Category: pyridine-derivatives

Zhang, Xian Man published the artcileEquilibrium acidities and homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in N-substituted trimethylammonium and pyridinium cations, Related Products of pyridine-derivatives, the publication is Journal of Organic Chemistry (1993), 58(11), 3060-6, database is CAplus.

Equilibrium acidities (pK_HA) of the cations in 16 N-substituted trimethylammonium salts, one N-phenacylquinuclidinium salt, 8 N-substituted pyridinium salts, and N-(ethoxycarbonyl)isoquinolinium bromide, together with the oxidation potentials of their conjugate bases, have been determined in Me₂SO. The acidifying effects of the α-trimethylammonium groups (α-Me₃N⁺) and the α-pyridinium groups (α-PyN⁺) on the adjacent acidic C-H bonds in these cations were found to average about 10 and 18 pK_HA units, resp. The homolytic bond dissociation energies of the acidic C-H bonds in these cations, estimated by the combination of the equilibrium acidities with the oxidation potentials of their corresponding conjugate bases (ylides), show that the α-trimethylammonium groups destabilize adjacent radicals by 2-6 kcal/mol, whereas α-pyridinium groups stabilize adjacent radicals by 3-6 kcal/mol. The effects of α-pyridinium groups on the stabilization energies of the radicals derived from these cations were ca. 4-10 kcal/mol smaller than those of the corresponding Ph groups, whereas their effects on the equilibrium acidities of the cations were 5.4-13.1 pK_HA units larger. The pK_HA value of tetramethylammonium cation (Me₄N⁺) was estimated by extrapolation to be about 42 in Me₂SO.

Journal of Organic 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 C8H11BO3, Related Products of pyridine-derivatives.

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

Largeau, Berenger published the artcileGabapentinoid-induced peripheral edema and acute heart failure: A translational study combining pharmacovigilance data and in vitro animal experiments, Category: pyridine-derivatives, the publication is Biomedicine & Pharmacotherapy (2022), 112807, database is CAplus and MEDLINE.

Gabapentinoids are ligands of the α2-δ subunit of voltage-gated calcium channels (Cav) that have been associated with a risk of peripheral edema and acute heart failure in connection with a potentially dual mechanism, vascular and cardiac. All cases of peripheral edema or heart failure involving gabapentin or pregabalin reported to the French Pharmacovigilance Centers between Jan. 1, 1994 and Apr. 30, 2020 were included to describe their onset patterns (e.g., time to onset). Based on these data, we investigated the impact of gabapentinoids on the myogenic tone of rat third-order mesenteric arteries and on the electrophysiol. properties of rat ventricular cardiomyocytes. A total of 58 reports were included (gabapentin n = 5, pregabalin n = 53). The female-to-male ratio was 4:1 and the median age was 77 years (IQR 57-85, range 32-95). The median time to onset were 23 days (IQR 10-54) and 17 days (IQR 3-30) for non-cardiogenic edema and acute heart failure, resp. Cardiogenic and non-cardiogenic peripheral edema occurred frequently after a dose escalation (27/45, 60%), and the course was rapidly favorable after discontinuation of gabapentinoid (median 7 days, IQR 5-13). On rat mesenteric arteries, gabapentinoids significantly decreased the myogenic tone to the same extent as verapamil and nifedipine. Acute application of gabapentinoids had no significant effect on Cav1.2 currents of ventricular cardiomyocytes. Gabapentinoids can cause concentration-dependent peripheral edema of early onset. The primary mechanism of non-cardiogenic peripheral edema is vasodilatory edema secondary to altered myogenic tone, independent of Cav1.2 blockade under the exptl. conditions tested.

Biomedicine & Pharmacotherapy published new progress about 21829-25-4. 21829-25-4 belongs to pyridine-derivatives, auxiliary class Membrane Transporter/Ion Channel,Calcium Channel, name is Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, and the molecular formula is C17H18N2O6, Category: pyridine-derivatives.

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

Shimeno, Hiroshi published the artcileInhibition of rat liver tryptophan pyrrolase activity and elevation of brain tryptophan concentration by administration of DL-α-amino-β-pyridinepropanoic acid (pyridylalanine) analogs, Computed Properties of 18437-58-6, the publication is Journal of Enzyme Inhibition (1987), 2(1), 57-66, database is CAplus and MEDLINE.

Single doses of DL-α-amino-β-(2-pyridine)propanoic acid (2-PA, 100 mg/kg) decreased the holoenzyme and apoenzyme activities of rat liver tryptophan pyrrolase (TP) and increased brain tryptophan, serotonin (5-HT) and 5-hydroxyindole-3-ylacetic acid concentrations 2-PA had no inhibitory effect on either of the enzyme activities in vitro, but its expected metabolites were effective. Single doses of DL-α-amino-β-(3-pyridine)propanoic acid (3-PA, 100 mg/kg) decreased only the holoenzyme activity and elevated brain tryptophan and its metabolites levels in rats. 3-PA and its metabolite, 3-pyridylpyruvate, inhibited only the holoenzyme activity in vitro. DL-α-Amino-β-(4-pyridine)propanoic acid (4-PA) caused changes in liver TP (holo- and apoenzyme forms) activity and brain tryptophan concentration only after repeated administration (100 mg/kg/day). 4-PA was a weak inhibitor of the holoenzyme, but its metabolites apparently inhibited the holo- and apoenzyme activities in vitro. These findings suggest that PA analogs (and(or) their metabolites) increased brain tryptophan (and hence 5-HT synthesis) by directly inhibiting liver TP activity.

Journal of Enzyme Inhibition published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C8H11NO, Computed Properties of 18437-58-6.

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

Besmer, Manuel Luca published the artcileExploring the Coordination Chemistry of N₂ with Technetium PNP Pincer-Type Complexes, COA of Formula: C23H43NP2, the publication is Inorganic Chemistry (2021), 60(9), 6696-6701, database is CAplus and MEDLINE.

Dinitrogen (N₂) complexes of technetium (⁹⁹Tc) are rare, and only two examples have been reported. To complement this important class of complexes also for ⁹⁹Tc, two different pincer-type complexes of ⁹⁹Tc were studied to assess their abilities for coordinating dinitrogen. The reactions of the ⁹⁹Tc^III complex [⁹⁹TcCl₃(PPh₃)₂(NCCH₃)] with the pincer ligands PNP^tBu and ^PyrPNP^tBu resp. gave [⁹⁹Tc(PNP^tBu)Cl₂] and [⁹⁹Tc(^PyrPNP^tBu)Cl₃], the first structurally characterized ⁹⁹Tc complexes with mer-coordinated pincer ligands. Reductions with [Co(Cp*)₂] under N₂ gave the mononuclear bis-dinitrogen complex [⁹⁹Tc^I(PNP^tBu)(N₂)₂] and the dinuclear complex [⁹⁹Tc^I(^PyrPNP^tBu)(N₂)Cl]₂(μ-N₂) with both a bridging and a terminal N₂ ligand. Spectroscopy and crystal structures confirm their identities. The complexes are stable under a dinitrogen atm., and the N₂ ligands are tightly bound. The results for the complexes with the PNP^tBu pincer allow a comparison to its rhenium homolog, which has recently been shown to split the N₂ ligand with the formation of a nitrido complex.

Inorganic Chemistry published new progress about 338800-13-8. 338800-13-8 belongs to pyridine-derivatives, auxiliary class Bis-phosphine Ligands, name is 2,6-Bis((di-tert-butylphosphino)methyl)pyridine, and the molecular formula is C23H43NP2, COA of Formula: C23H43NP2.

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

Lim, Xin Rui published the artcileFast voltage-dependent sodium (Na_v) currents are functionally expressed in mouse corpus cavernosum smooth muscle cells, Synthetic Route of 21829-25-4, the publication is British Journal of Pharmacology (2022), 179(5), 1082-1101, database is CAplus and MEDLINE.

Corpus cavernosum smooth muscle (CCSM) exhibits phasic contractions that are coordinated by ion channels. Mouse models are commonly used to study erectile dysfunction, but there are few published electrophysiol. studies of mouse CCSM. We describe the voltage-dependent sodium (NaV) currents in mouse CCSM and investigate their function. We used electrophysiol., pharmacol. and immunocytochem. methods to study the NaV currents in isolated CCSM cells from C57BL/6 mice. Tension measurements were carried out using crural sections of the corpus cavernosum in whole tissue. Fast, voltage-dependent, sodium currents in mouse CCSM were induced by depolarising steps. Steady-state activation and inactivation curves revealed a window current between -60 and -30 mV. Two populations of NaV currents, ′TTX-sensitiveâ€?and ′TTX-insensitiveâ€? were identified. TTX-sensitive currents showed 48% block with the NaV channel subtype-specific blockers ICA-121431 (NaV1.1-1.3), PF-05089771 (NaV1.7) and 4,9-anhydro-TTX (NaV1.6). TTX-insensitive currents were resistant to blockade by A803467, specific for NaV1.8 channels. Immunocytochem. confirmed expression of NaV1.5 and NaV1.4 in freshly dispersed CCSM cells. Veratridine, a NaV channel activator, reduced time-dependent inactivation of NaV currents and increased duration of evoked action potentials. Veratridine induced phasic contractions in CCSM strips, reversible with TTX and nifedipine but not KB-R7943. There are fast, voltage-dependent, sodium currents in mouse CCSM. Stimulation of these currents increased contractility of CCSM in vitro, suggesting an involvement in detumescence and potentially providing a clin. relevant target in erectile dysfunction. Further work will be necessary to define its role.

British Journal of Pharmacology published new progress about 21829-25-4. 21829-25-4 belongs to pyridine-derivatives, auxiliary class Membrane Transporter/Ion Channel,Calcium Channel, name is Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, and the molecular formula is C17H18N2O6, Synthetic Route of 21829-25-4.

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

Thomas, Michael published the artcileScaffold-Hopping Strategy on a Series of Proteasome Inhibitors Led to a Preclinical Candidate for the Treatment of Visceral Leishmaniasis, Product Details of C5H6BNO2, the publication is Journal of Medicinal Chemistry (2021), 64(9), 5905-5930, database is CAplus and MEDLINE.

There is an urgent need for new treatments for visceral leishmaniasis (VL), a parasitic infection which impacts heavily large areas of East Africa, Asia, and South America. We previously reported on the discovery of GSK3494245/DDD01305143 (1) as a preclin. candidate for VL and, herein, we report on the medicinal chem. program that led to its identification. A hit from a phenotypic screen was optimized to give a compound with in vivo efficacy, which was hampered by poor solubility and genotoxicity. The work on the original scaffold failed to lead to developable compounds, so an extensive scaffold-hopping exercise involving medicinal chem. design, in silico profiling, and subsequent synthesis was utilized, leading to the preclin. candidate. The compound was shown to act via proteasome inhibition, and we report on the modeling of different scaffolds into a cryo-EM structure and the impact this has on our understanding of the series’ structure-activity relationships.

Journal of Medicinal Chemistry published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C12H10O4S, Product Details of C5H6BNO2.

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

Roth, H. J. published the artcileRing formation and β-elimination by the reaction of triphenylboron on tertiary amines, SDS of cas: 971-66-4, the publication is Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft (1964), 297(12), 766-72, database is CAplus.

Tertiary amino alcs. and tertiary amines of the Mannich-base types were treated with Ph₃B to yield a boron-containing heterocyclic N compound and elimination of an unsaturated moiety. Freshly-prepared, moist Ph₃B (3 g.) in 5 ml. EtOH was added to 2.05 g. 1-phenyl-2-piperidino-l-ethanol in 20 ml. EtOH, and the mixture heated several min. on a steam bath and cooled to give 81% the triphenylboroxazolidine (I), m. 190-1°. N-Methyl-L-ephedrin (1.8 g.), and 1.1 g. 1-phenyl-3-piperidino-1-propanol gave 89% II, m. 207-8°, and 78% III, m. 198-200°, resp. Concentrated EtOH solutions of Et₃N and Ph₃B (stoichiometric equivalents) were allowed to react in the cold and kept a short time to give quant. B,B,B-triphenyl-N,N,N-triethylaminoborane, m. 108-12°. B,B,B-Triphenyl-1-ethylpiperidineborane, m. 114-16°, was similarly prepared from 1-ethylpiperidine. The pyridinyl analog C₅H₅NBPh₃, m. 214-15° (decomposition), was prepared from pyridine and Ph₃B. A solution of 3 g. Ph₃B in 10 ml. absolute EtOH was added to 1.56 g. 2-piperidinomethylcyclohexanone (Mannich base) in 10 ml. EtOH and the solution was evaporated to half its volume on a steam bath and cooled several hrs. to precipitate 85% B,B,B-triphenylpiperidineborane (IV), m. 213-14°. The mother liquor was evaporated in vacuo to a sirup which was dissolved in glacial HOAc and the solution treated with 1 ml. HCl to give 88% the hydrated dimeric cyclohexanone (V), m. 153°. Ph₃B (1.5 g.) in 5 ml. EtOH was added to 5 ml. of an EtOH solution of 2-diethylaminomethylphenol, prepared from 1 g. of the HCl salt by usual procedures. The precipitate, C₄₆H₅₀B₂N₂O, m. 169° (EtOH-acetone). No phenolic, other OH, or NH groups were present, as shown by ir. A similar reaction was carried out with 2-piperidinomethyl-4-methylphenol and Ph₃B. The compound, C₅₀H₅₄B₂N₂O, m. 230° (decomposition), likewise showed no OH or NH groups. IV was obtained by similar reaction of piperidinomethylbenzamide or piperidinomethylsalicylamide with Ph₃B along with BzNH₂, or salicylamide, resp.

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft published new progress about 971-66-4. 971-66-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is Triphenyl(pyridin-1-ium-1-yl)borate, and the molecular formula is C23H20BN, SDS of cas: 971-66-4.

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

Mallet, Marc published the artcileMigration of lithium in a series of pyridines: double catalysis and reforming. Access to derivatives of 2-bromo-3-lithiopyridine and 4-bromo-2-halo-3-lithiopyridines, Related Products of pyridine-derivatives, the publication is Journal of Organometallic Chemistry (1990), 382(3), 319-32, database is CAplus.

The lithium of an organolithio-pyridinic derivative can be moved from one position to another by an intermol. reaction. Two new reactions are possible for pyridinic organic synthesis; their isomerization of any lithio derivative to a more stable one, and a reaction that transforms a mixture of various bromo-lithio derivatives into a single one. The processes involved and the exptl. tools used are described in terms of the 2-bromo-3-lithio- and 4-bromo-2-halogeno-3-lithiopyridines derivatives synthesis. Thus, 2,6-dibromopyridine was treated with Me₃CLi and (Me₂CH)₂NH in THF followed by DMF to give 40% 2-bromo-3-pyridinecarboxaldehyde.

Journal of Organometallic Chemistry published new progress about 128071-77-2. 128071-77-2 belongs to pyridine-derivatives, auxiliary class Pyridine,Fluoride,Bromide,Aldehyde,Pyridine, name is 4-Bromo-2-fluoronicotinaldehyde, and the molecular formula is C6H3BrFNO, Related Products of pyridine-derivatives.

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

Simler, Thomas published the artcileChromium(II) Pincer Complexes with Dearomatized PNP and PNC Ligands: A Comparative Study of Their Catalytic Ethylene Oligomerization Activity, Category: pyridine-derivatives, the publication is Organometallics (2016), 35(24), 4044-4049, database is CAplus.

Monodeprotonation of the 2,6-bis(di-tert-butylphosphinomethyl)pyridine (^tBuPN^tBuP) at the α-lutidinyl-CH₂ position with 1 equiv of KCH₂C₆H₅ and concomitant dearomatization of the heterocycle afforded K(^tBuP^*N_a^tBuP) (^tBuP^* = di-tert-Bu vinylic P donor, ^tBuP = PtBu₂, N_a = anionic amido N donor); its transmetalation with [CrCl₂(THF)₂] afforded the Cr(II) complex [Cr(^tBuP^*N_a^tBuP)Cl] (A). The x-ray diffraction anal. of A established a slightly distorted square-planar coordination geometry at the metal center and confirmed retention of the dearomatized coordinated ligand. The catalytic activity of A in ethylene oligomerization was studied and compared with that of the related Cr(II) complexes [Cr(^tBuP^*N_aC^NHC)Cl] (B) and [Cr{Cr(^tBuP^*N_a^tBuP^*)Cl}₂] (C) previously reported.

Organometallics published new progress about 338800-13-8. 338800-13-8 belongs to pyridine-derivatives, auxiliary class Bis-phosphine Ligands, name is 2,6-Bis((di-tert-butylphosphino)methyl)pyridine, and the molecular formula is C5H5N3S, Category: pyridine-derivatives.

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

Ortgies, Stefan published the artcileSelenium-Catalyzed Oxidative C(sp²)-H Amination of Alkenes Exemplified in the Expedient Synthesis of (Aza-)Indoles, Category: pyridine-derivatives, the publication is Organic Letters (2015), 17(11), 2748-2751, database is CAplus and MEDLINE.

A new selenium-catalyzed protocol for the direct, intramol. amination of C(sp²)-H bonds using N-fluorobenzenesulfonimide as the terminal oxidant is reported. This method enables the facile formation of a broad range of diversely functionalized indoles and azaindoles derived from easily accessible ortho-vinyl anilines and vinylated aminopyridines, resp. The procedure exploits the pronounced carbophilicity of selenium electrophiles for the catalytic activation of alkenes and leads to the formation of C(sp²)-N bonds in high yields and with excellent functional group tolerance.

Organic Letters 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, Category: pyridine-derivatives.

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