Month: October 2022

In 2015,Kobayashi, Toshiki; Furusawa, Yuki; Yamada, Shoya; Akehi, Masaru; Takenaka, Fumiaki; Sasaki, Takanori; Akahoshi, Akiya; Hanada, Takahisa; Matsuura, Eiji; Hirano, Hiroyuki; Tai, Akihiro; Kakuta, Hiroki published 《Positron Emission Tomography to Elucidate Pharmacokinetic Differences of Regioisomeric Retinoid X Receptor Agonists》.ACS Medicinal Chemistry Letters published the findings.Safety of 5-Bromo-2-chloropyridine The information in the text is summarized as follows:

RXR partial agonist NEt-4IB (2a, 6-[ethyl-(4-isobutoxy-3-isopropylphenyl)amino]pyridine-3-carboxylic acid: EC50 = 169 nM, Emax = 55%) showed a blood concentration higher than its Emax after single oral administration at 30 mg/kg to mice, and repeated oral administration at 10 mg/kg/day to KK-Ay mice afforded antitype 2 diabetes activity without the side effects caused by RXR full agonists. However, RXR full agonist NEt-3IB (1a), in which the isobutoxy and iso-Pr groups of 2a are interchanged, gave a much lower blood concentration than 2a. Here we used positron emission tomog. (PET) with tracers [11C]1a, [11C]2a and fluorinated derivatives [18F]1b, [18F]2b, which have longer half-lives, to examine the reason why 1a and 2a exhibited significantly different blood concentrations As a result, the reason for the high blood concentration of 2a after oral administration was found to be linked to higher intestinal absorbability together with lower biliary excretion, compared with 1a. The experimental part of the paper was very detailed, including the reaction process of 5-Bromo-2-chloropyridine(cas: 53939-30-3Safety 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. Safety of 5-Bromo-2-chloropyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Ding, Shi; Dai, Rui-Yang; Wang, Wen-Ke; Cao, Qiao; Lan, Le-Fu; Zhou, Xian-Li; Yang, Yu-She published 《Design, synthesis and structure-activity relationship evaluation of novel LpxC inhibitors as Gram-negative antibacterial agents》.Bioorganic & Medicinal Chemistry Letters published the findings.SDS of cas: 29682-15-3 The information in the text is summarized as follows:

LpxC inhibitors are new-type antibacterial agents developed in the last twenty years, mainly against Gram-neg. bacteria infections. To develop novel LpxC inhibitors with good antibacterial activities and biol. metabolism, the authors summarized the basic skeleton of reported LpxC inhibitors, designed and synthesized several series of compounds and tested their antibacterial activities against Escherichia coli and Pseudomonas aeruginosa in vitro. Structure-activity relations are discussed. The metabolism stability of YDL-2, YDL-5, YDL-8, YDL-14, YDL-20-YDL-23 were evaluated in liver microsomes, which indicated that the 2-amino iso-Pr group may be a preferred structure than the 2-hydroxy Et group in the design of LpxC inhibitors. In addition to this study using Methyl 5-bromopicolinate, there are many other studies that have used Methyl 5-bromopicolinate(cas: 29682-15-3SDS of cas: 29682-15-3) was used in this study.

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.SDS of cas: 29682-15-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Kim, Jun Ki; Lim, Hwan Jung; Jeong, Kyung Chae; Park, Seong Jun published 《One-pot sequential synthesis of tetrasubstituted thiophenes via sulfur ylide-like intermediates》.Beilstein Journal of Organic Chemistry published the findings.HPLC of Formula: 31106-82-8 The information in the text is summarized as follows:

A novel approach for the practical synthesis of tetrasubstituted thiophenes was developed. The mechanism for this reaction was based on the formation of a sulfur ylide-like intermediate. It was clearly suggested by (i) the intramol. cyclization of ketene N,S-acetals to the corresponding thiophenes, (ii) 1H NMR studies of Meldrum’s acid-substituted aminothioacetals and (iii) substitution studies of the methoxy group on Meldrum’s acid containing N,S-acetals. Notably, in terms of structural effects on the reactivity and stability of sulfur ylide-like intermediates, 2-pyridyl substituted compound exhibited superior properties over those of others. In the experiment, the researchers used 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8HPLC of Formula: 31106-82-8)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) 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. HPLC of Formula: 31106-82-8

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Journal of Heterocyclic Chemistry included an article by Heppell, Jacob T.; Islam, Amirul Md.; McAlpine, Shelli R.; Al-Rawi, Jasim M. A.. Synthetic Route of C5H6BNO2. The article was titled 《Functionalization of Quinazolin-4-ones Part 3: Synthesis, Structures Elucidation, DNA-PK, PI3K, and Cytotoxicity of Novel 8-Aryl-2-morpholino-quinazolin-4-ones》. The information in the text is summarized as follows:

A series of novel 8-aryl-2-morpholino quinazolines I (X = H, Cl; Ar = C6H5, 4-ClC6H4, 3-pyridyl, etc.) and II (X = H, Cl; R1 = Me, Bn; Ar = C6H5, 4-MeOC6H4, 3-H2NC6H4, etc.) were synthesized from the precursor 2-thioxo quinazolin-4-one. The compounds I and II were assayed for DNA-dependent protein kinase (DNA-PK) and phosphatidylinositol 3-kinase (PI3K). All compounds showed low DNA-PK % inhibition activity at 10 μM compound concertation, and the compound I (X = H; Ar = dibenzo[b,d]thiophen-4-yl) was most active with 38% inhibition. Similar pattern of PI3K α, β, γ, and δ isoforms inhibition activity at 10 μM were observed and the most active isoform was PI3K δ of 41% inhibition for compound I (X = Cl; Ar = dibenzo[b,d]thiophen-4-yl). Most compounds were less active than expected in spite of the strong structural resemblance to known inhibitors. Loss of activity could be attributed to the tautomerization to the aromatic enol (4-OH), which could specify that the carbonyl (C=O) group is important functional group for the activity. Selected compounds displayed appreciable cytotoxicity and compound I (X = Cl; Ar = dibenzo[b,d]thiophen-4-yl) exhibiting the greatest activity with an IC50 of 9.95 μM, therefore, the mechanism of the cytotoxicity of this compd, were not through DNA-PK or PI3K inhibition activity. The experimental part of the paper was very detailed, including the reaction process of Pyridin-3-ylboronic acid(cas: 1692-25-7Synthetic Route of C5H6BNO2)

Pyridin-3-ylboronic acid(cas: 1692-25-7) 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.Synthetic Route of C5H6BNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,European Journal of Inorganic Chemistry included an article by Wang, Ping; Liang, Guangchao; Boyd, Chanteal Laquita; Webster, Charles Edwin; Zhao, Xuan. Electric Literature of C6H7Br2N. The article was titled 《Catalytic H2 Evolution by a Mononuclear Cobalt Complex with a Macrocyclic Pentadentate Ligand》. The information in the text is summarized as follows:

The use of H2 as fuel is considered as a potential solution for future energy demand, and there has been great interest in the design of metal catalysts for the H2 evolution from water with light and/or electricity over the past years. A mononuclear water soluble polypyridyl cobalt complex [Co(N4-Py)(H2O)](PF6)3 (4b) (N4-Py = N-methylpyridine-2,11-diaza[3,3](2,6)pyridinophane) was synthesized and characterized by elemental anal., mass spectrum, electrochem., and theor. calculations 4B can catalyze both electro- and photocatalytic H2 production in aqueous solutions Photocatalytic H2 production is achieved with a turnover number (TON) of 200 at pH 6 while electrolytic H2 production is accomplished with a TON of 140 at pH 7. Results from DFT computations indicate that the pentacoordinated CoII species is the active catalyst in the homogeneous H2 evolution by 4b, and the generation of H2 from a CoII-H species occurring via mononuclear heterolytic coupling is favorable by -23.0 kcal/mol. In the experimental materials used by the author, we found 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Electric Literature of C6H7Br2N)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) 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. Electric Literature of C6H7Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,ACS Medicinal Chemistry Letters included an article by Harrison, Tyler J.; Bauer, Daniel; Berdichevsky, Alina; Chen, Xin; Duvadie, Rohit; Hoogheem, Benjamin; Hatsis, Panos; Liu, Qian; Mao, Justin; Miduturu, Vasumathy; Rocheford, Erik; Zecri, Frederic; Zessis, Richard; Zheng, Rui; Zhu, Qingming; Streeper, Ryan; Patel, Sejal J.. Application of 13534-97-9. The article was titled 《Successful Strategies for Mitigation of a Preclinical Signal for Phototoxicity in a DGAT1 Inhibitor》. The information in the text is summarized as follows:

Diacylglycerol O-acyltransferase 1 (DGAT1) inhibitor Pradigastat (1) was shown to be effective at decreasing postprandial triglyceride levels in a patient population with familial chylomicronemia syndrome (FCS). Although pradigastat does not cause photosensitization in humans at the high clin. dose of 40 mg, a pos. signal was observed in preclin. models of phototoxicity. Herein, we describe a preclin. phototoxicity mitigation strategy for diarylamine containing mols. utilizing the introduction of an amide or suitable heterocyclic function. This strategy led to the development of two second-generation compounds with low risk of phototoxicity, disparate exposure profiles, and comparable efficacy to 1 in a rodent lipid bolus model for post-prandial plasma triglycerides. After reading the article, we found that the author used 6-Bromopyridin-3-amine(cas: 13534-97-9Application of 13534-97-9)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Application of 13534-97-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Excited-State Quenching of Porphyrins by Hydrogen-Bonded Phenol-Pyridine Pair: Evidence of Proton-Coupled Electron Transfer》 were Venkatesan, Munisamy; Mandal, Haraprasad; Chakali, Madhu; Bangal, Prakriti Ranjan. And the article was published in Journal of Physical Chemistry C in 2019. Synthetic Route of C6H4N2 The author mentioned the following in the article:

A series of porphyrins containing methoxy-substituted phenols were treated with different pyridine bases. Besides hydrogen bonding (H-bonding), the pyridine bases have imparted oxidation to the phenol rings resulting in coupled electron and proton movement. It has been shown that reduction of an excited substrate/porphyrin macrocycle by phenols with adjacent methoxy groups is facilitated by the movement or transfer of the phenolic proton toward H-bonded bases. Rates of electron transfer are accomplished by associated proton displacements within the redox reaction complex. Demonstrated fluorescence quenching of meso-(4-hydroxyphenyl derivatives)-substituted porphyrins in aprotic solvents is attributed to electron transfer from the phenol moiety by added bases (different pyridine derivatives), and rates of quenching are found to be correlated with Brönsted base strength rather than H-bonding equilibrium The rate of quenching is observed to be a function of the extent of hydroxy and methoxy substitutions to the phenyls and the solvent polarities. Replacement of 4-hydroxy by 4-methoxy completely eliminated the quenching indicating the disappearance of reduction in the porphyrin macrocycle. The dependence of the extent of fluorescence quenching of studied porphyrins on pyridine concentration led to phenol-pyridine H-bonding equilibrium constants, and these values closely resemble the values obtained directly from the corresponding absorption spectra. The quenching agent is thus revealed to be H-bonded phenol. Further, pos. deuterium isotope effects on quenching upon deuteration of the hydroxyl confirm that the electron transfer is coupled to the proton movement. In the experiment, the researchers used many compounds, for example, 4-Cyanopyridine(cas: 100-48-1Synthetic Route of C6H4N2)

4-Cyanopyridine(cas: 100-48-1) 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 C6H4N2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Streamlined Synthesis of Diaminopyridines by Pd-Catalyzed Ammonia Coupling with Deactivated Amino-Chloropyridines》 were Bourriquen, Florian; Bruneau-Voisine, Antoine; Jeandin, Alienor; Stihle, Etienne; Fantasia, Serena. And the article was published in Chemistry – A European Journal in 2019. Recommanded Product: 5-Bromo-2-chloropyridine The author mentioned the following in the article:

An efficient and cost-effective two-step synthesis of diaminopyridines, fundamental building blocks of biol. active compounds, is reported. The advantages over previously reported routes include cost and wider availability of the bromo-chloropyridine starting materials and the straightforward accessibility to an extended array of diaminopyridine regioisomers. The key enabler of this synthetic strategy is the development of an unprecedented palladium-catalyzed coupling reaction of ammonia with chloropyridines deactivated by the presence of an alkylamino substituent. The coupling reaction was accomplished with very low catalyst loadings under remarkably mild reaction conditions, making the system particularly suitable for both academic and industrial applications. The utility of this methodol. is exemplified by the application to the synthesis of highly relevant scaffolds, including the synthetic intermediates of the marketed drugs Ribociclib and Palbociclib. After reading the article, we found that the author used 5-Bromo-2-chloropyridine(cas: 53939-30-3Recommanded Product: 5-Bromo-2-chloropyridine)

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: 5-Bromo-2-chloropyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Convenient Continuous Flow Synthesis of N-Methyl Secondary Amines from Alkyl Mesylates and Epoxides》 was published in Organic Process Research & Development in 2020. These research results belong to Mathieu, Gary; Patel, Heena; Lebel, Helene. Related Products of 103-74-2 The article mentions the following:

The first continuous flow process was developed to synthesize N-Me secondary amines from alkyl mesylates and epoxides via a nucleophilic substitution using aqueous methylamine. A variety of N-Me secondary amines were produced in good to excellent yields, including a number of bioactive compounds, or their precursors. Up to 10.6 g (88% yield) of a N-Me secondary amine was produced in 140 min process time. The amination procedure included an in-line workup, and the starting mesylate material was also produced in continuous flow from the corresponding alc. Finally, an in-line process combining the mesylate synthesis and nucleophilic substitution was developed. The experimental process involved the reaction of 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Related Products of 103-74-2)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.Related Products of 103-74-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Millimeter-wave spectrum of 4-cyanopyridine in its ground state and lowest-energy vibrationally excited states, ν20 and ν30》 was published in Journal of Molecular Spectroscopy in 2020. These research results belong to Dorman, P. Matisha; Esselman, Brian J.; Park, Jieun E.; Woods, R. Claude; McMahon, Robert J.. Category: pyridine-derivatives The article mentions the following:

The rotational spectrum of 4-cyanopyridine (μa = 1.96 D) was recorded from 130 to 360 GHz, and the anal. of the ground state and two lowest-energy excited vibrational states was completed. Over 3900 new rotational transitions were measured for the ground state, allowing the determination of spectroscopic constants for a partial octic, distorted-rotor Hamiltonian. Over 5600 new transitions were measured for the Coriolis-coupled dyad, ν20 and ν30. A coupled-state least-squares fit of the dyad was obtained, which resulted in the precise determination of several parameters addressing the Coriolis coupling between the two states: Ga, GJa, Fbc, and FKbc. With inclusion of these terms, numerous resonance transitions associated with selection rules ΔKa = 2 or ΔKa = 4 between vibrational states were assigned and fit to low error (σfit < 50 kHz). The precise energy difference between ν20 and ν30 was determined, ΔE = 18.806554 (11) cm-1, along with the Coriolis coupling coefficient ζa20,30 = 0.8432 (8). Determination of the spectroscopic and perturbation parameters for the vibrational states permits comparison to other arenes bearing -CN or -NC substituents and sharing a similar Coriolis-coupled dyad ∼150 cm-1 above the ground state. This new data provides the foundation for an astrochem. search for 4-cyanopyridine in the interstellar medium. After reading the article, we found that the author used 4-Cyanopyridine(cas: 100-48-1Category: pyridine-derivatives)

4-Cyanopyridine(cas: 100-48-1) 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. Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem