Day: January 6, 2023

Design and synthesis of 7H-pyrrolo[2,3-d]pyrimidines as focal adhesion kinase inhibitors. Part 1 was written by Choi, Ha-Soon;Wang, Zhicheng;Richmond, Wendy;He, Xiaohui;Yang, Kunyong;Jiang, Tao;Sim, Taebo;Karanewsky, Donald;Gu, Xiang-Ju;Zhou, Vicki;Liu, Yi;Ohmori, Osamu;Caldwell, Jeremy;Gray, Nathanael;He, Yun. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2006.Category: pyridine-derivatives This article mentions the following:

(amino)(aryl)pyrrolo[2,3-d]pyrimidines such as I and II and pyridopyrimidines such as III are prepared as inhibitors of focal adhesion kinase (FAK). The structure-activity relationships for pyrrolopyrimidines are determined; electron-donating arylamino substituents at the 2-position and pyridinyl substituents at the 9-position lead to moderately active FAK inhibitors, while oxo-substituted analogs have reduced activities. I, II, and III inhibit FAK with IC₅₀ values of 0.1 μM, 0.1 μM, and 0.2 μM, resp., comparable to the initial lead compound IV (IC₅₀ = 0.1 μM). In the experiment, the researchers used many compounds, for example, 3-Bromo-4-fluoropyridine (cas: 116922-60-2Category: pyridine-derivatives).

3-Bromo-4-fluoropyridine (cas: 116922-60-2) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Metal-Free Difunctionalization of Pyridines: Selective Construction of N-CF₂H and N-CHO Dihydropyridines was written by Zhou, Sen;Sun, Ze-Ying;Zhu, Kongying;Zhao, Wentao;Tang, Xiangyang;Guo, Minjie;Wang, Guangwei. And the article was included in Organic Letters in 2021.HPLC of Formula: 626-64-2 This article mentions the following:

A novel nucleophilic addition of N-difluoromethylpyridinium salts with nitroalkanes to synthesize N-CF₂H-dihydropyridines and N-CHO-dihydropyridines in a highly efficient and regioselective pathway was reported. This protocol exhibited good functional group tolerance and good to excellent yields. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2HPLC of Formula: 626-64-2).

Pyridin-4-ol (cas: 626-64-2) 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. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.HPLC of Formula: 626-64-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Copper-Mediated Perfluoroalkylation of Heteroaryl Bromides with (phen)CuR_F was written by Mormino, Michael G.;Fier, Patrick S.;Hartwig, John F.. And the article was included in Organic Letters in 2014.COA of Formula: C7H4F3NO This article mentions the following:

The attachment of perfluoroalkyl groups onto organic compounds has been a major synthetic goal over the past several decades. Previously, our group reported phenanthroline-ligated perfluoroalkyl copper reagents, (phen)CuR_F, which react with aryl iodides and aryl boronates to form the corresponding benzotrifluorides. Herein the perfluoroalkylation of a series of heteroaryl bromides with (phen)CuCF₃ and (phen)CuCF₂CF₃ is reported. The mild reaction conditions allow the process to tolerate many common functional groups. Perfluoroethylation with (phen)CuCF₂CF₃ occurs in somewhat higher yields than trifluoromethylation with (phen)CuCF₃, creating a method to generate fluoroalkyl heteroarenes that are less accessible from trifluoroacetic acid derivatives In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethyl)nicotinaldehyde (cas: 116308-35-1COA of Formula: C7H4F3NO).

2-(Trifluoromethyl)nicotinaldehyde (cas: 116308-35-1) 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.COA of Formula: C7H4F3NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Interfering with Metabolic Profile of Triple-Negative Breast Cancers Using Rationally Designed Metformin Prodrugs was written by Babak, Maria V.;Chong, Kai Ren;Rapta, Peter;Zannikou, Markella;Tang, Hui Min;Reichert, Lisa;Chang, Meng Rui;Kushnarev, Vladimir;Heffeter, Petra;Meier-Menches, Samuel M.;Lim, Zhi Chiaw;Yap, Jian Yu;Casini, Angela;Balyasnikova, Irina V.;Ang, Wee Han. And the article was included in Angewandte Chemie, International Edition in 2021.Formula: C12H9NO This article mentions the following:

Triple-neg. breast cancer (TNBC) is the most aggressive subtype of breast cancer, characterized by an aberrant metabolic phenotype with high metastatic capacity, resulting in poor patient prognoses and low survival rates. We designed a series of novel AuIII cyclometalated prodrugs of energy-disrupting Type II antidiabetic drugs namely, metformin and phenformin. Prodrug activation and release of the metformin ligand was achieved by tuning the cyclometalated AuIII fragment. The lead complex 3met was 6000-fold more cytotoxic compared to uncoordinated metformin and significantly reduced tumor burden in mice with aggressive breast cancers with lymphocytic infiltration into tumor tissues. These effects was ascribed to 3met interfering with energy production in TNBCs and inhibiting associated pro-survival responses to induce deadly metabolic catastrophe. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Formula: C12H9NO).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) 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 derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Formula: C12H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Thermal stability limits of imidazolium, piperidinium, pyridinium, and pyrrolidinium ionic liquids immobilized on metal oxides was written by Kurtoglu-Oztulum, Samira F.;Jalal, Ahsan;Uzun, Alper. And the article was included in Journal of Molecular Liquids in 2022.COA of Formula: C10H16BrN This article mentions the following:

Twenty-nine different ionic liquids (ILs) consisting of imidazolium, pyridinium, piperidinium, and pyrrolidinium cations and I^–, Cl^–, Br^–, PF^–₆, BF^–₄, [DCA]^–, and [NTf₂]^– anions were immobilized on MgO and SiO₂. Their short-term thermal stability limits were investigated by thermogravimetric anal. and compared with those of the corresponding bulk ILs. Data showed that the thermal stability limits of ILs change significantly when the ILs are immobilized on metal oxides. These changes were evaluated based on the structural interactions determined by IR spectroscopy. Systematic structural differences were considered to investigate the factors affecting the thermal stability of bulk ILs, and their counterparts immobilized on MgO and SiO₂. These structural changes were the change in the alkyl chain length, the methylation on C2 site in imidazolium ILs, the change in substituent position in the pyridinium ring, the change in the anion, and the change in the IL family. The strongest factor controlling the thermal stability limits of both bulk ILs and their supported counterparts was determined as the anion type. Accordingly, the basicity of the anion and the surface acidity of the metal oxide and their resulting interactions were found to have a significant effect on the thermal stability limits. Data presented here offer the opportunity to pick a suitable anion and cation pair according to the metal oxide, so that the supported IL can withstand the desired operation conditions in various applications, such as catalysis or gas separation In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6COA of Formula: C10H16BrN).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) 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. 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.COA of Formula: C10H16BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Triplet-triplet energy transfer study in hydrogen bonding systems was written by Wang, Zhijia;Zhao, Jianzhang;Guo, Song. And the article was included in Chimia in 2015.HPLC of Formula: 1075-62-3 This article mentions the following:

The 2,6-diiodoBodipy-styrylBodipy hydrogen bonding system was prepared to study the effect of hydrogen bonding on the triplet-triplet-energy-transfer (TTET) process. 2,6-DiiodoBodipy linked with N-acetyl-2,6-diaminopyridine (D-2) was used as the triplet energy donor, and the styrylBodipy connected with thymine (A-1) was used as triplet energy acceptor, thus the TTET process was established upon photoexcitation. The photophys. processes of the hydrogen bonding system were studied with steady-state UV-vis absorption spectroscopy, fluorescence spectroscopy, fluorescence lifetime measurement and nanosecond time-resolved transient absorption spectroscopies. The TTET of the intramol./hydrogen bonding/intermol. systems were compared through nanosecond transient absorption spectroscopy. The TTET process of the hydrogen bonding system is faster and more efficient (kTTET = 6.9 × 104 s-1, ΦTTET = 94.0%) than intermol. triplet energy transfer (kTTET = 6.0 × 104 s-1, ΦTTET = 90.9%), but slower and less efficient than intramol. triplet energy transfer (kTTET > 108 s-1). These results are valuable for designing self-assembly triplet photosensitizers and for the study of the TTET process of hydrogen bonding systems. In the experiment, the researchers used many compounds, for example, N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3HPLC of Formula: 1075-62-3).

N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. 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.HPLC of Formula: 1075-62-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Aqueous Suzuki-Miyaura Reaction with 0.6 Equivalent of Base: Green and Efficient Access to Biaryls and Unsymmetrical Terphenyls was written by Li, Xinmin;Teng, Yong;Feng, Fangfang;Hu, Qinghong;Yuan, Zeli. And the article was included in ChemistrySelect in 2018.Related Products of 4373-61-9 This article mentions the following:

A green and efficient protocol for the synthesis of biaryls by a Pd(OAc)₂-catalyzed ligand-free Suzuki-Miyaura reaction was described. The reaction proceeded smoothly in water and gives good yields in the presence of 0.6 equivalent of base. Addnl., using bromo-N-methyliminodiacetic acid (MIDA) boronates as building block, one-pot double Suzuki-Miyaura reaction was achieved by controlling the amount of base and various unsym. terphenyls were prepared in moderate to good yields. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Related Products of 4373-61-9).

2-(m-Tolyl)pyridine (cas: 4373-61-9) 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. 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 4373-61-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Nickel-Catalyzed Reaction of Aryl 2-Pyridyl Ethers with Silylzinc Chlorides: Silylation of Aryl 2-Pyridyl Ethers via Cleavage of the Carbon-Oxygen Bond was written by Kong, Ying-Ying;Wang, Zhong-Xia. And the article was included in Advanced Synthesis & Catalysis in 2019.COA of Formula: C11H9NO This article mentions the following:

Ni-catalyzed C-O(Py) bond activation and silylation of aryl 2-pyridyl ethers with silylzinc chlorides were carried out. This protocol allowed the 2-pyridyloxy group to be substituted by a silyl group with short reaction times, mild reaction conditions, and good compatibility of functional groups. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0COA of Formula: C11H9NO).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. COA of Formula: C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Palladium-Catalyzed Directed Halogenation of Bipyridine N-Oxides was written by Zucker, Sina P.;Wossidlo, Friedrich;Weber, Manuela;Lentz, Dieter;Tzschucke, C. Christoph. And the article was included in Journal of Organic Chemistry in 2017.Computed Properties of C8H8BrNO2 This article mentions the following:

The palladium-catalyzed directed C-H halogenation of bipyridine N-oxides was investigated. Using NCS or NBS (N-chloro- or N-bromosuccinimide) and 5 mol % Pd(OAc)₂ in chlorobenzene (0.10 M) at 110 °C, pyridine-directed functionalization took place and 3-chloro- or 3-bromobipyridine N-oxides were obtained in high yields. The reaction is sensitive to steric hindrance by 4- and 6′-substituents. Only in the latter case, where coordination of palladium by the pyridine is hindered, 3′-halogenation directed by the N-oxide function was observed The halogenated products were deoxygenated by PCl₃ or PBr₃. In the experiment, the researchers used many compounds, for example, Ethyl 2-bromoisonicotinate (cas: 89978-52-9Computed Properties of C8H8BrNO2).

Ethyl 2-bromoisonicotinate (cas: 89978-52-9) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. 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.Computed Properties of C8H8BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Direct dissolution and NMR analysis of the plant cell walls via perdeuterated pyridinium-based ionic liquid was written by Jiang, Nan;Pu, Yunqiao;Samuel, Reichel;Ragauskas, Arthur J.. And the article was included in Preprints of Symposia – American Chemical Society, Division of Fuel Chemistry in 2010.Formula: C7H7ClN2 This article mentions the following:

This article presents the perdeuterated pyridinium ionic liquid system for direct dissolution and NMR anal. of the Wiley milled and ball-milled plant cell walls to reveal the detailed structure of the plant cell walls. The unique properties and easy preparation of pyridinium-based ionic liquid [Hpyr]Cl-d₆ offer significant benefits over imidazolium-based ionic liquids for NMR characterization of the non-ball-milled plant cell walls. Further applications of this novel ionic liquid-based solvent system include the determination of lignin content, H:S:G ratios and inter-unit lignin bonding arrangements, without the need for lengthy lignin isolation procedures. In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3Formula: C7H7ClN2).

1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) 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. 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.Formula: C7H7ClN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem