40114-83-8

Upstream product

• 485-47-2 indan-1,2,3-trione hydrate 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 938-24-9 indantrione 

Downstream Products

• 1357383-94-8 6'-amino-3,4,3'-trimethyl-1'-phenylspiro[indeno[1,2-b]quinoxaline-11,4′-[1′H]pyrano[2,3-c]pyrazole]-5'-carbonitrile 

Relevant academic research and scientific papers

An efficient multicomponent and stereoselective synthesis of new spiro[indeno[1,2-b]quinoxaline-11,2′-pyrrolidine] derivatives

New spiro[indeno[1,2-b]quinoxaline-11,2′-pyrrolidine] derivatives were prepared in high yield stereoselectively from an efficient multicomponent 1,3-dipolar cycloaddition reaction between ninhydrin, phenylenediamine, sarcosine, and chalcones. The regiochemistry and stereochemistry of resultant cycloadducts have been determined by several 2D NMR spectroscopic techniques and X-ray single crystal diffraction..

Regio- And Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1- a ]isoquinolines Bearing Indeno[1,2- b ]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

A regio- and diastereoselective synthesis of 2,3-dihydro-10b′ H -spiro[indeno[1,2- b ]quinoxaline-11,1′-pyrrolo[2,1- a ]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N -ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92percent) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

Design and synthesis of novel spirooxindole–indenoquinoxaline derivatives as novel tryptophanyl-tRNA synthetase inhibitors

Abstract: In the current study, we used an integrated approach combining bioinformatics, rational drug design, one-pot synthesis, and biological experiments in vitro for the potential discovery of novel tryptophanyl-tRNA synthetase (TrpRS) inhibitors. Atom economic and diastereoselective syntheses were used to generate several Spirooxindole–indenoquinoxaline derivatives in situ from isatin and amino acids viz. proline, phenylglycine, and sarcosine through targeting the 1,3-dipolar cycloaddition of azomethine ylides. These compounds were assayed by biochemical TrpRS inhibition, using in vitro experiments to test against various gram-positive and gram-negative strains, and using diffuse large B cell lymphoma (DLBCL) cell lines. Compound 6e was found to be the most active in vitro with IC50 values of 225 and 74?nM for tests against hmTrpRS and ecTrpRS, respectively. We also found a MIC90 value of 4?μg/mL for tests against S. aureus and IC50 values which ranged from 2.9 to 4.8?μM for tests against proliferation of DLBCL cell lines. Moreover, compound 6e was remarkably good at inducing bacterial autolysis in MRSA strains. Our results suggested that such an integrated approach could be an attractive and viable strategy for the discovery of novel TrpRS inhibitors as potential lead compounds for antibiotics and as novel anticancer agents. Graphic abstract: Discovery of novel spirooxindole-indenoquinoxaline TrpRS inhibitors as potential lead compounds with antibacterial and antitumor activities.[Figure not available: see fulltext.].

Asymmetric synthesis approach of enantiomerically pure spiro-indenoquinoxaline pyrrolidines and spiro-indenoquinoxaline pyrrolizidines

An efficient, one-pot, four-component procedure for the synthesis of a small library of novel chiral spiro-indenoquinoxaline pyrrolidines and chiral spiro-indenoquinoxaline pyrrolizidines with high regio-, diastereo- (up to 96 dr), and enantioselectivity (up to 99% ee), through a 1,3-dipolar cycloaddition reaction of azomethine ylides and an optically active cinnamoyl-crotonoyl oxazolidinone is described. This methodology was very simple and was utilized to construct complex products from simple starting materials. The process was carried out in aqueous ethanol as an eco-friendly solvent and in the absence of any Lewis acids catalysts. The oxazolidinone chiral auxiliary was removed through a non-destructive protocol. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts and using quantum mechanical calculations. The regio- and stereoselectivity were described on the basis of transition states' stabilities and global and local reactivity indices of the reactants. The results of the theoretical calculations are in agreement with the experimental outcomes.

Green synthesis of novel spiro-indenoquinoxaline derivatives and their cholinesterases inhibition activity

A convenient synthesis of substituted spiroindenoquinoxalines at mild and green conditions was developed. Multicomponent reaction of substituted phenylene diamines, ninhydrin, malononitrile and N,N′-substituted-2-nitroethene-1,1-diamines produced the targ

Discovery of Nonquinone Substrates for NAD(P)H: Quinone Oxidoreductase 1 (NQO1) as Effective Intracellular ROS Generators for the Treatment of Drug-Resistant Non-Small-Cell Lung Cancer

The elevation of oxidative stress preferentially in cancer cells by efficient NQO1 substrates, which promote ROS generation through redox cycling, has emerged as an effective strategy for cancer therapy, even for treating drug-resistant cancers. Here, we described the identification and structural optimization studies of the hit compound 1, a new chemotype of nonquinone substrate for NQO1 as an efficient ROS generator. Further structure-activity relationship studies resulted in the most active compound 20k, a tricyclic 2,3-dicyano indenopyrazinone, which selectively inhibited the proliferation of NQO1-overexpressing A549 and A549/Taxol cancer cells. Furthermore, 20k dramatically elevated the intracellular ROS levels through NQO1-catalyzed redox cycling and induced PARP-1-mediated cell apoptosis in A549/Taxol cells. In addition, 20k significantly suppressed the growth of A549/Taxol xenograft tumors in mice with no apparent toxicity observed in vivo. Together, 20k acts as an efficient NQO1 substrate and may be a new option for the treatment of NQO1-overexpresssing drug-resistant NSCLC.

One-pot three-component synthesis of functionalized spirolactones by means of reaction between aromatic ketones, dimethyl acetylenedicarboxylate, and N-heterocycles

A simple and convenient one-pot multi-component reaction has been described for the synthesis of functionalized spirolactones. This strategy demonstrated three-component reaction between aromatic ketones (11H-indeno[1,2-b]quinoxalin- 11-one) and dimethyl acetylenedicarboxylate (DMAD) in the presence of N-heterocycles, such as pyridine, quinoline, and isoquinoline in CH 2Cl2 at ambient temperature without use of any catalyst or activator.

CURABLE COMPOSITION, CURED PRODUCT, OPTICAL MEMBER, LENS, AND METHOD FOR MANUFACTURING OPTICAL MEMBER

A curable composition containing a compound represented by General Formula A and a salt of an acidic phosphoric acid ester is provided as a curable composition for forming a cured product that has a small Abbe number and a large partial dispersion ratio and has excellent moldability. In General Formula A, Ar represents an n-valent group containing a nitrogen-containing aromatic ring as a partial structure, L represents a linking group such as —O— and —C(═O)O—, Sp represents a single bond or a divalent linking group, Pol represents a hydrogen atom or a polymerizable group, and n represents 1 or 2; and the compound represented by General Formula A has at least one polymerizable group.

Imidazolium-based ionic liquid promoted facile and efficient one-pot four-component synthesis of spiro[furan-2,11'-indeno[1,2-b]quinoxaline]s under ambient conditions

Spiro compounds are one of the most important organic molecules. Spiro rings such as spiroketals are present in numerous natural products; simple spiroketals are known insect pheromones. A small number of spiro containing drugs has been investigated durin

Synthesis and characterization of acetic acid functionalized poly (4-vinylpyridinium) salt as new catalyst for the synthesis of spiropyran derivatives and their biological activity

Acetic acid functionalized poly(4-vinylpyridinium) bromide (APVPB), as a new and heterogeneous catalyst, was designed and successfully tested on the synthesis of 2-aminospiro[indoline-3,4?pyran]-2-one and spiro[indeno[1,2-b]quinoxaline-11,4-pyran]-2?-amine derivatives. Also, infrared spectroscopy (FT-IR), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), scanning electron microscope (SEM), X-ray diffraction analysis (XRD) and energy dispersive X-ray analysis (EDX) of the catalyst has been studied in the presented work. The prepared spiro-pyrans were solved in DMSO and subjected to antioxidant activity screening by DPPH free radical scavenging assay and antifungal activity against Fusarium oxysporum. Results showed that the synthesized spiro-pyran possess strong antioxidant activity (IC50; 0.161 ± 0.009 to 1.509 ± 0.007 mg/ml) and also good inhibition activity against Fusarium oxysporum (65.8 ± 1.4% to 88.3 ± 2.2% at 500 ppm concentration and 89.2 ± 3.2% to 100 ± 0.0% at 1000 ppm concentration). For their biological activities, the prepared spiro-pyran compounds may be suggested to apply as alternative systems in medicine and agriculture.