24623-25-4

Basic information

• Product Name: 4-Nitroindanone
• Synonyms: 4-Nitro-1-Indanone;4-nitro-2,3-dihydro-1H-inden-1-one;4-Nitroindanone;1H-Inden-1-one, 2,3-dihydro-4-nitro-;4-Nitroindan-1-one;2,3-Dihydro-4-nitroinden-1-one;Einecs 246-367-2
• CAS NO: 24623-25-4
• Molecular Formula: C₉H₇NO₃
• Molecular Weight: 177.16
• EINECS: 246-367-2
• Product Categories: Indanone & Indene
• Mol File: 24623-25-4.mol

Chemical Properties

• Melting Point: 104-105 °C
• Boiling Point: 332.9 °C at 760 mmHg
• Flash Point: 170.4 °C
• Appearance: /
• Density: 1.396 g/cm³
• Vapor Pressure: 0.000141mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-Nitroindanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitroindanone(24623-25-4)
• EPA Substance Registry System: 4-Nitroindanone(24623-25-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 24623-25-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Nitroindanone is used as a versatile building block for the synthesis of various chemical compounds. Its ability to undergo microwave-assisted oxidation makes it a valuable precursor in the formation of ninhydrins, which have a wide range of applications in different industries.
Used in Pharmaceutical Industry:
4-Nitroindanone is used as a key intermediate in the development of pharmaceutical products. Specifically, its thiosemicarbazone derivative has demonstrated anti-Trypanosoma cruzi properties, making it a promising candidate for the treatment of Chagas disease, a tropical parasitic disease caused by the protozoan parasite Trypanosoma cruzi.

InChI:InChI=1/C9H7NO3/c11-9-5-4-6-7(9)2-1-3-8(6)10(12)13/h1-3H,4-5H2

Upstream product

• 83-33-0 inden-1-one 
• 2001-32-3 3-(2-nitrophenyl)propionic acid 
• 7440-44-0 pyrographite 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 59803-35-9 (2-nitro-benzyl)-malonic acid diethyl ester 
• 612-23-7 2-nitrobenzyl chloride 
• 496-11-7 INDANE 
• 34701-14-9 4-nitroindane 
• 85397-21-3 3-(2-nitro-phenyl)-propionyl chloride 

Downstream Products

• 51135-91-2 4-amino-2,3-dihydro-1H-inden-1-one 
• 135586-75-3 2-(p-nitrobenzylidene)-4-nitro-1-indanone 
• 60031-14-3 (E)-2-benzylidene-4-nitro-2,3-dihydro-1Hinden-1-one 
• 65887-63-0 5-nitro-3,4-dihydro-1H-quinolin-2-one 
• 135586-68-4 3,3a-cis-2-acetyl-3-phenyl-2,3,3a,4-tetrahydroindeno<1,2-c>pyrazole 
• 135586-69-5 3,3a-cis-2-acetyl-3-(p-nitrophenyl)-2,3,3a,4-tetrahydro-4-nitroindeno<1,2-c>pyrazole 
• 80960-26-5 2,2-dihydroxy-4-nitro-1H-indene-1,3(2H)-dione 
• 1253416-88-4 2-oxo-1-(4-phenyl-2,3-dihydro-1H-inden-1-yl)-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide 
• 1416258-22-4 4-amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dione 
• 1416258-20-2 2-azido-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione 
• 1416258-19-9 2-chloro-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione 
• 1416258-17-7 2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione 
• 69975-65-1 6-aminoindan-1-one 
• 58130-38-4 5-amino-3,4-dihydro-1H-quinolin-2-one 

Relevant articles and documents

Discovery of novel 2,3-dihydro-1H-inden-1-amine derivatives as selective monoamine oxidase B inhibitors

Inhibition of MAO-B has been an effective strategy for the treatment of Parkinson's disease. To find more potent and selective MAO-B inhibitors with novel chemical scaffold, we designed and synthesized a series of new 2,3-dihydro-1H-inden-1-amine derivatives on basis of our previous study. Furthermore, the corresponding structure-activity relationship (SAR) of these compounds is detailedly discussed. Compounds L4 (IC50 = 0.11 μM), L8 (IC50 = 0.18 μM), L16 (IC50 = 0.27 μM) and L17 (IC50 = 0.48 μM) showed similar MAO-B inhibitory activity as Selegiline. Moreover, L4, L16 and L17 also exhibited comparable selectivity with Selegiline, indicating that L4, L16 and L17 could be promising selective MAO-B inhibitors for further study.

Synthesis of haloindenes

The subject invention provides an expedited synthesis of 5, 6, and 7-iodoindenes from the corresponding aminoindan-1-ones in more than 70% yield, employing readily available precursors and reagents. A three-step sequence involves diazotization-iodination of aminoindan-1-one followed by reduction and dehydration. The method has a general character and can be extended for the preparation of various 4-, 5-, 6- or 7-haloindenes using different halogen sources for diazotization-halogenation reaction.

Novel 1-(prop-2-yn-1-ylamino)-2,3-dihydro-1H-indene-4-thiol derivatives as potent selective human monoamine oxidase B inhibitors: Design, SAR development, and biological evaluation

Successes have been achieved in developing human monoamine oxidase B (hMAO-B) inhibitors as anti-Parkinson's disease (PD) drugs. However, low efficiency and unwanted side effects of the marketed hMAO-B inhibitors hamper their medical applications, therefore, novel potent selective hMAO-B inhibitors are still of great interest. Herein we report 1-(prop-2-yn-1-ylamino)-2,3-dihydro-1H-indene-4-thiol derivatives as hMAO-B inhibitors, which were designed by employing a fragment-based drug design strategy to link rasagiline to hydrophobic fragments. Among the synthesized 31 compounds, K8 and K24 demonstrated very encouraging hMAO-B inhibitory activities and selectivity over hMAO-A, better than rasagiline and safinamide. In vitro studies indicated that K8 and K24 are nontoxic to nervous tissue cells and they have considerable effects against ROS formation and potential neuroprotective activity. Further mice behavioral tests demonstrated these two compounds have good therapeutic effects on MPTP-induced PD model mice. All these experiment results suggest that compounds K8 and K24 can be promising candidates for further research for treatment of PD.

METHODS FOR MAKING QUINOLINYLDIAMINES

The present disclosure provides methods for making quinolinyldiamine products from quinolinyl starting materials. In addition, the quinolinyldiamines can be used as ligands or ligand precursors for catalysts, e.g. for use in olefin polymerization.

Iodoindenes: Synthesis and application to cross-coupling

An expeditious synthesis of 5-, 6-, and 7-iodoindenes from the corresponding aminoindan-1-ones in more than 70% yield employing readily available precursors and ubiquitous reagents is reported. The 4-iodoindene has been prepared analogously in 40% overall yield. A three-step sequence involves diazotization-iodination of aminoindan-1-one followed by the reduction and dehydration. The iodoindenes serve as effective substrates for the regioselective Stille coupling with vinyl stannanes but isomeric mixtures are produced during Sonogashira coupling with alkynes in the presence of triethylamine.

COVALENT TARGETING OF E3 LIGASES

Disclosed herein, inter alia, are compositions and methods for targeting E3 ligases. In an aspect is a targeted protein degrader including 1) a targeted protein binder and 2) an E3 Ubiquitin ligase binder, wherein the E3 Ubiquitin ligase is human RNF4 or human RNF114. In an aspect is provided a pharmaceutical composition including a compound as described herein, including embodiments, and a pharmaceutically acceptable excipient.

Discovery of N-indanyl benzamides as potent RORγt inverse agonists

The retinoic acid receptor-related orphan receptor-gamma-t (RORγt) is a promising therapeutic target for treatment of Th17 cell-mediated autoimmune diseases. Based on a scaffold hopping/conformational restriction strategy, a series of N-indanyl benzamides as novel RORγt inverse agonists was discovered. Exploration of structure-activity relationship on the piperazine ring, benzoyl moiety and cyclopentyl moiety of N-indanyl benzamides 2a and 2d led to identification of potent RORγt inverse agonists. Compound 5c with (S)-enantiomer was found having an IC50 of 153.7 nM in Fluorescence Resonance Energy Transfer (FRET) assay, and an IC50 of 47.1 nM in mouse Th17 cell differentiation assay, which represents a promising starting point for developing potent small molecule RORγt inverse agonists. Binding modes of the two enantiomers 5c and 5d in RORγt ligand binding domain were also discussed.

THERAPEUTIC COMPOUNDS

The invention provides compounds of formula (I): wherein, A, C, D, X, and Y have any of the values defined in the specification, and salts thereof. The compounds are SIRT2 inhibitors and are useful for treating SIRT2 associated conditions.

Thiosemicarbazones derived from 1-indanones as new anti-Trypanosoma cruzi agents

In the present work, we synthesized a series of thiosemicarbazones derived from 1-indanones with good anti-Trypanosoma cruzi activity. Most of them displayed remarkable trypanosomicidal activity. All the compounds showed nonspecific cytotoxicity on human erythrocytes. The ability of the new compounds to inhibit cruzipain, the major cysteine protease of T. cruzi, was also explored. Thiosemicarbazones 12 and 24 inhibited this enzyme at the dose assayed. This interaction was also studied in terms of molecular docking.