14697-49-5Relevant articles and documents
Crystal structures of 4-(oxiran-2-ylmethoxy) benzoic acid and 4-acetoxybenzoic acid
Obreza, A.,Perdih, F.
, p. 793 - 799,7 (2012)
Compounds 4-(oxiran-2-ylmethoxy)benzoic acid (2) and 4-acetoxybenzoic acid (4) are synthesized by a new synthetic route and studied by X-ray crystallography. Compound 2 crystallizes in the monoclinic system, P21/n space group, a = 5.1209(2) A, b = 30.3429(16) A, c = 5.9153(3) A, β = 96.725(3)°, V = 912.81(8) A3, Z = 4. Compound 4 crystallizes in the triclinic system, P-1 space group, a = 7.3400(4) A, b = 8.0819(3) A, c = 15.6548(9) A, α = 85.754(3)°, β = 84.268(2)°, γ = 70.023(3)°, V = 867.63(8) A3, Z = 4. The crystal structure of 2 comprises two crystallographically independent molecules of the compound. In the crystal structures of 2 and 4, pairs of molecules form carboxyl dimers. Original Russian Text Copyright
Amino Alcohol Acrylonitriles as Activators of the Aryl Hydrocarbon Receptor Pathway: An Unexpected MTT Phenotypic Screening Outcome
Baker, Jennifer R.,Gilbert, Jayne,McCluskey, Adam,Russell, Cecilia C.,Sakoff, Jennette A.
, (2020/03/11)
Lead (Z)-N-(4-(2-cyano-2-(3,4-dichlorophenyl)vinyl)phenyl)acetamide, 1 showed MCF-7 GI50=30 nM and 400-fold selective c.f. MCF10A (normal breast tissue). Acetamide moiety modification (13 a-g) to introduce additional hydrophobicity was favoured with MCF-7 breast cancer cell activity enhanced at 1.3 nM. Other analogues were potent against the HT29 colon cancer cell line at 23 nM. Textbook SAR data was observed in the MCF-7 cell line, in an MTT assay, via the ortho (17 a), meta (17 b) and para (13 f). The amino alcohol -OH moiety was pivotal, but no stereochemical preference noted. But, these data did not fit our homology modelling expectations. Aberrant MTT ((3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide) screening results and metabolic interference confirmed by sulforhodamine B (SRB) screening. Interfering analogues resulted in 120 and 80-fold CYP1A1 and CYP1A2 amplification, with no upregulation of SULT1A1. This is consistent with activation of the AhR pathway. Piperidine per-deuteration reduced metabolic inactivation. 3-OH / 4-OH piperidine analogues showed differential MTT and SRB activity supporting MTT assay metabolic inactivation. Data supports piperidine 3-OH, but not the 4-OH, as a CYP substrate. This family of β-amino alcohol substituted 3,4-dichlorophenylacetonitriles show broad activity modulated via the AhR pathway. By SRB analysis the most potent analogue was 23 b, (Z)-3-(4-(3-(4-phenylpiperidin-1-yl)-2-hydroxypropoxy)phenyl)-2-(3,4-dichlorophenyl)-acrylonitrile.
Epoxy thermosets from model mixtures of the lignin-to-vanillin process
Fache,Boutevin,Caillol
, p. 712 - 725 (2016/02/12)
Epoxy thermosets were prepared from mixtures of phenolics modelling the product stream of the lignin-to-vanillin process. Vanillin is one of the only mono-aromatic compounds produced on an industrial scale from lignin. This process leads to mixtures of phenolic compounds. Isolation of pure vanillin is costly both economically and environmentally. The present work demonstrates that these purification steps are not necessary in order to prepare high-performance epoxy thermosets from biomass. Model mixtures of depolymerization products of lignins from both softwood and hardwood were prepared. These mixtures were subjected in a first step to a Dakin oxidation in order to increase their phenolic functionality. In the second step, they were glycidylated to obtain mixtures of epoxy monomers. Each of the components of the mixtures was individually subjected to the same reactions to provide further insights on their reactivity. Epoxy thermosets were conveniently prepared from these epoxy monomer mixtures. These potentially bio-based epoxy thermosets displayed outstanding thermo-mechanical properties while avoiding environmentally damaging purification steps. Thus, their production could advantageously be integrated in a biorefinery as a high value added product from lignin processing.
Discovery and structure-activity relationship of novel 2,3- dihydrobenzofuran-7-carboxamide and 2,3-dihydrobenzofuran-3(2 h)-one-7-carboxamide derivatives as poly(ADP-ribose)polymerase-1 Inhibitors
Patel, Maulik R.,Bhatt, Aaditya,Steffen, Jamin D.,Chergui, Adel,Murai, Junko,Pommier, Yves,Pascal, John M.,Trombetta, Louis D.,Fronczek, Frank R.,Talele, Tanaji T.
, p. 5579 - 5601 (2014/08/05)
Novel substituted 2,3-dihydrobenzofuran-7-carboxamide (DHBF-7-carboxamide) and 2,3-dihydrobenzofuran-3(2H)-one-7-carboxamide (DHBF-3-one-7-carboxamide) derivatives were synthesized and evaluated as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1). A structure-based design strategy resulted in lead compound 3 (DHBF-7-carboxamide; IC50 = 9.45 μM). To facilitate synthetically feasible derivatives, an alternative core was designed, DHBF-3-one-7-carboxamide (36, IC50 = 16.2 μM). The electrophilic 2-position of this scaffold was accessible for extended modifications. Substituted benzylidene derivatives at the 2-position were found to be the most potent, with 3′,4′-dihydroxybenzylidene 58 (IC50 = 0.531 μM) showing a 30-fold improvement in potency. Various heterocycles attached at the 4′-hydroxyl/4′-amino of the benzylidene moiety resulted in significant improvement in inhibition of PARP-1 activity (e.g., compounds 66-68, 70, 72, and 73; IC50 values from 0.718 to 0.079 μM). Compound 66 showed selective cytotoxicity in BRCA2-deficient DT40 cells. Crystal structures of three inhibitors (compounds (-)-13c, 59, and 65) bound to a multidomain PARP-1 structure were obtained, providing insights into further development of these inhibitors.
