Tag: 245.082

Copper-Mediated Radiofluorination of Aryl Pinacolboronate Esters: A Straightforward Protocol by Using Pyridinium Sulfonates was written by Antuganov, Dmitrii;Zykov, Michail;Timofeev, Vasilii;Timofeeva, Ksenija;Antuganova, Yulija;Orlovskaya, Victoriya;Fedorova, Olga;Krasikova, Raisa. And the article was included in European Journal of Organic Chemistry in 2019.Application of 936902-12-4 This article mentions the following:

Radiofluorination of arylboronic acids pinacol esters (arylBPin) mediated by copper triflate pyridine complex is one of the more promising synthetic approaches for the direct introduction of nucleophilic [¹⁸F]fluoride into non-activated arenes and heteroarenes. However, the application of this method to the production of positron emission tomog. (PET) radiotracers in automated synthesizers remains a challenging task. The choice of phase-transfer catalyst (PTC) and corresponding base used for the generation of reactive [¹⁸F]fluoride species has a profound impact on the efficiency of the ¹⁸F-fluorination process. Herein the authors report the development of a simple procedure involving trapping of the aqueous [¹⁸F]fluoride on a weak anion-exchange resin (WAX) and its release by elution with pyridinium sulfonate in di-Me acetamide. Obtained reactive [¹⁸F]fluoride was used as-is in a copper-catalyzed fluorination reaction employing pyridinium salt as both PTC and base. High radiochem. conversion rates (RCCs) achieved for a series of simple arylBPin substrates and 4-[¹⁸F]fluoro-D,L-phenylalanine demonstrate the efficiency of this novel ¹⁸F-processing approach. Notably, the proposed method obviates conventional azeotropic drying steps, solvents evaporation and/or changeover and can be implemented on com. automated synthesizers. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4Application of 936902-12-4).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Benzoxazole derivatives have gained a lot of importance in the past few years because of their use in intermediates for the preparation of new biological materials. A number of marketed drugs are available having benzoxazole as core active moiety like, nonsteroidal anti-inflammatory drug (NSAID)—flunoxaprofen, benoxaprofen, antibiotic—calcimycin.Application of 936902-12-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Discovery of 4-Arylindolines Containing a Thiazole Moiety as Potential Antitumor Agents Inhibiting the Programmed Cell Death-1/Programmed Cell Death-Ligand 1 Interaction was written by Qin, Mingze;Meng, Yangyang;Yang, Haoshen;Liu, Lei;Zhang, Haotian;Wang, Simeng;Liu, Chunyang;Wu, Xia;Wu, Di;Tian, Ye;Hou, Yunlei;Zhao, Yanfang;Liu, Yajing;Xu, Congjun;Wang, Lihui. And the article was included in Journal of Medicinal Chemistry in 2021.SDS of cas: 936902-12-4 This article mentions the following:

Through specific structural modification of a 4-phenylindoline precursor, new 4-arylindolines containing a thiazole moiety were developed and found to be promising modulators of the programmed cell death-1 (PD-1)/programmed cell death-ligand 1 (PD-L1) axis. Compound A30(I) exhibited outstanding biochem. activity, with an IC₅₀ of 11.2 nM in a homogeneous time-resolved fluorescence assay. In the cell-based assay, A30 significantly promoted IFN-γ secretion and rescued T-cell proliferation, which were inhibited by PD-1 activation. Furthermore, A30 showed favorable in vivo antitumor activity in a mouse 4T1 breast carcinoma model. Moreover, in mouse CT26 colon carcinoma models, A30 potently suppressed the growth of CT26/PD-L1 tumor but did not obviously affect the growth of CT26/vector tumor. The results of flow cytometry anal. indicated that A30 inhibited tumor growth by activating the immune microenvironment. We concluded that A30 is a new starting point for further development of PD-1/PD-L1 interaction inhibitors as antitumor agents. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4SDS of cas: 936902-12-4).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Benzoxazole derivatives have different biological activities. Benzoxazoles are prominent in medicinal chemistry due to their wide spectrum of pharmacological activities such as antibacterial, antifungal, anticancer.SDS of cas: 936902-12-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Defluorinative Functionalization of Pd(II) Fluoroalkyl Complexes was written by Wade Wolfe, Michael M.;Shanahan, James P.;Kampf, Jeff W.;Szymczak, Nathaniel K.. And the article was included in Journal of the American Chemical Society in 2020.Safety of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole This article mentions the following:

When subjected to arylboranes, anionic trifluoromethyl and difluorobenzyl palladium(II) complexes undergo fluoride abstraction followed by 1,1-migratory insertion. The resulting intermediate fluoroalkyl species can be induced to undergo a subsequent transmetalation and reductive elimination from either an in situ formed fluoroboronate (FB(Ar₃)^–) or an exogenous boronic acid/ester (ArB(OR)₂) and nucleophilic activator, representing a net defluorinative arylation reaction. The latter method enabled a structurally diverse substrate scope to be prepared from either an isolated palladium-CF₃ complex, or from Pd(PPh₃)₄ and other com. available reagents. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4Safety of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Benzoxazole derivatives have gained a lot of importance in the past few years because of their use in intermediates for the preparation of new biological materials. Benzoxazoles are prominent in medicinal chemistry due to their wide spectrum of pharmacological activities such as antiparkinson, inhibition of hepatitis C virus, 5-HT3 antagonistic effect.Safety of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Copper-Mediated Radiofluorination of Aryl Pinacolboronate Esters: A Straightforward Protocol by Using Pyridinium Sulfonates was written by Antuganov, Dmitrii;Zykov, Michail;Timofeev, Vasilii;Timofeeva, Ksenija;Antuganova, Yulija;Orlovskaya, Victoriya;Fedorova, Olga;Krasikova, Raisa. And the article was included in European Journal of Organic Chemistry in 2019.Application of 936902-12-4 This article mentions the following:

Radiofluorination of arylboronic acids pinacol esters (arylBPin) mediated by copper triflate pyridine complex is one of the more promising synthetic approaches for the direct introduction of nucleophilic [¹⁸F]fluoride into non-activated arenes and heteroarenes. However, the application of this method to the production of positron emission tomog. (PET) radiotracers in automated synthesizers remains a challenging task. The choice of phase-transfer catalyst (PTC) and corresponding base used for the generation of reactive [¹⁸F]fluoride species has a profound impact on the efficiency of the ¹⁸F-fluorination process. Herein the authors report the development of a simple procedure involving trapping of the aqueous [¹⁸F]fluoride on a weak anion-exchange resin (WAX) and its release by elution with pyridinium sulfonate in di-Me acetamide. Obtained reactive [¹⁸F]fluoride was used as-is in a copper-catalyzed fluorination reaction employing pyridinium salt as both PTC and base. High radiochem. conversion rates (RCCs) achieved for a series of simple arylBPin substrates and 4-[¹⁸F]fluoro-D,L-phenylalanine demonstrate the efficiency of this novel ¹⁸F-processing approach. Notably, the proposed method obviates conventional azeotropic drying steps, solvents evaporation and/or changeover and can be implemented on com. automated synthesizers. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4Application of 936902-12-4).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Benzoxazole derivatives have gained a lot of importance in the past few years because of their use in intermediates for the preparation of new biological materials. A number of marketed drugs are available having benzoxazole as core active moiety like, nonsteroidal anti-inflammatory drug (NSAID)—flunoxaprofen, benoxaprofen, antibiotic—calcimycin.Application of 936902-12-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Copper-Mediated Radiofluorination of Aryl Pinacolboronate Esters: A Straightforward Protocol by Using Pyridinium Sulfonates was written by Antuganov, Dmitrii;Zykov, Michail;Timofeev, Vasilii;Timofeeva, Ksenija;Antuganova, Yulija;Orlovskaya, Victoriya;Fedorova, Olga;Krasikova, Raisa. And the article was included in European Journal of Organic Chemistry in 2019.Application of 936902-12-4 This article mentions the following:

Radiofluorination of arylboronic acids pinacol esters (arylBPin) mediated by copper triflate pyridine complex is one of the more promising synthetic approaches for the direct introduction of nucleophilic [¹⁸F]fluoride into non-activated arenes and heteroarenes. However, the application of this method to the production of positron emission tomog. (PET) radiotracers in automated synthesizers remains a challenging task. The choice of phase-transfer catalyst (PTC) and corresponding base used for the generation of reactive [¹⁸F]fluoride species has a profound impact on the efficiency of the ¹⁸F-fluorination process. Herein the authors report the development of a simple procedure involving trapping of the aqueous [¹⁸F]fluoride on a weak anion-exchange resin (WAX) and its release by elution with pyridinium sulfonate in di-Me acetamide. Obtained reactive [¹⁸F]fluoride was used as-is in a copper-catalyzed fluorination reaction employing pyridinium salt as both PTC and base. High radiochem. conversion rates (RCCs) achieved for a series of simple arylBPin substrates and 4-[¹⁸F]fluoro-D,L-phenylalanine demonstrate the efficiency of this novel ¹⁸F-processing approach. Notably, the proposed method obviates conventional azeotropic drying steps, solvents evaporation and/or changeover and can be implemented on com. automated synthesizers. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4Application of 936902-12-4).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Benzoxazole derivatives have gained a lot of importance in the past few years because of their use in intermediates for the preparation of new biological materials. A number of marketed drugs are available having benzoxazole as core active moiety like, nonsteroidal anti-inflammatory drug (NSAID)—flunoxaprofen, benoxaprofen, antibiotic—calcimycin.Application of 936902-12-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Discovery of 4-Arylindolines Containing a Thiazole Moiety as Potential Antitumor Agents Inhibiting the Programmed Cell Death-1/Programmed Cell Death-Ligand 1 Interaction was written by Qin, Mingze;Meng, Yangyang;Yang, Haoshen;Liu, Lei;Zhang, Haotian;Wang, Simeng;Liu, Chunyang;Wu, Xia;Wu, Di;Tian, Ye;Hou, Yunlei;Zhao, Yanfang;Liu, Yajing;Xu, Congjun;Wang, Lihui. And the article was included in Journal of Medicinal Chemistry in 2021.SDS of cas: 936902-12-4 This article mentions the following:

Through specific structural modification of a 4-phenylindoline precursor, new 4-arylindolines containing a thiazole moiety were developed and found to be promising modulators of the programmed cell death-1 (PD-1)/programmed cell death-ligand 1 (PD-L1) axis. Compound A30(I) exhibited outstanding biochem. activity, with an IC₅₀ of 11.2 nM in a homogeneous time-resolved fluorescence assay. In the cell-based assay, A30 significantly promoted IFN-γ secretion and rescued T-cell proliferation, which were inhibited by PD-1 activation. Furthermore, A30 showed favorable in vivo antitumor activity in a mouse 4T1 breast carcinoma model. Moreover, in mouse CT26 colon carcinoma models, A30 potently suppressed the growth of CT26/PD-L1 tumor but did not obviously affect the growth of CT26/vector tumor. The results of flow cytometry anal. indicated that A30 inhibited tumor growth by activating the immune microenvironment. We concluded that A30 is a new starting point for further development of PD-1/PD-L1 interaction inhibitors as antitumor agents. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4SDS of cas: 936902-12-4).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Benzoxazole derivatives have different biological activities. Benzoxazoles are prominent in medicinal chemistry due to their wide spectrum of pharmacological activities such as antibacterial, antifungal, anticancer.SDS of cas: 936902-12-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Defluorinative Functionalization of Pd(II) Fluoroalkyl Complexes was written by Wade Wolfe, Michael M.;Shanahan, James P.;Kampf, Jeff W.;Szymczak, Nathaniel K.. And the article was included in Journal of the American Chemical Society in 2020.Safety of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole This article mentions the following:

When subjected to arylboranes, anionic trifluoromethyl and difluorobenzyl palladium(II) complexes undergo fluoride abstraction followed by 1,1-migratory insertion. The resulting intermediate fluoroalkyl species can be induced to undergo a subsequent transmetalation and reductive elimination from either an in situ formed fluoroboronate (FB(Ar₃)^–) or an exogenous boronic acid/ester (ArB(OR)₂) and nucleophilic activator, representing a net defluorinative arylation reaction. The latter method enabled a structurally diverse substrate scope to be prepared from either an isolated palladium-CF₃ complex, or from Pd(PPh₃)₄ and other com. available reagents. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4Safety of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Benzoxazole derivatives have gained a lot of importance in the past few years because of their use in intermediates for the preparation of new biological materials. Benzoxazoles are prominent in medicinal chemistry due to their wide spectrum of pharmacological activities such as antiparkinson, inhibition of hepatitis C virus, 5-HT3 antagonistic effect.Safety of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Small Molecule Disruptors of the Glucokinase-Glucokinase Regulatory Protein Interaction: 4. Exploration of a Novel Binding Pocket was written by Hong, Fang-Tsao;Norman, Mark H.;Ashton, Kate S.;Bartberger, Michael D.;Chen, Jie;Chmait, Samer;Cupples, Rod;Fotsch, Christopher;Jordan, Steven R.;Lloyd, David J.;Sivits, Glenn;Tadesse, Seifu;Hale, Clarence;St. Jean, David J. Jr.. And the article was included in Journal of Medicinal Chemistry in 2014.Product Details of 936902-12-4 This article mentions the following:

Structure-activity relationship investigations conducted at the 5-position of the N-pyridine ring of a series of N-arylsulfonyl-N’-2-pyridinyl-piperazines led to the identification of a novel bis-pyridinyl piperazine sulfonamide I that was a potent disruptor of the glucokinase-glucokinase regulatory protein (GK-GKRP) interaction. Anal. of the x-ray cocrystal of compound I bound to hGKRP revealed that the 3-pyridine ring moiety occupied a previously unexplored binding pocket within the protein. Key features of this new binding mode included forming favorable contacts with the top face of the Ala27-Val28-Pro29 (“shelf region”) as well as an edge-to-face interaction with the Tyr24 side chain. Compound I was potent in both biochem. and cellular assays (IC₅₀ = 0.005 μM and EC₅₀ = 0.205 μM, resp.) and exhibited acceptable pharmacokinetic properties for in vivo evaluation. When administered to db/db mice (100 mg/kg, po), compound I demonstrated a robust pharmacodynamic effect and significantly reduced blood glucose levels up to 6 h postdose. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4Product Details of 936902-12-4).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization. In the past years, numerous benzoxazole derivatives have been synthesised and evaluated for their biological potential.Product Details of 936902-12-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Discovery of Potent and Selective Inhibitors of Cdc2-Like Kinase 1 (CLK1) as a New Class of Autophagy Inducers was written by Sun, Qi-Zheng;Lin, Gui-Feng;Li, Lin-Li;Jin, Xi-Ting;Huang, Lu-Yi;Zhang, Guo;Yang, Wei;Chen, Kai;Xiang, Rong;Chen, Chong;Wei, Yu-Quan;Lu, Guang-Wen;Yang, Sheng-Yong. And the article was included in Journal of Medicinal Chemistry in 2017.Product Details of 936902-12-4 This article mentions the following:

Autophagy inducers represent new promising agents for the treatment of a wide range of medical illnesses. However, safe autophagy inducers for clin. applications are lacking. Inhibition of cdc2-like kinase 1 (CLK1) was recently found to efficiently induce autophagy. Unfortunately, most of the known CLK1 inhibitors have unsatisfactory selectivity. Herein, we report the discovery of a series of new CLK1 inhibitors containing the 1H-[1,2,3]triazolo[4,5-c]quinoline scaffold. Among them, compound 25 was the most potent and selective, with an IC₅₀ value of 2 nM against CLK1. The crystal structure of CLK1 complexed with compound 25 was solved, and the potency and kinase selectivity of compound 25 were interpreted. Compound 25 was able to induce autophagy in in vitro assays and displayed significant hepatoprotective effects in the acetaminophen (APAP)-induced liver injury mouse model. Collectively, due to its potency and selectivity, compound 25 could be used as a chem. probe or agent in future mechanism-of-action or autophagy-related disease therapy studies. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4Product Details of 936902-12-4).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Benzoxazole derivatives have gained a lot of importance in the past few years because of their use in intermediates for the preparation of new biological materials. Benzoxazoles are prominent in medicinal chemistry due to their wide spectrum of pharmacological activities such as anti-inflammatory, antimycobacterial, antihistamine.Product Details of 936902-12-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Fluorination-¹⁸F using tri-tert-butanol ammonium iodide as phase-transfer catalyst: an alternative minimalist approach was written by Shinde, Sandip S.;Bolik, Kim-Viktoria;Maschauer, Simone;Prante, Olaf. And the article was included in Pharmaceuticals in 2021.HPLC of Formula: 936902-12-4 This article mentions the following:

The ¹⁸F syntheses of tracers for positron emission tomog. (PET) typically require several steps, including extraction of [¹⁸F]fluoride from H_2[¹⁸O]O, elution, and drying, prior to nucleophilic substitution reaction, being a laborious and time-consuming process. The elution of [¹⁸F]fluoride is commonly achieved by phase transfer catalysts (PTC) in aqueous solution, which makes azeotropic drying indispensable. The ideal PTC is characterized by a slightly basic nature, its capacity to elute [¹⁸F]fluoride with anhydrous solvents, and its efficient complex formation with [¹⁸F]fluoride during subsequent labeling. Herein, we developed tri-(tert-butanol)-methylammonium iodide (TBMA-I), a quaternary ammonium salt serving as the PTC for ¹⁸F-fluorination reactions. The favorable elution efficiency of [¹⁸F]fluoride using TBMA-I was demonstrated with aprotic and protic solvents, maintaining high ¹⁸F-recoveries of 96-99%. ¹⁸F-labeling reactions using TBMA-I as PTC were studied with aliphatic 1,3-ditosylpropane and aryl pinacol boronate esters as precursors, providing ¹⁸F-labeled products in moderate-to-high radiochem. yields. TBMA-I revealed adequate properties for application to ¹⁸F-fluorination reactions and could be used for elution of [¹⁸F]fluoride with MeOH, omitting an addnl. base and azeotropic drying prior to ¹⁸F-labeling. We speculate that the tert-alc. functionality of TBMA-I promotes intermol. hydrogen bonding, which enhances the elution efficiency and stability of [¹⁸F]fluoride during nucleophilic ¹⁸F-fluorination. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4HPLC of Formula: 936902-12-4).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Benzoxazoles belong to the group of well-known antifungal agents with antioxidant, antiallergic, antitumoral and antiparasitic activity. Due to its versatile biological properties, benzoxazole has been incorporated as an essential pharmacophore and substructure in many medicinal compounds.HPLC of Formula: 936902-12-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem