31084-54-5Relevant articles and documents
Development and radiosynthesis of the first 18F-labeled inhibitor of monocarboxylate transporters (MCTs)
Sadeghzadeh, Masoud,Moldovan, Rare?-Petru,Fischer, Steffen,Wenzel, Barbara,Ludwig, Friedrich-Alexander,Teodoro, Rodrigo,Deuther-Conrad, Winnie,Jonnalagadda, Shirisha,Jonnalagadda, Sravan K.,Gudelis, Emilis,?a?kus, Algirdas,Higuchi, Kei,Ganapathy, Vadivel,Mereddy, Venkatram R.,Drewes, Lester R.,Brust, Peter
, p. 411 - 424 (2019)
Monocarboxylate transporters 1 and 4 (MCT1 and MCT4) are involved in tumor development and progression. Their expression levels are related to clinical disease prognosis. Accordingly, both MCTs are promising drug targets for treatment of a variety of human cancers. The noninvasive imaging of these MCTs in cancers is regarded to be advantageous for assessing MCT-mediated effects on chemotherapy and radiosensitization using specific MCT inhibitors. Herein, we describe a method for the radiosynthesis of [18F]FACH ((E)-2-cyano-3-{4-[(3-[18F]fluoropropyl)(propyl)amino]-2-methoxyphenyl}acrylic acid), as a novel radiolabeled MCT1/4 inhibitor for imaging with PET. A fluorinated analog of α-cyano-4-hydroxycinnamic acid (FACH) was synthesized, and the inhibition of MCT1 and MCT4 was measured via an L-[14C]lactate uptake assay. Radiolabeling was performed by a two-step protocol comprising the radiosynthesis of the intermediate (E)/(Z)-[18F]tert-Bu-FACH (tert-butyl (E)/(Z)-2-cyano-3-{4-[(3-[18F]fluoropropyl)(propyl)amino]-2-methoxyphenyl}acrylate) followed by deprotection of the tert-butyl group. The radiofluorination was successfully implemented using either K[18F]F-K2.2.2-carbonate or [18F]TBAF. The final deprotected product [18F]FACH was only obtained when [18F]tert-Bu-FACH was formed by the latter procedure. After optimization of the deprotection reaction, [18F]FACH was obtained in high radiochemical yields (39.6?±?8.3%, end of bombardment (EOB) and radiochemical purity (greater than 98%).
Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation
Matsubara, Yoshio,Hirakawa, Saori,Yamaguchi, Yoshihiro,Yoshida, Zen-Ichi
experimental part, p. 7670 - 7673 (2011/10/05)
Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright
One-pot reductive monoalkylation of nitro aryls with hydrogen over Pd/C
Sydnes, Magne O.,Isobe, Minoru
, p. 1199 - 1202 (2008/09/17)
A range of different nitro aryls were converted in one-pot to the corresponding secondary alkyl amino aryls in good to excellent yields by using aldehydes as alkyl source and hydrogen over Pd/C (10%) as reducing agent. In all examples, but one, the second