24767-82-6Relevant articles and documents
Fluorinated Analogues of the Histone Deacetylase Inhibitor Vorinostat (Zolinza): Validation of a Chiral Hybrid Bioisostere, BITE
Erdeljac, Nathalie,Bussmann, Kathrin,Sch?ler, Andrea,Hansen, Finn K.,Gilmour, Ryan
, p. 1336 - 1340 (2019)
A chiral, hybrid bioisostere of the CF3 and Et groups (BITE) was installed in a series of vorinostat (Zolinza) analogues, and their histone deacetylase (HDAC) inhibitory behavior was studied relative to that of their nonfluorinated counterparts. Several of these compounds containing the 1,2-difluoroethylene unit showed in vitro potency greater than that of the clinically approved drug itself against HDAC1. This trend was found to be general with the BITE-modified HDAC inhibitors performing significantly better than the ethyl derivatives. Installed by the direct, catalytic vicinal difluorination of terminal alkenes using an I(I)/I(III) manifold, this underexplored chiral bioisostere shows potential in drug discovery.
Combinatorial discovery of thermoresponsive cycloammonium ionic liquids
Chu, Yen-Ho,Hwang, Chun-Chieh,Chen, Chien-Yuan,Tseng, Min-Jen
, p. 11855 - 11858 (2020)
This work demonstrated, for the first time, the combinatorial discovery and rational identification of small-molecule cycloammonium-based thermoresponsive ionic liquids that exhibit LCST phase transition and carry attractiveTcvalues in water.
Preparation method of higher fatty alcohol 2-alkoxy ethanol
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Paragraph 0030-0032, (2021/08/25)
The invention provides a preparation method of higher fatty alcohol 2-alkoxy ethanol, and relates to the technical field of organic synthesis, higher fatty alcohol and sulfonyl halide are used as raw materials for cascade reaction, the higher fatty alcohol is completely converted into sulfonate under the action of alkali, and then the sulfonate is subjected to phase transfer reaction under the promotion of a phase transfer catalyst (the used phase transfer catalyst comprises quaternary ammonium salt or crown ether), sulfonate directly performs nucleophilic substitution reaction with ethylene glycol, and the reaction temperature is controlled to complete the reaction within half an hour to obtain the corresponding higher fatty alcohol 2-alkoxy ethanol. The method is low in raw material and reagent cost, simple in process operation, small in pollution, high in product yield and purity, and suitable for large-scale preparation.
Exploring physicochemical space: Via a bioisostere of the trifluoromethyl and ethyl groups (BITE): Attenuating lipophilicity in fluorinated analogues of Gilenya for multiple sclerosis
Erdeljac, Nathalie,Kehr, Gerald,Ahlqvist, Marie,Knerr, Laurent,Gilmour, Ryan
supporting information, p. 12002 - 12005 (2018/11/21)
The direct, catalytic vicinal difluorination of terminal alkenes via an I(i)/I(iii) manifold was exploited to install a chiral, hybrid bioisostere of the CF3 and Et groups (BITE) in Gilenya; the first orally available drug for the clinical management of Multiple Sclerosis (MS). This subtle fluorination pattern allows lipophilicity (logD) to be tempered compared to the corresponding CF3 and Et derivatives (CH2CH3 > CH2CF3 > CHFCH2F).
Synthesis of structural analogues of hexadecylphosphocholine and their antineoplastic, antimicrobial and amoebicidal activity
Timko, Luká?,Fischer-Fodor, Eva,Garajová, Mária,Mrva, Martin,Chereches, Gabriela,Ondriska, Franti?ek,Bukovsky, Marián,Luká?, Milo?,Karlovská, Janka,Kubincová, Janka,Devínsky, Ferdinand
, p. 263 - 273 (2015/05/26)
Twelve derivatives of hexadecylphosphocholine (miltefosine) were synthesized to determine how the position and length of the alkyl chain within the molecule influence their biological activities. The prepared alkylphosphocholines have the same molecular formula as miltefosine. Activity of the compounds was studied against a spectrum of tumour cells, two species of protozoans, bacteria and yeast. Antitumour efficacy of some alkylphosphocholines measured up on MCF-7, A2780, HUT-78 and THP-1 cell lines was higher than that of miltefosine. The compounds showed antiprotozoal activity against Acanthamoeba lugdunensis and Acanthamoeba quina. Some of them also possess fungicidal activity against Candida albicans equal to miltefosine. No antibacterial activity was observed against Staphylococcus aureus and Escherichia coli. A difference in position of a long hydrocarbon chain within the structure with maximum efficacy was observed for antitumour, antiprotozoal and antifungal activity.
Soluble and reusable poly(norbornene) supports with high loading capacities for peptide synthesis
Naganna, Nimmashetti,Madhavan, Nandita
supporting information, p. 5870 - 5873 (2013/12/04)
Poly(norbornene) supports comprising solubilizing ethylene glycol units and multiple amino acid attachment sites have been developed for peptide synthesis. A variety of amino acids have been efficiently loaded (0.6-1.1 mmol/g) onto the support in high yields (83-98%). Several tripeptides have been synthesized in moderate-to-good overall yields (41-66%) using only 1.2 equiv of coupling reagents/amino acids, and the support could be efficiently recycled up to 3 times.
Amphiphilic organocatalyst for schotten-baumann-type tosylation of alcohols under organic solvent free condition
Asano, Keisuke,Matsubara, Seijiro
supporting information; experimental part, p. 1757 - 1759 (2009/09/06)
A Tosylation of primary alcohol with tosyl chloride was performed effectively with an W-hexadecylimidazole catalyst in water containing K 2CO3 aggregation of the catalyst carrying a hydrophobic methylene chain worked as a substitute for organic solvent.
Process for preparation of oxyglutaric acid ester derivatives
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, (2008/06/13)
A process for preparing an oxyglutaric acid ester derivative of the formula: STR1 in which each of R1 and R2 is C1-5 alkoxy, C1-7 aralkyloxy, C7-9 halogenated aralkyloxy or phenyl, R4 is a hydroxyl-protecting group, and R5 is C1-10 alkyl which may have a substituent, comprises the steps of reacting a methyl phosphonate derivative or methyl phosphine oxide derivative with an oxyglutaric acid mono-ester to give a reaction product which comprises an oxyglutaric acid derivative having a phosphorus-containing group and a pentenedioic acid mono-ester (by-product), removing the pendenedioic acid mono-ester from the reaction product to isolate the oxyglutaric acid derivative, and converting the isolated oxyglutaric acid derivative into the oxyglutaric acid ester derivative. A process for obtaining an optically active oxyglutaric acid ester derivative is also disclosed.
Scope and utility of a new soluble copper catalyst [CuBr-LiSPh-LiBr-THF]: A comparison with other copper catalysts in their ability to couple one equivalent of a Grignard reagent with an alkyl sulfonate
Burns, Dennis H.,Miller, Jeffrey D.,Chan, Ho-Kit,Delaney, Michael O.
, p. 2125 - 2133 (2007/10/03)
A mixture of equal amounts of CuBr-SMe2, LiBr, and LiSPh in THF at 0°C furnished a new soluble copper catalyst that was highly efficient at coupling primary, secondary, tertiary, aryl, vinyl, and allylic Grignard reagents to primary tosylates and primary Grignard reagents to secondary tosylates and mesylates, all with the use of only 1 equiv of Grignard reagent. The new catalyst was shown to be much more reactive than copper catalysts CuBr and Li2CuCl4 and more efficient in the transference of secondary and tertiary alkyl groups than lower order cuprates (Gilman reagents) and demonstrated more reactivity than the lower order cuprates with its ability to couple primary Grignard reagents to secondary sulfonates. The Grignard reagent/catalyst system was compatible with an ester functionalized tosylate, thus proving to be more chemoselective than a Grignard reagent without the catalyst. The catalyst exhibited good reactivity below room temperature, and with the addition of 6% v/v of HMPA to the catalyst solution, excellent yields of coupled product were obtained within a 25-67°C temperature range. 1H NMR demonstrated that the catalyst solution consisted of several species that most likely were composed of copper ligated with thiophenol, THF, and LiBr in aggregated forms.
Novel Ion Containing Liquid Crystals and Liquid Crystalline Main Chain Polymers Based on Trans-1,2-Bis(4-Pyridyl Ethylene) Mesogen
Cheng, P.,Blumstein, A.,Subramanyam, S.
, p. 1 - 38 (2007/10/02)
Ion bearing liquid crystalline compounds based on trans-1,2-bis(4-pyridinium)ethylene were synthesized and studied.These compounds included low molecular mass analogues, twin model compounds and main chain ionomers.Most of these exhibited liquid crystallinity of the smectic type.As a general rule the introduction of charges into the mesogenic moiety increased the stability (transition temperature) of the mesophase.Large supercooling effects, broad mesophase intervals and tendency to polymorphism are common features of these ionic mesogenic compounds.In the case of twin model compounds a variety of smectic phases were observed.The nature of these was dependent on the nature of the counterion and the thermal history of the compound.Tosylate or p.toluene sulfonate counterions promoted a higher degree of order in smectic mesophases as well as higher transition tempertures compared to methylsulfonate counterions.A pronounced odd-even effect of the isotropisation temperature of the twin compounds was observed.Compounds with even numbered methylene spacers display higher transition temperatures than those with an odd spacer.Only polymers with methylsulfonate and toluenesulfonate counterions were found to exhibit both, thermotropic and lyotropic mesophases.Thermotropic mesophases were characterized as smectic mesophases of lower order (SA).The nature of lyotropic mesophases were not determined.High transition temperatures and concommitant oxydative crosslinking made the study of polymers with halogen counterions difficult.Polymers with halogen and perchlorate counterions were found fo be poorly soluble in water precluding the formation of lyotropic mesophases.The introduction of a few siloxane bonds into the flexible spacer joining the charged mesogen moieties has a dramatic effect on lowering the transition temparatures and making possible the study of mesophases up to their isotropisation temperature.Preliminary characterization of polymers with siloxane containing spacer and methylsulfonate/tosylate counterions suggest a smectic mesophase of lower order. - Keywords: Ion containing liquid crystals, liquid crystal ionomers
