53963-10-3Relevant articles and documents
Synthesis and Preliminary PET Imaging Studies of a FAAH Radiotracer ([11C]MPPO) Based on α-Ketoheterocyclic Scaffold
Wang, Lu,Yui, Joji,Wang, Qifan,Zhang, Yiding,Mori, Wakana,Shimoda, Yoko,Fujinaga, Masayuki,Kumata, Katsushi,Yamasaki, Tomoteru,Hatori, Akiko,Rotstein, Benjamin H.,Collier, Thomas Lee,Ran, Chongzhao,Vasdev, Neil,Zhang, Ming-Rong,Liang, Steven H.
, p. 109 - 118 (2016)
Fatty acid amide hydrolase (FAAH) is one of the principle enzymes for metabolizing endogenous cannabinoid neurotransmitters such as anandamide, and thus regulates endocannabinoid (eCB) signaling. Selective pharmacological blockade of FAAH has emerged as a potential therapy to discern the endogenous functions of anandamide-mediated eCB pathways in anxiety, pain, and addiction. Quantification of FAAH in the living brain by positron emission tomography (PET) would help our understanding of the endocannabinoid system in these conditions. While most FAAH radiotracers operate by an irreversible ("suicide") binding mechanism, a FAAH tracer with reversibility would facilitate quantitative analysis. We have identified and radiolabeled a reversible FAAH inhibitor, 7-(2-[11C]methoxyphenyl)-1-(5-(pyridin-2-yl)oxazol-2-yl)heptan-1-one ([11C]MPPO) in 13% radiochemical yield (nondecay corrected) with >99% radiochemical purity and 2 Ci/μmol (74 GBq/μmol) specific activity. The tracer showed moderate brain uptake (0.8 SUV) with heterogeneous brain distribution. However, blocking studies with a potent FAAH inhibitor URB597 demonstrated a low to modest specificity to the target. Measurement of lipophilicity, metabolite, and efflux pathway analysis were also performed to study the pharmacokinetic profile of [11C]MPPO. In all, we reported an efficient radiolabeling and preliminary evaluation of the first-in-class FAAH inhibitor [11C]MPPO with α-ketoheterocyclic scaffold. (Chemical Equation Presented).
Synthesis of Oct-1-ene
Read, Gordon,Townsend, Ian
, p. 2901 - 2902 (1982)
Oct-1-ene, with 98percent and 93percent deuterium incorporation at C-2 and C-8, respectively, is prepared from 6-bromohexan-1-ol in a six-step synthesis which offers access to a wide range of ω-labelled acyclic aliphatic compounds.
The synthesis of 14-membered macrocyclic ethers
Clyne, Dean S.,Weiler, Larry
, p. 13659 - 13682 (1999)
As part of an ongoing study of the chemistry of macrocyclic compounds, 14-membered macrocyclic ethers with a variety of methyl substitution patterns were synthesized. The preparation of these macrocyclic ethers involved either the Baeyer-Villiger ring expansion of a cyclic ketone, or the macrolactonization of a hydroxy acid to give a lactone. The lactone carbonyl was removed either by conversion to an intermediate thionolactone obtained by reaction with Lawesson's reagent and reduction, or by direct reduction using a boron trifluoride etherate mediated sodium borohydride reaction.
Modular Assembly of Vibrationally and Electronically Coupled Rhenium Bipyridine Carbonyl Complexes on Silicon
Allegretti, Francesco,Amati, Matteo,Barth, Johannes V.,Bartl, Johannes D.,Bondino, Federica,Cattani-Scholz, Anna,Deimel, Peter S.,Gregoratti, Luca,Henning, Alex,Magnano, Elena,Nickel, Bert,Ober, Martina F.,Ochsenfeld, Christian,Paulus, Claudia,Rieger, Bernhard,Savasci, G?kcen,Sharp, Ian D.,Stutzmann, Martin,Thomas, Christopher,Yazdanshenas, Bahar,Zeller, Patrick
supporting information, p. 19505 - 19516 (2021/11/26)
Hybrid inorganic/organic heterointerfaces are promising systems for next-generation photocatalytic, photovoltaic, and chemical-sensing applications. Their performance relies strongly on the development of robust and reliable surface passivation and functionalization protocols with (sub)molecular control. The structure, stability, and chemistry of the semiconductor surface determine the functionality of the hybrid assembly. Generally, these modification schemes have to be laboriously developed to satisfy the specific chemical demands of the semiconductor surface. The implementation of a chemically independent, yet highly selective, standardized surface functionalization scheme, compatible with nanoelectronic device fabrication, is of utmost technological relevance. Here, we introduce a modular surface assembly (MSA) approach that allows the covalent anchoring of molecular transition-metal complexes with sub-nanometer precision on any solid material by combining atomic layer deposition (ALD) and selectively self-assembled monolayers of phosphonic acids. ALD, as an essential tool in semiconductor device fabrication, is used to grow conformal aluminum oxide activation coatings, down to sub-nanometer thicknesses, on silicon surfaces to enable a selective step-by-step layer assembly of rhenium(I) bipyridine tricarbonyl molecular complexes. The modular surface assembly of molecular complexes generates precisely structured spatial ensembles with strong intermolecular vibrational and electronic coupling, as demonstrated by infrared spectroscopy, photoluminescence, and X-ray photoelectron spectroscopy analysis. The structure of the MSA can be chosen to avoid electronic interactions with the semiconductor substrate to exclusively investigate the electronic interactions between the surface-immobilized molecular complexes.
Method for synthesizing (E)-7-dodecen-1-ol acetate
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Paragraph 0011; 0023-0025, (2019/01/08)
The invention belongs to the technical field of insect pheromone synthesis, and discloses a novel method for synthesizing (E)-7-dodecen-1-ol acetate. The method comprises the following steps: reactinga starting raw material 6-bromo-1-hexanol with 2,3-dihydropyran to obtain 1-tetrahydropyranyloxy-6-bromohexane, and carrying out a coupling reaction on the 1-tetrahydropyranyloxy-6-bromohexane and 1-hexyne in the presence of n-butyllithium to generate 1-tetrahydropyranyloxy-7-dodecyne; reducing the 1-tetrahydropyranyloxy-7-dodecyne by lithium aluminum hydroxide in diethylene glycol dimethyl etherto obtain (E)-tetrahydropyranyloxy-7-dodecene; and removing tetrahydropyran protecting groups by using p-toluenesulfonic acid to synthesize (E)-7-dodecen-1-ol acetate, and finally reacting the (E)-7-dodecen-1-ol acetate with acetyl chloride to obtain the target product (E)-7-dodecen-1-ol acetate. The method has the advantages of simple synthesis route, mild reaction conditions, and realization ofthe total yield reaching 49%.
Synthesis and Cytotoxicity of 1,4-Naphthoquinone Oxime Derivatives
Zhang,Dong,Meng,Huang,Li
, p. 2388 - 2393 (2019/01/04)
A series of hydroxylated 1,4-naphthoquinone oximes were designed and synthesized. The in vitro cytotoxicity of these compounds was evaluated against five human cancer cell lines and human skin fibroblast cell line. Among them, compounds (1E,4E)-6-{1-[(5-Hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8- dimethoxynaphthalene-1,4-dione dioxime and (1E,4E)-6-{1-[(6-Hydroxyhexyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione dioxime displayed higher cytotoxicity in three cancer cell lines than the positive drug 5-fluorouracil.
A (Z, Z, E) - 7, 11, 13 - sixteen carbon three activated olefinic ketones synthesis method (by machine translation)
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Page/Page column 2; 3; 8; 11, (2018/07/15)
The invention relates to an improved synthetic method of (Z,Z,E)-7,11,13-hexadecatrienal, wherein the (Z,Z,E)-7,11,13-hexadecatrienal is an important component in a sex pheromone compound of phyllocnistis citrella. The improved synthetic method is carried out with 6-bromo-1-hexanol as an initial raw material and through a coupled reaction, a Wittig reaction and other reactions to synthesize the (Z,Z,E)-7,11,13-hexadecatrienal. The improved synthetic method is advantaged in that the raw material is low in cost and easy to get, and the reactions are safe and convenient in operations and is short in step periods. The improved synthetic method is high in product yield, is free of environmental pollution and can achieve better economic benefit.
Donepezil–melatonin hybrids as butyrylcholinesterase inhibitors: Improving binding affinity through varying mode of linking fragments
?ozińska, Iwona,?wierczyńska, Aleksandra,Mol?da, Zuzanna,Hartman, Alwin M.,Hirsch, Anna K. H.,Czarnocki, Zbigniew
, (2018/10/15)
Hybrid inhibitors of acetyl- and butyrylcholinesterase are compounds that combine structural motifs of two different classical inhibitors, leading to a dual binding ligand. A rapidly growing collection of those compounds involves a wide diversity of structural motifs, but the way of linking two active fragments and its impact on the affinity toward cholinesterases usually remains beyond the extent of investigation. We present hereby a detailed analysis of this aspect using melatonin–donepezil hybrids. A new series of compounds, in which two fragments are connected using a carbamate linker, exhibits excellent activity and selectivity toward butyrylcholinesterase.
Identification of β-hydroxy fatty acid esters and primary, secondary-alkanediol esters in cuticular waxes of the moss Funaria hygrometrica
Busta, Lucas,Budke, Jessica M.,Jetter, Reinhard
, p. 38 - 49 (2015/12/01)
The plant cuticle, a multi-layered membrane that covers plant aerial surfaces to prevent desiccation, consists of the structural polymer cutin and surface-sealing waxes. Cuticular waxes are complex mixtures of ubiquitous, typically monofunctional fatty acid derivatives and taxon-specific, frequently bifunctional specialty compounds. To further our understanding of the chemical diversity of specialty compounds, the waxes on the aerial structures of the leafy gametophyte, sporophyte capsule, and calyptra of the moss Funaria hygrometrica were surveyed. Respective moss surfaces were extracted, and resulting lipid mixtures were analyzed by gas chromatography-mass spectrometry (GC-MS). The extracts contained ubiquitous wax compound classes along with two prominent, unidentified classes of compounds that exhibited some characteristics of bifunctional structures. Microscale transformations led to derivatives with characteristic MS fragmentation patterns suggesting possible structures for these compounds. To confirm the tentative structure assignments, one compound in each of the suspected homologous series was synthesized. Based on GC-MS comparison with the authentic standards, the first series of compounds was identified as containing esters formed by β-hydroxy fatty acids and wax alcohols, with ester chain lengths varying from C42 to C50 and the most prominent homolog being C46. The second series consisted of fatty acid esters of 1,7-alkanediols, linked via the primary hydroxyl group, with ester chain lengths C40-C52 also dominated by the C46 homolog. The β-hydroxy acid esters were restricted to the sporophyte capsule, and the diol esters to the leafy gametophyte and calyptra. Based on their homolog and isomer distributions, and the presence of free 1,7-triacontanediol, possible biosynthetic reactions leading to these compounds are discussed.
The molecular structure of thio-ether fatty acids influences PPAR-dependent regulation of lipid metabolism
Lund, Jenny,Stensrud, Camilla,Rajender,Bohov, Pavol,Thoresen, G. Hege,Berge, Rolf K.,Wright, Michael,Kamal, Ahmed,Rustan, Arild C.,Miller, Andrew D.,Skorve, Jon
, p. 1191 - 1203 (2016/03/01)
Thio-ether fatty acids (THEFAs), including the parent 2-(tetradecylthio)acetic acid (TTA), are modified fatty acids (FAs) that have profound effects on lipid metabolism given that they are blocked for β-oxidation, and able to act as peroxisome proliferator-activated receptor (PPAR) agonists. Therefore, TTA in particular has been tested clinically for its therapeutic potential against metabolic syndrome related disorders. Here, we describe the preparation of THEFAs based on the TTA scaffold with either a double or a triple bond. These are tested in cultured human skeletal muscle cells (myotubes), either as free acid or following esterification as phospholipids, lysophospholipids or monoacylglycerols. Metabolic effects are assessed in terms of cellular bioavailabilities in myotubes, by FA substrate uptake and oxidation studies, and gene regulation studies with selected PPAR-regulated genes. We note that the inclusion of a triple bond promotes THEFA-mediated FA oxidation. Furthermore, esterification of THEFAs as lysophospholipids also promotes FA oxidation effects. Given that the apparent clinical benefits of TTA administration were offset by dose limitation and poor bioavailability, we discuss the possibility that a selection of our latest THEFAs and THEFA-containing lipids might be able to fulfill the therapeutic potential of the parent TTA while minimizing required doses for efficacy, side-effects and adverse reactions.
