78326-88-2

Usage

Uses

Used in Pharmaceutical Industry:
5-(benzyloxy)-2,3-dihydroinden-1-one is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
In the realm of chemical research, 5-(benzyloxy)-2,3-dihydroinden-1-one is utilized as a building block for the creation of fine chemicals, contributing to advancements in chemical synthesis and compound development.
Used as a Precursor in Organic Synthesis:
5-(benzyloxy)-2,3-dihydroinden-1-one is employed as a precursor in the synthesis of biologically active compounds, highlighting its importance in the discovery and production of novel organic molecules with potential applications in various fields.

Upstream product

• 3470-49-3 5-hydroxy-2,3-dihydro-1H-indene-1-one 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 100-51-6 benzyl alcohol 
• 1265683-76-8 2-(4-hydroxy-2-methylphenyl)-2-oxoethyl formate 
• 1265683-77-9 2-(4-(benzyloxy)-2-methylphenyl)-2-oxoethyl formate 
• 608119-82-0 1-(4-(benzyloxy)-2-methylphenyl)ethanone 
• 41877-16-1 2-bromo-1-(4-hydroxy-2-methylphenyl)-1-ethanone 
• 875-59-2 4'-hydroxy-2'methylacetophenone 
• 5111-70-6 5-methoxy-1-indanone 

Downstream Products

• 3199-73-3 2,3-dihydro-5-(phenylmethoxy)-1H-inden-1-ol 
• 88628-63-1 5-Benzyloxy-indan-1,2-dione 2-oxime 
• 90606-44-3 dimethyl 5-benzyloxy-1-oxo-2,2-indandipropionate 
• 90606-46-5 5-(benzyloxy)-1-hydroxy-2,2-indandipropionic acid δ-lactone 
• 90606-45-4 5-(benzyloxy)-1-oxo-2,2-indandipropionic acid 
• 88628-64-2 (1S,2R)-2-Amino-5-benzyloxy-indan-1-ol; hydrochloride 
• 88628-02-8 (1S,2R)-5-Benzyloxy-2-isopropylamino-indan-1-ol; hydrochloride 
• 88627-99-0 cis-5-hydroxy-2-(1-methyl-3-phenylpropyl)aminoindan-1-ol 
• 88628-01-7 (1S,2R)-5-Benzyloxy-2-(1-methyl-3-phenyl-propylamino)-indan-1-ol; compound with (E)-but-2-enedioic acid 
• 1382490-72-3 5-(benzyloxy)-2,3-dihydro-1-oxo-1H-inden-2-yl acetate 
• 856169-08-9 methyl 2-(5-hydroxy-2,3-dihydro-1H-inden-1-yl)acetate 

Relevant academic research and scientific papers

Adenosine A2AR/A1R Antagonists Enabling Additional H3R Antagonism for the Treatment of Parkinson’s Disease

Adenosine A1/A2Areceptors (A1R/A2AR) represent targets in nondopaminergic treatment of motor disorders such as Parkinson’s disease (PD). As an innovative strategy, multitargeting ligands (MTLs) were developed to achieve comprehensive PD therapies simultaneously addressing comorbid symptoms such as sleep disruption. Recognizing the wake-promoting capacity of histamine H3receptor (H3R) antagonists in combination with the “caffeine-like effects” of A1R/A2AR antagonists, we designed A1R/A2AR/H3R MTLs, where a piperidino-/pyrrolidino(propyloxy)phenyl H3R pharmacophore was introduced with overlap into an adenosine antagonist arylindenopyrimidine core. These MTLs showed distinct receptor binding profiles with overall nanomolar H3R affinities (Kii(A1R) = 11.5 nM,Ki(A2AR) = 7.25 nM) and 12( ST-1992,Ki(A1R) = 11.2 nM,Ki(A2AR) = 4.01 nM) were evaluatedin vivo.l-DOPA-induced dyskinesia was improved after administration of compound 4(1 mg kg-1, i.p. rats). Compound 12(2 mg kg-1, p.o. mice) increased wakefulness representing novel pharmacological tools for PD therapy.

METHODS OF TREATING OR PREVENTING COGNITIVE IMPAIRMENT USING INDANE ACETIC ACID DERIVATIVES BASED ON APOE4 GENOTYPE

The present invention provides indane acetic acid and their derivatives and methods for the treating and/or preventing of cognitive disorders based on the ApoE4 genotype of human subjects.

METHODS OF DOSE ADMINISTRATION FOR TREATING OR PREVENTING COGNITIVE IMPAIRMENT USING INDANE ACETIC ACID DERIVATIVES

The present invention provides indane acetic acid and their derivatives and methods for the treating and/or preventing of cognitive disorders.

Indanones as high-potency reversible inhibitors of monoamine oxidase

Recent reports document that α-tetralone (3,4-dihydro-2H-naphthalen-1-one) is an appropriate scaffold for the design of high-potency monoamine oxidase (MAO) inhibitors. Based on the structural similarity between α-tetralone and 1-indanone, the present stu

A photo-favorskii ring contraction reaction: The effect of ring size

The effect of ring size on the photo-Favorskii induced ring-contraction reaction of the hydroxybenzocycloalkanonyl acetate and mesylate esters (7a-d, 8a-c) has provided new insight into the mechanism of the rearrangement. By monotonically decreasing the ring size in these cyclic derivatives, the increasing ring strain imposed on the formation of the elusive bicyclic spirocyclopropanone 20 results in a divergence away from rearrangement and toward solvolysis. Cycloalkanones of seven or eight carbons undergo a highly efficient photo-Favorskii rearrangement with ring contraction paralleling the photochemistry of p-hydroxyphenacyl esters. In contrast, the five-carbon ring does not rearrange but is diverted to the photosolvolysis channel avoiding the increased strain energy that would accompany the formation of the spirobicyclic ketone, the "Favorskii intermediate 20". The six-carbon analogue demonstrates the bifurcation in reaction channels, yielding a solvent-sensitive mixture of both. Employing a combination of time-resolved absorption measurements, quantum yield determinations, isotopic labeling, and solvent variation studies coupled with theoretical treatment, a more comprehensive mechanistic description of the rearrangement has emerged.

Identification of fused-ring alkanoic acids with improved pharmacokinetic profiles that Act as G protein-coupled receptor 40/free fatty acid receptor 1 agonists

The G protein-coupled receptor 40 (GPR40)/free fatty acid receptor 1 (FFA1) has emerged as an attractive target for a novel insulin secretagogue with glucose dependency. We previously identified phenylpropanoic acid derivative 1 (3-{4-[(2′,6′-dimethylbiphenyl-3-yl)methoxy]-2-fluorophenyl} propanoic acid) as a potent and orally available GPR40/FFA1 agonist; however, 1 exhibited high clearance and low oral bioavailability, which was likely due to its susceptibility to β-oxidation at the phenylpropanoic acid moiety. To identify long-acting compounds, we attempted to block the metabolically labile sites at the phenylpropanoic acid moiety by introducing a fused-ring structure. Various fused-ring alkanoic acids with potent GPR40/FFA1 activities and good PK profiles were produced. Further optimizations of the lipophilic portion and the acidic moiety led to the discovery of dihydrobenzofuran derivative 53 ((6-{[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methoxy} -2,3-dihydro-1-benzofuran-3-yl)acetic acid), which acted as a GPR40/FFA1 agonist with in vivo efficacy during an oral glucose tolerance test (OGTT) in rats with impaired glucose tolerance.

The power of solvent in altering the course of photorearrangements

A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)-hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzofuranones occurs abruptly at low water concentrations (～8%). The surprisingly clean yields suggest that such reactions are synthetically promising.

Synthesis and inhibition study of monoamine oxidase, indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by 3,8-substituted 5H-indeno[1,2-c]pyridazin-5-one derivatives

Previous studies on 5H-indeno[1,2-c]pyridazin-5-one derivatives as inhibitors of MAO-B revealed that it was possible to increase the MAO-B inhibitory potency of 5H-indeno[1,2-c]pyridazin-5-ones by substituting the central heterocycle in the 3-position or

METHODS OF TREATING OR PREVENTING PSORIASIS, AND/OR ALZHEIMER'S DISEASE USING INDANE ACETIC ACID DERIVATIVES

The present invention provides indane acetic acid and their derivatives and methods for the treating and/or preventing psoriasis and/or Alzheimer's diseases.

CONFORMATIONALLY CONSTRAINED CARBOXYLIC ACID DERIVATIVES USEFUL FOR TREATING METABOLIC DISORDERS

The present invention provides compounds useful, for example, for treating metabolic disorders in a subject. Such compounds have the general formula I or the general formula III: where the definitions of the variables are provided herein. The present invention also provides compositions that include, and methods for using, the compounds in preparing medicaments and for treating metabolic disorders such as, for example, type II diabetes.