Tag: 200-300

Electric Literature of C6H5Br2NOOn June 1, 2011, Allcock, Robert W.; Blakli, Haakon; Jiang, Zhong; Johnston, Karen A.; Morgan, Keith M.; Rosair, Georgina M.; Iwase, Kazuhiko; Kohno, Yasushi; Adams, David R. published an article in Bioorganic & Medicinal Chemistry Letters. The article was 《Phosphodiesterase inhibitors. Part 1: Synthesis and structure-activity relationships of pyrazolopyridine-pyridazinone PDE inhibitors developed from ibudilast》. The article mentions the following:

Ibudilast [1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one] is a nonselective phosphodiesterase inhibitor used clin. to treat asthma. Efforts to selectively develop the PDE3- and PDE4-inhibitory activity of ibudilast led to replacement of the iso-Pr ketone by a pyridazinone heterocycle. Structure-activity relationship exploration in the resulting 6-(pyrazolo[1,5-a]pyridin-3-yl)pyridazin-3(2H)-ones revealed that the pyridazinone lactam functionality is a critical determinant for PDE3-inhibitory activity, with the nitrogen preferably unsubstituted. PDE4 inhibition is strongly promoted by introduction of a hydrophobic substituent at the pyridazinone N(2) center and a methoxy group at C-7′ in the pyrazolopyridine. Migration of the pyridazinone ring connection from the pyrazolopyridine 3′-center to C-4′ strongly enhances PDE4 inhibition. These studies establish a basis for development of potent PDE4-selective and dual PDE3/4-selective inhibitors derived from ibudilast. In addition to this study using 2,3-Dibromo-6-methoxypyridine, there are many other studies that have used 2,3-Dibromo-6-methoxypyridine(cas: 909720-21-4Electric Literature of C6H5Br2NO) was used in this study.

2,3-Dibromo-6-methoxypyridine(cas: 909720-21-4) 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.Electric Literature of C6H5Br2NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromideIn 2017 ,《(Aminomethylene)phosphonate Analogues as ZnII Chelators: Synthesis and Characterization》 appeared in European Journal of Inorganic Chemistry. The author of the article were Hevroni, Bosmat Levi; Jantz, Thomas; Gottlieb, Hugo E.; Fischer, Bilha. The article conveys some information:

A series of (aminomethylene)phosphonate (AMP) analogs, 8-14, bearing one or two heterocyclic moieties (imidazolyl, pyridyl, and thiazolyl) on the aminomethylene group, were synthesized as potential ZnII chelators. The complexes of analogs 8-14 with ZnII ions were characterized by their stoichiometry, geometry, coordination sites, acid/base equilibrium, and stability constants Analogs 8-14 form stable water-soluble 2:1 L/ZnII complexes, as established by ZnII titration, monitored by UV/visible spectrophotometry and by 1H and 31P NMR spectroscopy. Acidity and stability constants were established for each derivative by potentiometric pH titrations ML2 type ZnII complexes of AMP, bearing either an imidazolyl or pyridyl moiety, 8, 10, and 12, exhibit high log β values (17.68, 16.92, and 16.65, resp.), while for the AMP-thiazolyl (14) complex with ZnII, log β is 12.53. Generally, ligands 9, 11, and 13, bearing two heterocyclic moieties, present higher log β values (22.25, 21.00, and 18.28, resp.) vs. analogs bearing one heterocyclic moiety. Addnl., based on 1H, 13C, and 31P NMR spectroscopic data, the authors propose a structure of the AMP-(Im)2-ZnII complex in solution, where the ZnII coordination sites involve the phosphonate moiety and both imidazolyl rings of the two binding mols., forming an octahedral geometry around the ZnII ion. In summary, the authors propose a new family of water-soluble high-affinity ZnII chelators, in particular AMP-(Im)2, which forms the most stable complex (log β 22).2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide) was used in this study.

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) 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.Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lisboa, Lynn S.; Riisom, Mie; Vasdev, Roan A. S.; Jamieson, Stephen M. F.; Wright, L. James; Hartinger, Christian G.; Crowley, James D. published an article in 2021. The article was titled 《Cavity-containing [Fe2L3] 4+ helicates: an examination of host-guest chemistry and cytotoxicity》, and you may find the article in Frontiers in Chemistry (Lausanne, Switzerland).Electric Literature of C5H3Br2N The information in the text is summarized as follows:

Two new di(2,2′-bipyridine) ligands, 2,6-bis([2,2′-bipyridin]-5-ylethynyl)pyridine (L1) and bis(4-([2,2′-bipyridin]-5-ylethynyl)phenyl)methane (L2) were synthesized and used to generate two metallosupramol. [Fe2(L)3](BF4)4 cylinders. The ligands and cylinders were characterized using elemental anal., electrospray ionization mass spectrometry, UV-vis, 1H-, 13C and DOSY NMR (NMR) spectroscopies. The mol. structures of the [Fe2(L)3](BF4)4 cylinders were confirmed using X-ray crystallog. Both the [Fe2(L1)3](BF4)4 and [Fe2(L2)3](BF4)4 complexes crystallized as racemic (rac) mixtures of the δδ (P) and λλ (M) helicates. However, 1H NMR spectra showed that in solution the larger [Fe2(L2)3](BF4)4 was a mixture of the rac δδ/λλ and meso-δλ isomers. The host-guest chem. of the helicates, which both feature a central cavity, was examined with several small drug mols. However, none of the potential guests were found to bind within the helicates. In vitro cytotoxicity assays demonstrated that both helicates were active against four cancer cell lines. The smaller [Fe2(L1)3](BF4)4 system displayed low μM activity against the HCT116 (IC50 = 7.1 ± 0.5 μM) and NCI-H460 (IC50 = 4.9 ± 0.4 μM) cancer cells. While the antiproliferative effects against all the cell lines examined were less than the well-known anticancer drug cisplatin, their modes of action would be expected to be very different. The experimental part of the paper was very detailed, including the reaction process of 2,6-Dibromopyridine(cas: 626-05-1Electric Literature of C5H3Br2N)

2,6-Dibromopyridine(cas: 626-05-1) 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. Electric Literature of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《The Suzuki-Miyaura Cross-Coupling as the Key Step in the Synthesis of 2-Aminobiphenyls and 2,2′-Diaminobiphenyls: Application in the Synthesis of Schiff Base Complexes of Zn》 was published in European Journal of Organic Chemistry in 2020. These research results belong to Hylland, Knut Tormodssoenn; Oien-Odegaard, Sigurd; Tilset, Mats. Computed Properties of C5H3Br2N The article mentions the following:

2-Nitrophenylboronic acids serve as interesting starting materials for the construction of biphenyl- and terphenyl-based amines if subjected to the Suzuki-Miyaura reaction. Unfortunately, these boronic acids suffer from low reactivity in Suzuki reactions, alongside their low stability in the presence of Pd. Herein, a general method for the construction of 2-nitro-substituted bi- and terphenyls is presented, with special emphasis on the synthesis of 2-amino-2′-nitrobi- and terphenyls. Comparisons are made with other boronic acids that have some of the aforementioned issues. Finally, the application of the obtained 2-amino-2′-nitrobi- and terphenyls as starting materials for the synthesis of bi- and terphenyl based di- and triamines is encountered for, with emphasis on the use of these amines as precursors for Schiff base ligands. In addition, the synthesis of some Zn complexes of these ligands is presented. In the part of experimental materials, we found many familiar compounds, such as 2,5-Dibromopyridine(cas: 624-28-2Computed Properties of C5H3Br2N)

2,5-Dibromopyridine(cas: 624-28-2) 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.Computed Properties of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Heterogeneous photocatalytic degradation of picloram, dicamba, and floumeturon in aqueous suspensions of titanium dioxide》 was published in Journal of Environmental Science and Health in 2005. These research results belong to Rahman, M. Atiqur; Muneer, M.. COA of Formula: C6H2Cl3NO2 The article mentions the following:

Heterogeneous photocatalytic degradation of picloram, dicamba and floumeturon has been investigated in aqueous suspensions of titanium dioxide under a variety of conditions. The degradation was studied by monitoring the change in substrate concentration employing UV spectroscopic technique and decrease in total organic carbon (TOC) content as a function of irradiation time under a variety of conditions. The degradation of the herbicide was studied under different conditions such as pH, catalyst concentration, substrate concentration, different types of TiO2, and in the presence of electron acceptors such as H2O2, KBrO3, and (NH4)2S2O8 besides mol. oxygen. The degradation rates were found to be strongly influenced by all the above parameters. The photocatalyst Degussa P25 was found to be more efficient as compared with other photocatalysts in the case of dicamba and floumeturon, whereas Hombikat UV100 was found to be better for the degradation of picloram. The herbicide picloram was found to degrade faster as compared to dicamba and floumeturon. The degradation products were analyzed by gas chromatog.-mass spectrometry (GC/MS) technique, and plausible mechanisms for the formation of products have been proposed. The experimental part of the paper was very detailed, including the reaction process of 3,5,6-Trichloropicolinic acid(cas: 40360-44-9COA of Formula: C6H2Cl3NO2)

3,5,6-Trichloropicolinic acid(cas: 40360-44-9) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.COA of Formula: C6H2Cl3NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Mitochondria targeted and NADH triggered photodynamic activity of chloromethyl modified Ru(II) complexes under hypoxic conditions》 were Tian, Na; Sun, Weize; Guo, Xusheng; Lu, Jian; Li, Chao; Hou, Yuanjun; Wang, Xuesong; Zhou, Qianxiong. And the article was published in Chemical Communications (Cambridge, United Kingdom) in 2019. COA of Formula: C12H10Cl2N2 The author mentioned the following in the article:

Three chloromethyl-modified Ru(II) complexes were designed and synthesized as mitochondria targeting photosensitizers, which can generate carbon radicals in the presence of NADH under visible light irradiation, cause DNA cleavage and covalent binding in Ar-saturated solutions, and lead to apoptosis of human ovarian carcinoma SKOV-3 cells under hypoxic conditions (3% O2), demonstrating a new mode of type I mechanism to overcome the limitation of hypoxia in photodynamic therapy (PDT). The results came from multiple reactions, including the reaction of 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4COA of Formula: C12H10Cl2N2)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. 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. COA of Formula: C12H10Cl2N2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Name: 2,6-DibromopyridineIn 2020 ,《A novel approach for rhodium(III)-catalyzed C-H functionalization of 2,2′-bipyridine derivatives with alkynes: a significant substituent effect》 appeared in Chemical Communications (Cambridge, United Kingdom). The author of the article were Wu, Shaonan; Wang, Zhuo; Bao, Yinwei; Chen, Chen; Liu, Kun; Zhu, Bolin. The article conveys some information:

The authors described a novel approach for the C-H functionalization of 2,2′-bipyridine derivatives with alkynes. DFT calculations and exptl. data showed a significant substituent effect at the 6-position of 2,2′-bipyridine, which weakened the adjacent N-Rh bond and provided the possibility of subsequent rollover cyclometalation, C-H activation, and functionalization.2,6-Dibromopyridine(cas: 626-05-1Name: 2,6-Dibromopyridine) was used in this study.

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. Pyridine and pyridine-derived structures are privileged pharmacophores in medicinal chemistry and an essential functionality for organic chemists. As the prototypical π-deficient heterocycle, pyridine illustrates distinctive chemistry as both substrate and reagent. Name: 2,6-Dibromopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《A conjugated microporous polymer as a recyclable heterogeneous ligand for highly efficient regioselective hydrosilylation of allenes》 was written by Jiang, Ya-Nan; Zeng, Jia-Hao; Yang, Ying; Liu, Zhi-Kai; Chen, Jun-Jia; Li, Ding-Chang; Chen, Li; Zhan, Zhuang-Ping. Electric Literature of C5H3Br2N And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020. The article conveys some information:

Pyridines containing adjacent CC bonds were utilized as ligand units and integrated into the skeleton of conjugated microporous polymers. The resultant Pd-CMP-1 was first applied as a highly efficient heterogeneous catalytic system for Pd-catalyzed allene hydrosilylation towards a wide range of allenes to produce branched allylsilanes with high regioselectivity. The ligand units of the polymer, along with the confinement effect of the porous structure, jointly regulated the regioselectivity. The parts-per-million (ppm) levels of Pd, coordinated with the recyclable heterogeneous ligand, show promise for industrial applications. This work opens a new front of using CMP as an intriguing platform for developing highly efficient catalysts to control the regioselectivities in allene hydrosilylation. The results came from multiple reactions, including the reaction of 2,6-Dibromopyridine(cas: 626-05-1Electric Literature of C5H3Br2N)

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. Pyridines form stable salts with strong acids. Pyridine itself is often used to neutralize acid formed in a reaction and as a basic solvent. Electric Literature of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Kariofillis, Stavros K.; Jiang, Shutian; Zuranski, Andrzej M.; Gandhi, Shivaani S.; Martinez Alvarado, Jesus I.; Doyle, Abigail G. published an article in 2022. The article was titled 《Using Data Science To Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources》, and you may find the article in Journal of the American Chemical Society.Product Details of 29682-15-3 The information in the text is summarized as follows:

Ni/photoredox-catalyzed (deutero)methylation and alkylation of aryl halides RX (R = Ph, Ac, t-Bu, etc.; X = Br, Cl) and benzaldehyde di(alkyl) acetals R1CH(OR2)2 (R1 = Ph, 4-(1H-imidazol-4-yl)benzen-1-yl, 5-tert-butyl-2-chlorophenyl, etc.; R2 = Me, Et, Bn, etc.) that serve as alc.-derived radical sources were reported. Reaction development, mechanistic studies, and late-stage derivatization of a biol. relevant aryl chloride, fenofibrate, are presented. Then, the integration of data science techniques, including DFT featurization, dimensionality reduction, and hierarchical clustering, to delineate a diverse and succinct collection of aryl bromides that is representative of the chem. space of the substrate class was described. By superimposing scope examples from published Ni/photoredox methods on this same chem. space, areas of sparse coverage and high vs. low average yields were identified, enabling comparisons between prior art and this new method. Addnl., it was demonstrated that the systematically selected scope of aryl bromides RBr can be used to quantify population-wide reactivity trends and reveal sources of possible functional group incompatibility with supervised machine learning. In the experiment, the researchers used many compounds, for example, Methyl 5-bromopicolinate(cas: 29682-15-3Product Details of 29682-15-3)

Methyl 5-bromopicolinate(cas: 29682-15-3) 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.Product Details of 29682-15-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lauzon, Samuel; Ollevier, Thierry published their research in Chemical Communications (Cambridge, United Kingdom) in 2021. The article was titled 《2,2′-Bipyridine-α,α’-trifluoromethyl-diol ligand: Synthesis and application in the asymmetric Et2Zn alkylation of aldehydes》.Synthetic Route of C5H3Br2N The article contains the following contents:

A chiral 2,2′-bipyridine ligand I, bearing α,α’-trifluoromethyl-alcs. at the 6,6′-positions, was designed in five steps affording either the R,R/S,S enantiomer with excellent stereoselectivities, i.e., 97% de, >99% ee and >99.5% de, >99.5% ee, resp. The key step for reaching high levels of stereoselectivity was demonstrated to be the resolution of the α-CF3-alc. using (S)-ibuprofen as the resolving agent. An initial application for the 2,2′-bipyridine-α,α’-CF3-diol ligand was highlighted in the Zn(II)-catalyzed asym. ethylation reaction of aromatic, heteroaromatic, and aliphatic aldehydes RCHO (R = 4-chlophenyl, thiophen-2-yl, Pr, etc.). Synergistic electron deficiency and steric hindrance properties of the newly developed ligand afforded the corresponding alcs. in good to excellent yields (up to 99%) and enantioselectivities (up to 95% ee). In the part of experimental materials, we found many familiar compounds, such as 2,6-Dibromopyridine(cas: 626-05-1Synthetic Route of C5H3Br2N)

2,6-Dibromopyridine(cas: 626-05-1) 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.Synthetic Route of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem