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).
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.
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%.
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.
