1133-72-8

Usage

Uses

Used in Analytical Chemistry:
2-Acetyl-1,3-indanedione is used as a reagent for the detection and analysis of various metal ions, particularly lanthanide ions, due to its ability to form coordination complexes with these ions. The strong luminescence of these complexes upon UV light irradiation allows for sensitive and selective detection methods.
Used in Material Science:
In the field of material science, 2-Acetyl-1,3-indanedione is used as a precursor for the development of advanced luminescent materials. The strong luminescence properties of the AID-lanthanide complexes make them suitable for applications such as light-emitting diodes (LED), sensors, and other optoelectronic devices.
Used in Pharmaceutical Industry:
2-Acetyl-1,3-indanedione is used as an intermediate in the synthesis of various pharmaceutical compounds. Its ability to form coordination complexes with metal ions can be exploited in the development of drugs with enhanced bioavailability and targeted delivery.
Used in Environmental Science:
In environmental science, 2-Acetyl-1,3-indanedione can be used for the detection and monitoring of metal ion pollution in water and soil samples. The strong luminescence of the AID-lanthanide complexes provides a sensitive and reliable method for assessing the presence and concentration of these ions in the environment.

InChI:InChI=1/C11H8O3/c1-6(12)9-10(13)7-4-2-3-5-8(7)11(9)14/h2-5,9H,1H3

Upstream product

• 606-23-5 1H-indene-1,3(2H)-dione 
• 108-24-7 acetic anhydride 
• 15435-71-9 sodium acetylacetonate 
• 88-95-9 Phthaloyl dichloride 
• 131-11-3 phthalic acid dimethyl ester 
• 67-64-1 acetone 
• 141-97-9 ethyl acetoacetate 
• 98-88-4 benzoyl chloride 
• 75-36-5 acetyl chloride 
• 115851-78-0 ethyl 2-benzoyl-3-oxobutanoate 
• 601-70-7 3,3-dichlorophthalide 
• 60-29-7 diethyl ether 
• 7446-70-0 aluminium trichloride 
• 108-05-4 vinyl acetate 

Downstream Products

• 85301-71-9 2-(1'-amino)ethylidenyl-1,3-indandione 
• 39560-80-0 2-(1-hydrazono-ethyl)-indan-1,3-dione 
• 73636-26-7 2-Acetoxy-1,3-indandione 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 72307-22-3 α-(1,3-dioxoindane-2-yl)-ethylidene-p-toluidine 
• 70600-41-8 C₂₉H₂₀O₆ 
• 70600-29-2 2-[(Z)-3-(2,4-Dimethoxy-phenyl)-acryloyl]-indan-1,3-dione 
• 70600-40-7 2-(3-Oxo-5-phenyl-cyclohex-1-enyl)-indan-1,3-dione 
• 25083-69-6 2-[1-(N-phenyamino)-1-ethylidene]-indane-1,3-dione 
• 130946-60-0 1-(4'-methylquinol-2-yl)-3-methyl-indeno<1,2-c>pyrazol-(1H)-4-one 

Relevant academic research and scientific papers

Friedel-crafts coordinated processes: Selective cyclooligomerization of acyl chlorides

Adducts AlCl3.RCOCl undergo highly regioselective self- and cross-condensation. 4-Hydroxy-2-pyrones and 2-acetyl-indan-l,3-diones are synthesized in good yields.

Synthesis, Type II Diabetes Inhibitory Activity, and Antimicrobial Tests of Benzothiazole Derivatives Bridged with Indenedione by Methylenehydrazone

Benzothiazolyl hydrazones are synthesized and tested as hypoglycemic and antimicrobial agents. Condensation of 2-acyl-(1H)-indene-1,3(2H)-diones with 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles gives the corresponding hydrazones in high yields. Preliminary biological assay of the products reveals significant antidiabetic and antimicrobial activities. The α-amylase and α-glucosidase inhibition assay is used for determination of Type II diabetes inhibitory activity.

Quantum chemical and spectroscopic study of the structure of 2-acetylindan-1,3-dione complexes with metal(II) ions

A series of M(II) (M = Cu, Zn, Cd, Pb) complexes with the physiologically active 1-acetylindan-1,3-dione were synthezed. All complexes were obtained with the metal to ligand ratio 1:2. The presence of two water molecules in the inner coordination sphere of the Zn(II) and Cd(II) complexes was proven. The structure and coordination mode of the newly synthesized Cd(II) and Pb(II) complexes were investigated using NMR (13C CPMAS and 13C NMR in DMF-d7 solution) method. Semi-empirical (PM3) and ab initio (ECP-312G) calculations of the structure and IR spectra of the free ligand and corresponding metal(II) complexes were performed. It is shown that the structure of the Pp(II) complex differs significantly from the distorted tetrahedral structure of the Cu(II), Zn(II), and Cd(II) complexes.

Synthesis, antimicrobial evaluation, α-amylase inhibitory ability and molecular docking studies of 3-alkyl-1-(4-(aryl/heteroaryl)thiazol-2-yl)indeno[1,2-c]pyrazol-4(1H)-ones

A series of thiazole tethered indenopyrazoles has been synthesized and assayed for their antimicrobial and α-amylase inhibitory activities. Ciprofloxacin and Fluconazole were used as standard drugs for antibacterial and antifungal evaluation, respectively while Acarbose was used as standard reference for α-amylase inhibitory activity. The antimicrobial activity evaluation results revealed that derivative 3d showed highest potency against two Gram-positive bacterial strains (Bacillus subtilis and Staphylococcus aureus), two Gram-negative bacterial strains (Escherichia coli and Pseudomonas aeruginosa) with MIC values of 0.0541 μmol/mL, 0.0270 μmol/mL, 0.0270 μmol/mL, 0.0270 μmol/mL, respectively and two fungal strains (Candida albians and Aspergillus niger) with MIC values of 0.0067 μmol/mL and 0.0270 μmol/mL, respectively in comparison to the standard drugs Ciprofloxacin (MIC = 0.0094 μmol/mL) and Fluconazole (MIC = 0.0408 μmol/mL). Interestingly, all the compounds of the series except 3e exhibited better inhibitory activity against C. albicans with MIC value ranging from 0.0067 to 0.0297 μmol/mL than the standard drug Fluconazole. However, derivatives 3j with IC50 value of 0.79 μM and 3k with IC50 value of 0.46 μM were recognized as good α-amylase inhibitors as compared to the reference drug Acarbose (IC50 = 0.11 μM). Further, the docking studies were performed to support the results of biological activities.

Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones

We report a convenient and efficient synthesis of indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) by the reaction of a variety of 2-acyl-(1H)-indene-1,3(2H)-diones (1) and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles (2) in the presence of glacial acetic acid in good yields. The structure of the compounds thus prepared were confirmed by analytical and spectral (FT-IR, 1H NMR, 13C NMR, and HRMS) techniques. All the synthesized indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) were assayed for their in vitro Type II diabetes inhibitory activity by using Acarbose as standard drug and in vitro antimicrobial activity utilizing Streptomycin and Fluconazole as reference drugs. Among the synthesized derivatives, 4e (IC50 = 6.71 μg/mL) was found to be more potent against α-glucosidase enzyme as compared with the standard Acarbose (IC50 = 9.35 μg/mL) and 4i (IC50 = 11.90 μg/mL) exhibited good inhibitory activity against α-amylase enzyme as compared with the standard Acarbose (IC50 = 22.87 μg/mL). Also, all the titled compounds showed good antimicrobial activity. In addition, in vitro α-glucosidase and α-amylase inhibition were supported by docking studies performed on the derivatives 4e and 4o, respectively. [Figure not available: see fulltext.].

Acylation of Aroyl Chlorides via a Template Friedel-Crafts Process: Synthesis of Indan-1,3-diones

Variously substituted indan-1,3-diones have been regioselectively prepared in a one-pot synthesis by sequential cross-condensation-cycloacylation of aromatic acyl chlorides and acetyl chloride or malonyl dichloride, electrophilic acylation of aromatic acyl chlorides representing the key step in the process.The synergism of the aromatic carbonyl enolization and the organization of the reacting system promoted by the metal is emphasized to account for the mild reaction conditions.