Category: 932738-80-2

Discovery and in vitro and in vivo profiles of 4-fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide as novel class of an orally active metabotropic glutamate receptor 1 (mGluR1) antagonist was written by Satoh, Atsushi;Nagatomi, Yasushi;Hirata, Yukari;Ito, Satoru;Suzuki, Gentaroh;Kimura, Toshifumi;Maehara, Shunsuke;Hikichi, Hirohiko;Satow, Akio;Hata, Mikiko;Ohta, Hisashi;Kawamoto, Hiroshi. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2009.Application In Synthesis of 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine The following contents are mentioned in the article:

We identified 4-fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide 27 (I) as a potent mGluR1 antagonist. The compound possessed excellent subtype selectivity and good PK profile in rats. It also demonstrated relatively potent antipsychotic-like effects in several animal models. Suitable for development as a PET tracer, compound 27 would have great potential for elucidation of mGluR1 functions in human. This study involved multiple reactions and reactants, such as 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2Application In Synthesis of 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine).

4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Application In Synthesis of 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

A concise method for fully automated radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM via Cu-mediated ¹⁸F-fluorination of organoboranes was written by Yuan, Gengyang;Shoup, Timothy M.;Moon, Sung-Hyun;Brownell, Anna-Liisa. And the article was included in RSC Advances in 2020.COA of Formula: C8H7ClN4S The following contents are mentioned in the article:

A modified alc.-enhanced 18F-fluorodeboronation has been developed for the radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM. Unlike the [¹⁸F]KF/K222 approach, this method tolerates the presence of sensitive heterocycles in Bpin precursors 4 and 8 allowing a one-step ¹⁸F-fluorodeboronation on the fully automated TRACERlab FXFN platform. This study involved multiple reactions and reactants, such as 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2COA of Formula: C8H7ClN4S).

4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.COA of Formula: C8H7ClN4S

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Derisking the Cu-Mediated ¹⁸F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands was written by Taylor, Nicholas J.;Emer, Enrico;Preshlock, Sean;Schedler, Michael;Tredwell, Matthew;Verhoog, Stefan;Mercier, Joel;Genicot, Christophe;Gouverneur, Veronique. And the article was included in Journal of the American Chemical Society in 2017.Electric Literature of C8H7ClN4S The following contents are mentioned in the article:

The compatibility of various heterocycles, particularly nitrogen heterocycles, towards the copper-mediated ¹⁸F-fluorination of aryl pinacolboronates with ¹⁸F-fluoride was determined using fluorination reactions of a model substrate in the presence of exogenous heterocycles and the fluorination reactions of substrates possessing heterocycles with fluorination on an attached aromatic ring or directly attached to the heterocycle of interest. Using this information, syntheses of seven ¹⁸F-labeled structurally complex pharmaceutically relevant heterocycle-containing mols. were designed and executed. The method may be useful in designing syntheses of other radiolabeled compounds and delineating the scope of utility of other radiolabeling methods. This study involved multiple reactions and reactants, such as 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2Electric Literature of C8H7ClN4S).

4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Electric Literature of C8H7ClN4S

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Synthesis and Evaluation in Monkey of [¹⁸F]4-Fluoro-N-methyl-N-(4-(6-(methylamino)pyrimidin-4-yl)thiazol-2-yl)benzamide ([¹⁸F]FIMX): A Promising Radioligand for PET Imaging of Brain Metabotropic Glutamate Receptor 1 (mGluR1) was written by Xu, Rong;Zanotti-Fregonara, Paolo;Zoghbi, Sami S.;Gladding, Robert L.;Woock, Alicia E.;Innis, Robert B.;Pike, Victor W.. And the article was included in Journal of Medicinal Chemistry in 2013.Recommanded Product: 932738-80-2 The following contents are mentioned in the article:

We sought to develop a PET radioligand that would be useful for imaging human brain metabotropic subtype 1 receptors (mGluR1) in neuropsychiatric disorders and in drug development. 4-Fluoro-N-methyl-N-(4-(6-(methylamino)pyrimidin-4-yl)-thiazol-2-yl)-benzamide (FIMX) was identified as having favorable properties for development as a PET radioligand. We developed a method for preparing [¹⁸F]FIMX in useful radiochem. yield and in high specific activity from [¹⁸F]-fluoride ion and an N-Boc-protected (phenyl)aryliodonium salt precursor. In baseline experiments in the rhesus monkey, [¹⁸F]FIMX gave high brain radioactivity uptake, reflecting the expected distribution of mGluR1 with notably high uptake in cerebellum, which became 47% lower by 120 min after radioligand injection. Pharmacol. challenges demonstrated that a very high proportion of the radioactivity in monkey brain was bound specifically and reversibly to mGluR1. [¹⁸F]FIMX is concluded to be an effective PET radioligand for imaging mGluR1 in monkey brain and therefore merits further evaluation in human subjects. This study involved multiple reactions and reactants, such as 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2Recommanded Product: 932738-80-2).

4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Recommanded Product: 932738-80-2

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Development of N-[4-[6-(Isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methyl-4-[¹¹C]methylbenzamide for Positron Emission Tomography Imaging of Metabotropic Glutamate 1 Receptor in Monkey Brain was written by Fujinaga, Masayuki;Yamasaki, Tomoteru;Maeda, Jun;Yui, Joji;Xie, Lin;Nagai, Yuji;Nengaki, Nobuki;Hatori, Akiko;Kumata, Katsushi;Kawamura, Kazunori;Zhang, Ming-Rong. And the article was included in Journal of Medicinal Chemistry in 2012.COA of Formula: C8H7ClN4S The following contents are mentioned in the article:

Three novel 4-substituted benzamides have been synthesized as potential ligands for the positron emission tomog. (PET) imaging of metabotropic glutamate 1 (mGlu1) receptor in the brain. Of these compounds, N-(4-(6-(isopropylamino)pyrimidin-4-yl)-1,3-thiazol-2-yl)-N,4-dimethylbenzamide (4) exhibited the highest binding affinity (K_i = 13.6 nM) for mGlu1 and was subsequently labeled with carbon-11. In vitro autoradiog. using rat brain sections showed that [¹¹C]4 binding was consistent with the distribution of mGlu1, with high specific binding in the cerebellum and thalamus. PET studies with [¹¹C]4 in monkey showed a high brain uptake and a kinetic profile suitable for quant. anal. Pretreatment with a mGlu1-selective ligand 16 largely decreased the brain uptake, indicating high in vivo specific binding of [¹¹C]4 to mGlu1. In metabolite anal., only unchanged [¹¹C]4 was found in the brain. [¹¹C]4 is a useful PET ligand for the imaging and quant. anal. of mGlu1 in monkey brain and merits further evaluation in humans. This study involved multiple reactions and reactants, such as 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2COA of Formula: C8H7ClN4S).

4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.COA of Formula: C8H7ClN4S

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Radiosynthesis and preliminary evaluation of 4-[¹⁸F]fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide as a new positron emission tomography ligand for metabotropic glutamate receptor subtype 1 was written by Yamasaki, Tomoteru;Fujinaga, Masayuki;Yoshida, Yuichiro;Kumata, Katsushi;Yui, Joji;Kawamura, Kazunori;Hatori, Akiko;Fukumura, Toshimitsu;Zhang, Ming-Rong. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Category: thiazole The following contents are mentioned in the article:

The purpose of this study was to develop 4-[¹⁸F]fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide ([¹⁸F]I) as a new PET ligand for imaging metabotropic glutamate receptor subtype 1 (mGluR1). [¹⁸F]I was synthesized by [¹⁸F]fluorination of a novel nitro precursor with [¹⁸F]KF in the presence of Kryptofix 222. At the end of synthesis, 429-936 MBq (n = 8) of [¹⁸F]I was obtained with >99% radiochem. purity and 204-559 GBq/μmol specific activity starting from 6.7 to 13.0 GBq of [¹⁸F]F^–. The brain distribution of [¹⁸F]I was determined by the in vitro and ex vivo autoradiog. using rat brain sections. The in vitro and in vivo specific binding of [¹⁸F]I to mGluR1 was detected in the cerebellum, thalamus, hippocampus, and striatum. These results suggest that [¹⁸F]I is a promising PET ligand for the in vivo evaluation of mGluR1. This study involved multiple reactions and reactants, such as 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2Category: thiazole).

4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Category: thiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Synthesis and Evaluation of 4-Halogeno-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-[¹¹C]methylbenzamide for Imaging of Metabotropic Glutamate 1 Receptor in Melanoma was written by Fujinaga, Masayuki;Xie, Lin;Yamasaki, Tomoteru;Yui, Joji;Shimoda, Yoko;Hatori, Akiko;Kumata, Katsushi;Zhang, Yiding;Nengaki, Nobuki;Kawamura, Kazunori;Zhang, Ming-Rong. And the article was included in Journal of Medicinal Chemistry in 2015.Category: thiazole The following contents are mentioned in the article:

Isopropylaminopyrimidinylthiazolyl halobenzamides I (R = H, Me; R¹ = Cl, Br, I) were prepared as inhibitors of metabotropic glutamate 1 (mGlu1) receptors for potential use in the treatment of melanoma; I (R = ¹¹CH₃; R¹ = Cl, Br, I) were prepared and tested as PET imaging agents for mGlu1-containing melanomas with decreased affinities for concentration in brain tissue. I (R = Me; R¹ = Cl, Br, I) bound to mGlu1 with K_i values of 22-143 nM. In vivo biodistribution studies of I (R = ¹¹CH₃; R¹ = Cl, Br, I) in mice implanted with B16F10 melanoma cells confirmed high radioactive uptake in tumor and low uptake in blood, skin, and muscles; inhibition of mGlu1 receptor using an mGlu1-selective ligand led to reduced radioactive uptake in the tumor. I (R = ¹¹CH₃; R¹ = I) displayed the highest ratio of uptake between tumor and nontarget tissue and may prove useful as a PET tracer for mGlu1 imaging in melanoma. This study involved multiple reactions and reactants, such as 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2Category: thiazole).

4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Category: thiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Synthesis and Evaluation of Novel Radioligands for Positron Emission Tomography Imaging of Metabotropic Glutamate Receptor Subtype 1 (mGluR1) in Rodent Brain was written by Fujinaga, Masayuki;Yamasaki, Tomoteru;Yui, Joji;Hatori, Akiko;Xie, Lin;Kawamura, Kazunori;Asagawa, Chiharu;Kumata, Katsushi;Yoshida, Yuichiro;Ogawa, Masanao;Nengaki, Nobuki;Fukumura, Toshimitsu;Zhang, Ming-Rong. And the article was included in Journal of Medicinal Chemistry in 2012.Quality Control of 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine The following contents are mentioned in the article:

Three novel positron emission tomog. ligands, N-(4-(6-(isopropylamino)pyrimidin-4-yl)-1,3-thiazol-2-yl)-4-[¹¹C]methoxy-N-methylbenzamide ([¹¹C]I), 4-[¹⁸F]fluoroethoxy-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide ([¹⁸F]II), and 4-[¹⁸F]fluoropropoxy-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide ([¹⁸F]III), were designed for imaging metabotropic glutamate receptor type 1 (mGluR1) in rodent brain. Unlabeled compound I was synthesized by benzoylation of 4-pyrimidinyl-2-methylaminothiazole, followed by reaction with isopropylamine. Removal of the Me group in I gave the phenol precursor for radiosynthesis. Two fluoroalkoxy analogs II and III were prepared by reacting the phenol with the corresponding fluorine-containing tosylates. Radioligands [¹¹C]I, [¹⁸F]II, and [¹⁸F]III were synthesized by O-[¹¹C]methylation or [¹⁸F]fluoroalkylation of the phenol precursor. Compound I showed high in vitro binding affinity for mGluR1, whereas II and III had weak affinity. Autoradiog. using rat brain sections showed that [¹¹C]I binding is aligned with the reported distribution of mGluR1 with high specific binding in the cerebellum and thalamus. PET study with [¹¹C]I in rats showed high brain uptake and a similar distribution pattern to that in autoradiog., indicating the usefulness of [¹¹C]I for imaging brain mGluR1. This study involved multiple reactions and reactants, such as 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2Quality Control of 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine).

4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Quality Control of 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica