Category: pyridine-derivatives

Recommanded Product: 3510-66-5In 2021 ,《A study of the structure-affinity relationship in SYA16263; is a D2 receptor interaction essential for inhibition of apormorphine-induced climbing behavior in mice?》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Onyameh, Edem K.; Bricker, Barbara A.; Eyunni, Suresh V. K.; Voshavar, Chandrashekhar; Gonela, Uma M.; Ofori, Edward; Jenkins, Andrea; Ablordeppey, Seth Y.. The article conveys some information:

Dopamine (DA) and serotonin (5-HT) receptors are prime targets for the development of antipsychotics. The specific role of each receptor subtype to the pharmacol. effects of antipsychotic drugs remains unclear. Understanding the relationship between antipsychotic drugs and their binding affinities at DA and 5-HT receptor subtypes is very important for antipsychotic drug discovery and could lead to new drugs with enhanced efficacies. We have previously disclosed SYA16263 (5) as an interesting compound with moderate radioligand binding affinity at the D2 & D3 receptors (Ki = 124 nM & 86 nM resp.) and high binding affinities towards D4 and 5-HT1A receptors (Ki = 3.5 nM & 1.1 nM resp.). Furthermore, we have demonstrated SYA16263 (5) is functionally selective and produces antipsychotic-like behavior but without inducing catalepsy in mice. Based on its pharmacol. profile, we selected SYA16263 (5) to study its structure-affinity relationship with a view to obtaining new analogs that display receptor subtype selectivity. In this study, we present the synthesis of structurally modified SYA16263 (5) analogs and their receptor binding affinities at the DA and 5-HT receptor subtypes associated with antipsychotic action. Furthermore, we have identified compound 21 with no significant binding affinity at the D2 receptor subtype but with moderate binding affinity at the D3 and D4 receptors subtypes. However, because 21 is able to demonstrate antipsychotic-like activity in a preliminary test, using the reversal of apomorphine-induced climbing behavior experiment in mice with SYA16263 and haloperidol as pos. controls, we question the essential need of the D2 receptor subtype in reversing apomorphine-induced climbing behavior. In the experiment, the researchers used many compounds, for example, 2-Bromo-5-methylpyridine(cas: 3510-66-5Recommanded Product: 3510-66-5)

2-Bromo-5-methylpyridine(cas: 3510-66-5) belongs to pyridine. The basicity and metallophilic high donor number of these π-deficient systems has long favored them as ligands in metal catalysis. The last decade saw pyridine assume a stronger role as functional group for directed C–H oxidation/activation.Recommanded Product: 3510-66-5

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Formula: C5H3Br2NIn 2019 ,《Pyrenylpyridines: Sky-Blue Emitters for Organic Light-Emitting Diodes》 appeared in ACS Omega. The author of the article were Deepthika De Silva, Thenahandi Prasanthi; Youm, Sang Gil; Tamas, George G.; Yang, Boqian; Wang, Chun-Han; Fronczek, Frank R.; Sahasrabudhe, Girija; Sterling, Sierra; Quarels, Rashanique D.; Chhotaray, Pratap K.; Nesterov, Evgueni E.; Warner, Isiah M.. The article conveys some information:

A novel sky-blue-emitting tripyrenylpyridine derivative, 2,4,6-tri(1-pyrenyl)pyridine (2,4,6-TPP), has been synthesized using a Suzuki coupling reaction and compared with three previously reported isomeric dipyrenylpyridine (DPP) analogs (2,4-di(1-pyrenyl)pyridine (2,4-DPP), 2,6-di(1-pyrenyl)pyridine (2,6-DPP), and 3,5-di(1-pyrenyl)pyridine (3,5-DPP)). As revealed by single-crystal X-ray anal. and computational simulations, all compounds possess highly twisted conformations in the solid state with interpyrene torsional angles of 42.3°-57.2°. These solid-state conformations and packing variations of pyrenylpyridines could be correlated to observed variations in phys. characteristics such as photo/thermal stability and spectral properties, but showed only marginal influence on electrochem. properties. The novel derivative, 2,4,6-TPP, exhibited the lowest degree of crystallinity as revealed by powder X-ray diffraction anal. and formed amorphous thin films as verified using grazing-incidence wide-angle X-ray scattering. This compound also showed high thermal/photo stability relative to its disubstituted analogs (DPPs). Thus, a nondoped organic light-emitting diode (OLED) prototype was fabricated using 2,4,6-TPP as the emissive layer, which displayed a sky-blue electroluminescence with Commission Internationale de L’Eclairage (CIE) coordinates of (0.18, 0.34). This OLED prototype achieved a maximum external quantum efficiency of 6.0 ± 1.2% at 5 V. The relatively high efficiency for this simple-architecture device reflects a good balance of electron and hole transporting ability of 2,4,6-TPP along with efficient exciton formation in this material and indicates its promise as an emitting material for design of blue OLED devices. The experimental part of the paper was very detailed, including the reaction process of 2,6-Dibromopyridine(cas: 626-05-1Formula: C5H3Br2N)

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. The basicity and metallophilic high donor number of these π-deficient systems has long favored them as ligands in metal catalysis. The last decade saw pyridine assume a stronger role as functional group for directed C–H oxidation/activation.Formula: C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Patel, P. N.; Desai, D. H.; Patel, N. C. published an article in Russian Journal of Organic Chemistry. The title of the article was 《Novel Terpyridine Derivatives of Benzothiazole and Copper(II) Complex: Synthesis and Spectral Studies》.Synthetic Route of C7H7NO The author mentioned the following in the article:

Novel terpyridine derivatives of benzothiazole were synthesized by simple multicomponent 1-pot reaction of benzothiazole-2-carbaldehyde, ammonium hydroxide, and isomeric acetyl pyridines with isolated yields of 92-98%. All the prepared derivatives were characterized by NMR, IR, and high-resolution mass spectra. A Cu(II) complex was prepared selectively from the terpyridine derivative obtained from 2-acetylpyridine and was characterized by single-crystal x-ray anal. UV-visible spectra were recorded for all the synthesized compounds In the experiment, the researchers used 4-Acetylpyridine(cas: 1122-54-9Synthetic Route of C7H7NO)

4-Acetylpyridine(cas: 1122-54-9) 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. Synthetic Route of C7H7NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Tolmachova, Kateryna A.; Moroz, Yurii S.; Konovets, Angelika; Platonov, Maxim O.; Vasylchenko, Oleksandr V.; Borysko, Petro; Zozulya, Sergey; Gryniukova, Anastasia; Bogolubsky, Andrey V.; Pipko, Sergey; Mykhailiuk, Pavel K.; Brovarets, Volodymyr S.; Grygorenko, Oleksandr O. published 《(Chlorosulfonyl)benzenesulfonyl Fluorides-Versatile Building Blocks for Combinatorial Chemistry: Design, Synthesis and Evaluation of a Covalent Inhibitor Library》.ACS Combinatorial Science published the findings.Electric Literature of C5H5BrN2 The information in the text is summarized as follows:

Multigram synthesis of (chlorosulfonyl)benzenesulfonyl fluorides is described. Selective modification of these building blocks at the sulfonyl chloride function under parallel synthesis conditions is achieved. It is shown that the reaction scope includes the use of (hetero)aromatic and electron-poor aliphatic amines (e.g., amino nitriles). Utility of the method is demonstrated by preparation of the sulfonyl fluoride library for potential use as covalent fragments, which is demonstrated by a combination of in silico and in vitro screening against trypsin as a model enzyme. As a result, several inhibitors were identified with activity on par with that of the known inhibitor. In the part of experimental materials, we found many familiar compounds, such as 6-Bromopyridin-3-amine(cas: 13534-97-9Electric Literature of C5H5BrN2)

6-Bromopyridin-3-amine(cas: 13534-97-9) 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.Electric Literature of C5H5BrN2

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

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 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,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,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,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