5426-11-9

Usage

Appearance

Yellow crystalline The compound has a yellow color and forms crystalline structures.

Solubility

Soluble in organic solvents It dissolves easily in organic solvents such as ethanol and acetone.

Type of compound

Diketone The compound is classified as a diketone, which means it contains two carbonyl groups (C=O) within its structure.

Synthesis

Derived from condensation of 2-methylpropanoyl and 1H-indene-1,3(2H)-dione The compound is formed by the condensation reaction of 2-methylpropanoyl and 1H-indene-1,3(2H)-dione.

Applications

Production of drugs, dyes, and fragrances It is used in the manufacturing of pharmaceuticals, dyes, and fragrances due to its chemical properties.

Use as a reagent

Chemical reactions 2-(2-methylpropanoyl)-1H-indene-1,3(2H)-dione is also employed as a reagent in various chemical reactions, contributing to the synthesis of other compounds.

Biological and pharmacological properties

Potential for study The compound has been researched for its possible biological and pharmacological properties, indicating that it may have potential uses in medicine or other fields.

Upstream product

• 606-23-5 1H-indene-1,3(2H)-dione 
• 79-31-2 isobutyric Acid 
• 563-80-4 3-methyl-butan-2-one 
• 131-11-3 phthalic acid dimethyl ester 
• 84-66-2 Diethyl phthalate 
• 609-67-6 2-Iodobenzoyl chloride 
• 88-67-5 2-Iodobenzoic acid 
• 1864-94-4 phenyl formate 

Downstream Products

• 109473-24-7 3-isopropyl-1(2)H-indeno[1,2-c]pyrazol-4-one hydrazone 
• 121068-12-0 2-isobutyryl-3-(N-pyrrolidino)-2-inden-1-one 
• 121068-09-5 2-(1-Amino-2-methyl-propylidene)-indan-1,3-dione 

Relevant academic research and scientific papers

Convenient synthesis, anticancer evaluation and QSAR studies of some thiazole tethered indenopyrazoles

Abstract: A convenient one-pot synthesis of twelve new thiazole tethered indeno[1,2-c]pyrazol-4-ones (3a–3l) was carried out by three-component reaction between 1,3-diketones, thiosemicarbazide and α-bromoketones in high yields. Wolff-Kishner reduction of indeno[1,2-c]pyrazol-4-ones (3a–3l) led to the formation of corresponding indeno[1,2-c]pyrazoles (4a–4l) in moderate-to-good yields. The structures of all the synthesized indenopyrazoles were elucidated by IR, 1H NMR, 13C NMR and mass spectral techniques. In vitro cytotoxicity of thiazole tethered indenopyrazoles (3a–3l & 4a–4l) was evaluated against different human cancer cell lines, viz. human renal carcinoma (A498), human colorectal adenocarcinoma (HT29), human breast adenocarcinoma (MCF-7), human hepatocellular carcinoma (HepG2) and normal cell line, i.e., normal rat kidney epithelial (NRK). Among all the tested derivatives, 4a, 4d and 4h exhibited better activity against HT29 cancer cell line. The statistically significant QSAR models were developed for all the cancer cell lines using multiple linear regression analysis to understand the observed activity trend on structural basis. Graphical Abstract: [Figure not available: see fulltext.]

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.].

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.

A method for C2 acylation of 1,3-indandiones

The 1,3-indandione scaffold is an important structural motif used in the preparation of a large number of industrial chemical and pharmaceutical compounds. However, few approaches allow for the direct C2 acylation on these building blocks. A method was developed using DMAP and EDCI, which is mild in reactivity, covers a diverse range of carboxylic acid acylating agents, is compatible with electron releasing and withdrawing substituents on the 1,3-indandione partner, and performs well in a polar aprotic solvent (for solubility reasons) This method cleanly afforded twenty five different products in yields of 32–96%.

Palladium-Catalyzed Carbonylative Annulation Reactions Using Aryl Formate as a CO Source: Synthesis of 2-Substituted Indene-1,3(2H)-dione Derivatives

An efficient synthesis of 2-substituted indene-1,3(2H)-diones from stable and readily available 1-(2-halophenyl)-1,3-diones by employing phenyl formate as a CO source has been developed. The reaction occurred via palladium-catalyzed intramolecular carbonylative annulation using K3PO4 as a base and DMSO as a solvent at 95 °C. In this protocol, the reaction showed a broad substrate scope with good to excellent yields.