124702-80-3

Basic information

• Product Name: 56-dihydroxy-indan-1-
• Synonyms: 56-dihydroxy-indan-1-;1H-Inden-1-one, 2,3-dihydro-5,6-dihydroxy-;5,6-Dihydroxy-2,3-dihydro-1H-inden-1-one;5,6-dihydroxy-2,3-dihydroinden-1-one
• CAS NO: 124702-80-3
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.15802
• Mol File: 124702-80-3.mol

Chemical Properties

• Melting Point: 107-109℃
• Appearance: /
• Density: 1.467
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 56-dihydroxy-indan-1-(CAS DataBase Reference)
• NIST Chemistry Reference: 56-dihydroxy-indan-1-(124702-80-3)
• EPA Substance Registry System: 56-dihydroxy-indan-1-(124702-80-3)

Safety Data

• Hazardous Substances Data: 124702-80-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Dihydroxy-indan-1-one is used as a pharmaceutical candidate for its potential antioxidant properties, which can help in the development of treatments targeting oxidative stress-related conditions. Its free radical scavenging ability also makes it a promising agent for the prevention and treatment of various diseases associated with oxidative damage.
Used in Organic Synthesis:
In the field of organic synthesis, 5,6-dihydroxy-indan-1-one serves as a valuable building block. Its unique structure allows for the synthesis of various complex organic compounds, contributing to the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Antioxidant Formulations:
5,6-Dihydroxy-indan-1-one is used as an antioxidant in various formulations, such as food additives, cosmetics, and industrial applications, to prevent oxidation and extend the shelf life of products. Its ability to scavenge free radicals helps protect against oxidative damage and degradation.
Used in Research and Development:
Due to its unique structure and properties, 5,6-dihydroxy-indan-1-one is utilized in research and development for the exploration of new chemical reactions, synthesis pathways, and potential applications in various industries. Its study contributes to the advancement of knowledge in chemistry and biochemistry, paving the way for future innovations.

Upstream product

• 1078-61-1 dihydrocaffeic acid 
• 90843-62-2 6-hydroxy-5-methoxyindan-1-one 
• 2107-69-9 5,6-dimethoxy-1-indanone 
• 2107-70-2 3,4-methoxycinnamic acid 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 100446-13-7 5,6-dibenzyloxy-2,3-dihydro-1H-inden-1-one 
• 383382-44-3 5-benzyloxy-6-hydroxy-indan-1-one 
• 90843-62-2 6-hydroxy-5-methoxyindan-1-one 
• 383382-47-6 5,6-dihydroxy-7-nitro-indan-1-one 
• 383382-45-4 5-benzyloxy-6-hydroxy-7-nitro-indan-1-one 
• 124702-67-6 5,6-dibenzyloxy-2-hydroximino-2,3-dihydro-1H-inden-1-one 
• 124702-69-8 5,6-dibenzyloxy-2-amino-2,3-dihydro-1H-inden-1-one 
• 124702-69-8 cis-5,6-dibenzyloxy-2-amino-2,3-dihydro-1H-inden-1-ol 
• 124702-73-4 cis-5,6-dibenzyloxy-2-acetamido-2,3-dihydro-1H-inden-1-one 
• 1402063-08-4 2-(4-(dimethylamino)benzylidene)-5,6-dihydroxy-2,3-dihydro-1H-inden-1-one 4-methylbenzene-1-sulfonic acid 
• 1402063-06-2 6-hydroxy-5-methoxy-2-(4-(methyl(propyl)amino)-benzylidene)-2,3-dihydro-1H-inden-1-one hydrochloride 

Relevant articles and documents

Cyanopyridyl containing 1,4-dihydroindeno[1,2-c]pyrazoles as potent checkpoint kinase 1 inhibitors: Improving oral biovailability

A series of 1,4-dihydroindeno[1,2-c]pyrazole compounds with a cyanopyridine moiety at the 3-position of the tricyclic pyrazole core was explored as potent CHK-1 inhibitors. The impact of substitutions at the 6 and/or 7-position of the core on pharmacokinetic properties was studied in detail. Compounds carrying a side chain with an ether linker at the 7-position and a terminal morpholino group, such as 29 and 30, exhibited much-improved oral biovailability in mice as compared to earlier generation inhibitors. These compounds also possessed desirable cellular activity in potentiating doxorubicin and will serve as valuable tool compounds for in vivo evaluation of CHK-1 inhibitors to sensitize DNA-damaging agents.

Synthesis, characterization and nonlinear optical studies of novel blue-light emitting room temperature truxene discotic liquid crystals

A new series of discotic liquid crystals based on a truxene core has been synthesized to study the structure-property relationship in view of the self-assembling property and their linear and nonlinear optical properties. All these branched alkyl chain truxene derivatives show a mesogenic property in a columnar hexagonal fashion at room temperature which is studied by a combination of different techniques. The newly synthesized truxene discotic 7a possesses a clearing temperature of 117 °C, one of the lowest clearing temperatures known in truxene discotic liquid crystals. We have discovered that the introduction of branching near to the core even in a small alkyl chain drastically reduces the isotropic temperature. Due to their C3 symmetry and their large first hyperpolarizability, these truxene derivatives show long-lived emissions in the solution state at room temperature. We also report large effective three-photon absorption in these materials under nanosecond laser pulse excitation at 532 nm, which makes them suitable candidates for optical limiting applications.

Efficient demethylation of aromatic methyl ethers with HCl in water

A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.

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.

Indanone derivative 5,6-dyhydroxy-2,3-dihydrocaroone-1H-indene-1-ketone and preparation method thereof

The invention provides indanone derivative 5,6-dyhydroxy-2,3-dihydrocaroone-1H-indene-1-ketone and a preparation method thereof, relates to indanone derivatives and a preparation method thereof and aims to solve the technical problems that in the prior art, the operation process is complex, controllability is poor, the product yield is low, and stability is poor. The structural formula of the indanone derivative can be found in the specification. The preparation method includes the steps that 1, a 5,6-dimethoxy-2,3-dihydrocaroone-1H-indene-1-ketone solution is prepared; 2, boron tribromide is added for a reaction; 3, a saturated sodium bicarbonate solution is added for neutralizing the boron tribromide; 4, extraction and spin steaming are conducted. A product obtained through the method has good stability and a high yield; by means of the method, two methoxyl functional groups adjacent to indanone are converted into hydroxyl, and the activity of the indanone is greatly improved so that indanone derivatives provided with different substituent groups can be synthesized on the indanone, and crystal complexes of different spacial structures are configured. The preparation method is used for preparing the 5,6-dyhydroxy-2,3-dihydrocaroone-1H-indene-1-ketone.

Multitarget-directed benzylideneindanone derivatives: Anti-β-amyloid (Aβ) aggregation, antioxidant, metal chelation, and monoamine oxidase B (MAO-B) inhibition properties against Alzheimer's disease

A novel series of benzylideneindanone derivatives were designed, synthesized, and evaluated as multitarget-directed ligands against Alzheimer's disease. The in vitro studies showed that most of the molecules exhibited a significant ability to inhibit self-induced β-amyloid (Aβ 1-42) aggregation (10.5-80.1%, 20 μM) and MAO-B activity (IC 50 of 7.5-40.5 μM), to act as potential antioxidants (ORAC-FL value of 2.75-9.37), and to function as metal chelators. In particular, compound 41 had the greatest ability to inhibit Aβ1-42 aggregation (80.1%), and MAO-B (IC50 = 7.5 μM) was also an excellent antioxidant and metal chelator. Moreover, it is capable of inhibiting Cu(II)-induced Aβ1-42 aggregation and disassembling the well-structured Aβ fibrils. These results indicated that compound 41 is an excellent multifunctional agent for the treatment of AD.

INDANONE INHIBITORS OF ACETYLCHOLINESTERASE

The present invention relates to new indanone inhibitors of acetylcholinesterase, pharmaceutical compositions thereof, and methods of use thereof.

Synthesis and biological evaluation of 4′-(6,7-disubstituted-2,4-dihydro-indeno[1,2-c]pyrazol-3-yl)-biphenyl-4-ol as potent Chk1 inhibitors

A new series of potent tricyclic pyrazole-based Chk1 inhibitors are described. Analogues disubstituted on the 6- and 7-positions show improved Chk1 inhibition potency compared with analogues with a single substituent on either the 6- or 7-position. Based

Simple and regioselective bromination of 5,6-disubstituted-indan-1-ones with Br2 under acidic and basic conditions

Bromination of 5,6-dimethoxyindan-1-one with Br2 in acetic acid at room temperature produced exclusively the corresponding 2,4-dibromo compound in 95% yield. Reaction of 5,6-dimethoxyindan-1-one with Br2 in the presence of KOH, K2CO3 or Cs2CO3 at ～0°C gave the monobrominated product 4-bromo-5,6-dimethoxyindan-3-one in 79%, 81% and 67% yield, respectively. 5,6-Dihydroxyindan-1-one was dibrominated on the aromatic ring affording 4,7-dibromo-5,6-dihydroxyindan-1-one both in acetic acid at room temperature and in the presence of KOH at ～0° C. 5,6-Difluoroindan-1-one and 1-indanone were α-monobrominated in acetic acid and α,aα-dibrominated under KOH conditions at room temperature.