13476-55-6

Usage

InChI:InChI=1/C13H19NO2/c1-2-3-4-5-10-16-13(15)11-6-8-12(14)9-7-11/h6-9H,2-5,10,14H2,1H3

Upstream product

• 869657-87-4 6-bromohexyl 4-nitrobenzoate 
• 6835-50-3 hex-5-enyl 4-nitrobenzoate 
• 150-13-0 4-amino-benzoic acid 
• 111-27-3 hexan-1-ol 
• 6268-24-2 n-hexyl p-nitrobenzoate 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 1246881-86-6 hexyl 4-amino-3-bromobenzoate 
• 299965-41-6 4-(4-(hexyloxycarbonyl)phenylamino)-3,5-dinitrobenzoic acid 
• 1610566-94-3 methyl 3-(4-(hexyloxycarbonyl)phenylamino)-5-nitrobenzoate 

Relevant academic research and scientific papers

Computational techniques are valuable tools for the discovery of protein-protein interaction inhibitors: The 14-3-3σ case

Targeting the binding site of 14-3-3 proteins lets the release of partner proteins involved in cell cycle progression, apoptosis, cytoskeletal rearrangement and transcriptional regulation and may therefore be regarded as an alternative strategy to integra

Competitive homolytic and heterolytic decomposition pathways of gas-phase negative ions generated from aminobenzoate esters

An alkyl-radical loss and an alkene loss are two competitive fragmentation pathways that deprotonated aminobenzoate esters undergo upon activation under mass spectrometric conditions. For the meta and para isomers, the alkyl-radical loss by a homolytic cleavage of the alkyl-oxygen bond of the ester moiety is the predominant fragmentation pathway, while the contribution from the alkene elimination by a heterolytic pathway is less significant. In contrast, owing to a pronounced charge-mediated ortho effect, the alkene loss becomes the predominant pathway for the ortho isomers of ethyl and higher esters. Results from isotope-labeled compounds confirmed that the alkene loss proceeds by a specific γ-hydrogen transfer mechanism that resembles the McLafferty rearrangement for radical cations. Even for the para compounds, if the alkoxide moiety bears structural motifs required for the elimination of a more stable alkene molecule, the heterolytic pathway becomes the predominant pathway. For example, in the spectrum of deprotonated 2-phenylethyl 4-aminobenzoate, m/z 136 peak is the base peak because the alkene eliminated is styrene. Owing to the fact that all deprotonated aminobenzoate esters, irrespective of the size of the alkoxy group, upon activation fragment to form an m/z 135 ion, aminobenzoate esters in mixtures can be quantified by precursor ion discovery mass spectrometric experiments.

Discovery of 14-3-3 protein-protein interaction inhibitors that sensitize multidrug-resistant cancer cells to doxorubicin and the Akt inhibitor GSK690693

14-3-3 is a family of highly conserved adapter proteins that is attracting much interest among medicinal chemists. Small-molecule inhibitors of 14-3-3 protein-protein interactions (PPIs) are in high demand, both as tools to increase our understanding of 14-3-3 actions in human diseases and as leads to develop innovative therapeutic agents. Herein we present the discovery of novel 14-3-3 PPI inhibitors through a multidisciplinary strategy combining molecular modeling, organic synthesis, image-based high-content analysis of reporter cells, and in vitro assays using cancer cells. Notably, the two most active compounds promoted the translocation of c-Abl and FOXO pro-apoptotic factors into the nucleus and sensitized multidrug-resistant cancer cells to apoptotic inducers such as doxorubicin and the pan-Akt inhibitor GSK690693, thus becoming valuable lead candidates for further optimization. Our results emphasize the possible role of 14-3-3 PPI inhibitors in anticancer combination therapies. Pièce de résistance! Multidrug resistance (MDR) is the main obstacle toward effective anticancer therapy. Herein we report the discovery of two small-molecule 14-3-3 protein-protein interaction inhibitors that promote the translocation of c-Abl and FOXO pro-apoptotic factors into the nucleus and sensitize MDR cancer cells to doxorubicin and the pan-Akt inhibitor GSK690693.

Synthesis and phase behaviors of side-chain liquid-crystalline polymers containing azobenzene mesogen with the different length alkyl tail

A series of side-chain liquid-crystal polymers, poly[6-[4-(4′-n-alkyl benzoateazo)phenoxy]-hexylmethacrylate]s (PMAzoCOORm, m = 1, 2, 3, 4, 5, 6, 8, 10, 14, and 18) have been prepared by two synthetic methods. The chemical structure of the monomers was confirmed by 1H NMR and mass spectrometry. The molecular characterizations of the polymers were performed with 1H NMR and gel permeation chromatograph. The phase behaviors of polymers were investigated by the combination of techniques including differential scanning calorimetry, polarized optical microscopy, and small-angle X-ray scattering. For m = 1, 2, 3, 4, 5, and 6, the polymers exhibited a monosmectic A phase in which the smectic layer period was almost identical to the side-chain length. In addition, for m = 2, 3, 4, and 5, they presented the monosmectic C phase in low temperature; moreover, the tilt angle increased from 23.3 to 40.5°. For m = 8, 10, 14, and 18, the polymers showed a bilayer smectic A phase in which the layer spacing was larger than a fully extended side chain but less than two extended chains. On the other hand, for the clearing point, with the increasing of m, it first decreased, and then increased. All of these indicated that the length of alkyl tails played an important role in the phase behaviors of these polymers.

Synthesis of symmetric diester-functionalised Troeger's base analogues

The yields of ester-functionalised Troeger's base analogues are dramatically improved by incorporating an electron-donating group on the aromatic ring and/or enhancing solubil- ity of the aniline unit. In addition to 2,8-diester compounds, 1,7-, 3,9- and 4,10-diester-functionalised Troeger's base analogues have been prepared for the first time.

Palladium-catalyzed silane/siloxane reductions in the one-pot conversion of nitro compounds into their amines, hydroxylamines, amides, sulfonamides, and carbamates

A combination of palladium(II) acetate, aqueous potassium fluoride, and polymethylhydrosiloxane (PMHS) facilitates the room-temperature reduction of aromatic nitro compounds to anilines. These reactions tend to be quick (30 min), high-yielding, and tolerate a range of other functional groups. Replacement of PMHS/KF with triethylsilane allows for the reduction of aliphatic nitro compounds to their corresponding hydroxylamines. Depending on the substrate, both conditions can allow for the in situ conversion of the product amines into amides, sulfonamides, and carbamates. Georg Thieme Verlag Stuttgart.

Smectogenic Salts Formed by Combination of Alkyl p-Aminobenzoates and p-Ethyl- or p-Chlorobenzenesulfonic Acid

Two series of smectogenic salts were obtained by combining alkyl p-aminobenzoates with p-ethyl- and p-chlorobenzenesulfonic acids, respectively.The shortest ester alkyl chain required to generate a smectic A phase is nonyl when the former sulfonic acid is employed but the chain may be as short as butyl when the latter is employed.The smectic A-isotropic transition temperature in the second series is significantly higher than that in the first series, indicating that the terminal substituent on the anion is as crucial as that in non-ionic mesogens in determining the mesophase stability. - Keywords: Smectic, alkyl p-aminobenzoates, benzenesulfonates

EFFECTS OF BRANCHING OF THE ALKYL CHAIN ON THE LIQUID CRYSTALLINE PROPERTIES OF N-(p-PHENYLBENZYLIDENE)-p-ALKOXYCARBONYLANILINES.

The liquid crystal behavior of twenty-three N-(p-phenylbenzylidene)-p-alkoxycarbonylanilines has been examined by optical microscopy and differential scanning calorimetry in order to study the effects of branching of the alkyl groups.