Tag: 100-200

《Synthesis and Structure-Activity Relationships of 5′-Aryl-14-alkoxypyridomorphinans: Identification of a μ Opioid Receptor Agonist/δ Opioid Receptor Antagonist Ligand with Systemic Antinociceptive Activity and Diminished Opioid Side Effects》 was written by Vekariya, Rakesh H.; Lei, Wei; Ray, Abhisek; Saini, Surendra K.; Zhang, Sixue; Molnar, Gabriella; Barlow, Deborah; Karlage, Kelly L.; Bilsky, Edward J.; Houseknecht, Karen L.; Largent-Milnes, Tally M.; Streicher, John M.; Ananthan, Subramaniam. Related Products of 197958-29-5 And the article was included in Journal of Medicinal Chemistry in 2020. The article conveys some information:

We previously identified a pyridomorphinan (6, SRI-22138) possessing a 4-chlorophenyl substituent at the 5′-position on the pyridine and a 3-phenylpropoxy at the 14-position of the morphinan as a mixed μ opioid receptor (MOR) agonist and δ/κ opioid receptor (DOR/KOR) antagonist with potent antinociceptive activity and diminished tolerance and dependence in rodents. Structural variations at the 5′- and 14-positions of this mol. gave insights into the structure-activity relationships for binding and functional activity. Subtle structural changes exerted significant influence, particularly on the ability of the compounds to function as agonists at the MOR. In vivo evaluation identified compound 20(I) (SRI-39067) as a MOR agonist/DOR antagonist that produced systemically active potent antinociceptive activity in tail-flick assay in mice, with diminished tolerance, dependence/withdrawal, reward liability, and respiratory depression vs. morphine. These results support the hypothesis that mixed MOR agonist/DOR antagonist ligands may emerge as novel opioid analgesics with reduced side effects. The experimental part of the paper was very detailed, including the reaction process of 2-Pyridinylboronic acid(cas: 197958-29-5Related Products of 197958-29-5)

2-Pyridinylboronic acid(cas: 197958-29-5) 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.Related Products of 197958-29-5

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate》 was published in Journal of the American Chemical Society in 2020. These research results belong to Sato, Yukiya; Nakamura, Kei; Sumida, Yuto; Hashizume, Daisuke; Hosoya, Takamitsu; Ohmiya, Hirohisa. Safety of 4-Cyanopyridine The article mentions the following:

The generation of tertiary, secondary, and primary alkyl radicals has been achieved by the direct visible-light excitation of a boracene-based alkylborate. This system is based on the photophys. properties of the organoboron mol. The protocol is applicable to decyanoalkylation, Giese addition, and nickel-catalyzed carbon-carbon bond formations such as alkyl-aryl cross-coupling or vicinal alkylarylation of alkenes, enabling the introduction of various C(sp3) fragments to organic mols. After reading the article, we found that the author used 4-Cyanopyridine(cas: 100-48-1Safety of 4-Cyanopyridine)

4-Cyanopyridine(cas: 100-48-1) belongs to pyridine. Pyridine’s structure is isoelectronic with that of benzene, but its properties are quite different. Pyridine is completely miscible with water, whereas benzene is only slightly soluble. Like all hydrocarbons, benzene is neutral (in the acid–base sense), but because of its nitrogen atom, pyridine is a weak base.Safety of 4-Cyanopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,European Journal of Medicinal Chemistry included an article by Li, Xue-Meng; Lv, Wei; Guo, Si-Yang; Li, Ya-Xin; Fan, Bing-Zhi; Cushman, Mark; Kong, Fan-Sheng; Zhang, Jun; Liang, Jian-Hua. Computed Properties of C5H5BrN2. The article was titled 《Synthesis and structure-bactericidal activity relationships of non-ketolides: 9-Oxime clarithromycin 11,12-cyclic carbonate featured with three-to eight-atom-length spacers at 3-OH》. The information in the text is summarized as follows:

In general, potent non-ketolide versions of erythromycin possessed conformationally constricted two- or three-atom-length sidechains at 3-OH. Novel 14-membered non-ketolides possessing long spacers beyond three-atom length were evaluated for antibacterial activitcy. The most potent one is 34a, featuring a five-atom-length flexible linker from of a pyridine ring to the aglycon. Conversion of the pyridine of 34a to other aryl groups, changing the linker’s length of 34a to longer or shorter ones, and variation of the linker flexibility to a rigid olefin or alkyne led to decreased antibacterial activity. The hybrids of macrolides and quinolones 28b, 31 and 34b possessing various sidechains, unlike their 15-membered counterparts, were ineffective compared to 34a. Similar to the marketed ketolide telithromycin, the non-ketolide 34a proved to be a time-dependent bactericidal agent, but it exhibited superior in vivo pharmacokinetic properties such as longer half-life, higher plasma concentration, lower clearance and shorter time to reach the highest drug concentration relative to telithromycin. Mol. docking suggested 34a might π – π interact with the bacterial rRNA base G2505Ec. This study suggested that the bacteriostatic agent erythromycin can be structurally modified to afford a new bactericidal chemotype that targets the ribosome and is superior to ciprofloxacin with regard to its min. bactericidal concentration After reading the article, we found that the author used 6-Bromopyridin-3-amine(cas: 13534-97-9Computed Properties of C5H5BrN2)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Computed Properties of C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Fu, Haiyan; Shen, Peng-Xiang; He, Jian; Zhang, Fanglin; Li, Suhua; Wang, Peng; Liu, Tao; Yu, Jin-Quan published 《Ligand-Enabled Alkynylation of C(sp3)-H Bonds with Palladium(II) Catalysts》.Angewandte Chemie, International Edition published the findings.HPLC of Formula: 128071-75-0 The information in the text is summarized as follows:

The palladium(II)-catalyzed β- and γ-alkynylation of amide C(sp3)-H bonds is enabled by pyridine-based ligands. This alkynylation reaction is compatible with substrates containing α-tertiary or α-quaternary carbon centers. The β-methylene C(sp3)-H bonds of various carbocyclic rings were also successfully alkynylated. The experimental process involved the reaction of 2-Bromonicotinaldehyde(cas: 128071-75-0HPLC of Formula: 128071-75-0)

2-Bromonicotinaldehyde(cas: 128071-75-0) 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.HPLC of Formula: 128071-75-0

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

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

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

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

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

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