622-04-8Relevant academic research and scientific papers
Molecular structure of PhOCH2CH(OH)CH2OPH
Koide, Yoshihiro,Bott, Simon G.,Barron, Andrew R.
, p. 247 - 250 (1999)
The molecular structure of PhOCH2CH(OH)CH2OPh has been determined. The C - O -C - C - C - O - C backbone adopts an anti-anti-anti-anti conformation. Inter-molecular O - H ... O hydrogen-bonding results in dimeric units which stack into zig-zag tapes. Crystal data: orthorhombic, Pbca, a = 10.383(1), b = 8.0532(0), c = 31.295(3) A, V = 2616.8(3) A3, and Z = 8.
Full atom-efficiency transformation of wasted polycarbonates into epoxy thermosets and the catalyst-free degradation of the thermosets for environmental sustainability
Abu-Omar, Mahdi M.,Chan, Jian Ren,Chen, Chien Han,Juang, Tzong Yuan,Lin, Ching Hsuan,Shao, Shih Wei
, p. 4683 - 4696 (2020/08/10)
We report two sustainable features in this work. The first feature is that we successfully applied wasted polycarbonate (WPC) as an epoxy curing agent for epoxy resins to prepare WPC-cured epoxy thermosets. The curing of WPC and epoxy is based on the reaction of a carbonate and an epoxide, which is proven by a model reaction of diphenyl carbonate (DPC) and glycidyl phenyl ether (GPE) in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP). The WPC-cured epoxy thermosets show comparable thermal properties to commercial-based, phenol novolac (PN)-cured epoxy thermosets. Interestingly, the films of WPC-cured epoxy thermosets are foldable, while those of PN-cured epoxy thermosets are brittle, demonstrating the advantage of using WPC as a curing agent over PN. Since the WPC was used directly without any digestion or pyrolysis process, the atomic efficiency is 100percent, making this WPC recycling strategy economically attractive. The second feature is that we successfully degraded the WPC-cured epoxy thermosets to phenoxy resins through a catalyst-free aminolysis process, that is, the products based on the WPC-cured epoxy thermosets are degradable when their lifespans are expired. The transformation of WPC into epoxy thermosets, along with the degradation of the epoxy thermosets, makes this work attractive for sustainability.
An innovative synthesis pathway to benzodioxanes: The peculiar reactivity of glycerol carbonate and catechol
Tabanelli,Giliberti,Mazzoni,Cucciniello,Cavani
, p. 329 - 338 (2019/01/28)
A peculiar reactivity of glycerol carbonate (GlyC) as an innovative and highly reactive alkylating agent for phenolic compounds is investigated in this article. In particular, 2-hydroxymethyl-1,4-benzodioxane (HMB), a key intermediate for the pharmaceutical industry, has been selectively synthesized by the reaction of a slight excess of GlyC with catechol in the presence of a basic catalyst (NaOCH3, Na-mordenite, MgO), without requiring a reaction solvent. Both reagents have been quantitatively converted in just one hour at 170 °C with a HMB yield, up to 88%, in the presence of a homogeneous basic catalyst (NaOCH3). Notably, the main side product, the HMB isomer, may be an interesting intermediate for the synthesis of calone analogues, which are important scaffolds used in fragrances. A detailed mechanistic study, supported by kinetics, GC-MS, and HMBC NMR characterization, is also reported. Accordingly, this paper describes a completely innovative and greener synthesis pathway to benzodioxanes.
Synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines
Lavorato, Stefania N.,Duarte, Mariana C.,Lage, Daniela P.,Tavares, Carlos A. P.,Coelho, Eduardo A. F.,Alves, Ricardo J.
, p. 1052 - 1072 (2017/04/14)
We describe herein the antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines, prepared in four simple steps from epichlorohydrin. Among the evaluated compounds, three (4o, 4q, and 4r) displayed considerable activity against Leishmania amazonensis promastigote forms, with IC50 values below 10 μM. We also analyzed the effects of the nature and the position of ring substituent on activity. Two amines (4m and 4o) showed excellent profiles in the treatment of L. amazonensis-infected macrophages, reducing the parasite burden by more than 95% in tested concentrations.
1,3-Bis(aryloxy)propan-2-ols as potential antileishmanial agents
Lavorato, Stefania N.,Duarte, Mariana C.,Lage, Daniela P.,Tavares, Carlos A. P.,Coelho, Eduardo A. F.,Alves, Ricardo J.
, p. 981 - 986 (2017/10/05)
We describe herein the synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-ols. Five compounds (2, 3, 13, 17, and 18) exhibited an effective antileishmanial activity against stationary promastigote forms of Leishmania amazonensis (IC50??15.0?μm), and an influence of compound lipophilicity on activity was suggested. Most of the compounds were poorly selective, as they showed toxicity toward murine macrophages, except 17 and 18, which presented good selective indexes (SI?≥?10.0). The five more active compounds (2, 3, 13, 17, and 18) were selected for the treatment of infected macrophages, and all of them were able to reduce the number of internalized parasites by more than 80%, as well as the number of infected macrophages by more than 70% in at least one of the tested concentrations. Altogether, these results demonstrate the potential of these compounds as new hits of antileishmanial agents and open future possibilities for them to be tested in in vivo studies.
New bent-shaped azomethine monomers for optical applications
Ovdenko, Valeriia,Kolendo, Aleksey
, p. 113 - 121 (2016/12/22)
It was convenient preparative method of new methacrylic monomers with banana-shaped structure and photoactive azomethine fragments synthesis. To determine the effect of large azomethine fragment on the process of homopolymerization, symmetrical model compounds with simpler structure were synthesized. The kinetic of its thermally initiated radical polymerization in DMF solution was studied and compared with the kinetics of model compounds does not containing bulky photochromic fragment. Peculiarities of photo initiated processes of E,Z-isomerization were studied.
Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases
Tassi, Marco,Bartollini, Elena,Adriaensens, Peter,Bianchi, Luca,Barkakaty, Balaka,Carleer, Robert,Chen, Jihua,Hensley, Dale K.,Marrocchi, Assunta,Vaccaro, Luigi
, p. 107200 - 107208 (2016/01/08)
In view of searching for efficient polymeric supports for organic bases to be used in environmentally friendly reaction conditions, novel gel-type cross-linked polystyrenes functionalized with diethylamine and 1,5,7-triazabicyclo[4.4.0]dec-5-ene, have been prepared. The structural properties and morphology of these catalysts have been determined by extensive solid state NMR experiments, FTIR spectroscopy and SEM/TEM microscopy. SPACeR-supported bases were found to exhibit high catalytic activity in the epoxide ring opening by phenols. A range of β-substituted alcohols have been readily and regioselectively synthesized.
Continuous and convergent access to vicinyl amino alcohols
Nobuta, Tomoya,Xiao, Guozhi,Ghislieri, Diego,Gilmore, Kerry,Seeberger, Peter H.
supporting information, p. 15133 - 15136 (2015/10/12)
Five active pharmaceutical ingredients (APIs) containing the vicinyl amino alcohol moiety were synthesized using a convergent chemical assembly system. The continuous system is composed of four flow reaction modules: biphasic oxidation, Corey-Chaykovsky epoxidation, phenol alkylation, and epoxide aminolysis. Judicious choice of reagents and module order allowed for two classes of β-amino alcohols, aryl and aryloxy, to be synthesized in good (27-69%) overall yields.
Monovalent mannose-based DC-SIGN antagonists: Targeting the hydrophobic groove of the receptor
Toma?i?, Tihomir,Haj?ek, David,?vajger, Urban,Luzar, Jernej,Obermajer, Nata?a,Petit-Haertlein, Isabelle,Fieschi, Franck,Anderluh, Marko
, p. 308 - 326 (2014/03/21)
Dendritic cell-specific, intercellular adhesion molecule-3-grabbing non-integrin (DC-SIGN) is a C-type lectin expressed specifically on dendritic cells. It is a primary site for recognition and binding of various pathogens and thus a promising therapeutic target for inhibition of pathogen entry and subsequent prevention of immune defense cell infection. We report the design and synthesis of d-mannose-based DC-SIGN antagonists bearing diaryl substituted 1,3-diaminopropanol or glycerol moieties incorporated to target the hydrophobic groove of the receptor. The designed glycomimetics were evaluated by in vitro assay of the isolated DC-SIGN extracellular domain for their ability to compete with HIV-1 gp120 for binding to the DC-SIGN carbohydrate recognition domain. Compounds 14d and 14e, that display IC50 values of 40 μM and 50 μM, are among the most potent monovalent DC-SIGN antagonists reported. The antagonistic effect of all the synthesized compounds was further evaluated by a one-point in vitro assay that measures DC adhesion. Compounds 14d, 14e, 18d and 18e were shown to act as functional antagonists of DC-SIGN-mediated DC adhesion. The binding mode of 14d was also studied by molecular docking and molecular dynamics simulation, which revealed flexibility of 14d in the binding site and provides a basis for further optimization.
Synergistic dual activation catalysis by palladium nanoparticles for epoxide ring opening with phenols
Seth, Kapileswar,Roy, Sudipta Raha,Pipaliya, Bhavin V.,Chakraborti, Asit K.
supporting information, p. 5886 - 5888 (2013/07/25)
Synergistic dual activation catalysis has been devised for epoxide phenolysis wherein palladium nanoparticles induce electrophilic activation via coordination with the epoxide oxygen followed by nucleophilic activation through anion-π interaction with the aromatic ring of the phenol, and water (reaction medium) also renders assistance through 'epoxide-phenol' dual activation.
