Month: December 2022

Pd-Catalyzed Synthesis of Aryl and Heteroaryl Triflones from Reactions of Sodium Triflinate with Aryl (Heteroaryl) Triflates was written by Smyth, Lynette A.;Phillips, Eric M.;Chan, Vincent S.;Napolitano, Jose G.;Henry, Rodger;Shekhar, Shashank. And the article was included in Journal of Organic Chemistry in 2016.Safety of 5-Hydroxy-2-methoxylpyridine This article mentions the following:

A novel method for Pd-catalyzed triflination of aryl and heteroaryl triflates using NaSO₂CF₃ as the nucleophile is described. The combination of Pd₂(dba)₃ and RockPhos formed the most effective catalyst. A broad range of functional groups and heteroaromatic compounds were tolerated under the neutral reaction conditions. The order of reactivity ArOTf ≥ ArCl ≥ ArBr is consistent with transmetalation being a slow step of the reaction. In the experiment, the researchers used many compounds, for example, 5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0Safety of 5-Hydroxy-2-methoxylpyridine).

5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Safety of 5-Hydroxy-2-methoxylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Meso-pyridinium substituted BODIPY dyes as mitochondria-targeted probes for the detection of cysteine in living cells and in vivo was written by Ji, Xin;Wang, Nannan;Zhang, Jian;Xu, Shuang;Si, Yubing;Zhao, Weili. And the article was included in Dyes and Pigments in 2021.Synthetic Route of C5H5NO This article mentions the following:

Cysteine (Cys) is a crucial bio-thiol attributing to its significant role in many physiol. and pathol. processes and maintaining redox dynamic balance. In mitochondria, ROS can cause oxidative damage, and Cys can solve this problem by acting as an antioxidant. Herein, we designed and synthesized a series of meso-pyridin and meso-pyridinium substituted BODIPY dyes as fluorescent probes to distinguish Cys. Through screening the responsive behaviors of the all probes toward biothiols, we obtained an appropriate mitochondria-targeted probe BDP-S-o-Py⁺ for Cys-specific detection. D. functional theory (DFT) calculations were used to demonstrate the different reactivity of the probes. BDP-S-o-Py⁺ could detect Cys with fast response under biol. environment. The probe BDP-S-o-Py⁺ had a low limit of detection (LOD, 72 nM) at the linear dynamic range from 0 to 50 μM. In particularly, BDP-S-o-Py⁺ could be used for imaging of mitochondrial Cys in living cells, and was capable of monitoring endogenous Cys in vivo, successfully. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Synthetic Route of C5H5NO).

Pyridin-4-ol (cas: 626-64-2) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Synthetic Route of C5H5NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Late-stage synthesis and application of photoreactive probes derived from direct benzoylation of heteroaromatic C-H bonds was written by Hesp, Kevin D.;Xiao, Jun;West, Graham M.. And the article was included in Organic & Biomolecular Chemistry in 2020.SDS of cas: 59718-84-2 This article mentions the following:

A C-H functionalization strategy for the expedient access to photoreactive chem. probes of commonly found heterocyclic fragments RC₆H₄C(O)R¹ [R = H, 4-(CHCCH₂O), 4-N₃, 3-(CHC), etc.; R¹ = pyrazin-2-yl, isoquinolin-1-yl, pyridazin-4-yl, etc.] or drug mols. of pharmaceutical relevance is described. A series of aryl glyoxylic acid reagents featuring pendant alkyne or azide clickable handles RC₆H₄C(O)C(O)OH have been developed for application in the radical-mediated appendage of benzoyl fragments onto simple heteroaromatic fragments RC₆H₄C(O)R¹, as well as more complex drug-like compounds This unprecedented strategy of chem. probe synthesis allows for direct access to photoreactive chem. probes without any requirement of fragment pre-functionalization or significant synthetic re-evaluation. In the experiment, the researchers used many compounds, for example, Methyl 3-methylpicolinate (cas: 59718-84-2SDS of cas: 59718-84-2).

Methyl 3-methylpicolinate (cas: 59718-84-2) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.SDS of cas: 59718-84-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Development of an ionization method using hydrogenated plasma for mass analysis of surface adhesive compounds was written by Aida, Mari;Iwai, Takahiro;Okamoto, Yuki;Miyahara, Hidekazu;Seto, Yasuo;Okino, Akitoshi. And the article was included in Journal of Analytical Atomic Spectrometry in 2018.Synthetic Route of C8H11N This article mentions the following:

Currently, atm. plasmas are applied to the desorption and ionization of surface adhesive materials for rapid and highly sensitive anal. One widely used chem. ionization method applies protons generated from atm. water mols. to a desorbed sample; however, a detailed study of the ionization mechanism has not been addressed thus far. Therefore, this paper proposes an ionization method that adds a small, optimized amount of hydrogen to the helium plasma for generating protons in the sample ionization source. Using this technique, mass spectrometry was performed on the sample surface deposits of 2-isopropylpyridine and 4-isopropylaniline. The hydrogen flow rate was optimized to the addition ratio of 2%, and the lowest limit of detection achieved is 0.1 and 42 pmol for 2-isopropylpyridine and 4-isopropylaniline, resp. By optimizing the hydrogen addition flow rate, the optimum number of protons for sample ionization was attained, and it became possible to realize control of proton content in the sample, irresp. of humidity and surrounding environmental factors during mass spectrometry. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Synthetic Route of C8H11N).

2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Synthetic Route of C8H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Discovery of 3-Benzyl-1-(trans-4-((5-cyanopyridin-2-yl)amino)cyclohexyl)-1-arylurea Derivatives as Novel and Selective Cyclin-Dependent Kinase 12 (CDK12) Inhibitors was written by Ito, Masahiro;Tanaka, Toshio;Toita, Akinori;Uchiyama, Noriko;Kokubo, Hironori;Morishita, Nao;Klein, Michael G.;Zou, Hua;Murakami, Morio;Kondo, Mitsuyo;Sameshima, Tomoya;Araki, Shinsuke;Endo, Satoshi;Kawamoto, Tomohiro;Morin, Gregg B.;Aparicio, Samuel A.;Nakanishi, Atsushi;Maezaki, Hironobu;Imaeda, Yasuhiro. And the article was included in Journal of Medicinal Chemistry in 2018.Safety of 6-Fluoronicotinonitrile This article mentions the following:

Cyclin-dependent kinase 12 (CDK12) plays a key role in the coordination of transcription with elongation and mRNA processing. CDK12 mutations found in tumors and CDK12 inhibition sensitize cancer cells to DNA-damaging reagents and DNA-repair inhibitors. This suggests that CDK12 inhibitors are potential therapeutics for cancer that may cause synthetic lethality. Here, we report the discovery of 3-benzyl-1-(trans-4-((5-cyanopyridin-2-yl)amino)cyclohexyl)-1-arylurea derivatives as novel and selective CDK12 inhibitors. Structure-activity relationship studies of a HTS hit, structure-based drug design, and conformation-oriented design using the Cambridge Structural Database afforded the optimized compound 2, which exhibited not only potent CDK12 (and CDK13) inhibitory activity and excellent selectivity but also good physicochem. properties. Furthermore, 2 inhibited the phosphorylation of Ser2 in the C-terminal domain of RNA polymerase II and induced growth inhibition in SK-BR-3 cells. Therefore, 2 represents an excellent chem. probe for functional studies of CDK12 and could be a promising lead compound for drug discovery. In the experiment, the researchers used many compounds, for example, 6-Fluoronicotinonitrile (cas: 3939-12-6Safety of 6-Fluoronicotinonitrile).

6-Fluoronicotinonitrile (cas: 3939-12-6) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Safety of 6-Fluoronicotinonitrile

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Recyclable ionic liquid iodinating reagent for solvent-free, regioselective iodination of activated aromatic and heteroaromatic amines was written by Deshmukh, Amarsinh;Gore, Babasaheb;Thulasiram, Hirekodathakallu V.;Swamy, Vincent P.. And the article was included in RSC Advances in 2015.Synthetic Route of C10H16ClN This article mentions the following:

A simple, efficient method for iodination of activated aromatic amines [C₆H₅NH₂, 2-BrC₆H₄NH₂, 2,6-(H₃C)₂C₆H₃NH₂, etc.] and heteroaromatic amines such as 1-methylimidazole, 8-hydroxyquinoline, 5-chloro-8-hydroxyquinoline using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCl) as an ionic liquid iodinating reagent, in the absence of any solvent has been described. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3Synthetic Route of C10H16ClN).

1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Synthetic Route of C10H16ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of 2-arylfuro[3,2-b]pyridines: Effect of the C2-aryl group on melatoninergic activity was written by Couhert, Audrey;Delagrange, Philippe;Caignard, Daniel-Henri;Chartier, Agnes;Suzenet, Franck;Guillaumet, Gerald. And the article was included in European Journal of Medicinal Chemistry in 2016.Category: pyridine-derivatives This article mentions the following:

An efficient synthesis of 2-substituted furo[3,2-b]pyridines and their biol. evaluation as melatonin receptors ligands was reported. The proposed eight-step sequence ending with a Suzuki coupling allowed a rapid access to various analogs. The steric hindrance and the conformation of the aryl group in C2-position were evaluated regarding the selectivity of the mol. for one of the two high affinity melatonin receptors as well as the activity profile of the compound Introduction of 1-naphthyl substituent gave the best result in terms of selectivity with a MT₁/MT₂ ratio of about 150 (MT₁ K_i = 198 nM, MT₂ K_i = 1.3 nM). In the experiment, the researchers used many compounds, for example, 5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0Category: pyridine-derivatives).

5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of Decahydrocyclobuta[cd]indene Skeletons: Rhodium(III)-Catalyzed Hydroarylation and Relay Thiophene-Promoted Intramolecular [2+2] Cycloaddition was written by Gao, Dingding;Wang, Feng;Liu, Xing-Yu;Feng, Kai-Rui;Zhao, Jia-Ying;Wang, Yu-Hui;Yang, Xiao-Di;Tian, Ping;Lin, Guo-Qiang. And the article was included in Advanced Synthesis & Catalysis in 2020.Related Products of 54151-74-5 This article mentions the following:

The preparation of decahydrocyclobuta[cd]indene skeleton was accomplished through rhodium(III)-catalyzed hydroarylation and relay thiophene-promoted intramol. [2+2] cycloaddition This tandem reaction exhibited broad substrate scope (24 examples) and good functional group compatibility. Control experiments revealed the important role of sulfur (S) heteroatom, thus a tentative mechanism with thiophene-promoted double Michael additions was proposed to explain this formal [2+2] cycloaddition Moreover, the resulting polycyclic products displayed potent anti-cancer activities against breast cancer cell lines MDA-MB-468. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-phenylpyridine (cas: 54151-74-5Related Products of 54151-74-5).

2-Bromo-4-phenylpyridine (cas: 54151-74-5) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Related Products of 54151-74-5

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Mild C(sp³)-H Alkylation of 8-Methylquinolines with α,β-Unsaturated Carbonyl Compounds by Rhodium(III) Catalysis was written by Han, Shengnan;Ma, Wenbo;Zhang, Zhao;Liu, Lei;Tang, Mengyao;Li, Jie. And the article was included in Asian Journal of Organic Chemistry in 2017.Related Products of 644-98-4 This article mentions the following:

A straightforward approach to the synthesis of γ-quinolyl carbonyl compounds RCH₂CH₂CH₂C(O)R¹ (R = quinolin-8-yl, 6-chloroquinolin-8-yl, 7-methylquinolin-8-yl, etc.; R¹ = Me, cyclohexyl, 1-naphthyl, furan-2-yl, benzo[d][1,3]dioxol-5-yl, etc.) has been developed by a rhodium(III)-catalyzed C(sp³)-H alkylation of 8-methylquinolines such as 8-methylquinoline, 5-chloro-8-methylquinoline, 5-styryl-8-methylquinoline, etc. with conjugated C=C multiple bonds. Remarkably, this C(sp³)-H functionalization proceeds under mild reaction conditions, obviates the need for external oxidants, and features high atom-economy, ample substrate scope and wide functional group tolerance. Mechanistic studies provided strong support for an irreversible C(sp³)-H bond activation. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Related Products of 644-98-4).

2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Related Products of 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Selective C-H trifluoromethoxylation of (hetero)arenes as limiting reagent was written by Deng, Zhijie;Zhao, Mingxin;Wang, Feng;Tang, Pingping. And the article was included in Nature Communications in 2020.Product Details of 626-64-2 This article mentions the following:

A general late-stage C-H trifluoromethoxylation of arenes and heteroarenes RH (R = 4-methoxypyridin-2-yl, 4-t-butylphenyl, 3-acetylbenzothien-2-yl, etc.) as limiting reagent with trifluoromethoxide anion was described. The reaction is mediated by silver salts under mild reaction conditions, exhibiting broad substrate scope and wide functional-group compatibility. In addition, ortho-position selective C-H trifluoromethoxylation of pyridines is observed The method is not only applicable to the gram-scale synthesis of trifluoromethoxylated products ROCF₃ but also allows efficient late-stage C-H trifluoromethoxylation of marketed small-mol. drugs, common pharmacophores and natural products. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Product Details of 626-64-2).

Pyridin-4-ol (cas: 626-64-2) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Product Details of 626-64-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem