Category: 26218-78-0

Pang, Lijuan; Bezencon, Jacqueline; Kleeb, Simon; Rabbani, Said; Sigl, Anja; Smiesko, Martin; Sager, Christoph P.; Eris, Deniz; Schwardt, Oliver; Ernst, Beat published the article 《FimH antagonists – solubility vs. permeability》. Keywords: FimH antagonist solubility permeability.They researched the compound: Methyl 6-bromonicotinate( cas:26218-78-0 ).SDS of cas: 26218-78-0. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:26218-78-0) here.

Urinary tract infections (UTIs) caused by uropathogenic Escherichia coli (UPEC) are among the most prevalent infections worldwide. Since frequent antibiotic treatment favors the emergence of antibiotic resistance, efficient non-antibiotic strategies are urgently needed. The first step of the pathogenesis of UTI is the bacterial adherence to urothelial host cells, a process mediated by the mannose-binding adhesin FimH located at the tip of bacterial pili. In a preliminary study, biphenyl α-D-mannopyranosides with an electron-withdrawing carboxylate on the aglycon were identified as potent FimH antagonists. Although passive permeability could be established by masking the carboxylate as an ester, insufficient solubility and fast hydrolysis did not allow to maintain the therapeutic concentration in the bladder for the requested period of time. By modifying the substitution pattern, mol. planarity and symmetry of the biphenyl aglycon could be disrupted leading to improved solubility In addition, when heteroatoms were introduced to the aglycon, antagonists with further improved solubility, metabolic stability as well as passive permeability were obtained. The best representative, the pyrrolylphenyl mannoside 42f exhibited therapeutic urine concentration for up to 6 h and is therefore a promising oral candidate for UTI prevention and/or treatment.

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Reference:
Tetrahydrofuran – Wikipedia,
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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 26218-78-0, is researched, SMILESS is C1=NC(=CC=C1C(=O)OC)Br, Molecular C7H6BrNO2Journal, Heterocycles called Synthesis of pyrrolo[2,3-d]pyrimidine analogues: “”pyridine ring”” analogues of pemetrexed, Author is Xu, Yun; Yu, Mingfeng; Long, Yan; Wu, Han; Mao, Zhenmin, the main research direction is pyridine analog pemetrexed preparation anticancer.Category: tetrahydrofurans.

Two analogs of pemetrexed with its Ph ring replaced with a pyridine ring were synthesized as novel anticancer agents. Preliminary in-vitro evaluation indicated that replacement of the Ph moiety of pemetrexed by the pyridine ring with the 6-5 bicyclic ring system showed low cytotoxicity, that departs from the findings with antifolates bearing a 6-6 bicyclic system.

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Tetrahydrofuran – Wikipedia,
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Computed Properties of C7H6BrNO2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about Enantioselective Dearomative [3 + 2] Umpolung Annulation of N-Heteroarenes with Alkynes. Author is Yang, Peng; Wang, Qiang; Cui, Bing-Hui; Zhang, Xiao-Dong; Liu, Hang; Zhang, Yue-Yuan; Liu, Jia-Liang; Huang, Wen-Yu; Liang, Ren-Xiao; Jia, Yi-Xia.

Enantioselective [3 + 2] annulation of N-heteroarenes such as 2-(2-bromophenyl)quinoline with alkynes R1CCR2 [R1 = Me, Ph, benzyloxymethyl, (thiophen-2-ylmethoxy)methyl, etc.; R2 = Me, Ph, benzyloxymethyl, (thiophen-2-ylmethoxy)methyl, etc.] has been developed via a cobalt-catalyzed dearomative umpolung strategy in the presence of chiral ligand e.g., [(2R,3R)-3-(diphenylphosphanyl)butan-2-yl]diphenylphosphane and reducing reagent. A variety of electron-deficient N-heteroarenes e.g., 2-(2-bromophenyl)quinoline and internal or terminal alkynes are employed in this reaction, showing a broad substrate scope and good functionality tolerance. Annulation of electron-rich indoles I (R = H, 5-Cl) with alkynes is also developed. This protocol provides a straightforward access to a variety of N-spiroheterocyclic mols. such as II and in excellent enantioselectivities (76 examples, up to 99% ee).

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Reference:
Tetrahydrofuran – Wikipedia,
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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, N.I.H., Extramural, Nature Chemistry called Concerted nucleophilic aromatic substitutions, Author is Kwan, Eugene E.; Zeng, Yuwen; Besser, Harrison A.; Jacobsen, Eric N., which mentions a compound: 26218-78-0, SMILESS is C1=NC(=CC=C1C(=O)OC)Br, Molecular C7H6BrNO2, Electric Literature of C7H6BrNO2.

Nucleophilic aromatic substitution (SNAr) is one of the most widely applied reaction classes in pharmaceutical and chem. research, providing a broadly useful platform for the modification of aromatic ring scaffolds. The generally accepted mechanism for SNAr reactions involves a two-step addition-elimination sequence via a discrete, non-aromatic Meisenheimer complex. Here the authors use 12C/13C kinetic isotope effect (KIE) studies and computational analyses to provide evidence that prototypical SNAr reactions in fact proceed through concerted mechanisms. The KIE measurements were made possible by a new technique that leverages the high sensitivity of 19F as an NMR nucleus to quantitate the degree of isotopic fractionation. This sensitive technique permits the measurement of KIEs on 10 mg of natural abundance material in one overnight acquisition. As a result, it provides a practical tool for performing detailed mechanistic analyses of reactions that form or break C-F bonds.

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Tetrahydrofuran – Wikipedia,
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SDS of cas: 26218-78-0. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about Bistrifluoromethylated organocuprate [Ph4P]+[Cu(CF3)2]-: synthesis, characterization and its application for trifluoromethylation of activated heteroaryl bromides, chlorides and iodides. Author is Liu, He; Shen, Qilong.

The synthesis and characterization of a bistrifluoromethylated organocuprate [Ph4P]+[Cu(CF3)2]- and its reactions with a variety of activated heteroaryl bromides, chlorides and iodides were described. These results showed that complex [Ph4P]+[Cu(CF3)2]- can serve as a trifluoromethylating reagent.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Electric Literature of C7H6BrNO2. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about Probing the metabotropic glutamate receptor 5 (mGlu5) positive allosteric modulator (PAM) binding pocket: discovery of point mutations that engender a “”molecular switch”” in PAM pharmacology. Author is Gregory, Karen J.; Nguyen, Elizabeth D.; Reiff, Sean D.; Squire, Emma F.; Stauffer, Shaun R.; Lindsley, Craig W.; Meiler, Jens; Conn, P. Jeffrey.

Pos. allosteric modulation of metabotropic glutamate receptor subtype 5 (mGlu5) is a promising novel approach for the treatment of schizophrenia and cognitive disorders. Allosteric binding sites are topog. distinct from the endogenous ligand (orthosteric) binding site, allowing for co-occupation of a single receptor with the endogenous ligand and an allosteric modulator. Neg. allosteric modulators (NAMs) inhibit and pos. allosteric modulators (PAMs) enhance the affinity and/or efficacy of the orthosteric agonist. The mol. determinants that govern mGlu5 modulator affinity vs. cooperativity are not well understood. Focusing on the modulators based on the acetylene scaffold, the authors sought to determine the mol. interactions that contribute to PAM vs. NAM pharmacol. Generation of a comparative model of the transmembrane-spanning region of mGlu5 served as a tool to predict and interpret the impact of mutations in this region. Application of an operational model of allosterism allowed for determination of PAM and NAM affinity estimates at receptor constructs that possessed no detectable radioligand binding as well as delineation of effects on affinity vs. cooperativity. Novel mutations within the transmembrane domain (TM) regions were identified that had differential effects on acetylene PAMs vs. 2-methyl-6-(phenylethynyl)-pyridine, a prototypical NAM. Three conserved amino acids (Y658, T780, and S808) and two non-conserved residues (P654 and A809) were identified as key determinants of PAM activity. Interestingly, the authors identified two point mutations in TMs 6 and 7 that, when mutated, engender a mode switch in the pharmacol. of certain PAMs.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Application In Synthesis of Methyl 6-bromonicotinate. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about Catalytic enantioselective synthesis of heterocyclic vicinal fluoroamines using asymmetric protonation: a method development and mechanistic study. Author is Ashford, Matthew W.; Xu, Chao; Molloy, John J.; Carpenter-Warren, Cameron; Slawin, Alexandra M. Z.; Leach, Andrew G.; Watson, Allan J. B..

A catalytic enantioselective synthesis of heterocyclic vicinal fluoroamines is reported. A chiral Bronsted acid promotes aza-Michael addition to fluoroalkenyl heterocycles to give a prochiral enamine intermediate, which undergoes asym. protonation upon rearomatization [e.g., I + aniline → II (82%, 96:4 R:S)]. The reaction accommodates a range of azaheterocycles and nucleophiles, generating the C-F stereocenter in high enantioselectivity, and is also amenable to stereogenic C-CF3 bonds. Extensive DFT calculations have provided insight into the reaction mechanism and the origin of catalyst selectivity. Crystal structure data shows the dominance of non-covalent interactions in the core structure conformation, enabling modulation of the conformational landscape. Ramachandran-type anal. of conformer distribution and protein data bank mining has indicated benzylic fluorination using this approach has potential for improved potency in several marketed drugs.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Methyl 6-bromonicotinate( cas:26218-78-0 ) is researched.Category: tetrahydrofurans.Young, Tom A.; Silcock, Joseph J.; Sterling, Alistair J.; Duarte, Fernanda published the article 《autodE: Automated Calculation of Reaction Energy Profiles- Application to Organic and Organometallic Reactions》 about this compound( cas:26218-78-0 ) in Angewandte Chemie, International Edition. Keywords: organic organometallic compound potential energy surface machine learning; automation; reaction mechanisms; sampling; transition states. Let’s learn more about this compound (cas:26218-78-0).

Calculating reaction energy profiles to aid in mechanistic elucidation has long been the domain of the expert computational chemist. Here, we introduce autodE (), an open-source Python package capable of locating transition states (TSs) and min. and delivering a full reaction energy profile from 1D or 2D chem. representations. autodE is broadly applicable to study organic and organometallic reaction classes, including addition, substitution, elimination, migratory insertion, oxidative addition, and reductive elimination; it accounts for conformational sampling of both min. and TSs and is compatible with many electronic structure packages. The general applicability of autodE is demonstrated in complex multi-step reactions, including cobalt- and rhodium-catalyzed hydroformylation and an Ireland-Claisen rearrangement.

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Tetrahydrofuran – Wikipedia,
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Name: Methyl 6-bromonicotinate. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about Mechanistic Insight into Copper-Mediated Trifluoromethylation of Aryl Halides: The Role of CuI. Author is Liu, He; Wu, Jian; Jin, Yuxuan; Leng, Xuebing; Shen, Qilong.

The synthesis, characterization, and reactivity of key intermediates [Cu(CF3)(X)]-Q+ (X = CF3 or I, Q = PPh4) in copper-mediated trifluoromethylation of aryl halides were studied. Qual. and quant. studies showed [Cu(CF3)2]-Q+ and [Cu(CF3)(I)]-Q+ were not highly reactive. Instead, a much more reactive species, ligand-less [CuCF3] or DMF-ligated species [(DMF)CuCF3], was generated in the presence of excess CuI. On the basis of these results, a general mechanistic map for CuI-promoted trifluoromethylation of aryl halides was proposed. Furthermore, on the basis of this mechanistic understanding, a HOAc-promoted protocol for trifluoromethylation of aryl halides with [Ph4P]+[Cu(CF3)2]- was developed.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Application In Synthesis of Methyl 6-bromonicotinate. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about Catalytic enantioselective synthesis of heterocyclic vicinal fluoroamines using asymmetric protonation: a method development and mechanistic study. Author is Ashford, Matthew W.; Xu, Chao; Molloy, John J.; Carpenter-Warren, Cameron; Slawin, Alexandra M. Z.; Leach, Andrew G.; Watson, Allan J. B..

A catalytic enantioselective synthesis of heterocyclic vicinal fluoroamines is reported. A chiral Bronsted acid promotes aza-Michael addition to fluoroalkenyl heterocycles to give a prochiral enamine intermediate, which undergoes asym. protonation upon rearomatization [e.g., I + aniline → II (82%, 96:4 R:S)]. The reaction accommodates a range of azaheterocycles and nucleophiles, generating the C-F stereocenter in high enantioselectivity, and is also amenable to stereogenic C-CF3 bonds. Extensive DFT calculations have provided insight into the reaction mechanism and the origin of catalyst selectivity. Crystal structure data shows the dominance of non-covalent interactions in the core structure conformation, enabling modulation of the conformational landscape. Ramachandran-type anal. of conformer distribution and protein data bank mining has indicated benzylic fluorination using this approach has potential for improved potency in several marketed drugs.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem