative energy sources were used for the total synthesis in order to improve yields, regioselectively, and rate of each synthetic step and to reduce the coproduction of waste at the same time. For all products, characterized by an improved structural rigidity respect to donepezil, the inhibitor activity on AChE, the selectivity vs BuChE, the side-activity on BACE-1, and the effect on SHSY-5Y neuroblastoma cells viability were tested. Two potential new lead compounds for a dual therapeutic strategy against Alzheimers disease were envisaged.

Synthesis of 1-indanones by intramolecular Friedel-Crafts reaction of 3-arylpropionic acids catalyzed by Tb(OTf)3

Intramolecular Friedel-Crafts acylation reaction of 3-arylpropionic acids was efficiently catalyzed by Tb(OTf)3 at 250°C to give 1-indanones. Even deactivated 3-arylpropionic acids with halogen atoms on the aromatic ring can be cyclized in moderation to good yields.

A concise synthesis of 2-benzoyl-1-indanones and 1-indanones from 2-aryl-1-tetralones

Methyl-2-(3-oxo-3-aryl) benzoates derived from acid catalyzed air oxidative fragmentation of 2-aryl-1-tetralones were efficiently undergone intramolecular-Claisen condensation in the presence of potassium tertiary butoxide. The resulting 2-benzoyl-1-indanones formed in two-step ring contractions were further subjected to indium triflate mediated retro-Claisen condensation to get 1-indanones.

Synthesis and biological evaluation of pyridine-linked indanone derivatives: Potential agents for inflammatory bowel disease

A series of pyridine-linked indanone derivatives were designed and synthesized to discover new small molecules for the treatment of inflammatory bowel disease (IBD). Compounds 5b and 5d exhibited strongest inhibitory activity against TNF-α-induced monocyte adhesion to colon epithelial cells (an in vitro model of colitis). In TNBS (2,4,6-trinitrobenzenesulfonic acid)-induced rat colitis model, oral administration of the compounds 5b and 5d ameliorated colitis with significant recovery in altered expressions of E-cadherin, TNF-α and IL-1β expressions, indicating 5b and 5d as potential agents for therapeutics development against IBD.

Effect of ring size on photoisomerization properties of stiff stilbene macrocycles

A series of stiff stilbene macrocycles have been studied to investigate the possible impact of the macrocycle ring size on their photodynamic properties. The results show that reducing the ring size counteracts the photoisomerization ability of the macrocycles. However, even the smallest macrocycle studied (stiff stilbene subunits linked by a six carbon chain) showed some degree of isomerization when irradiated. DFT calculations of the energy differences between the E- and Z-isomers show the same trend as the experimental results. Interestingly the DFT study highlights that the energy difference between the E- and Z-isomers of even the largest macrocycle (linked by a twelve carbon chain) is significantly higher than that of the stiff stilbene unit itself. In general, it is indicated that addition of even a flexible chain to the stiff stilbene unit may significantly affect its photochemical properties and increase the photostability of the resulting macrocycle.

Bipolar carrier transport in Tri-Substituted octyloxy-Truxene DLC

In this study, bipolar charge carrier transport of 2,7,12- trioctyloxytruxene has been studied by a time-of-flight method. The substance studied exhibits a hexagonal columnar mesophase of which melting and clearing points are 118C and 133C, respectively. Ambipolar electronic carrier transports were observed in the mesophase. The drift mobility measurements reveal it is in the order of 10-2cm2 V-1 s-1 in the Colh and it increases to 10-1cm2 V-1 s-1 at the columnar mesophase - metastable phase transition, indicating truxene is an interesting molecular core for mesophase semiconductors. Copyright Taylor & Francis Group, LLC.

Non-conventional methodologies in the synthesis of 1-indanones

1-Indanones have been successfully prepared by means of three different non-conventional techniques, namely microwaves, high-intensity ultrasound and a Q-tube reactor. A library of differently substituted 1-indanones has been prepared via one-pot intramolecular Friedel-Crafts acylation and their efficiency and "greenness" have been compared.

Kinetics-Driven Drug Design Strategy for Next-Generation Acetylcholinesterase Inhibitors to Clinical Candidate

The acetylcholinesterase (AChE) inhibitors remain key therapeutic drugs for the treatment of Alzheimer's disease (AD). However, the low-safety window limits their maximum therapeutic benefits. Here, a novel kinetics-driven drug design strategy was employed to discover new-generation AChE inhibitors that possess a longer drug-target residence time and exhibit a larger safety window. After detailed investigations, compound 12 was identified as a highly potent, highly selective, orally bioavailable, and brain preferentially distributed AChE inhibitor. Moreover, it significantly ameliorated cognitive impairments in different mouse models with a lower effective dose than donepezil. The X-ray structure of the cocrystal complex provided a precise binding mode between 12 and AChE. Besides, the data from the phase I trials demonstrated that 12 had good safety, tolerance, and pharmacokinetic profiles at all preset doses in healthy volunteers, providing a solid basis for its further investigation in phase II trials for the treatment of AD.