38753-50-3

Usage

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. A skin and eye irritant. Whenheated to decomposition it emits toxic fumes of NOx. Seealso NITRO COMPOUNDS OF AROMATICHYDROCARBONS.

InChI:InChI=1/C9H11NO3/c1-7(2)13-9-6-4-3-5-8(9)10(11)12/h3-7H,1-2H3

Upstream product

• 6831-82-9 potassium isopropoxide 
• 1493-27-2 ortho-nitrofluorobenzene 
• 75-26-3 isopropyl bromide 
• 88-75-5 2-hydroxynitrobenzene 
• 75-30-9 2-iodo-propane 
• 683-60-3 sodium isopropylate 
• 88-73-3 2-Chloronitrobenzene 
• 1992-48-9 Tetraisopropoxysilan 
• 15163-59-4 potassium o-nitrobenzoate 
• 552-16-9 ortho-nitrobenzoic acid 
• 91-23-6 2-Nitroanisole 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 29026-74-2 2-isopropoxy-phenylamine 
• 88-75-5 2-hydroxynitrobenzene 
• 98772-03-3 2-(2-Isopropoxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid 
• 98771-57-4 ethyl 1,6-dihydro-2-[2-(1-methylethoxy)anilino]-6-oxo-5-pyrimidinecarboxylate 
• 908554-54-1 N-(2-isopropoxyphenyl)benzamide 
• 870249-29-9 2-[(2-hydroxy-ethyl)-(2-isopropoxy-phenyl)-amino]-ethanol 
• 870249-31-3 4-[4-(2-isopropoxy-phenyl)-piperazin-1-yl]-cyclohexylamine 
• 1538593-65-5 2-((4-(2-(4-chlorophenoxy)ethanoyl)piperazin-1-yl)methyl)-3-(2-isopropoxyphenyl)quinazolin-4(3H)-one 
• 1538593-64-4 3-(2-isopropoxyphenyl)-2-(piperazin-1-ylmethyl)quinazolin-4(3H)-one 
• 1538593-63-3 2-(chloromethyl)-3-(2-isopropoxyphenyl)quinazolin-4(3H)-one 
• 1400637-48-0 C₂₀H₂₄FNO₄ 
• 1400637-91-3 C₁₈H₂₃NO₃ 
• 1400637-76-4 C₂₀H₂₄BrNO₄ 
• 1323064-53-4 C₄₂H₃₁NO₄ 

Relevant academic research and scientific papers

Boron-Promoted Ether Interchange Reaction: Synthesis of Alkyl Nitroaromatic Ethers from Methoxynitroarenes

The first protocol for boron-promoted ether interchange reaction of methoxynitroarenes was described. A series of methoxynitroarenes and alcohols, including primary, secondary, as well as tertiary alcohols were reacted smoothly in moderate to good yields under the optimized reaction conditions. This protocol constitutes an operationally simple and scalable strategy for the synthesis of alkyl nitroaromatic ethers. Moreover, the new reactivity of boron reagents was discovered.

Discovery of new ATP-competitive inhibitors of human DNA topoisomerase IIα through screening of bacterial topoisomerase inhibitors

Human DNA topoisomerase II is one of the major targets in anticancer therapy, however ATP-competitive inhibitors of this target have not yet reached their full potential. ATPase domain of human DNA topoisomerase II belongs to the GHKL ATPase superfamily and shares a very high 3D structural similarity with other superfamily members, including bacterial topoisomerases. In this work we report the discovery of a new chemotype of ATP-competitive inhibitors of human DNA topoisomerase IIα that were discovered through screening of in-house library of ATP-competitive inhibitors of bacterial DNA gyrase and topoisomerase IV. Systematic screening of this library provided us with 20 hit compounds. 1,2,4-Substituted N-phenylpyrrolamides were selected for a further exploration which resulted in 13 new analogues, including 52 with potent activity in relaxation assay (IC50 = 3.2 μM) and ATPase assay (IC50 = 0.43 μM). Cytotoxic activity of all hits was determined in MCF-7 cancer cell line and the most potent compounds, 16 and 20, showed an IC50 value of 8.7 and 8.2 μM, respectively.

Modulators of the nuclear hormone receptor ROR

The invention provides small molecule modulators of retinoic acid receptor-related orphan receptors such as RORα, RORβ, or RORγ, of formula with the variable atoms as defined herein and R1 comprising a hydroxyl- or alkoxyl-substituted fluoroalkyl group. Compounds of the invention can be effective modulators at concentrations ineffective to act on LXR receptors, or on other nuclear receptors, or other biological targets. Methods of modulation the RORs and methods of treating metabolic disorders, immune disorders, cancer, and CNS disorders wherein modulation of an ROR is medically indicated are also provided.

QUINAZOLINONE-BASED ONCOGENIC-RAS-SELECTIVE LETHAL COMPOUNDS AND THEIR USE

The present invention provides, inter alia, compounds having the structure (1) compositions containing such compounds are also provided. Methods for using such compounds or compositions for treating or ameliorating the effects of a cancer having a cell that harbors an oncogenic RAS mutation, for modulating a lipoxygenase in a ferroptosis cell death pathway, and for depleting reduced glutathione (GSH) in a cell harboring an oncogenic RAS mutation are further provided.

Synthesis of aryl ethers from aromatic carboxylic acids

A silver/copper bimetallic catalyst system promotes the decarboxylative Chan-Evans-Lam alkoxylation of ortho-substituted aromatic carboxylate salts with tetraalkyl orthosilicates or triaryl borates. Non-ortho-substituted carboxylates are alkoxylated via an ortho-C-H-alkoxylation with concomitant cleavage of the carboxylate directing group via protodecarboxylation. This way, meta-substituted carboxylates are converted into para-substituted alkoxyarenes and vice versa. The combined processes provide a convenient synthetic entry to the important class of aromatic ethers from widely available carboxylic acids.

Exploration of the structure-activity relationship of the diaryl anilide class of ligands for translocator protein - Potential novel positron emitting tomography imaging agents

A series of novel ligands based on the diaryl anilide (DAA) class of translocator protein (TSPO) ligands was synthesised and evaluated as potential positron emitting tomography (PET) ligands for imaging TPSO in vivo. Fluorine-18 labelling of the molecules was achieved using direct radiolabelling or synthon based labelling approaches. Several of the ligands prepared have promising profiles as potential TSPO PET imaging ligands and will be evaluated further as potential clinical imaging agents.

Decarboxylative etherification of aromatic carboxylic acids

Decarboxylative Chan-Evans-Lam-type couplings are presented as a new strategy for the regiospecific construction of diaryl and alkyl aryl ethers starting from easily available aromatic carboxylic acids. They allow converting various aromatic carboxylate salts into the corresponding aryl ethers by reaction with alkyl orthosilicates or aryl borates, under aerobic conditions in the presence of silver carbonate as the decarboxylation catalyst and copper acetate as the cross-coupling catalyst.

A molecular balance for measuring aliphatic CH-π interactions

A series of conformationally flexible bicyclic N-arylimides were employed as molecular balances to study the weak aliphatic CH-π interaction between alkyl and arene groups. The formation of intramolecular CH-π interactions in the folded conformers was characterized by X-ray crystallography. The strengths of the interactions were characterized in CDCl3 by the changes in the folded/unfolded ratios, as measured by 1H NMR. The CH-π interaction between a methyl group and an aromatic surface was ～1.0 kcal/mol and was easily disrupted or masked by conformational entropy and repulsive steric interactions.

Iodine-mediated cyclisation of thiobenzamides to produce benzothiazoles and benzoxazoles

Synthesis of benzothiazoles by reaction of iodine with thiobenzamides, which do not possess an ortho alkoxy or ester group, is described. The unlikely synthesis of benzoxazoles from reaction of 2-alkoxythiobenzamides with iodine is also reported.

Structure-activity relationships in the binding of chemically derivatized CD4 to gp120 from human immunodeficiency virus

The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.