Journal of Labelled Compounds and Radiopharmaceuticals 
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This is an RSS file. You can use it to subscribe to this data in your favourite RSS reader or to display this data on your own website or blog.Synthesis of [2H5]baricitinib via [2H5]ethanesulfonyl chloride
Baricitinib, typically applied as a treatment for rheumatoid arthritis, has recently attracted the attention of clinicians and researchers as a potential treatment for COVID-19. Naturally, there has been a need for the preparation of the isotope-labelled analogue of baricitinib to probe the pharmacokinetics of baricitinib in this new role. As such, we have developed a simple synthetic route to deuterated [2H5]baricitinib, facilitating its formation over 4 steps and in a 29% overall yield based on starting [2H5]ethanethiol (19% if we start with [2H5]bromoethane instead). A critical component of the overall process involves ...
Source: Journal of Labelled Compounds and Radiopharmaceuticals - March 12, 2022 Category: Biochemistry Authors: Ross D. Jansen ‐van Vuuren,
Rahul Vohra Tags: PRACTITIONER PROTOCOL ‐ SYNTHESIS Source Type: research
Synthesis of a dual carbon ‐14‐labeled calcitonin gene‐related peptide receptor antagonist for use in a human absorption–distribution–metabolism–elimination study
Oral calcitonin gene-related peptide (CGRP) receptor antagonists have been shown to be effective in the acute and preventive treatment of migraine. Bristol Myers Squibb discovered high-affinity CGRP receptor antagonist BMS-927711 (Nurtec ® ODT [rimegepant]). Dual-labeled [14C]-BMS-927711 was prepared and used in a human absorption–distribution–metabolism–elimination (ADME) study. A dual-labeled analog of BMS-927711 was required to fully track the compound's metabolic transformation. The carbon-14-labeled synthesis of both rig ht side and left side portions of [14C]-BMS-927711 is described. Oral calcitonin gene-relat...
Source: Journal of Labelled Compounds and Radiopharmaceuticals - March 11, 2022 Category: Biochemistry Authors: Wesley A. Turley,
John A. Easter,
Richard C. Burrell,
Samuel J. Bonacorsi Tags: RESEARCH ARTICLE Source Type: research
Synthesis of deuterium ‐labeled CCR2 antagonist JNJ‐26131300, [4‐(1H‐indol‐ 3‐yl)‐piperidin‐1‐yl]‐{1‐[3‐(3,4,5‐trifluoro‐phenyl)‐acryloyl]‐piperidin‐4‐yl}‐acetic acid
Synthesis of multiple deuterium-labeled CCR2 antagonist JNJ-26131300, [4-(1H-indol-3-yl)-piperidin-1-yl]-{1-[3-(3,4,5-trifluoro-phenyl)-acryloyl]-piperidin-4-yl}-acetic acid, is described. First, condensation of indole-D7 with 4-piperidone produced 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-D5, which subsequently underwent catalytic hydrogenation to give 3-piperidin-4-yl-1H-indole-D5. Next, bromo-{1-[3-(3,4,5-trifluoro-phenyl)-acryloyl]-piperidin-4-yl}-acetic acid was prepared through multiple steps from 3-(3,4,5-trifluoro-phenyl)-acrylic acid and bromo-piperidin-4-yl-acetic acid ethyl ester. Nucleophilic coupling of 3-p...
Source: Journal of Labelled Compounds and Radiopharmaceuticals - March 9, 2022 Category: Biochemistry Authors: Ronghui Lin,
Yong Gong,
Rhys Salter Tags: PRACTITIONER PROTOCOL ‐ SYNTHESIS Source Type: research
High ‐yielding, automated radiosynthesis of [11C]martinostat using [11C]methyl triflate
An efficient, automated radiosynthesis of [11C]martinostat using [11C]methyl triflate as the alkylating agent in anhydrous ethanol is presented. Histone deacetylases (HDACs) mediate epigenetic mechanisms implicated in a broad range of central nervous system dysfunction, including neurodegenerative diseases and neuropsychiatric disorders. [11C]Martinostat allows in vivo quantification of class I/IIb HDACs and may be useful for the quantification of drug –occupancy relationship, facilitating drug development for disease modifying therapies. The present study reports a radiosynthesis of [11C]martinostat using [11C]methyl tr...
