Day: October 17, 2022

Application In Synthesis of 4,4′-Bis(chloromethyl)-2,2′-bipyridineOn October 24, 2018 ,《Extending Hypochlorite Sensing from Cells to Elesclomol-Treated Tumors in Vivo by Using a Near-Infrared Dual-Phosphorescent Nanoprobe》 was published in ACS Applied Materials & Interfaces. The article was written by Meng, Xiangchun; Shi, Yuxiang; Chen, Zejing; Song, Linna; Zhao, Menglong; Zou, Liang; Liu, Shujuan; Huang, Wei; Zhao, Qiang. The article contains the following contents:

Reactive oxygen species (ROS), when beyond the threshold, can exhaust the capacity of cellular antioxidants and ultimately trigger cell apoptosis in tumor biol. However, the roles of hypochlorite (ClO-) in this process are much less clear compared with those of ROS, and its detection is easily obstructed by tissue penetration and endogenous fluorophores. Herein, the authors first synthesized a near-IR (NIR) ratiometric ClO- probe (Ir NP) composed of two kinds of phosphorescent iridium(III) complexes (Ir1 and Ir2) encapsulated with amphiphilic DSPE-mPEG5000. Ir NPs are dual-emissive and show obvious changes in phosphorescence intensity ratios and lifetimes of two emission bands upon exposure to ClO-. During the ClO- detection, ratiometric photoluminescence imaging is much more reliable over the intensity-based one for its self-calibration, while time-resolved photoluminescence imaging (TRPI) could distinguish the phosphorescence with long lifetime of Ir NPs from short-lived autofluorescence of tissues, resulting in the high accuracy of ClO- determination With NIR emission, a long phosphorescence lifetime, fast response, and excellent biocompatibility, Ir NPs were applied to the detection of ClO- in vitro and in vivo by means of ratiometric phosphorescence imaging and TRPI with high signal-to noise-ratios (SNR). Importantly, the authors demonstrated the elevated ClO- in elesclomol-stimulated tumors in living mice for the first time, which holds great potential for the visualization of the boost of ClO- in anticarcinogen-treated tumors and the further investigation of ROS-related oncotherapeutics. The experimental process involved the reaction of 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Application In Synthesis of 4,4′-Bis(chloromethyl)-2,2′-bipyridine)

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. Application In Synthesis of 4,4′-Bis(chloromethyl)-2,2′-bipyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 4-Amino-2-picolineOn October 24, 2019 ,《Development of Chemical Entities Endowed with Potent Fast-Killing Properties against Plasmodium falciparum Malaria Parasites》 was published in Journal of Medicinal Chemistry. The article was written by Matralis, Alexios N.; Malik, Adnan; Penzo, Maria; Moreno, Inmaculada; Almela, Maria J.; Camino, Isabel; Crespo, Benigno; Saadeddin, Anas; Ghidelli-Disse, Sonja; Rueda, Lourdes; Calderon, Felix; Osborne, Simon A.; Drewes, Gerard; Boesche, Markus; Fernandez-Alvaro, Elena; Martin Hernando, Jose Ignacio; Baker, David A.. The article contains the following contents:

One of the attractive properties of artemisinins is their extremely fast-killing capability, quickly relieving malaria symptoms. Nevertheless, the unique benefits of these medicines are now compromised by the prolonged parasite clearance times and the increasing frequency of treatment failures, attributed to the increased tolerance of Plasmodium falciparum to artemisinin. This emerging artemisinin resistance threatens to undermine the effectiveness of antimalarial combination therapies. Herein, we describe the medicinal chem. efforts focused on a cGMP-dependent protein kinase (PKG) inhibitor scaffold, leading to the identification of novel chem. entities with very potent, similar to artemisinins, fast-killing potency against asexual blood stages that cause disease, and activity against gametocyte activation that is required for transmission. Furthermore, we confirm that selective PKG inhibitors have a slow speed of kill, while chemoproteomic anal. suggests for the first time serine/arginine protein kinase 2 (SRPK2) targeting as a novel strategy for developing antimalarial compounds with extremely fast-killing properties. After reading the article, we found that the author used 4-Amino-2-picoline(cas: 18437-58-6Reference of 4-Amino-2-picoline)

4-Amino-2-picoline(cas: 18437-58-6) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Reference of 4-Amino-2-picoline

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Formula: C5H5BrN2On March 20, 2020, Li, Jianqing; Smith, Daniel; Krishnananthan, Subramaniam; Mathur, Arvind published an article in Organic Process Research & Development. The article was 《A Practical Synthesis of the TGFβRI Inhibitor N-(4-(3-(6-(Difluoromethyl)pyridin-2-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)pyridin-2-yl)acetamide via One-pot Sequential Sonogashira and Cacchi Reactions Catalyzed by Pd(OAc)2/BINAP》. The article mentions the following:

N-(4-(3-(6-(Difluoromethyl)pyridin-2-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)pyridin-2-yl)acetamide is a potent inhibitor of TGFβRI kinase that provides durable antitumor activity when combined with an anti-PD-1 antibody. In order to conduct a full range of preclin. studies, over 150 g of high quality material were required. The original discovery route through a step-wise, copper-mediated Sonogashira reaction, trifluoroacetamide formation and Cacchi reaction suffered from scale-up issues, mainly associated with tedious chromatog. purification of intermediates. This communication describes a chromatog.-free, one-pot synthesis of tittle compound via sequential Sonogashira and Cacchi reactions promoted by the superior catalyst Pd(OAc)2/BINAP, which was discovered by catalyst screening. In the experiment, the researchers used many compounds, for example, 2-Bromopyridin-3-amine(cas: 39856-58-1Formula: C5H5BrN2)

2-Bromopyridin-3-amine(cas: 39856-58-1) 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.Formula: C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 39856-58-1On September 17, 2021 ,《Phosphine Oxides (-POMe2) for Medicinal Chemistry: Synthesis, Properties, and Applications》 was published in Journal of Organic Chemistry. The article was written by Stambirskyi, Maksym V.; Kostiuk, Tetiana; Sirobaba, Serhii I.; Rudnichenko, Alexander; Titikaiev, Dmytro L.; Dmytriv, Yurii V.; Kuznietsova, Halyna; Pishel, Iryna; Borysko, Petro; Mykhailiuk, Pavel K.. The article contains the following contents:

A general practical approach to hetero(aromatic) and aliphatic P(O)Me2-substituted derivatives is elaborated. The key synthetic step was a [Pd]-mediated C-P coupling of (hetero)aryl bromides/iodides with HP(O)Me2. The P(O)Me2 substituent was shown to dramatically increase solubility and decrease lipophilicity of organic compounds This tactic was used to improve the solubility of the antihypertensive drug prazosin without affecting its biol. profile.2-Bromopyridin-3-amine(cas: 39856-58-1Related Products of 39856-58-1) was used in this study.

2-Bromopyridin-3-amine(cas: 39856-58-1) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Related Products of 39856-58-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

HPLC of Formula: 58498-61-6On October 31, 1989 ,《Carbon-13 and proton NMR spectra of 2-pyridone derivatives》 appeared in Journal of Molecular Structure. The author of the article were De Kowalewski, D. G.; Contreras, R. H.; De los Santos, C.. The article conveys some information:

The 13C- and 1H-NMR of substituted pyridines (e.g. I) were studied to determine through additivity properties of 13C shielding constants and of the 13C-1H spin-spin coupling constants, the structure of the ring and of the lateral chains. In the part of experimental materials, we found many familiar compounds, such as 5-Chloro-3-methylpyridin-2-ol(cas: 58498-61-6HPLC of Formula: 58498-61-6)

5-Chloro-3-methylpyridin-2-ol(cas: 58498-61-6) 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.HPLC of Formula: 58498-61-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Bobbio, Carla; Schlosser, Manfred published their research in European Journal of Organic Chemistry on December 31 ,2001. The article was titled 《Regiochemical flexibility: the optional functionalization of 2,3,5-trihalopyridines at the 4- or 6-position》.Product Details of 40360-44-9 The article contains the following contents:

A deprotonation study was performed using 2,3,5-trichloropyridine, 3,5-dichloro-2-fluoropyridine, and 5-chloro-2,3-difluoropyridine as the substrates. Upon reaction with lithium diisopropylamide (LDA), deprotonation occurred exclusively at the 4-position. Subsequent carboxylation and iodination led to the acids and 4-iodopyridines. The exposure of the latter compounds to lithium 2,2,6,6-tetramethylpiperidide (LITMP) caused deprotonation and immediately ensuing iodine migration. The intermediates were trapped with dry ice to afford the carboxylic acids. Upon neutralization, the 6-iodopyridines were obtained. These compounds readily exchanged the heavy halogen for metal when treated with isopropylmagnesium chloride. In this way, functional groups could be selectively introduced in the 6-position. Employing carbon dioxide routinely as the model electrophile, trihalopyridinecarboxylic acids were formed which, all unknown so far, should provide valuable new building blocks for pharmaceutical research. Moreover, the selective nucleophilic displacement of the halogen at the 2-position could give rise to an immense variety of new structures. In the experimental materials used by the author, we found 3,5,6-Trichloropicolinic acid(cas: 40360-44-9Product Details of 40360-44-9)

3,5,6-Trichloropicolinic acid(cas: 40360-44-9) 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.Product Details of 40360-44-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhu, Heping; Ying, Shilong; Zhou, Bingluo; Liang, Xiao; He, Quan; Song, Ping; Hu, Xinyang; Shi, Keqiang; Xiong, Mingteng; Jin, Hongchuan; Pan, Yuanjiang published an article on February 5 ,2021. The article was titled 《Discovery of novel 2-aryl-3-sulfonamido-pyridines (HoAns) as microtubule polymerization inhibitors with potent antitumor activities》, and you may find the article in European Journal of Medicinal Chemistry.Application In Synthesis of 2-Bromopyridin-3-amine The information in the text is summarized as follows:

In this study, a series of novel 2-aryl-3-sulfonamido-pyridines had been designed, synthesized, and evaluated for their antiproliferative activities in vitro and in vivo. Among them, compound I exhibited the most potent activity with IC50 values ranging from 0.170 to 1.193μM in a panel of cancer cell lines. Mechanistic studies indicated that compound I bound to the colchicine site of β-tubulin, resulting in colony formation inhibition, G2/M phase cell cycle arrest, cell apoptosis as well as increased the generation of ROS in both RKO and SW620 cells. In addition, compound I showed potent anti-vascular activity in vitro. Furthermore, compound I also exhibited outstanding antitumor activity in SW620 xenograft tumor models without observable toxic effects, which was more potent than that of ABT-751. In conclusion, these findings suggest that compound I may be a promising microtubule destabilizing agent and deserves for further development in cancer therapy. The experimental process involved the reaction of 2-Bromopyridin-3-amine(cas: 39856-58-1Application In Synthesis of 2-Bromopyridin-3-amine)

2-Bromopyridin-3-amine(cas: 39856-58-1) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Application In Synthesis of 2-Bromopyridin-3-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2008,Reisner, Erwin; Lippard, Stephen J. published 《Synthesis of dicarboxylate “”C-clamp”” 1,2-diethynylarene compounds as potential transition-metal ion hosts》.European Journal of Organic Chemistry published the findings.Formula: C7H6BrNO2 The information in the text is summarized as follows:

An efficient convergent synthesis is reported for a new type of C-clamp ligand with a 1,2-diethynylarene scaffold involving a chelate host capable of binding a guest mol. in its endo-dicarboxylate pocket. The chem. involves a combination of palladium-catalyzed Sonogashira, Heck, and Suzuki cross-coupling reactions. The compounds 2,3-bis[2-(2′-carboxybiphenyl-4-yl)ethynyl]triptycene and 4,5-bis[2-(2′-carboxybiphenyl-4-yl)ethynyl]veratrole and their 2′-carboxy-m-terphenyl-4-yl analogs were designed as dinucleating ligands to assemble carboxylate-bridged transition-metal complexes with a windmill geometry. The X-ray crystal structure of one such C-clamp compound containing co-crystallized water mols. reveals strong hydrogen bonds of the aqua guest to the endo-oriented carboxylic acid entities of the C-clamp host. In addition, two syn-N-donor ligands were prepared as a synthetic scaffold to mimic the geometric arrangement of N-donor atoms in carboxylate-bridged dinuclear proteins. In the experiment, the researchers used many compounds, for example, Methyl 5-bromopicolinate(cas: 29682-15-3Formula: C7H6BrNO2)

Methyl 5-bromopicolinate(cas: 29682-15-3) 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. Formula: C7H6BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2009,Kuwabara, Junpei; Mori, Hironori; Teratani, Takuya; Akita, Munetaka; Kanbara, Takaki published 《Regioregulated Syntheses of Poly(aminopyridine)s by Pd-catalyzed Amination Reaction》.Macromolecular Rapid Communications published the findings.SDS of cas: 13534-97-9 The information in the text is summarized as follows:

Regioregulated poly(aminopyridine)s were synthesized by a Pd-catalyzed C-N coupling reaction. The polymerization using Pd(0) and a bulky monodentate phosphine ligand distinctively produced the para-linked and meta-linked poly(aminopyridine)s, without the need for a protection process. The regioregularity of the polymer was confirmed by 1H NMR spectroscopy. Model reactions were studied to evaluate the possibility of crosslinkage in the polymer. A large difference in reactivity was observed between 5-amino-2-bromopyridine and 2-amino-5-bromopyridine, which should have afforded same product. D. functional theory (DFT) calculations indicated that electron densities of the Br-bound carbon atom and the pyridine-nitrogen atom determine the reactivity of the monomers. The experimental part of the paper was very detailed, including the reaction process of 6-Bromopyridin-3-amine(cas: 13534-97-9SDS of cas: 13534-97-9)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.SDS of cas: 13534-97-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2015,Godeau, Julien; Harari, Marine; Laclef, Sylvain; Deau, Emmanuel; Fruit, Corinne; Besson, Thierry published 《Cu/Pd-Catalyzed C-2-H Arylation of Quinazolin-4(3H)-ones with (Hetero)aryl Halides》.European Journal of Organic Chemistry published the findings.Category: pyridine-derivatives The information in the text is summarized as follows:

The regiospecific C-2-H arylation of N-3-substituted quinazolin-4(3H)-ones with a wide range of aryl or (hetero)aryl halides under microwave irradiation was studied. A ligand-dependent palladium/copper bicatalytic system was developed and allowed direct cross-coupling with a variety of (hetero)aryl halides. This useful and scalable procedure promotes the construction of C(sp2)-C(sp2) bonds from arenes or (hetero)arenes and aryl or (hetero)aryl bromides and chlorides in a time-efficient strategy. The extension of the reaction to various N-3-substituted quinazolin-4(3H)-ones with iodobenzene as well as the scope and limitations of the method were also investigated. In the part of experimental materials, we found many familiar compounds, such as 5-Bromo-2-chloropyridine(cas: 53939-30-3Category: pyridine-derivatives)

5-Bromo-2-chloropyridine(cas: 53939-30-3) 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.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem