239088-81-4

Usage

Uses

Used in Organic Synthesis:
(E)-ETHYL 3-(4-(TERT-BUTOXYCARBONYLAMINO)PHENYL)ACRYLATE is used as a building block for the synthesis of various compounds and materials, due to its unique molecular structure and reactivity.
Used in Research Applications:
In the field of research, (E)-ETHYL 3-(4-(TERT-BUTOXYCARBONYLAMINO)PHENYL)ACRYLATE is used as a key compound for studying its properties and potential applications in chemical reactions and material development.
Used in Chemical Industry:
(E)-ETHYL 3-(4-(TERT-BUTOXYCARBONYLAMINO)PHENYL)ACRYLATE is used as an intermediate in the chemical industry for the production of various specialty chemicals and materials, taking advantage of its specific functional groups and reactivity.

Upstream product

• 140-88-5 ethyl acrylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 623-04-1 4-aminobenzenemethanol 
• 144072-29-7 tert-butyl N-[4-(hydroxymethyl)phenyl]carbamate 
• 5048-82-8 (E)-ethyl 3-(4-aminophenyl)acrylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 144072-30-0 4-((tert-butoxycarbonyl)amino)benzaldehyde 
• 94-09-7 p-aminoethylbenzoate 
• 110969-44-3 4-tert-butyloxycarbonylaminobenzoic acid ethyl ester 
• 150-13-0 4-amino-benzoic acid 
• 5048-82-8 ethyl 4-aminocinnamate 
• 71026-66-9 N-(tert-butoxycarbonyl)-1,4-phenylenediamine 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis and Evaluation of PPARδAgonists That Promote Osteogenesis in a Human Mesenchymal Stem Cell Culture and in a Mouse Model of Human Osteoporosis

We synthesized a directed library of compounds to explore the structure-activity relationships of peroxisome proliferator-activated receptor δ(PPARδ) activation relative to mesenchymal stem cell (MSC) osteogenesis. Our scaffold used para-substituted cinnamic acids as a polar headgroup, a heteroatom and heterocycle core connecting units, and substituted phenyl groups for the lipophilic tail. Compounds were screened for their ability to increase osteogenesis in MSCs, and the most promising were examined for subunit specificity using a quantitative PPAR transactivation assay. Six compounds were selected for in vivo studies in an ovariectomized mouse model of human postmenopausal osteoporosis. Four compounds improved bone density in vivo, with two (12d and 31a) having activity comparable to that of GW0742, a well-studied PPARδ-selective agonist. 31a (2-methyl-4-[N-methyl-N-[5-methylene-4-methyl-2-[4-(trifluoromethyl)phenyl]thiazole]]aminocinnamic acid) had the highest selectivity for PPARδcompared to other subtypes, its selectivity far exceeding that of GW0742. Our results confirm that PPARδis a new drug target for possible treatment of osteoporosis via in situ manipulation of MSCs.

Synthesis of Nitrogen-Containing Goniothalamin Analogues with Higher Cytotoxic Activity and Selectivity against Cancer Cells

Two series of racemic goniothalamin analogues displaying nitrogen-containing groups were designed and synthesized. A total of 19 novel analogues were evaluated against a panel of four different cancer cell lines, along with the normal prostate cell line PNT2 to determine their selectivity. Among them, goniothalamin chloroacrylamide 13 e displayed the lowest IC50 values for both MCF-7 (0.5 μm) and PC3 (0.3 μm) cells, about 26-fold more potent than goniothalamin (1). Besides its higher potency, compound 13 e also displayed much higher selectivity than goniothalamin. In contrast, goniothalamin isobutyramide 13 c was the most potent analogue against Caco-2 cells (IC50=0.8 μm), about 10-fold more potent and 17-fold more selective than 1. These results reveal the potential of compounds 13 c and 13 e for further in vivo studies, representing the first goniothalamin analogues with IC50 values in the low micromolar range and high selectivity against MCF-7, Caco-2, and PC3 cancer cell lines.

Olefination reactions using tetraarylphosphonium (TAP)-supported phosphorus ylides

Tetraarylphosphonium (TAP)-supported phosphorus ylides were prepared and used in copper-catalyzed olefination reactions with diazo compounds to produce conjugated esters, amides, and phosphonates. The TAP-phosphine oxide can easily be separated from the alkene product, recycled, and reused. Georg Thieme Verlag Stuttgart ? New York.

Dual emission from (E)-3-(4-methylamino-phenyl)-acrylic acid ethyl ester (MAPAEE) and its application as fluorescence probe for studying micellar and protein microenvironment

Steady state absorption, fluorescence and time resolved fluorescence spectroscopy have been used for studying the photoinduced intramolecular charge transfer reaction in (E)-3-(4-methylamino-phenyl)-acrylic acid ethyl ester (MAPAEE). The title molecule shows dual emission due to high energy local and a low energy charge transfer emission. Depending on the nature of solvent the red shifted emission band shows good correlation with the solvent polarity parameter, ET(30) parameter and hydrogen bonding parameter. Quantum chemicals calculations by density functional theory predict that a stabilized twisted intramolecular charge transfer excited state generated either by twisting of the donor group ({single bond}NHMe) or the acceptor (- = {single bond}COOEt) group is responsible for the red shifted charge transfer emission. The solvent polarity dependent red shifted emission from the excited charge transfer state of MAPAEE has been used as fluorosensor to study bovine serum albumin proteinous and sodium dodecyl sulphate micellar microenvironment.

Diazo reagents in copper(I)-catalyzed olefination of aldehydes

The olefination of aldehydes to synthesize unsaturated ketones, esters, amides and phosphonates using diazo reagents and triphenylphosphine in the presence of copper(I) iodide as catalyst, is described. Good to excellent E:Z selectivities as well as yields were obtained for a large variety of aliphatic, aromatic and heteroaromatic aldehydes. The reaction showed also an excellent functional group compatibility and aldehydes were selectively reacted in the presence of ketone, nitro, amine, ether, acetal, thioether and halide groups. The use of a cost-effective copper salt as a catalyst is advantageous compared to previously reported expensive transition metal complexes. The method was used in the total synthesis of the scutifoliamide A, a biologically active compound that exhibits antifungal activity.

An efficient procedure for the synthesis of crystalline aryldiazonium trifluoroacetates - Synthetic applications

We have developed a very mild procedure for the synthesis of crystalline aryldiazonium trifluoroacetate salts in high yields under anhydrous conditions. Over thirty mono- or polyfunctional aniline derivatives have been diazotized by this method, including water- and acid-sensitive substrates. The o- and p-hydroxyaryldiazonium salts, derived from the corresponding anilines, could be deprotonated by treatment with K2CO3 to yield pure diazoquinones. NMR and UV/Vis spectra have been recorded for all the synthesized salts; the data are in good agreement with the rather limited published data and constitute a first extensive report of 13C-NMR chemical shifts in diazonium salts. An excellent linear relationship emerged between Brown's substituent constants S+(p) and the 13C(ipso) chemical shifts. The diazonium salts obtained proved to be much more soluble in organic solvents than their tetrafluoroborate counterparts. They were tested in Pd-mediated coupling reactions of various carbon-carbon double bonds, and were found to give good yields within short reaction times under very mild conditions. We believe that diazonium trifluoroacetates represent a very attractive alternative to diazonium tetrafluoroborates.

BRADYKININ ANTAGONIST QUINOLINES

This invention relates to new heterocyclic compounds and pharmaceutically acceptable salts thereof. More particularly, this invention relates to new heterocyclic compounds and salts thereof which display bradykinin antagonist activity, to processes for preparing these compounds, to a pharmaceutical composition comprising these compounds, and to methods of using same in the prevention and/or the treatment of bradykinin-or bradykinin analogue-mediated diseases such as allergy, inflammation, autoimmune disease, shock, pain, or the like, in human beings or in animals.

Guanidinophenyl-Substituted Enol Lactones as Selective, Mechanism-Based Inhibitors of Trypsin-like Serine Proteases

We have synthesized four guanidinophenyl-substituted protio enol and iodo enol lactones (3-(4-guanidinophenyl)-6-methylidenetetrahydro-2-pyranone (1), 3-(4-guanidinophenyl)-6-(E)-(iodomethylidene)tetrahydro-2-pyranone (2), 4-(4-guanidinophenyl)-6-methylidenetetrahydro-2-pyranone (3), and 4-(4-guanidinophenyl)-6-(E)-(iodomethylidene)tetrahydro-2-pyranone (4)) and tested them for inhibitory activity against some trypsin-like enzymes, namely trypsin, urokinase, tissue plasminogen activator (t-PA), plasmin, and thrombin, as well as α-chymotrypsin and human neutrophil elastase (HNE).The β-aryl-substituted protio lactone 3 was a potent alternate substrate inhibitor of trypsin and urokinase.The α-aryl-substituted iodo lactone 2 was a permanent inactivator of urokinase, plasmin, t-PA, thrombin, and α-chymotrypsin, exhibiting a relatively high specificity for the former two enzymes.In general, these compounds showed a preference for inactivating trypsin-like enzymes over α-chymotrypsin and HNE.Also, within the class of trypsin-like enzymes, there was generally good selectivity of inhibition.