Day: October 17, 2022

Category: pyridine-derivativesOn November 1, 2013 ,《Novel complex crystal structure of prolyl hydroxylase domain-containing protein 2 (PHD2): 2,8-Diazaspiro[4.5]decan-1-ones as potent, orally bioavailable PHD2 inhibitors》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Deng, Guanghui; Zhao, Baowei; Ma, Yingli; Xu, Qiongfeng; Wang, Hailong; Yang, Liuqing; Zhang, Qing; Guo, Taylor B.; Zhang, Wei; Jiao, Yang; Cai, Xin; Zhang, Jinqiang; Liu, Houfu; Guan, Xiaoming; Lu, Hongtao; Xiang, Jianing; Elliott, John D.; Lin, Xichen; Ren, Feng. The article conveys some information:

We have discovered a novel complex crystal structure of the PHD2 enzyme with its inhibitor, the 2,8-diazaspiro[4.5]decan-1-one analog 4b. The widely reported salt bridge between Arg383 of the enzyme and its inhibitors in all complex structures published thus far was not observed in our case. In our complex structure compound 4b forms several novel interactions with the enzyme, which include a hydrogen bond with Arg322, a π-cation interaction with Arg322, a π-π stacking with Trp389, and a π-π stacking with His313. Guided by the structural information, SAR studies were performed on the 2,8-diazaspiro[4.5]decan-1-one series leading to the discovery of compound 9p with high potency and good oral pharmacokinetic profile in mice. The results came from multiple reactions, including the reaction of 5-Bromo-3-methyl-2-pyridinecarbaldehyde(cas: 376587-53-0Category: pyridine-derivatives)

5-Bromo-3-methyl-2-pyridinecarbaldehyde(cas: 376587-53-0) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Name: 2-Bromopyridin-3-amineOn May 3, 2020 ,《Synthesis of [3.4]-Spirooxindoles through Cascade Carbopalladation of Skipped Dienes》 appeared in Advanced Synthesis & Catalysis. The author of the article were Azizollahi, Hamid; Perez-Gomez, Marta; Mehta, Vaibhav P.; Garcia-Lopez, Jose-Antonio. The article conveys some information:

A synthetic route to [3.4]-spirooxindoles based on cascade carbopalladation reactions of 1,4-dienes was described. While carbopalladation of alkenes have been used to access mainly [4.4]- or [4.5]-spirocycles, 4-exo-trig carbopalladation was not been yet applied to the synthesis of relevant [3.4]-spirooxindole scaffolds bearing a cyclobutyl ring. In addition, the cascade reaction generates an exocyclic double bond that can serve as a platform to further diversify the substitution pattern of the spirooxindole nuclei. The experimental part of the paper was very detailed, including the reaction process of 2-Bromopyridin-3-amine(cas: 39856-58-1Name: 2-Bromopyridin-3-amine)

2-Bromopyridin-3-amine(cas: 39856-58-1) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.Name: 2-Bromopyridin-3-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Formula: C5H5BrN2On May 19, 2022 ,《Base-Mediated Remote Deuteration of N-Heteroarenes – Broad Scope and Mechanism》 appeared in European Journal of Organic Chemistry. The author of the article were Kopf, Sara; Liu, Jiali; Franke, Robert; Jiao, Haijun; Neumann, Helfried; Beller, Matthias. The article conveys some information:

Using KOtBu as base and DMSO-d6 as deuterium source, a general and applicable method was presented for the selective deuteration of a set of nitrogen-containing heterocycles (pyridines, azines and bioactive mols.). Exptl. and DFT mechanistic studies indicated that this reaction proceeded via deprotonation of the substrates by the dimsyl anion. The relative thermodn. stability of the heterocycle anions determines the distribution and degree of deuteration. In the experiment, the researchers used 2-Bromopyridin-3-amine(cas: 39856-58-1Formula: C5H5BrN2)

2-Bromopyridin-3-amine(cas: 39856-58-1) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Formula: C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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