Tag: 200-300

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 Anticonvulsant Activity Evaluation of 7-Alkoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-ones was written by Liu, Da-Chuan;Deng, Xian-Qing;Wang, Shi-Ben;Quan, Zhe-Shan. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2014.Computed Properties of C11H14N2OS The following contents are mentioned in the article:

A new series of 7-alkoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-ones were synthesized and evaluated for their anticonvulsant activities. Among these compounds, 7-propoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-one and 7-butoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-one (I) showed the highest activity against maximal electroshock (MES)-induced tonic extension [(ED)₅₀ = 11.4 and 13.6 mg/kg, resp.]. It is worth mentioning that compound I showed especially low neurotoxicity, which led to a high protective index (PI >51). The orally anticonvulsant activity data of compound I further confirmed its efficacy, in an MES test, and its high safety with a PI value of 50.2. In addition, the potency of compound I against seizures induced by pentylenetetrazole, 3-mercaptopropionic acid, and bicuculline in the chem.-induced seizure tests suggested that compound I may exert its anticonvulsant activity through affecting the GABAergic system. This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Computed Properties of C11H14N2OS).

6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Computed Properties of C11H14N2OS

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

Relation between physiological action and chemical structure. II. Pharmacological studies on various benzothiazole derivatives was written by Fujimura, Hajime. And the article was included in Bulletin of the Institute for Chemical Research, Kyoto University in 1950.Application of 15850-81-4 The following contents are mentioned in the article:

cf. Folia Pharmacol. Japon. 44, 6(1949). The potentiating effects of 2-amino-(I), 2-amino-6-methoxy-(II), 2-amino-6-ethoxy-(III), 2-amino-6-isopropoxy-(IV), 2-(2-diethylaminoethylamino)-6-methoxy-(V), and 2-(2-diethylaminoethylamino)-6-ethoxybenzothiazole (VI) on the hypnotic action of evipan and the analgesic action of morphine were studied. I-VI prolonged the duration of evipan action (30 min. by 50 mg./kg.) in mice 50, 150, 200, 500, 17, and 17%, resp., by injection of 20 mg./kg., 15 min. before the administration of evipan. As determined by Haffner’s method in mice, they did not increase the morphine action (5 mg./kg.). When administered with benadryl (10 mg./kg.), II, III, and IV increased it while I, V, and VI did not. The presence of an alkoxy radical in the 6-position of the benzothiazole ring appears to play an important role in increasing the actions of these 2 drugs, while further substitution of H of the amino radical in the 2-position by the diethylaminoethyl group may result in their inhibition. This study involved multiple reactions and reactants, such as 6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4Application of 15850-81-4).

6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4) 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 sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Application of 15850-81-4

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

Organic thiocyanogen compounds. XXXII. Fungistatic properties and skin tolerance of some thicyanophenols, thiocyanophenol ethers, and thiocyanophenol ketones was written by Hueller, H.;Luess, K. D.;Wollmann, H.;Pohloudek-Fabini, R.. And the article was included in Pharmazie in 1968.Electric Literature of C11H14N2OS The following contents are mentioned in the article:

Thiocyanophenols, thiocyanophenol ethers, and thiocyanophenol ketones were tested for their fungistatic activity with Candida albicans, Trichophyton mentagrophytes, Epidermophyton floccosum, and Penicillium waksmani. All the thiocyano compounds had stronger fungistatic activity than the corresponding thiocyano free original compounds as in 4-thiocyanophenol vs. phenol, 1-methoxy-2-thiocyanobenzene vs. methoxybenzene, and 4-thiocyanoacetophenone vs. acetophenone. Monothiocyanophenylalkyl ethers and monothiocyanophenylakyl ketones had higher activity than the corresponding dithiocyano compounds Addition of amino group to benzene nucleus of thiocyanophenyl ethers diminished the activity. Healthy skin of guinea pigs and rabbits could tolerate 4-thiocyanophenetole and 4-thiocyanoaceto-phenone up to 1%, 4-thiocyanophenol and 4-thiocyanopropoxybenzene up to 0.1%. Higher concentrations caused reddening and swelling of the skin, and 4-thiocyanopropoxylbenzene at 10% caused necrosis. 12 references. This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Electric Literature of C11H14N2OS).

6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) 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. 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.Electric Literature of C11H14N2OS

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

Design, synthesis, and apoptosis-promoting effect evaluation of novel pyrazole with benzo[d]thiazole derivatives containing aminoguanidine units was written by Liu, Da Chuan;Gao, Mei Jia;Huo, Qiang;Ma, Tao;Wang, Ying;Wu, Cheng Zhu. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2019.Synthetic Route of C11H14N2OS The following contents are mentioned in the article:

New pyrazole with benzo[d]thiazoles containing hydrazinecarboximidamide substituent was synthesized and evaluated for cytotoxicity and apoptotic activity using the MTT assay, flow cytometry, and Western blot anal. Among the compounds studied, (E)-2-((1-(6-((4-fluorobenzyl)oxy)benzo[d]thiazol-2-yl)-3-phenyl-1H-pyrazol-4-yl)methylene) hydrazinecarboximidamide (8l) was potent, with IC₅₀ values of 2.41 μM, 2.23 μM, 3.75 μM and 2.31 μM in vitro anti-proliferative activity testing against triple-neg. breast cancer cell line MDA-MB-231, non-triple-neg. breast cancer MCF-7 cells, and human hepatocarcinoma HepG2 cells, and SMMC-7721 cells, resp. Especially, the activity against MDA-MB-231 was similar to that of Doxorubicin, which was used as a pos. control in this study. Next, the Annexin V/PI flow cytometry assay was used at different concentrations of compound 8l to demonstrate that compound 8l induced apoptosis of MDA-MB-231 cells in a concentration-dependent manner. Finally, these results were further verified by Western blot anal. Taken together, the results of this study revealed that compound 8l may be a potential anticancer compound play a significant role in the subsequent researches. This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Synthetic Route of C11H14N2OS).

6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Synthetic Route of C11H14N2OS

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 biological evaluation of novel benzothiazole derivatives as potential anticonvulsant agents was written by Liu, Da-Chuan;Zhang, Hong-Jian;Jin, Chun-Mei;Quan, Zhe-Shan. And the article was included in Molecules in 2016.Quality Control of 6-Butoxybenzo[d]thiazol-2-amine The following contents are mentioned in the article:

New benzothiazoles with a mercapto-triazole and other heterocycle substituents I (R = Pr, benzyl, 3-trifluoromethylbenzyl, etc.; R¹ = 1H-1,2,4-triazol-3-ylthio, 1H-1,2,4-triazol-1-yl, 3-amino-1H-1,2,4-triazol-1-yl, 1H-imidazol-1-yl, 1H-1,2,3,4-tetrazol-1-yl) were synthesized and evaluated for their anticonvulsant activity and neurotoxicity by using the maximal electroshock (MES), s.c. pentylenetetrazole (scPTZ), and rotarod neurotoxicity (TOX) tests. Among the compounds studied, compounds I (R = 3-fluorobenzyl, 4-fluorobenzyl; R¹ = 1H-1,2,4-triazol-3-ylthio) were the most potent, with an ED₅₀ value of 50.8 mg/kg and 54.8 mg/kg in the MES test and 76.0 mg/kg and 52.8 mg/kg in the scPTZ seizures test, resp. They also showed lower neurotoxicity and therefore a higher protective index. In particular, compound I (R = 4-fluorobenzyl; R¹ = 1H-1,2,4-triazol-3-ylthio) showed high protective index (PI) values of 8.96 in the MES test and 9.30 in the scPTZ test, which were better than those of the standard drugs used as pos. controls in this study. This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Quality Control of 6-Butoxybenzo[d]thiazol-2-amine).

6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Quality Control of 6-Butoxybenzo[d]thiazol-2-amine

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