Day: January 5, 2023

Inhibitors of human immunodeficiency virus type 1 (HIV-1) attachment. 12. structure-activity relationships associated with 4-fluoro-6-azaindole derivatives leading to the identification of 1-(4-benzoylpiperazin-1-yl)-2-(4-fluoro-7-[1,2,3]triazol-1-yl-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione (BMS-585248) was written by Regueiro-Ren, Alicia;Xue, Qiufen M.;Swidorski, Jacob J.;Gong, Yi-Fei;Mathew, Marina;Parker, Dawn D.;Yang, Zheng;Eggers, Betsy;D’Arienzo, Celia;Sun, Yongnian;Malinowski, Jacek;Gao, Qi;Wu, Dedong;Langley, David R.;Colonno, Richard J.;Chien, Caly;Grasela, Dennis M.;Zheng, Ming;Lin, Pin-Fang;Meanwell, Nicholas A.;Kadow, John F.. And the article was included in Journal of Medicinal Chemistry in 2013.Computed Properties of C5H2BrFN2O2 This article mentions the following:

A series of highly potent HIV-1 attachment inhibitors with 4-fluoro-6-azaindole core heterocycles that target the viral envelope protein gp120 has been prepared Substitution in the 7-position of the azaindole core with amides, C-linked heterocycles, and N-linked heterocycles provided compounds with subnanomolar potency in a pseudotype infectivity assay and good pharmacokinetic profiles in vivo. A predictive model was developed from the initial SAR in which the potency of the analogs correlated with the ability of the substituent in the 7-position of the azaindole to adopt a coplanar conformation by either forming internal hydrogen bonds or avoiding repulsive substitution patterns. Compound I (BMS-585248) exhibited much improved in vitro potency and pharmacokinetic properties than the previous clin. candidate BMS-488043 (II). The predicted low clearance in humans, modest protein binding, and good potency in the presence of 40% human serum for I led to its selection for human clin. studies. In the experiment, the researchers used many compounds, for example, 2-Bromo-5-fluoro-3-nitropyridine (cas: 652160-72-0Computed Properties of C5H2BrFN2O2).

2-Bromo-5-fluoro-3-nitropyridine (cas: 652160-72-0) 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 groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Computed Properties of C5H2BrFN2O2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Gram-Scale Synthesis of Amines Bearing a gem-Difluorocyclopropane Moiety was written by Nosik, Pavel S.;Gerasov, Andrii O.;Boiko, Rodion O.;Rusanov, Eduard;Ryabukhin, Sergey V.;Grygorenko, Oleksandr O.;Volochnyuk, Dmitriy M.. And the article was included in Advanced Synthesis & Catalysis in 2017.Synthetic Route of C10H17NO2 This article mentions the following:

The synthesis of monocyclic, spirocyclic and fused bicyclic secondary amines bearing a gem-difluorocyclopropane moiety via difluorocyclopropanation of unsaturated N-Boc derivatives using the trifluoromethyl(trimethyl)silane/sodium iodide [CF₃SiMe₃-NaI] system is described. The relative order of the substrate reactivity is established. It is shown that for the reactive alkenes the standard reaction conditions can be used, whereas for the substrates with low reactivity, slow addition of the Ruppert-Prakash reagent is necessary. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4Synthetic Route of C10H17NO2).

tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. 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. Synthetic Route of C10H17NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lewis Acid/Bronsted Acid Controlled Pd(II)-Catalyzed Chemodivergent Functionalization of C(sp²)-H Bonds with N-(Arylthio)i(a)mides was written by Chaitanya, Manthena;Anbarasan, Pazhamalai. And the article was included in Organic Letters in 2018.Category: pyridine-derivatives This article mentions the following:

An efficient and chemodivergent palladium-catalyzed thiolation (C-S) and imidation (C-N) of directing group-assisted C-H bonds have been accomplished employing N-(arylthio)imides in combination with either Bronsted acid or Lewis acid, resp. Notable features of the developed methodologies include excellent diversity, high functional group tolerance, wide substrate scope, and use of a single N-S reagent. Importantly, the developed hypothesis was also successfully extended to the amidation of C-H bonds. A plausible mechanistic pathway was proposed based on the preliminary mechanistic study. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Category: pyridine-derivatives).

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. 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.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Visible-Light-Enabled Ortho-Selective Aminopyridylation of Alkenes with N-Aminopyridinium Ylides was written by Moon, Yonghoon;Lee, Wooseok;Hong, Sungwoo. And the article was included in Journal of the American Chemical Society in 2020.Quality Control of Phenyl(pyridin-2-yl)methanone This article mentions the following:

By utilizing an underexplored reactivity mode of N-aminopyridinium ylides, we developed the visible-light-induced ortho-selective aminopyridylation of alkenes via radical-mediated 1,3-dipolar cycloaddition The photocatalyzed single-electron oxidation of N-aminopyridinium ylides generates the corresponding radical cations that enable previously inaccessible 1,3-cycloaddition with a broader range of alkene substrates. The resulting cycloaddition adducts rapidly undergo subsequent homolytic cleavage of the N-N bond, conferring a substantial thermodn. driving force to yield various β-aminoethylpyridines. Remarkably, amino and pyridyl groups can be installed into both activated and unactivated alkenes with modular control of ortho-selectivity and 1,2-syn-diastereoselectivity under metal-free and mild conditions. Combined exptl. and computational studies are conducted to clarify the detailed reaction mechanism and the origins of site selectivity and diastereoselectivity. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Quality Control of Phenyl(pyridin-2-yl)methanone).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) 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. 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.Quality Control of Phenyl(pyridin-2-yl)methanone

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The Mn(Salen)-catalyzed oxidative kinetic resolution of secondary alcohols: reaction development and scope was written by Cheng, Qigan;Deng, Fanguo;Xia, Chungu;Sun, Wei. And the article was included in Tetrahedron: Asymmetry in 2008.HPLC of Formula: 65350-59-6 This article mentions the following:

A series of chiral Mn(Salen) complexes have been synthesized and submitted to the kinetic resolution of secondary alcs. bearing a large hindrance in the biphasic system, which is composed of water and CH₂Cl₂. After evaluating the appropriate complex, additive, and other conditions, chiral secondary alcs. were obtained with enantiomeric excesses of up to 98.6% in 6 min. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6HPLC of Formula: 65350-59-6).

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Suzuki-Miyaura cross-coupling for efficient synthesis of aryl-substituted N-heteroarenes catalyzed by recyclable N-phenylpiperazine-Palladium(II) complex was written by Perumgani, Pullaiah C.;Kodicherla, Balaswamy;Mandapati, Mohan Rao;Parvathaneni, Sai Prathima. And the article was included in Inorganica Chimica Acta in 2018.Product Details of 4373-61-9 This article mentions the following:

Polystyrene supported N-phenylpiperazine-Pd(II) complex was synthesized and characterized by various techniques, including Fourier transform IR spectroscopy (FTIR), scanning electronmicroscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and thermal anal. (TG-DTA). This heterogeneous Pd(II) complex showed high catalytic efficiency for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides, aryl chlorides to give the corresponding 2-arylpyridines and heteroarenes. The coupled products were formed in excellent yields at low catalyst loadings under mild reaction conditions. Further, this heterogeneous catalyst showed excellent recyclability and reused for four cycles with no significant decrease in its activity. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Product Details of 4373-61-9).

2-(m-Tolyl)pyridine (cas: 4373-61-9) 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, 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. Product Details of 4373-61-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

C-H Cyanation of 6-Ring N-Containing Heteroaromatics was written by Elbert, Bryony L.;Farley, Alistair J. M.;Gorman, Timothy W.;Johnson, Tarn C.;Genicot, Christophe;Lallemand, Benedicte;Pasau, Patrick;Flasz, Jakub;Castro, Jose L.;MacCoss, Malcolm;Paton, Robert S.;Schofield, Christopher J.;Smith, Martin D.;Willis, Michael C.;Dixon, Darren J.. And the article was included in Chemistry – A European Journal in 2017.Product Details of 644-98-4 This article mentions the following:

Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chem. and the biomedical sciences. Herein, we report an approach to heteroaromatic C-H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Product Details of 644-98-4).

2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Product Details of 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Easy and efficient S_NAr reactions on halopyridines in solvent free conditions was written by Loupy, Andre;Philippon, Noelle;Pigeon, Philippe;Galons, Herve. And the article was included in Heterocycles in 1991.Related Products of 4783-68-0 This article mentions the following:

Solid-liquid phase transfer catalysis without added solvent efficiently promotes S_NAr reactions on 2-fluoro-, 2-chloro-, and 2-bromopyridines with a variety of anionic nucleophiles (from PhOH, PHCH₂OH, Ph₂CHCN, PhCH₂CN, PhCHMeCN) generated in situ. This methodol. gives access to substituted pyridines I (Nu = PhO, PhCH₂O, Ph₂CCN, etc.) under very simplified conditions depending on halide nature. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Related Products of 4783-68-0).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). 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.Related Products of 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis, anti-bacterial evaluation, DFT study and molecular docking as a potential 3-chymotrypsin-like protease (3CLpro) of SARS-CoV-2 inhibitors of a novel Schiff bases was written by Al-Janabi, Ahmed S. M.;Elzupir, Amin O.;Yousef, Tarek A.. And the article was included in Journal of Molecular Structure in 2021.Computed Properties of C12H9NO This article mentions the following:

New Schiff bases (L¹H) I (I), (L²H) II (II), (L³H) III (III) were synthesized by reaction of 2-benzoylpyridine with different amines (2-amino-6-chlorobenzothiazole, isonicotinohydrazide and N¹-(naphthalen-1-yl)ethane-1,2-diamine) and characterized by ¹H-NMR, ¹³C-NMR, IR mass spectroscopy and elemental anal. The compounds (I), (II) and (III) were assayed by the disk diffusion method for anti-bacterial against five pathogenic bacteria species (Staphylococcus aureus, Micrococcus luteus, Staphylococcus pyogenes, Bacillus subtilis, and E. coli). All prepared Schiff bases (I), (II) and (III) showed good activity compared to pos. control (streptomycin). Moreover the L³H showed the highest activity against S. aureus, and M. luteus than the other compounds and streptomycin. In addnl. mol. docking studies with 3-chymotrypsin-like protease (3CLpro), the essential enzyme for SARS-CoV-2 proliferation. The rest of compounds have shown promising results as 3CLpro inhibitors interacting with the active sites of the enzymes. Finally, DFT’s estimated electrostatic mol. potential results were used to illustrate the mol. docking findings. The DFT calculations showed that L³H has the highest dipole moment and electrophilicity index. Interestingly, L²H of the largest energy gap ΔE = 2.49 eV, there are several hydrophilic interactions that could facilitate the binding with the receptors. All of these parameters could be shared to significantly affect the protein sites of binding affinity with different extent. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Computed Properties of C12H9NO).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Computed Properties of C12H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Bamboo pyroligneous acid as a novel insecticide, its mosquito repellency activity, chemical components and safety towards animals was written by Li, Zhikun;Maliang, Huidong;Liu, Qing;Chen, Anliang;Liu, Hongbo;Lin, Haiping;Ma, Jianyi;Wang, Pinwewi. And the article was included in Fresenius Environmental Bulletin in 2022.Reference of 626-64-2 This article mentions the following:

Mosquitoes transmit pathogens which cause human and mammalian diseases. We employed several practical and multidisciplinary approaches to discover a new natural mosquito repellent. The active ingredient tests revealed that bamboo vinegar (BV) showed 91% protective efficacy. The forearm skin landing test showed that 9% acetic acid water solution (AAWS) and BV had strong protective efficacy against Aedes albopictus. The limb skin landing test also showed that BV and AAWS had protective efficacy. The sugar-feeding behavioral bioassay showed that mosquitoes were repelled by the smell of AAWS. There was no significant difference between the number of mosquitoes that landed on the two Petri dishes treated with BV (6.6% acetic acid (AA)), 4.5% AAWS, 9% AAWS, and 4.5% DEBT, but a significant difference was found among BV (6.6% AA), 4.5% AAWS, 9.0% AAWS, DEBT, and distilled water. The arm-in-cage tests showed that there was a descending order for the duration of complete protection was DEBT (75-90 min) = BV (75-90 min) > formic acid (60-75 min) > AA (45-60 min) > propanoic acid (30-45 min) > butanoic acid (15-30 min) > water (0 min). The safety tests showed that the acute oral toxicity (LD50) of BV (6.6% AA) was > 5000 mg/kg for mice and produced no red spots or edema symptoms. Furthermore, the dermal sensitization rate was zero for rabbits, and the marrow micronucleus rates for mice were neg. In summary, BV can be safely used for volatilization and skin applications. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Reference 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. 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.Reference of 626-64-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem