Category: 107317-58-8

Pharmacophore-Based Design of Novel Oxadiazoles as Selective Sphingosine-1-phosphate (S1P) Receptor Agonists with in vivo Efficacy was written by Quattropani, Anna;Sauer, Wolfgang H. B.;Crosignani, Stefano;Dorbais, Jerome;Gerber, Patrick;Gonzalez, Jerome;Marin, Delphine;Muzerelle, Mathilde;Beltran, Fanny;Nichols, Anthony;Georgi, Katrin;Schneider, Manfred;Vitte, Pierre-Alain;Eligert, Valerie;Novo-Perez, Laurence;Hantson, Jennifer;Nock, Sebastien;Carboni, Susanna;Soares de Souza, Adriano Luis;Arrighi, Jean-Francois;Boschert, Ursula;Bombrun, Agnes. And the article was included in ChemMedChem in 2015.Recommanded Product: 107317-58-8 This article mentions the following:

Sphingosine-1-phosphate (S1P) receptor agonists have shown promise as therapeutic agents for multiple sclerosis (MS) due to their regulatory roles within the immune, central nervous system, and cardiovascular system. Here, the design and optimization of novel [1,2,4]oxadiazole derivatives as selective S1P receptor agonists are described. The structure-activity relation exploration was carried out on the three dominant segments of the series: modification of the polar head group (P), replacement of the oxadiazole linker (L) with different five-membered heterocycles, and the use of diverse 2,2′-disubstituted biphenyl moieties as the hydrophobic tail (H). All three segments have a significant impact on potency, S1P receptor subtype selectivity, physicochem. properties, and in vitro absorption, distribution, metabolism, excretion and toxicity (ADMET) profile of the compounds From these optimization studies, a selective S1P₁ agonist, N-methyl-N-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine (45), and a dual S1P_1,5 agonist, N-methyl-N-(3-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine (49), emerged as frontrunners. These compounds distribute predominantly in lymph nodes and brain over plasma and induce long lasting decreases in lymphocyte count after oral administration. When evaluated head-to-head in an exptl. autoimmune encephalomyelitis mouse model, together with the marketed drug fingolimod, a pan-S1P receptor agonist, S1P_1,5 agonist 49 demonstrated comparable efficacy while S1P₁-selective agonist 45 was less potent. Compound 49 is not a prodrug, and its improved property profile should translate into a safer treatment of relapsing forms of MS. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8Recommanded Product: 107317-58-8).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon闂佺偨鍎茶ぐ绲﹐mine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Recommanded Product: 107317-58-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium(0) catalyzed cross coupling reactions of hindered, double activated aryl halides with organozinc reagents – the effect of copper(I) cocatalysis was written by Weichert, Andreas;Bauer, Martina;Wirsig, Petra. And the article was included in Synlett in 1996.Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate This article mentions the following:

Various organozinc reagents undergo palladium(0) catalyzed Negishi-Kumada-type cross coupling reactions, cocatalyzed by copper(I) iodide, with electronically activated aryl halides in the presence of an electron withdrawing ortho or meta substituent and an ester group. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rational Design of a Red Fluorescent Sensor for ALDH1A1 Displaying Enhanced Cellular Uptake and Reactivity was written by Bearrood, Thomas E.;Aguirre-Figueroa, Guadalupe;Chan, Jefferson. And the article was included in Bioconjugate Chemistry in 2020.SDS of cas: 107317-58-8 This article mentions the following:

High aldehyde dehydrogenase 1A1 (ALDH1A1) activity has emerged as a reliable marker for the identification of both normal and cancer stem cells. To facilitate the detection, mol. imaging, and sorting of stem cells, a green fluorescent probe based on the xanthene dye scaffold was recently developed. However, green dyes are less amenable to multicolor imaging because most com. reagents are also green. Overcoming this limitation will enable the simultaneous tracking of multiple stem cell markers. Herein, we report the development of a red congener, red-AlDeSense. Through chem. tuning we were able to achieve excellent isoform selectivity and chemostability, a good turn on response, and enhanced cellular uptake and reactivity. Importantly, red-AlDeSense represents one of only a few turn-on sensors in the red region that use the d-PeT quenching mechanism. By employing red-AlDeSense and a green anti-CD44 antibody, we were able to demonstrate staining of these two stem cell markers is independent of one another in A549 lung adenocarcinoma cells. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8SDS of cas: 107317-58-8).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.SDS of cas: 107317-58-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

5-Phenyl-1,3,4-oxadiazol-2(3H)-ones Are Potent Inhibitors of Notum Carboxylesterase Activity Identified by the Optimization of a Crystallographic Fragment Screening Hit was written by Mahy, William;Willis, Nicky J.;Zhao, Yuguang;Woodward, Hannah L.;Svensson, Fredrik;Sipthorp, James;Vecchia, Luca;Ruza, Reinis R.;Hillier, James;Kjaer, Svend;Frew, Sarah;Monaghan, Amy;Bictash, Magda;Salinas, Patricia C.;Whiting, Paul;Vincent, Jean-Paul;Jones, E. Yvonne;Fish, Paul V.. And the article was included in Journal of Medicinal Chemistry in 2020.COA of Formula: C9H6BrF3O2 This article mentions the following:

Carboxylesterase Notum is a neg. regulator of the Wnt signaling pathway. There is an emerging understanding of the role Notum plays in disease, supporting the need to discover new small-mol. inhibitors. A crystallog. X-ray fragment screen was performed, which identified fragment hit 1,2,3-triazole (I) as an attractive starting point for a structure-based drug design hit-to-lead program. Optimization of I identified oxadiazol-2-one II as a preferred example with properties consistent with drug-like chem. space. Screening of II in a cell-based TCF/LEF reporter gene assay restored the activation of Wnt signaling in the presence of Notum. Mouse pharmacokinetic studies with oral administration of II demonstrated good plasma exposure and partial blood-brain barrier penetration. Significant progress was made in developing fragment hit I into lead II (>600-fold increase in activity), making it suitable as a new chem. tool for exploring the role of Notum-mediated regulation of Wnt signaling. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8COA of Formula: C9H6BrF3O2).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.COA of Formula: C9H6BrF3O2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

1-Ethoxy-3-trifluoromethyl-1,3-butadiene and congeners as Diels-Alder components opening an entry to functionalized (trifluoromethyl)benzenes and -pyridines was written by Volle, Jean-Noel;Schlosser, Manfred. And the article was included in European Journal of Organic Chemistry in 2002.Related Products of 107317-58-8 This article mentions the following:

1-Ethoxy-3-trifluoromethyl-1,3-butadiene and its 2-bromo- and 2-phenyl-substituted derivatives have been prepared by Wittig methylenation of the corresponding 4-ethoxy-1,1,1-trifluoro-3-buten-2-ones, which in turn are readily accessible from trifluoroacetic acid. The electron-rich/electron-poor dienes combine smoothly with di-Me acetylenedicarboxylate and Me propiolate to provide trifluoromethyl-substituted phthalates or benzoates. Satisfactory yields of 4-(trifluoromethyl)pyridinecarboxylic acids can even be achieved with Me cyanoformate, a less reactive dienophile, if a large excess of the dienophile is employed. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8Related Products of 107317-58-8).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Related Products of 107317-58-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Pharmacophore-Based Design of Novel Oxadiazoles as Selective Sphingosine-1-phosphate (S1P) Receptor Agonists with in vivo Efficacy was written by Quattropani, Anna;Sauer, Wolfgang H. B.;Crosignani, Stefano;Dorbais, Jerome;Gerber, Patrick;Gonzalez, Jerome;Marin, Delphine;Muzerelle, Mathilde;Beltran, Fanny;Nichols, Anthony;Georgi, Katrin;Schneider, Manfred;Vitte, Pierre-Alain;Eligert, Valerie;Novo-Perez, Laurence;Hantson, Jennifer;Nock, Sebastien;Carboni, Susanna;Soares de Souza, Adriano Luis;Arrighi, Jean-Francois;Boschert, Ursula;Bombrun, Agnes. And the article was included in ChemMedChem in 2015.Recommanded Product: 107317-58-8 This article mentions the following:

Sphingosine-1-phosphate (S1P) receptor agonists have shown promise as therapeutic agents for multiple sclerosis (MS) due to their regulatory roles within the immune, central nervous system, and cardiovascular system. Here, the design and optimization of novel [1,2,4]oxadiazole derivatives as selective S1P receptor agonists are described. The structure-activity relation exploration was carried out on the three dominant segments of the series: modification of the polar head group (P), replacement of the oxadiazole linker (L) with different five-membered heterocycles, and the use of diverse 2,2′-disubstituted biphenyl moieties as the hydrophobic tail (H). All three segments have a significant impact on potency, S1P receptor subtype selectivity, physicochem. properties, and in vitro absorption, distribution, metabolism, excretion and toxicity (ADMET) profile of the compounds From these optimization studies, a selective S1P₁ agonist, N-methyl-N-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine (45), and a dual S1P_1,5 agonist, N-methyl-N-(3-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine (49), emerged as frontrunners. These compounds distribute predominantly in lymph nodes and brain over plasma and induce long lasting decreases in lymphocyte count after oral administration. When evaluated head-to-head in an exptl. autoimmune encephalomyelitis mouse model, together with the marketed drug fingolimod, a pan-S1P receptor agonist, S1P_1,5 agonist 49 demonstrated comparable efficacy while S1P₁-selective agonist 45 was less potent. Compound 49 is not a prodrug, and its improved property profile should translate into a safer treatment of relapsing forms of MS. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8Recommanded Product: 107317-58-8).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Recommanded Product: 107317-58-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium(0) catalyzed cross coupling reactions of hindered, double activated aryl halides with organozinc reagents – the effect of copper(I) cocatalysis was written by Weichert, Andreas;Bauer, Martina;Wirsig, Petra. And the article was included in Synlett in 1996.Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate This article mentions the following:

Various organozinc reagents undergo palladium(0) catalyzed Negishi-Kumada-type cross coupling reactions, cocatalyzed by copper(I) iodide, with electronically activated aryl halides in the presence of an electron withdrawing ortho or meta substituent and an ester group. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rational Design of a Red Fluorescent Sensor for ALDH1A1 Displaying Enhanced Cellular Uptake and Reactivity was written by Bearrood, Thomas E.;Aguirre-Figueroa, Guadalupe;Chan, Jefferson. And the article was included in Bioconjugate Chemistry in 2020.SDS of cas: 107317-58-8 This article mentions the following:

High aldehyde dehydrogenase 1A1 (ALDH1A1) activity has emerged as a reliable marker for the identification of both normal and cancer stem cells. To facilitate the detection, mol. imaging, and sorting of stem cells, a green fluorescent probe based on the xanthene dye scaffold was recently developed. However, green dyes are less amenable to multicolor imaging because most com. reagents are also green. Overcoming this limitation will enable the simultaneous tracking of multiple stem cell markers. Herein, we report the development of a red congener, red-AlDeSense. Through chem. tuning we were able to achieve excellent isoform selectivity and chemostability, a good turn on response, and enhanced cellular uptake and reactivity. Importantly, red-AlDeSense represents one of only a few turn-on sensors in the red region that use the d-PeT quenching mechanism. By employing red-AlDeSense and a green anti-CD44 antibody, we were able to demonstrate staining of these two stem cell markers is independent of one another in A549 lung adenocarcinoma cells. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8SDS of cas: 107317-58-8).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.SDS of cas: 107317-58-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

5-Phenyl-1,3,4-oxadiazol-2(3H)-ones Are Potent Inhibitors of Notum Carboxylesterase Activity Identified by the Optimization of a Crystallographic Fragment Screening Hit was written by Mahy, William;Willis, Nicky J.;Zhao, Yuguang;Woodward, Hannah L.;Svensson, Fredrik;Sipthorp, James;Vecchia, Luca;Ruza, Reinis R.;Hillier, James;Kjaer, Svend;Frew, Sarah;Monaghan, Amy;Bictash, Magda;Salinas, Patricia C.;Whiting, Paul;Vincent, Jean-Paul;Jones, E. Yvonne;Fish, Paul V.. And the article was included in Journal of Medicinal Chemistry in 2020.COA of Formula: C9H6BrF3O2 This article mentions the following:

Carboxylesterase Notum is a neg. regulator of the Wnt signaling pathway. There is an emerging understanding of the role Notum plays in disease, supporting the need to discover new small-mol. inhibitors. A crystallog. X-ray fragment screen was performed, which identified fragment hit 1,2,3-triazole (I) as an attractive starting point for a structure-based drug design hit-to-lead program. Optimization of I identified oxadiazol-2-one II as a preferred example with properties consistent with drug-like chem. space. Screening of II in a cell-based TCF/LEF reporter gene assay restored the activation of Wnt signaling in the presence of Notum. Mouse pharmacokinetic studies with oral administration of II demonstrated good plasma exposure and partial blood-brain barrier penetration. Significant progress was made in developing fragment hit I into lead II (>600-fold increase in activity), making it suitable as a new chem. tool for exploring the role of Notum-mediated regulation of Wnt signaling. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8COA of Formula: C9H6BrF3O2).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.COA of Formula: C9H6BrF3O2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

1-Ethoxy-3-trifluoromethyl-1,3-butadiene and congeners as Diels-Alder components opening an entry to functionalized (trifluoromethyl)benzenes and -pyridines was written by Volle, Jean-Noel;Schlosser, Manfred. And the article was included in European Journal of Organic Chemistry in 2002.Related Products of 107317-58-8 This article mentions the following:

1-Ethoxy-3-trifluoromethyl-1,3-butadiene and its 2-bromo- and 2-phenyl-substituted derivatives have been prepared by Wittig methylenation of the corresponding 4-ethoxy-1,1,1-trifluoro-3-buten-2-ones, which in turn are readily accessible from trifluoroacetic acid. The electron-rich/electron-poor dienes combine smoothly with di-Me acetylenedicarboxylate and Me propiolate to provide trifluoromethyl-substituted phthalates or benzoates. Satisfactory yields of 4-(trifluoromethyl)pyridinecarboxylic acids can even be achieved with Me cyanoformate, a less reactive dienophile, if a large excess of the dienophile is employed. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8Related Products of 107317-58-8).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Related Products of 107317-58-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary