Tag: M.W=150-200

Plamthottam, Sheba published the artcileActivity and electrochemical properties: iron complexes of the anticancer drug triapine and its analogs, Name: 2-Bromopyridin-3-amine, the publication is JBIC, Journal of Biological Inorganic Chemistry (2019), 24(5), 621-632, database is CAplus and MEDLINE.

Abstract: Triapine (3-AP), is an iron-binding ligand and anticancer drug that is an inhibitor of human ribonucleotide reductase (RNR). Inhibition of RNR by 3-AP results in the depletion of dNTP precursors of DNA, thereby selectively starving fast-replicating cancer cells of nucleotides for survival. The redox-active form of 3-AP directly responsible for inhibition of RNR is the Fe(II)(3-AP)₂ complex. In this work, we synthesize 12 analogs of 3-AP, test their inhibition of RNR in vitro, and study the electronic properties of their iron complexes. The reduction and oxidation events of 3-AP iron complexes that are crucial for the inhibition of RNR are modeled with solution studies. We monitor the pH necessary to induce reduction in iron complexes of 3-AP analogs in a reducing environment, as well as the kinetics of oxidation in an oxidizing environment. The oxidation state of the complex is monitored using UV-Vis spectroscopy. Isoquinoline analogs of 3-AP favor the maintenance of the biol. active reduced complex and possess oxidation kinetics that allow redox cycling, consistent with their effective inhibition of RNR seen in our in vitro experiments In contrast, methylation on the thiosemicarbazone secondary amine moiety of 3-AP produces analogs that form iron complexes with much higher redox potentials, that do not redox cycle, and are inactive against RNR in vitro. Graphic abstract: The catalytic subunit of human Ribonucleotide Reductase (RNR), contains a tyrosyl radical in the enzyme active site. Fe(II) complexes of 3-AP and its analogs can quench the radical and, subsequently, inactivate RNR. The potency of RNR inhibitors is highly dependent on the redox properties of the iron complexes, which can be tuned by ligand modifications. Complexes are found to be active within a narrow redox window imposed by the cellular environment.[Figure not available: see fulltext.].

JBIC, Journal of Biological Inorganic Chemistry published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Name: 2-Bromopyridin-3-amine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Hou, Chuanfu published the artcileVisible-Light-Induced Decarboxylative Acylation of Pyridine N-Oxides with α-Oxocarboxylic Acids Using Fluorescein Dimethylammonium as a Photocatalyst, HPLC of Formula: 91-02-1, the publication is Advanced Synthesis & Catalysis (2021), 363(11), 2806-2812, database is CAplus.

The development of a visible-light-induced catalytic system achieved the decarboxylative acylation of pyridine N-oxides with α-oxocarboxylic acids, at room temperature and using the organic dye fluorescein dimethylammonium as a new type of photocatalyst was reported. A series of 2-arylacylpyridine N-oxides were selectively synthesized in moderate to good yields by controlling the polarity of the reaction solvent. The developed strategy was successfully applied in the synthesis of an important intermediate of the drug, acrivastine, on a gram scale. Notably, this is the first time that fluorescein dimethylammonium was used to catalyzed the Minisci-type C-H decarboxylative acylation reaction. The mechanism of decarboxylative acylation was studied by capturing adducts of acyl radicals and 1,1-diphenylethylene confirmed a radical mechanism. The disclosed catalytic system provided a green synthetic strategy for decarboxylative acylation without the use of addnl. oxidants or metal catalysts.

Advanced Synthesis & Catalysis published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C12H9NO, HPLC of Formula: 91-02-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Ishida, Akiharu published the artcileDiscovery and SAR Studies of Orally Active Somatostatin Receptor Subtype-2 (SSTR2) Agonists for the Treatment of Acromegaly, COA of Formula: C7H10BNO3, the publication is ACS Chemical Neuroscience (2020), 11(10), 1482-1494, database is CAplus and MEDLINE.

Acromegaly is a disease caused by the oversecretion of growth hormone. It is currently treated by i.v. injection with cyclic peptide drugs that activate somatostatin receptor subtype 2 (SSTR2). Here, novel nonpeptidic, small-mol., and orally active SSTR2 agonists were identified from a hit compound (13). Pharmacophore studies enabled scaffold hopping to obtain a unique 3,4,5-trisubstituted pyridine motif. Further optimization conferred potent SSTR2 agonistic activity and metabolic stability. Several compounds were evaluated and these showed good oral pharmacokinetic profiles in rats, and one representative compound (25)(I) showed highly potent inhibition of growth hormone secretion induced by growth hormone-releasing hormone in rats. Based on these results, 25 was identified as a promising lead for further optimization. A structure-activity relationship (SAR) study and the metabolic stability data for this compound are also described.

ACS Chemical Neuroscience published new progress about 612845-44-0. 612845-44-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Ether,Boronic Acids,Boronic acid and ester, name is (6-Ethoxypyridin-3-yl)boronic acid, and the molecular formula is C7H10BNO3, COA of Formula: C7H10BNO3.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Hurh, Byungserk published the artcilePurification and characterization of nicotinic acid dehydrogenase from Pseudomonas fluorescens TN5, Synthetic Route of 636-73-7, the publication is Journal of Fermentation and Bioengineering (1994), 78(1), 19-26, database is CAplus.

Membrane-bound nicotinic acid dehydrogenase, an enzyme that catalyzes the formation of 6-hydroxynicotinic acid from nicotinic acid, was solubilized with Triton X-100, and then purified 126-fold with an 11.1% overall recovery from nicotinic acid-induced cells of Pseudomonas fluorescens TN5. The purified enzyme appeared to be homogeneous from anal. by polyacrylamide gel electrophoresis. The enzyme had a mol. mass of approx. 80 kDa and consisted of one subunit. Some electron acceptors, such as phenazine methosulfate, K₃Fe(CN)₆ and nitro blue tetrazolium, acted as electron acceptors. The purified enzyme catalyzed the hydroxylation of nicotinic acid to 6-hydroxynicotinic acid at a rate of 672 μmol min^-1 mg^-1 of protein at 35°. It also catalyzed the hydroxylation of pyrazinecarboxylic acid, 3-pyridinesulfonic acid, and 3-cyanopyridine. The purified enzyme exhibited an optimum pH of 8.3, and was sensitive to thiol reagents such as HgCl₂ and p-chloromercuribenzoate. A reduction in the amount of the cytochrome c-like component in the respiratory particles was observed during the hydroxylation reaction of nicotinic acid. Thus, nicotinic acid dehydrogenase appeared to be linked to the cytochrome respiratory chain in the cells of P. fluorescens TN5.

Journal of Fermentation and Bioengineering published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C5H5NO3S, Synthetic Route of 636-73-7.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Hayashi, Eri published the artcileBase-Assisted Aerobic C-H Oxidation of Alkylarenes with a Murdochite-Type Oxide Mg₆MnO₈ Nanoparticle Catalyst, Safety of Phenyl(pyridin-2-yl)methanone, the publication is ACS Applied Materials & Interfaces (2022), 14(5), 6528-6537, database is CAplus and MEDLINE.

Heterogeneously catalyzed aerobic oxidative C-H functionalization under mild conditions is a chem. process to obtain desired oxygenated products directly. Nanosized murdochite-type oxide Mg₆MnO₈ (Mg₆MnO₈-MA) was successfully synthesized by the sol-gel method using malic acid. The sp. surface area reached up to 104 m² g^-1, which is about 7 times higher than those (2-15 m² g^-1) of Mg₆MnO₈ synthesized by previously reported methods. Mg₆MnO₈-MA exhibited superior catalytic performance to those of other Mn- and Mg-based oxides, including manganese oxides with Mn-O-Mn active sites for the oxidation of fluorene with mol. oxygen (O₂) as the sole oxidant under mild conditions (40°C). The present catalytic system was applicable to the aerobic oxidation of various substrates. The catalyst could be recovered by simple filtration and reused several times without obvious loss of its high catalytic performance. The correlation between the reactivity and the pK_a of the substrates, basic properties of catalysts, and kinetic isotope effects suggest a basicity-controlled mechanism of hydrogen atom transfer. The ¹⁸O-labeling experiments, kinetics, and mechanistic studies showed that H abstraction of the hydrocarbon proceeds via a mechanism involving O₂ activation. The structure of Mg₆MnO₈ consisting of isolated Mn⁴⁺ species located in a basic MgO matrix plays an important role in the present oxidation

ACS Applied Materials & Interfaces published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C12H9NO, Safety of Phenyl(pyridin-2-yl)methanone.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Neumann, Jennifer published the artcileBiodegradability of 27 pyrrolidinium, morpholinium, piperidinium, imidazolium and pyridinium ionic liquid cations under aerobic conditions, Synthetic Route of 17281-59-3, the publication is Green Chemistry (2014), 16(4), 2174-2184, database is CAplus.

The chem. and thermal stability of ionic liquids (ILs) makes them interesting for a large variety of applications in nearly all areas of the chem. industry. However, this stability is often reflected in their recalcitrance towards biodegradation, which comes with the risk of persistence when they are released into the environment. The authors carried out a systematic study of the biodegradability of pyrrolidinium, morpholinium, piperidinium, imidazolium and pyridinium-based IL cations substituted with different alkyl or functionalized side chains and using halide counterions. The authors examined their primary degradability by specific anal. and/or their ultimate biodegradability using BOD tests according to OECD guideline 301F. Biol. transformation products were studied using mass spectrometry. A comparison of the biodegradation potential of these ILs shows that for all five head groups, representatives can be found that are readily or inherently biodegradable, thus permitting the structural design of ILs with a reduced environmental hazard.

Green Chemistry published new progress about 17281-59-3. 17281-59-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitrile,Salt, name is 1-(Cyanomethyl)pyridin-1-ium chloride, and the molecular formula is C7H7ClN2, Synthetic Route of 17281-59-3.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Pischedda, Sara published the artcileSynthesis and characterization of new Pd(II) and Pt(II) complexes with 3-substituted 1-(2-pyridyl)imidazo[1,5-a]pyridine ligands, Quality Control of 91-02-1, the publication is Dalton Transactions (2021), 50(14), 4859-4873, database is CAplus and MEDLINE.

Several palladium(II) and platinum(II) complexes (1–20) of general formula [M(Lⁿ)(X)(Y)] [M = Pd, X = Y = Cl (1–Cl–4–Cl), X = Y = OAc (1–OAc–4–OAc); M = Pt: X = Y = Cl (5–8); M = Pd, X = Cl, Y = CH₃ (9–12); M = Pt, X = Cl, Y = CH₃ (13–16) or X = Y = CH₃ (17–20); n = 1-4] have been synthesized by reaction of different Pd(II) and Pt(II) derivatives with various 3-substituted 1-(2-pyridyl)-imidazo[1,5-a]pyridines; i.e. Lⁿ = 1-(2-pyridyl)-3-arylimidazo[1,5-a]pyridine (aryl = Ph, L¹; 2-o-Tolyl, L²; Mesityl, L³) and 1-(2-pyridyl)-3-benzylimidazo[1,5-a]pyridine (L⁴). Detailed spectroscopic investigation (including IR, mono- and bi-dimensional ¹H NMR) and elemental anal. has been performed for all these species, allowing their complete characterization. Lⁿ act as N,N-bidentate ligands and coordinate the metal centers in a chelate fashion through the pyridyl (N_py) and the pyridine-like nitrogen atom of the imidazo[1,5-a]pyridine group (N_im). The x-ray structural anal. performed on two of Pd(II) and three Pt(II) complexes, namely [Pd(L²)(CH₃)Cl] (10), [Pd(L³)(CH₃)Cl] (11) and [Pt(L¹)Cl₂] (5), [Pt(L⁴)Cl₂] (8), [Pt(L²)(CH₃)Cl] (14) confirmed the spectroscopic and anal. data. Finally DFT studies unveiled the structural reasons behind the inertia of the synthesized compounds toward metalation, identified as the higher angle steric strain in comparison with the analogous bipyridine complexes.

Dalton Transactions published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C12H9NO, Quality Control of 91-02-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Kader, Thomas published the artcileAzaindolo[3,2,1-jk]carbazoles: New Building Blocks for Functional Organic Materials, Application of 2-Bromopyridin-3-amine, the publication is Chemistry – A European Journal (2019), 25(17), 4412-4425, database is CAplus and MEDLINE.

The preparation and characterization of 12 azaindolo[3,2,1-jk]carbazoles, e.g., I was presented. Ring-closing C-H activation allowed for the convenient preparation of six singly and six doubly nitrogen-substituted indolo[3,2,1-jk]carbazole derivatives in which ten of the materials had not been described in the literature before. The detailed photophys. and electrochem. characterization of the developed materials revealed a significant impact of the incorporation of pyridine-like nitrogen into the fully planar indolo[3,2,1-jk]carbazole backbone. Furthermore, the nitrogen position decisively impacted intermol. hydrogen bonding and thus the solid-state alignment. Ultimately, the versatility of the azaindolo[3,2,1-jk]carbazoles scaffold makes this class of materials an attractive new building block for the design of functional organic materials.

Chemistry – A European Journal published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Application of 2-Bromopyridin-3-amine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Arning, Juergen published the artcileQualitative and quantitative structure activity relationships for the inhibitory effects of cationic head groups, functionalized side chains and anions of ionic liquids on acetylcholinesterase, Quality Control of 17281-59-3, the publication is Green Chemistry (2008), 10(1), 47-58, database is CAplus.

To contribute to a deeper insight into the hazard potential of ionic liquids to humans and the environment, an acetylcholinesterase (AchE) inhibition screening assay was used to identify toxicophore substructures and interaction potentials mediating enzyme inhibition. The pos. charged nitrogen atom, a widely delocalized aromatic system, and the lipophilicity of the side chains connected to the cationic head groups can be identified as the key structural elements in binding to the enzymes active site. With respect to this, the dimethylaminopyridinium, the quinolinium and the pyridinium head groups exhibit a very strong inhibitory potential to the enzyme with IC₅₀ values around 10 μM. In contrast, the polar and non-aromatic morpholinium head group is found to be only weakly inhibiting to the enzyme activity, with IC₅₀ values > 500 μM. The introduction of polar hydroxy, ether or nitrile functions into the alkyl side chain is shown to be a potent structural alteration to shift the corresponding ionic liquids to a lower inhibitory potential. Supporting this fact, for a series of imidazolium cations, a QSAR correlation was set up by the linear regression of the log IC₅₀ vs. the logarithm of the HPLC-derived lipophilicity parameter k₀. Addnl., a broad set of anion species (inorganic, organic and complex borate anions), commonly used as ionic liquid counterions, was tested and the vast majority exhibited no effect on AchE. Only the fluoride and fluoride containing anion species which readily undergo hydrolytic cleavage can be identified to act as AchE inhibitors.

Green Chemistry published new progress about 17281-59-3. 17281-59-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitrile,Salt, name is 1-(Cyanomethyl)pyridin-1-ium chloride, and the molecular formula is C7H7ClN2, Quality Control of 17281-59-3.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Yu, Miao published the artcileA Practical and Robust Multistep Continuous Process for Manufacturing 5-Bromo-N-(tert-butyl)pyridine-3-sulfonamide, Product Details of C5H5NO3S, the publication is Organic Process Research & Development (2019), 23(9), 2088-2095, database is CAplus.

A multistep continuous flow process involving (1) magnesium-halogen exchange, (2) sulfonylation with sulfuryl chloride, and (3) reaction with tert-butylamine was developed for the synthesis of an arylsulfonamide pharmaceutical intermediate in the synthesis of BMS-919373. The process was successfully implemented, including a robust control strategy to manage the levels of several process impurities, to produce 76 kg of 5-bromo-N-(tert-butyl)pyridine-3-sulfonamide (I). As the instability of the reactive intermediates and existence of strong exotherms made a batch process unsuitable for production beyond a 1 kg scale, the alternative continuous process led to a practical and robust manufacturing route to the active pharmaceutical ingredient.

Organic Process Research & Development published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C23H20BN, Product Details of C5H5NO3S.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem