29026-74-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Isopropoxyaniline is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications.
Used in Dye Industry:
2-Isopropoxyaniline is used as a precursor in the production of dyes, enabling the creation of a wide range of colorants for various applications.
Used in Organic Compounds Synthesis:
2-Isopropoxyaniline is utilized as a key component in the synthesis of other organic compounds, facilitating the production of diverse chemical products.

InChI:InChI=1/C9H13NO/c1-7(2)11-9-6-4-3-5-8(9)10/h3-7H,10H2,1-2H3

Upstream product

• 75-30-9 2-iodo-propane 
• 824-39-5 sodium o-nitrophenate 
• 1624-53-9 2-(benzylideneamino)phenol 
• 75-26-3 isopropyl bromide 
• 95-55-6 2-amino-phenol 
• 88-75-5 2-hydroxynitrobenzene 
• 38753-50-3 1-isopropoxy-2-nitrobenzene 

Downstream Products

• 98771-57-4 ethyl 1,6-dihydro-2-[2-(1-methylethoxy)anilino]-6-oxo-5-pyrimidinecarboxylate 
• 740028-28-8 2-(2-Isopropoxy-phenylamino)-1-phenyl-propan-1-one 
• 908554-54-1 N-(2-isopropoxyphenyl)benzamide 
• 870249-29-9 2-[(2-hydroxy-ethyl)-(2-isopropoxy-phenyl)-amino]-ethanol 
• 787519-45-3 N'-(tetrahydro-1H-pyrrolizin-7a(5H)-ylmethyl)-2-(2propyloxy)phenylurea 
• 54013-91-1 2-(1-methylethoxy)phenyl-1-piperazine 
• 1400637-91-3 C₁₈H₂₃NO₃ 
• 1400637-76-4 C₂₀H₂₄BrNO₄ 
• 1400637-48-0 C₂₀H₂₄FNO₄ 
• 914482-43-2 4-bromo-2-isopropoxyaniline 
• 98772-03-3 2-(2-Isopropoxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid 
• 748772-48-7 {2-[(2-isopropoxy-phenyl)-methyl-amino]-ethyl}-[3-(piperidine-1-carbonyl)-benzyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

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.

Investigation of hydro-lipophilic properties of n-alkoxyphenylhydroxynaphthalenecarboxamides ?

The evaluation of the lipophilic characteristics of biologically active agents is indispensable for the rational design of ADMET-tailored structure–activity models. N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides, and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently reported as a series of compounds with antimycobacterial, antibacterial, and herbicidal activity. As it was found that the lipophilicity of these biologically active agents determines their activity, the hydro-lipophilic properties of all three series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, a range of software lipophilicity predictors for the estimation of clogP values of a set of N-alkoxyphenylhydroxynaphthalenecarboxamides was employed and subsequently cross-compared with experimental parameters. Thus, the empirical values of lipophilicity (logk) and the distributive parameters (π) were compared with the corresponding in silico characteristics that were calculated using alternative methods for deducing the lipophilic features. To scrutinize (dis)similarities between the derivatives, a PCA procedure was applied to visualize the major differences in the performance of molecules with respect to their lipophilic profile, molecular weight, and violations of Lipinski’s Rule of Five.

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.

Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides

A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 μM against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 μM and 24 μM against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 μM) was the most active PET inhibitor. The structure-activity relationships are discussed.

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.

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.

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.

Selective alkylation of aminophenols

O-or N-Alkylated derivatives of aminophenols are important synthetic intermediates in organic synthesis. A series of aminophenols were selectively alkylated on their hydroxyl group in good yields via benzaldehyde protection of the amino group, subsequent alkylation, and hydrolysis; or on their amino group via imination and following reduction. ARKAT USA, Inc.

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.