104147-69-5

Usage

Chemical Properties

Pale yellow crystalline powder

InChI:InChI=1/C9H10BrNO3/c10-6-3-7-14-9-5-2-1-4-8(9)11(12)13/h1-2,4-5H,3,6-7H2

Upstream product

• 109-64-8 1,3-dibromo-propane 
• 88-75-5 2-hydroxynitrobenzene 
• 109-70-6 1.3-chlorobromopropane 

Downstream Products

• 47453-94-1 N-<2-(2-Methoxy-phenoxy)-aethyl>-3-(2-nitro-phenoxy)-propylamin 
• 190449-09-3 4-[3-(2-Nitro-phenoxy)-propoxy]-benzoic acid ethyl ester 
• 401802-28-6 C₁₃H₁₉N₃O₃ 
• 401803-26-7 1-methyl-4-(3-(2-nitrophenoxy)propyl)piperazine 
• 1254951-52-4 tert-butyl 4-(3-(2-nitrophenoxy)propyl)piperazine-1-carboxylate 
• 1082510-08-4 2-(3-(4-methylpiperazin-1-yl)propoxy)aniline 
• 1254951-09-1 1-adamantan-1-yl-3-(2-(3-(4-methylpiperazin-1-yl)propoxy)phenyl)urea 
• 190449-34-4 4-[3-(2-Nitro-phenoxy)-propoxy]-benzoic acid 
• 103546-10-7 3-(2-nitrophenoxy)-1-propylamine 

Relevant academic research and scientific papers

Photoresponsive ionic liquids with an azobenzene moiety

We examined photoresponsive ionic liquids containing an azobenzene moiety. Ionic liquids with a p,p-azobenzene or o,p- tetrafluoroazobenzene moiety exhibit a reversible solid-to-liquid phase transition induced by photo- and thermal-stimulation. o,p-Azobenzene, which exists as an ionic liquid with a bent structure, is in a liquid state even as a trans-isomer. Such photoresponsive ionic liquids may be useful as novel functional materials, such as in optical sensors.

A Comprehensive Study of the Ca2+ Ion Binding of Fluorescently Labelled BAPTA Analogues

Since its development, the ionophore BAPTA (1,2-bis(2-aminophenoxy)-ethane-N,N,N’,N’-tetraacetic acid) has been used unchanged in calcium sensing applications. In this work we present a comprehensive experimental and theoretical study of novel alterations in the structure of BAPTA, with a focus on the systematic modification of the chain connecting the two aromatic rings of the molecule (denoted as “linker”). A bis-(diethylamino)xantene fluorophore was also attached to the structures in a fixed position and the structure-fluorescence response relationship of these molecules was investigated in addition. The effect of the linker's length, the number of oxygen atoms in this chain and even the removal of one of the rings was tested; these all proved to significantly alter the characteristics of the compounds. For example, it was found that the second aromatic ring of BAPTA is not essential for the turn-on of the fluorescence. We also demonstrated that successful sensing can be realized even by replacing the chain with a single oxygen atom, which suggests the availability of a new calcium binding mode of the chelator. The reliable turn-on characteristic, the steep Ca2+ fluorescence titration curve and the intense fluorescence emission combine to make this compound a prospective candidate as a calcium sensing molecular probe in diagnostic neurobiological applications.

Piperazine substituted 1, 3 - di-substituted urea compound and piperazine substituted amide compounds and a method for its preparation and use

The present invention relates to a class of piperazine substituted 1,3-disubstitued urea compounds and piperazine substituted amide compounds, or pharmaceutically acceptable salts of the piperazine substituted 1,3-disubstitued urea compounds and the piper

Incorporation of piperazino functionality into 1,3-disubstituted urea as the tertiary pharmacophore affording potent inhibitors of soluble epoxide hydrolase with improved pharmacokinetic properties

The inhibition of the mammalian soluble epoxide hydrolase (sEH) is a promising new therapy in the treatment of hypertension, inflammation, and other disorders. However, the problems of limited water solubility, high melting point, and low metabolic stabil

Improved model of lanosterol 14α-demethylase by ligand-supported homology modeling: Validation by virtual screening and azole optimization

Lanosterol 14α-demethylase (CYP51) is an important target for antifungal drugs. An improved three-dimensional model of CYP51 from Candida albicans (CACYP51) was constructed by ligand-supported homology modeling and molecular dynamics simulations. The accuracy of the constructed model was evaluated by its performance in a small-scale virtual screen. The results show that known CYP51 inhibitors were efficiently discriminated by the model, and it performed better than our previous CACYP51 model. The active site of CACYP51 was characterized by multiple copy simultaneous search (MCSS) calculations. On the basis of the MCSS results, a series of novel azoles were designed and synthesized, and they showed good in vitro antifungal activity with a broad spectrum. The MIC80 value of four of these compounds against C. albicans is 0.001 μgmL-1, indicating that they are promising leads for the discovery of novel antifungal agents.

New azoles with potent antifungal activity: Design, synthesis and molecular docking

In response to the urgent need for novel antifungal agents with improved activity and broader spectrum, computer modeling was used to rational design novel antifungal azoles. On the basis of the active site of lanosterol 14α-demethylase from Candida albicans (CACYP51), a series of new azoles with substituted-phenoxypropyl piperazine side chains were rational designed and synthesized. In vitro antifungal activity assay indicates that the new azoles show good activity against most of the tested pathogenic fungi. Interestingly, the designed compounds are also active against an azole-resistant clinical strain. Compared to fluconazole and itraconazole, several compounds (such as 12i, 12j and 12n) show higher antifungal activity and broader spectrum, which are promising leads for the development of novel antifungal agents.

METHODS OF IDENTIFYING MODULATORS OF BROMODOMAINS

The present invention features compounds of the following general formula (I) wherein R1 is selected from the group consisting of hydrogen, lower alkyl, aryl, aralkyl; substituted aralkyl, heteroaryl; substituted heteroaryl, phenyl, SO2, NH2, NO2, SO2, CH2, CH2CH3, OCH3, OCOCH3, CH2COCH3, and OH, CN and halogen; R2 is selected from the group consisting of hydrogen; lower alkyl, aryl, phenyl, aralkyl; substituted aralkyl, heteroaryl; substituted heteroaryl, SO2 NH2NH3+NO2, SO2, CH3, CH2CH3, OCH3, OCOCH3, CH2COCH3, and OH, halogen, carboxy, and alkoxy; X is selected from the group consisting of lower alkyl, SO2, NH, NO2, , CH3, CH2CH3, OCH3, OCOCH3, CH2COCH3, and OH, carboxy, and alkoxy; and n is an integer from O to 10 and their pharmaceutically acceptable salts of acids or bases as well as pharmaceutical compositions comprising these compounds. The invention further provides methods for preventing or inhibiting the binding of bromodomains to acetyl-lysine residues of proteins and methods for treating HIV infection and HW related disease. The present invention also features compounds of the following general formula (II) wherein: R1R2 and R3 are independently selected from the group consisting of hydrogen; lower alkyl, aryl, phenyl, aralkyl; substituted aralkyl, heteroaryl; substituted heteroaryl, SO2, NH2, NH3+ NO2, SO2, CH3, CH2CH3, OCH3, OCOCH3, CH2COCH3, OH, SH, halogen, carboxy; and R4 is selected from the group consisting of lower alkyl, aryl, SO2, NH, NO2, CH3, CH2CH3, OCH3, OCOCH3, CH2COCH3, OH, carboxy, and alkoxy as well as pharmaceutical compositions comprising these compounds. The invention further provides methods for preventing or inhibiting the binding of bromodomains to acetyl-lysine residues of proteins and methods f treating HW infection and HIY related disease. The present invention also features compounds of formula (III) wherein R1, R2, R3, R4 R5, and R6 are independently selected from the group consisting of hydrogen; lower alkyl, aryl, phenyl, aralkyl; substituted aralkyl, heteroaryl, substituted heteroaryl, SO2 NH2, NH3+, NO2, SO2, CH3, CH2CH3, OCH3, OCOCH3, CH2COCH3, OCH2CH3, OCH(CH3)2, OCH2COOH, OCHCH3COOH, OCH2COCH3, OCH2CONH2, OCOCH(CH3)2, OCH2CH2OH, OCH2CH2CH3, O(CH2)3CH3, OCHCH3COOCH3, OCH2CON(CH3)2,NH(CH2)3N(CH3)2, NH(CH2)2N(CH3)2, NH(CH2)2OH, NH(CH2)3CH3, NHCH3, SH, halogen, carboxy, and alkoxy as well as pharmaceutical compositions comprising these compounds. The invention further provides methods for preventing or inhibiting the binding of bromodomains to acetyl-lysine residues of proteins and methods for treating HIV infection and HIV related disease.

Selective small molecules blocking HIV-1 tat and coactivator PCAF association

Development of drug resistance from mutations in the targeted viral proteins leads to continuation of viral production by chronically infected cells, contributing to HIV-mediated immune dysfunction. Targeting a host cell protein essential for viral reproduction, rather than a viral protein, may minimize the viral drug resistance problem as observed with HIV protease inhibitors. We report here the development of a novel class of N1-aryl-propane-1,3-diamine compounds using a structure-based approach that selectively inhibit the activity of the bromodomain of the human transcriptional co-activator PCAF, of which association with the HIV trans-activator Tat is essential for transcription and replication of the integrated HIV provirus. Copyright

Naphthalenylmethoxypiperidines as renin inhibitors

The present invention relates to compound of formula (I) wherein R1, R2and R3are as defined in the description and claims and pharmaceutically acceptable salts thereof. The compounds are useful for treating diseases associated with restenosis, glaucoma, cardiac infarct, high blood pressure and end organ damage, e.g. cardiac insufficiency and kidney insufficiency.

Synthesis and properties of liquid crystalline aniline monomers and semiconducting polyaniline with mesogenic side-chains

Novel aniline monomers substituted by mesogenic moieties with different spacer lengths are synthesised and preliminary data are reported on the conjugated polymers produced.