Source: Journal of Labelled Compounds and Radiopharmaceuticals - March 7, 2022 Category: Biochemistry Authors: Robert Hopewell,
Dean Jolly,
Qian Ying Li,
Karen Ross,
I ‐Huang Tsai,
Monica Lacatus‐Samoila,
Jean‐Paul Soucy,
Eliane Kobayashi,
Pedro Rosa‐Neto,
Gassan Massarweh Tags: SHORT NOTE Source Type: research
Synthesis of Deuterium ‐Labeled CCR2 Antagonist JNJ‐26131300, [4‐(1H‐Indol‐3‐yl)‐piperidin‐1‐yl]‐{1‐[3‐(3,4,5‐trifluoro‐phenyl)‐acryloyl]‐piperidin‐4‐yl}‐acetic acid
Synthesis of multiple deuterium-labeled CCR2 antagonist JNJ-26131300, i.e. [4-(1H-indol-3-yl)-piperidin-1-yl]-{1-[3-(3,4,5-trifluoro-phenyl)-acryloyl]-piperidin-4-yl}-acetic acid is described. First, condensation of indole-D7 with 4-piperidone produced 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-D5, which subsequently underwent catalytic hydrogenation to give 3-piperidin-4-yl-1H-indole-D5. Next, bromo-{1-[3-(3,4,5-trifluoro-phenyl)-acryloyl]-piperidin-4-yl}-acetic acid was prepared through multiple steps from 3-(3,4,5-trifluoro-phenyl)-acrylic acid and bromo-piperidin-4-yl-acetic acid ethyl ester. Nucleophilic coupling of...
Source: Journal of Labelled Compounds and Radiopharmaceuticals - February 26, 2022 Category: Biochemistry Authors: Ronghui Lin,
Yong Gong,
Rhys Salter Tags: PRACTITIONER PROTOCOL ‐ SYNTHESIS Source Type: research
High ‐yielding, automated radiosynthesis of [11C]martinostat using [11C]methyl triflate
Histone deacetylases (HDACs) mediate epigenetic mechanisms implicated in a broad range of central nervous system dysfunction, including neurodegenerative diseases and neuropsychiatric disorders. [11C]Martinostat allowsin vivo quantification of class I/IIb HDACs and may be useful for the quantification of drug-occupancy relationship, facilitating drug development for disease modifying therapies. The present study reports a radiosynthesis of [11C]martinostat using [11C]methyl triflate in ethanol, as opposed to the originally described synthesis using [11C]methyl iodide and DMSO. [11C]Methyl triflate is trapped in a solution ...
Source: Journal of Labelled Compounds and Radiopharmaceuticals - February 26, 2022 Category: Biochemistry Authors: Robert Hopewell,
Dean Jolly,
Qian Ying Li,
Karen Ross,
I ‐Huang Tsai,
Monica Lactus‐Samoila,
Jean‐Paul Soucy,
Eliane Kobayashi,
Pedro Rosa‐Neto,
Gassan Massarweh Tags: SHORT NOTE Source Type: research
Synthesis of a Dual Carbon ‐14 Labeled CGRP Receptor Antagonist For Use in a Human ADME Study
Oral calcitonin gene-related peptide (CGRP) receptor antagonists have been shown to be effective in the acute and preventive treatment of migraine. CGRP receptor antagonists offer safety advantages over triptans because they are not active vasoconstrictors, which reduces cardiovascular risks. Bristol Myers Squibb discovered a high affinity CGRP receptor antagonist BMS-927711 for the treatment of migraine now FDA approved as Nurtec ® ODT (rimegepant). Dual labeled [14C]-BMS-927711 was prepared and used in a human absorption-distribution-metabolism-elimination (ADME) study. A dual labeled analog of BMS-927711 was required t...
Source: Journal of Labelled Compounds and Radiopharmaceuticals - February 24, 2022 Category: Biochemistry Authors: Wesley A. Turley,
John A. Easter,
Richard C. Burrell,
Samuel J. Bonacorsi Tags: RESEARCH ARTICLE Source Type: research
Automated radiosynthesis of [11C]MTP38 —a phosphodiesterase 7 imaging tracer—using [11C]hydrogen cyanide for clinical applications
We successfully prepared the [11C]MTP38 radiopharmaceutical for clinical studies using the11C-labeling synthesizer and sterile isolator. The synthesis time and radiochemical yield of [11C]MTP38 was 34 –40 min and 33 ± 5.5% post-irradiation (n = 15), respectively. Radiochemical purity and molar activity were>97% and 47 ± 12 GBq/μmol, respectively, at the end of synthesis (n = 15). We have developed 8-amino-3-(2S,5R-dimethyl-1-piperidyl)-[1,2,4]triazolo[4,3-a]pyrazine-5-[11C]carbonitrile ([11C]MTP38) as a positron emission tomography (PET) tracer for the imaging of phosphodiesterase 7. For the fu...
Source: Journal of Labelled Compounds and Radiopharmaceuticals - February 9, 2022 Category: Biochemistry Authors: Kazunori Kawamura,
Hiroki Hashimoto,
Takayuki Ohkubo,
Masayuki Hanyu,
Masanao Ogawa,
Nobuki Nengaki,
Daisuke Arashi,
Yusuke Kurihara,
Tomoya Fujishiro,
Takahiro Togashi,
Toshiyuki Sakai,
Masatoshi Muto,
Makoto Takei,
Hideki Ishii,
Takeaki Sa Tags: PRACTITIONER PROTOCOL ‐ SYNTHESIS Source Type: research
Automated radiosynthesis of [11C]MTP38 —a phosphodiesterase 7 imaging tracer—using [11C]hydrogen cyanide for clinical applications
We have developed 8-amino-3-(2S,5R-dimethyl-1-piperidyl)-[1,2,4]triazolo[4,3-a]pyrazine-5-[11C]carbonitrile ([11C]MTP38) as a PET tracer for the imaging of phosphodiesterase 7. For the fully automated production of [11C]MTP38 routinely and efficiently for clinical applications, we determined the radiosynthesis procedure of [11C]MTP38 using [11C]hydrogen cyanide ([11C]HCN) as a PET radiopharmaceutical. Radiosynthesis of [11C]MTP38 was performed using an automated11C-labeling synthesizer developed in-house within 40 min after the end of irradiation. [11C]MTP38 was obtained with a relatively high radiochemical yield (33 ± 5....
Source: Journal of Labelled Compounds and Radiopharmaceuticals - February 5, 2022 Category: Biochemistry Authors: Kazunori Kawamura,
Hiroki Hashimoto,
Takayuki Ohkubo,
Masayuki Hanyu,
Masanao Ogawa,
Nobuki Nengaki,
Daisuke Arashi,
Yusuke Kurihara,
Tomoya Fujishiro,
Takahiro Togashi,
Toshiyuki Sakai,
Masatoshi Muto,
Makoto Takei,
Hideki Ishii,
Takeaki Sa Tags: PRACTITIONER PROTOCOL ‐ SYNTHESIS Source Type: research
Tritium hydrogen ‐isotope exchange with electron‐poor tertiary benzenesulfonamide moiety; application in late‐stage labeling of T0901317
Described is a late-stage tritium labeling of T0901317 using an HIE strategy in the electron-poor substrate lacking a goodortho-directing group for C ─H activation. Homogeneous catalysis with a Kerr-type catalyst provided [3H]T0901317 with SA of 10.8 Ci/mmol. Unprecedented translation issue of deuterium into tritium experiment during heterogeneous catalysis was observed, whereby efficient deuterium labeling conditions using Ir-black provided reasonable 0.72 D-enrichment of T0901317 but turned out to be ineffective when repeated under similar conditions in tritium experiments. The multifunctional radioligand [3H]T0901317 ...
Source: Journal of Labelled Compounds and Radiopharmaceuticals - February 3, 2022 Category: Biochemistry Authors: Tian Yongsong,
B řetislav Brož,
František Tureček,
Aleš Marek Tags: RESEARCH ARTICLE Source Type: research
Issue Information
No abstract is available for this article. (Source: Journal of Labelled Compounds and Radiopharmaceuticals)
Source: Journal of Labelled Compounds and Radiopharmaceuticals - February 3, 2022 Category: Biochemistry Tags: ISSUE INFORMATION Source Type: research
Exploring the enzyme ‐catalyzed synthesis of isotope labeled cyclopropanes
In this study, the use of enzyme-catalysis for the synthesis of labeled cyclopropanes was investigated. Two readily available (modified) enzymes were studied for the cyclopropanation of substituted styrenes with ethyl diazoacetate. This diazoacetate is highly energetic; therefore, alternatives were investigated. The final optimized cyclopropanation was successfully demonstrated using n-hexyl diazoacetate and used to synthesize stereoselective 13C-labeled cyclopropanes. This optimized procedure serves as a proof-of-concept for generating stereoselective-labeled cyclopropanes. Cyclopropanes are commonly employed structural m...
Source: Journal of Labelled Compounds and Radiopharmaceuticals - February 3, 2022 Category: Biochemistry Authors: Malvika Sardana,
Kim S. M ühlfenzl,
Sylvia T. M. Wenker,
Christian Åkesson,
Martin A. Hayes,
Charles S. Elmore,
Subhash Pithani Tags: RESEARCH ARTICLE Source Type: research
