Month: October 2022

Hansen, Helge-Boj; Wadepohl, Hubert; Enders, Markus published their research in Chemistry – A European Journal on August 2 ,2021. The article was titled 《The Stronger the Better: Donor Substituents Push Catalytic Activity of Molecular Chromium Olefin Polymerization Catalysts》.Computed Properties of C6H8N2 The article contains the following contents:

The donor strength of bifunctional pyridine-cyclopentadienyl ligands was altered systematically by the introduction of donating groups in the para-position of the pyridine. In the resulting chromium complexes an almost linear correlation between donor strength and the nitrogen-chromium distance as well as the electronic absorption maximum is exptl. observed The connection of electron-donating groups in the ligand backbone leads to an efficient transfer of the electronic influences to the catalytically active metal center without restricting it through steric effects. Therefore, catalytic olefin polymerization activity, which is already very high for the previously studied catalysts, increase considerably by attaching para-amino groups to the chelating pyridine or quinoline, resp. Combining electron-rich indenyl ligands with para-amino substituted pyridines lead to the highest catalytic activities observed so far for this class of organo chromium olefin polymerization catalysts. The resulting polymers are of ultra-high mol. weight and the ability of the catalysts to incorporate co-monomers is also very high. In the experiment, the researchers used 4-Amino-2-picoline(cas: 18437-58-6Computed Properties of C6H8N2)

4-Amino-2-picoline(cas: 18437-58-6) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Computed Properties of C6H8N2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2010,Yu, Ming; Lizarzaburu, Mike; Beckmann, Holger; Connors, Richard; Dai, Kang; Haller, Katrin; Li, Cong; Liang, Lingming; Lindstrom, Michelle; Ma, Ji; Motani, Alykhan; Wanska, Malgorzata; Zhang, Alex; Li, Leping; Medina, Julio C. published 《Identification of piperazine-bisamide GHSR antagonists for the treatment of obesity》.Bioorganic & Medicinal Chemistry Letters published the findings.Application of 29682-15-3 The information in the text is summarized as follows:

Piperazine-bisamide analogs I (X = 1,4-phenylene, 2-fluoro-1,4-phenylene, pyridine-2,5-diyl, thiazole-2,4-diyl, etc.; R1 = Ph, 6-indolyl, 8-quinolinyl, etc.; R2, R3 = H, Me; R4 = Ph, 3-MeOC6H4, 2-ClC6H4, 4-pyridyl, etc.) were synthesized and studied for their binding to human growth hormone secretagogue receptor (GHSR). Compounds I [X = 1,4-phenylene; R4 = (un)substituted phenyl] were shown to be partial agonists of GHSR in a high throughput screening. The partial agonists were optimized for potency and converted into antagonists through structure-activity relationship (SAR) studies. The efforts led to the identification of potent antagonist I [X = 3-fluoro-1,4-phenylene; R1 = 6-indolyl; R2 = (S)-Me; R3 = H; R4 = 4-pyridyl] with favorable PK profile suitable as a tool compound for in vivo studies.Methyl 5-bromopicolinate(cas: 29682-15-3Application of 29682-15-3) was used in this study.

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. Application of 29682-15-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2011,Feng, Li; Geisselbrecht, Yann; Blanck, Sebastian; Wilbuer, Alexander; Atilla-Gokcumen, G. Ekin; Filippakopoulos, Panagis; Kraling, Katja; Celik, Mehmet Ali; Harms, Klaus; Maksimoska, Jasna; Marmorstein, Ronen; Frenking, Gernot; Knapp, Stefan; Essen, Lars-Oliver; Meggers, Eric published 《Structurally Sophisticated Octahedral Metal Complexes as Highly Selective Protein Kinase Inhibitors》.Journal of the American Chemical Society published the findings.Application of 13534-97-9 The information in the text is summarized as follows:

The generation of synthetic compounds with exclusive target specificity is an extraordinary challenge of mol. recognition and demands novel design strategies, in particular for large and homologous protein families such as protein kinases with more than 500 members. Simple organic mols. often do not reach the necessary sophistication to fulfill this task. Here, we present six carefully tailored, stable metal-containing compounds in which unique and defined mol. geometries with natural-product-like structural complexity are constructed around octahedral ruthenium(II) or iridium(III) metal centers. Each of the six reported metal compounds displays high selectivity for an individual protein kinase, namely GSK3α, PAK1, PIM1, DAPK1, MLCK, and FLT4. Although being conventional ATP-competitive inhibitors, the combination of the unusual globular shape and rigidity characteristics, of these compounds facilitates the design of highly selective protein kinase inhibitors. Unique structural features of the octahedral coordination geometry allow novel interactions with the glycine-rich loop, which contribute significantly to binding potencies and selectivities. The sensitive correlation between metal coordination sphere and inhibition properties suggests that in this design, the metal is located at a “”hot spot”” within the ATP binding pocket, not too close to the hinge region where globular space is unavailable, and at the same time not too far out toward the solvent where the octahedral coordination sphere would not have a significant impact on potency and selectivity. This study thus demonstrates that inert (stable) octahedral metal complexes are sophisticated structural scaffolds for the design of highly selective chem. probes.6-Bromopyridin-3-amine(cas: 13534-97-9Application of 13534-97-9) was used in this study.

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Application of 13534-97-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2015,Schimler, Sydonie D.; Ryan, Sarah J.; Bland, Douglas C.; Anderson, John E.; Sanford, Melanie S. published 《Anhydrous Tetramethylammonium Fluoride for Room-Temperature SNAr Fluorination》.Journal of Organic Chemistry published the findings.Recommanded Product: 53939-30-3 The information in the text is summarized as follows:

This paper describes the room-temperature SNAr fluorination of aryl halides and nitroarenes using anhydrous tetramethylammonium fluoride (NMe4F). This reagent effectively converts aryl-X (X = Cl, Br, I, NO2, OTf) to aryl-F under mild conditions (often room temperature). Substrates for this reaction include electron-deficient heteroaromatics (22 examples) and arenes (5 examples). The relative rates of the reactions vary with X as well as with the structure of the substrate. However, in general, substrates bearing X = NO2 or Br react fastest. In all cases examined, the yields of these reactions are comparable to or better than those obtained with CsF at elevated temperatures (i.e., more traditional halex fluorination conditions). The reactions also afford comparable yields on scales ranging from 100 mg to 10 g. A cost anal. is presented, which shows that fluorination with NMe4F is generally more cost-effective than fluorination with CsF. The experimental process involved the reaction of 5-Bromo-2-chloropyridine(cas: 53939-30-3Recommanded Product: 53939-30-3)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. When pyridine is adsorbed on oxide surfaces or in porous materials, the following species are commonly observed: (i) pyridine coordinated to Lewis acid sites, (ii) pyridine H-bonded to weakly acidic hydroxyls, and (iii) protonated pyridine. At high coverage, physisorbed pyridine and protonated dimers can also be observed.Recommanded Product: 53939-30-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Saifuzzaman, Md.; Morrison, Rick; Zheng, Zhaohua; Orive, Stephanie; Hamilton, Justin; Thompson, Philip E.; Al-rawi, Jasim M. A. published 《Synthesis and biological evaluation of 8-aryl-2-morpholino-7-O-substituted benzo[e][1,3]oxazin-4-ones against DNA-PK, PI3K, PDE3A enzymes and platelet aggregation》.Bioorganic & Medicinal Chemistry published the findings.Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide The information in the text is summarized as follows:

A series of 40 7-(O-substituted)-2-morpholino-8-aryl-4H-benzo[e][1,3]oxazin-4-ones I [R1 = benzyl, 2-pyridylmethyl, (4-methylpiperazinyl)ethyl; R2 = 2-thiophenyl, 4-ClC6H4, dibenzo[b,d]thiophen-4-yl, etc.] were synthesized. They were prepared via synthesis of a key precursor, I [R1 = H; R2 = Br] which was amenable to ether synthesis at the 7-position and Suzuki coupling at the 8-position. The 2 protons of 7-OCH2 in compounds I [R1 = benzyl; R2 = benzo[b]thiophen-2-yl, dibenzo[b,d]thiophen-4-yl, dibenzo[b,d]furan-4-yl, naphthalen-1-yl, thianthren-1-yl] prove to be magnetically non-equivalent, atropisomerism (axial chirality), as result of sterically hindered rotation of the bulky 8-aryl-substituent. The products I were evaluated for their activities against PI3K isoforms, DNA-PK and PDE3. The results showed that this substitution pattern had a deleterious effect on PI3K activities, which may arise from steric hindrance in the active site. PI3Kδ was somewhat more tolerant of this substitution particularly where 8-(4-methoxylphenyl) substituents were present (IC50s ∼ 2-3 μM). Good activities against PDE3 were also obtained for compounds, with particular members of the 7-(2-pyridinyl) methoxy series showing good inhibition (IC50s ∼ 2-3 μM), comparable to previously described analogs. Compound I [R1 = (4-methylpiperazinyl)ethyl, R2 = Ph] effectively inhibited ADP-induced platelet aggregation with an IC50 of 8 μM. The results came from multiple reactions, including the reaction of 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Zhang, Fangfang; Yao, Qiyi; Yuan, Yang; Xu, Murong; Kong, Lingkai; Li, Yanzhong published 《Base-mediated insertion reaction of alkynes into carbon-carbon σ-bonds of ethanones: synthesis of hydroxydienone and chromone derivatives》.Organic & Biomolecular Chemistry published the findings.Computed Properties of C6H4BrNO The information in the text is summarized as follows:

Transition-metal free insertions of alkynes into C-C σ-bonds of ethanones are reported. These tandem reactions offer an efficient synthesis of hydroxydienones and multi-substituted chromones. This is the 1st example of base-promoted insertion reactions of isolated C-C triple bonds into C-C σ-bonds with active methylene compounds bearing only one electron-withdrawing group. The results came from multiple reactions, including the reaction of 2-Bromonicotinaldehyde(cas: 128071-75-0Computed Properties of C6H4BrNO)

2-Bromonicotinaldehyde(cas: 128071-75-0) belongs to pyridine. Pyridines are often used as catalysts or reagents; particular notice has been paid recently to how pyridine coordinates to metal centers enabling a wide range of valuable reactions. Computed Properties of C6H4BrNO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Robles, Andrew J.; McCowen, Shelby; Cai, Shengxin; Glassman, Michaels; Ruiz, Francisco; Cichewicz, Robert H.; McHardy, Stanton F.; Mooberry, Susan L. published 《Structure-Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells》.Journal of Medicinal Chemistry published the findings.Safety of 2-Bromonicotinaldehyde The information in the text is summarized as follows:

Targeted therapies for ER+/PR+ and HER2-amplified breast cancers have improved patient survival, but there are no therapies for triple neg. breast cancers (TNBC) that lack expression of estrogen and progesterone receptors (ER/PR), or amplification or overexpression of HER2. Gene expression profiling of TNBC has identified mol. subtypes and representative cell lines. An extract of the Texas native plant Amyris texana was found to have selective activity against MDA-MB-453 cells, a model of the luminal androgen receptor (LAR) subtype of TNBC. Bioassay-guided fractionation identified two oxazole natural products with selective activity against this cell line. Conducted analog synthesis and structure-activity relationship studies provided analogs with more potent and selective activity against two LAR subtype cell line models, culminating in the discovery of compound I (CIDD-0067106). Lead compounds discovered have potent and selective antiproliferative activities, and mechanisms of action studies show they inhibit the activity of the mTORC1 pathway. The experimental process involved the reaction of 2-Bromonicotinaldehyde(cas: 128071-75-0Safety of 2-Bromonicotinaldehyde)

2-Bromonicotinaldehyde(cas: 128071-75-0) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Safety of 2-Bromonicotinaldehyde

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Stepan, Antonia F.; Claffey, Michelle M.; Reese, Matthew R.; Balan, Gayatri; Barreiro, Gabriela; Barricklow, Jason; Bohanon, Michael J.; Boscoe, Brian P.; Cappon, Gregg D.; Chenard, Lois K.; Cianfrogna, Julie; Chen, Laigao; Coffman, Karen J.; Drozda, Susan E.; Dunetz, Joshua R.; Ghosh, Somraj; Hou, Xinjun; Houle, Christopher; Karki, Kapil; Lazzaro, John T.; Mancuso, Jessica Y.; Marcek, John M.; Miller, Emily L.; Moen, Mark A.; O’Neil, Steven; Sakurada, Isao; Skaddan, Marc; Parikh, Vinod; Smith, Deborah L.; Trapa, Patrick; Tuttle, Jamison B.; Verhoest, Patrick R.; Walker, Daniel P.; Won, Annie; Wright, Ann S.; Whritenour, Jessica; Zasadny, Kenneth; Zaleska, Margaret M.; Zhang, Lei; Shaffer, Christopher L. published 《Discovery and Characterization of (R)-6-Neopentyl-2-(pyridin-2-ylmethoxy)-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (PF-06462894), an Alkyne-Lacking Metabotropic Glutamate Receptor 5 Negative Allosteric Modulator Profiled in both Rat and Nonhuman Primates》.Journal of Medicinal Chemistry published the findings.Related Products of 31106-82-8 The information in the text is summarized as follows:

We previously observed a cutaneous type IV immune response in nonhuman primates (NHP) with the mGlu5 neg. allosteric modulator (NAM) 7. To determine if this adverse event was chemotype- or mechanism-based, we evaluated a distinct series of mGlu5 NAMs. Increasing the sp3 character of high-throughput screening hit 40 afforded a novel morpholinopyrimidone mGlu5 NAM series. Its prototype, (R)-6-neopentyl-2-(pyridin-2-ylmethoxy)-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (PF-06462894, 8), possessed favorable properties and a predicted low clin. dose (2 mg twice daily). Compound 8 did not show any evidence of immune activation in a mouse drug allergy model. Addnl., plasma samples from toxicol. studies confirmed that 8 did not form any reactive metabolites. However, 8 caused the identical microscopic skin lesions in NHPs found with 7, albeit with lower severity. Holistically, this work supports the hypothesis that this unique toxicity may be mechanism-based although addnl. work is required to confirm this and determine clin. relevance. After reading the article, we found that the author used 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Related Products of 31106-82-8)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.Related Products of 31106-82-8

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Gunaga, Prashantha; Lloyd, John; Mummadi, Somanadham; Banerjee, Abhisek; Dhondi, Naveen Kumar; Hennan, James; Subray, Veena; Jayaram, Ramya; Rajugowda, Nagendra; Umamaheshwar Reddy, Kommuri; Kumaraguru, Duraimurugan; Mandal, Umasankar; Beldona, Dasthagiri; Adisechen, Ashok Kumar; Yadav, Navnath; Warrier, Jayakumar; Johnson, James A.; Sale, Harinath; Putlur, Siva Prasad; Saxena, Ajay; Chimalakonda, Anjaneya; Mandlekar, Sandhya; Conder, MaryLee; Xing, Dezhi; Gupta, Arun Kumar; Gupta, Anuradha; Rampulla, Richard; Mathur, Arvind; Levesque, Paul; Wexler, Ruth R.; Finlay, Heather J. published 《Selective IKur Inhibitors for the Potential Treatment of Atrial Fibrillation: Optimization of the Phenyl Quinazoline Series Leading to Clinical Candidate 5-[5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide》.Journal of Medicinal Chemistry published the findings.Quality Control of 5-Bromo-2-chloropyridine The information in the text is summarized as follows:

We have recently disclosed 5-phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine (I) as a potent IKur current blocker with selectivity vs. hERG, Na and Ca channels and an acceptable preclin. PK profile. On further characterization in vivo, Compound I demonstrated an unacceptable level of brain penetration. In an effort to reduce the level of brain penetration while maintaining the overall profile, SAR was developed at the C2′ position for a series of close analogs by employing hydrogen bond donors. As a result, 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridine-3-sulfonamide (II) was identified as the lead compound in this series. Compound II showed robust effects in rabbit and canine pharmacodynamic models and an acceptable cross-species pharmacokinetic profile and was advanced as the clin. candidate. Further optimization of II to mitigate pH dependent absorption resulted in identification of the corresponding phosphoramide prodrug (29) with an improved solubility and pharmacokinetic profile. In the part of experimental materials, we found many familiar compounds, such as 5-Bromo-2-chloropyridine(cas: 53939-30-3Quality Control of 5-Bromo-2-chloropyridine)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. Quality Control of 5-Bromo-2-chloropyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Pomplun, Sebastian; Sippel, Claudia; Haehle, Andreas; Tay, Donald; Shima, Kensuke; Klages, Alina; Uenal, Can Murat; Riess, Benedikt; Toh, Hui Ting; Hansen, Guido; Yoon, Ho Sup; Bracher, Andreas; Preiser, Peter; Rupp, Jan; Steinert, Michael; Hausch, Felix published 《Chemogenomic Profiling of Human and Microbial FK506-Binding Proteins》.Journal of Medicinal Chemistry published the findings.Name: 2-(Bromomethyl)pyridine hydrobromide The information in the text is summarized as follows:

FK506-binding proteins (FKBPs) are evolutionarily conserved proteins that display peptidyl-prolyl isomerase activities and act as coreceptors for immunosuppressants. Microbial macrophage-infectivity-potentiator (Mip)-type FKBPs can enhance infectivity. However, developing druglike ligands for FKBPs or Mips has proven difficult, and many FKBPs and Mips still lack biol. useful ligands. To explore the scope and potential of C5-substituted [4.3.1]-aza-bicyclic sulfonamides as a broadly applicable class of FKBP inhibitors, we developed a new synthesis method for the bicyclic core scaffold and used it to prepare an FKBP- and Mip-focused library. This allowed us to perform a systematic structure-activity-relationship anal. across key human FKBPs and microbial Mips, yielding highly improved inhibitors for all the FKBPs studied. A cocrystal structure confirmed the mol.-binding mode of the core structure and explained the affinity gained as a result of the preferred substituents. The best FKBP and Mip ligands showed promising antimalarial, antileginonellal, and antichlamydial properties in cellular models of infectivity, suggesting that substituted [4.3.1]-aza-bicyclic sulfonamides could be a novel class of anti-infectives. In addition to this study using 2-(Bromomethyl)pyridine hydrobromide, there are many other studies that have used 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Name: 2-(Bromomethyl)pyridine hydrobromide) was used in this study.

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Name: 2-(Bromomethyl)pyridine hydrobromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem