Month: December 2022

Zhuang, Linghang published the artcileDiscovery of BI 135585, an in vivo efficacious oxazinanone-based 11β hydroxysteroid dehydrogenase type 1 inhibitor, Formula: C5H6BNO2, the publication is Bioorganic & Medicinal Chemistry (2017), 25(14), 3649-3657, database is CAplus and MEDLINE.

A potent, in vivo efficacious 11β hydroxysteroid dehydrogenase type 1 (11β HSD1) inhibitor (I) has been identified. Compound I inhibited 11β HSD1 activity in human adipocytes with an IC₅₀ of 4.3 nM and in primary human adipose tissue with an IC₈₀ of 53 nM. Oral administration of I to cynomolgus monkey inhibited 11β HSD1 activity in adipose tissue. Compound I exhibited >1000× selectivity over other hydroxysteroid dehydrogenases, displays desirable pharmacodynamic properties and entered human clin. trials in 2011.

Bioorganic & 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 C12H16O3, Formula: C5H6BNO2.

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

Zhang, Yongliang published the artcileN-alkylation of pyridylalanine and pyridinecarboxylic acids and their use in synthesis of GnRH antagonists, Synthetic Route of 636-73-7, the publication is Tetrahedron Letters (1993), 34(23), 3659-62, database is CAplus.

A mild N-alkylation method has been developed for the synthesis of N-alkylated pyridiniumcarboxylic acids using Ag₂O-H₂O catalysis to enhance the low reactivity of pyridinecarboxylic acids. Two approaches were undertaken for the synthesis of a series of GnRH antagonists containing pyridinium moieties at the side chain: (1) incorporation of alkylated D-pyridylalanine analogs I (Boc = Me₃CO₂C; R = Me, CH₂Ph, CHMe₂, Bu) during solid phase peptide chain assembly, and (2) coupling of the N-alkylated pyridiniumcarboxylic acid to a D-lysine ε-amino group on a solid support.

Tetrahedron Letters 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 C18H35NO, Synthetic Route of 636-73-7.

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

Banks, Ronald Eric published the artcileFluorocarbon derivatives of nitrogen. Part 11. Synthesis of some 2-(trifluoromethyl)imidazo[1,2-a]pyridines from trifluoroacetonitrile, Related Products of pyridine-derivatives, the publication is Journal of Fluorine Chemistry (1984), 26(4), 499-506, database is CAplus.

The title compound (I; R = Me₃CO₂C), prepared from CF₃CN and pyridinium t-butoxycarbonylmethylide, reacts smoothly with CF₃CO₂H to give the acid (I; R = HO₂C), which was decarboxylated to I (R = H) on heating. The cyano derivative (I; R = cyano) can be obtained via treatment of CF₃CN with pyridinium cyanomethylide, which is sufficiently reactive to effect nucleophilic displacement of fluorine from pentafluoropyridine under mild conditions to give II.

Journal of Fluorine 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, Related Products of pyridine-derivatives.

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

Abou, Diane S. published the artcileTowards the stable chelation of radium for biomedical applications with an 18-membered macrocyclic ligand, Recommanded Product: 6,6′-((1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-7,16-diyl)bis(methylene))dipicolinic acid, the publication is Chemical Science (2021), 12(10), 3733-3742, database is CAplus and MEDLINE.

Targeted alpha therapy is an emerging strategy for the treatment of disseminated cancer. [²²³Ra]RaCl₂ is the only clin. approved alpha particle-emitting drug, and it is used to treat castrate-resistant prostate cancer bone metastases, to which [²²³Ra]Ra²⁺ localizes. To specifically direct [²²³Ra]Ra²⁺ to non-osseous disease sites, chelation and conjugation to a cancer-targeting moiety is necessary. Although previous efforts to stably chelate [²²³Ra]Ra²⁺ for this purpose have had limited success, here we report a biol. stable radiocomplex with the 18-membered macrocyclic chelator macropa. Quant. labeling of macropa with [²²³Ra]Ra²⁺ was accomplished within 5 min at room temperature with a radiolabeling efficiency of >95%, representing a significant advancement over conventional chelators such as DOTA and EDTA, which were unable to completely complex [²²³Ra]Ra²⁺ under these conditions. [²²³Ra][Ra(macropa)] was highly stable in human serum and exhibited dramatically reduced bone and spleen uptake in mice in comparison to bone-targeted [²²³Ra]RaCl2, signifying that [²²³Ra][Ra(macropa)] remains intact in vivo. Upon conjugation of macropa to a single amino acid β-alanine as well as to the prostate-specific membrane antigen-targeting peptide DUPA, both constructs retained high affinity for 223Ra, complexing >95% of Ra²⁺ in solution Furthermore, [²²³Ra][Ra(macropa-β-alanine)] was rapidly cleared from mice and showed low 223Ra bone absorption, indicating that this conjugate is stable under biol. conditions. Unexpectedly, this stability was lost upon conjugation of macropa to DUPA, which suggests a role of targeting vectors in complex stability in vivo for this system. Nonetheless, our successful demonstration of efficient radiolabeling of the β-alanine conjugate with ²²³Ra and its subsequent stability in vivo establishes for the first time the possibility of delivering [²²³Ra]Ra²⁺ to metastases outside of the bone using functionalized chelators, marking a significant expansion of the therapeutic utility of this radiometal in the clinic.

Chemical Science published new progress about 1128304-86-8. 1128304-86-8 belongs to pyridine-derivatives, auxiliary class Pyridines, name is 6,6′-((1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-7,16-diyl)bis(methylene))dipicolinic acid, and the molecular formula is C26H36N4O8, Recommanded Product: 6,6′-((1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-7,16-diyl)bis(methylene))dipicolinic acid.

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

Lohse, Olivier published the artcileThe palladium-catalyzed Suzuki coupling of 2- and 4-chloropyridines, Name: 5-Nitro-2-phenylpyridine, the publication is Synlett (1999), 45-48, database is CAplus.

The Suzuki coupling of 2- and 4-chloropyridines with arylboronates is successfully performed under Pd(PPh₃)₄ catalysis. Moderate to good yields are obtained with 4-chloropyridines, while 2-chloropyridines give excellent yields. The corresponding pyridine N-oxides react in the same manner. An easy and cheap access to arylpyridines, is thus achieved.

Synlett published new progress about 89076-64-2. 89076-64-2 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitro Compound,Benzene, name is 5-Nitro-2-phenylpyridine, and the molecular formula is C11H8N2O2, Name: 5-Nitro-2-phenylpyridine.

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

Czyz, Milena L. published the artcileReductive Activation and Hydrofunctionalization of Olefins by Multiphoton Tandem Photoredox Catalysis, Related Products of pyridine-derivatives, the publication is ACS Catalysis (2021), 11(9), 5472-5480, database is CAplus.

The conversion of olefin feedstocks to architecturally complex alkanes represents an important strategy in the expedient generation of valuable mols. for the chem. and life sciences. Synthetic approaches are reliant on the electrophilic activation of unactivated olefins, necessitating functionalization with nucleophiles. However, the reductive functionalization of unactivated and less activated olefins with electrophiles remains an ongoing challenge in synthetic chem. Here, we report the nucleophilic activation of inert styrenes through a photoinduced direct single electron reduction to the corresponding nucleophilic radical anion. Central to this approach is the multiphoton tandem photoredox cycle of the iridium photocatalyst [Ir(ppy)₂(dtb-bpy)]PF₆, which triggers in situ formation of a high-energy photoreductant that selectively reduces styrene olefinic π bonds to radical anions without stoichiometric reductants or dissolving metals. This mild strategy enables the chemoselective reduction and hydrofunctionalization of styrenes to furnish valuable alkane and tertiary alc. derivatives Mechanistic studies support the formation of a styrene olefinic radical anion intermediate and a Birch-type reduction involving two sequential single electron transfers. Overall, this complementary mode of olefin activation achieves the hydrofunctionalization of less activated alkenes with electrophiles, adding value to abundant olefins as valuable building blocks in modern synthetic protocols.

ACS 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, Related Products of pyridine-derivatives.

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

Nishiwaki, Nagatoshi published the artcileThree components ring transformation affording substituted 5-nitropyridines and 4-nitroanilines, Recommanded Product: 5-Nitro-2-phenylpyridine, the publication is Letters in Organic Chemistry (2006), 3(8), 629-633, database is CAplus.

The ring transformation of 1-methyl-3,5-dinitro-2-pyridone afforded 2-aryl-5-nitropyridines upon treatment with aromatic ketones in the presence of ammonium acetate. In reactions with aliphatic ketones, 2,6-disubstituted 4-nitroanilines could be prepared in addition to 2,3-disubstituted 5-nitropyridines. In these reactions, dinitropyridone behaved as the synthetic equivalent of unstable nitromalonaldehyde.

Letters in Organic Chemistry published new progress about 89076-64-2. 89076-64-2 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitro Compound,Benzene, name is 5-Nitro-2-phenylpyridine, and the molecular formula is C11H8N2O2, Recommanded Product: 5-Nitro-2-phenylpyridine.

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

Woolston, Esther published the artcileComparison of the effects on maternal endothelial cell activation: an in vitro study of anti-hypertensive drugs clinically used in pre-eclampsia, Formula: C17H18N2O6, the publication is Journal of Human Hypertension (2022), 36(2), 192-200, database is CAplus and MEDLINE.

Endothelial cell dysfunction in pregnancy, which can be induced by placental factors, is the fundamental component of the pathogenesis of pre-eclampsia. The dysfunctional vascular endothelium disrupts the balance of vasodilatory and vasoconstrictive factors, resulting in increasing blood pressure. There is currently no effective treatment for pre-eclampsia and effective control of hypertension may reduce neonatal morbidity and mortality by prolonging gestation, especially in cases of early onset disease. To date methyldopa, labetalol, nifedipine and metoprolol are recommended for controlling blood pressure in pre-eclampsia. All of these drugs have different mechanisms of action. In this in vitro study we investigated whether different types of anti-hypertensive drugs could have different effects on improving maternal endothelial cell dysfunction. Endothelial cells (HMEC-1) were exposed to phorbol-12-myristate-13-acetate (PMA) or pre-eclamptic sera or extracellular vesicles (EVs) derived from pre-eclamptic placentae, in the presence of each of the studied anti-hypertensive drugs (methyldopa, labetalol, nifedipine and metoprolol) or placebo for 24 h. Endothelial cell-surface adhesion mol. (ICAM-1) and monocyte adhesion were measured. The expression of cell-face ICAM-1 by HMEC-1 cells and THP-1 monocyte adherent to HMEC-1 that were exposed to three sep. well-known activators of endothelial cells in the presence of four anti-hypertensive drugs was significantly reduced regardless of the dose. However, the effect on the reduction of ICAM-1 expression and monocyte adhesion was not significantly different between the four medications. Our data suggest that the beneficial effect on improving endothelial cell function by these commonly prescribed anti-hypertensive drugs is seemingly independent of the anti-hypertensive mechanisms of the medication.

Journal of Human Hypertension 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 C14H10N2O, Formula: C17H18N2O6.

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

Yamada, Yasuyuki published the artcileMetal-Induced Structural Switching of a Folded Quinone-Sandwiched Porphyrin, Category: pyridine-derivatives, the publication is Journal of Inorganic and Organometallic Polymers and Materials (2013), 23(1), 180-185, database is CAplus.

The authors report the synthesis of a novel quinone-sandwiched porphyrin in which two benzoquinones are connected oppositely at the meso positions of a porphyrin through rigid 3-amido 2,2′-bipyridine linkers. ¹H-NMR and single crystal x-ray analyses revealed that the quinone-sandwiched porphyrin has a folded structure in which the porphyrin unit was inserted into the two quinone moieties via π-stacking. Insertion of a Zn(II) ion into the porphyrin center induced a drastic conformational change which is resulted in coordination of the oxygen atoms of both benzoquinone moieties to the Zn-porphyrin to afford a 6-coordinated structure.

Journal of Inorganic and Organometallic Polymers and Materials 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 C7H13BrSi, Category: pyridine-derivatives.

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

Guo, Changchuan published the artcile[Determination of trace genotoxic impurities in nifedipine by ultra high performance liquid chromatography-electrostatic field orbitrap high resolution mass spectrometry]., Recommanded Product: Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, the publication is Se pu = Chinese journal of chromatography (2022), 40(3), 266-272, database is MEDLINE.

A method based on ultra high performance liquid chromatography-electrostatic field orbitrap high resolution mass spectrometry (UHPLC-Orbitrap HRMS) was established for the determination of genotoxic impurities 2, 6, and 12 in nifedipine. After extraction with methanol, the sample was injected into the UHPLC-Orbitrap HRMS system for analysis. An ACE EXCEL^TM 3 C18-AR column (150 mm×4.6 mm, 3 μm) was used for chromatographic separation. The mobile phase was methanol-0.1% formic acid aqueous solution (65âˆ?5, v/v). The flow rate was 0.6 mL/min, while the column temperature and autosampler temperature were set as 35 â„?and 8 â„? respectively. The divert valve switching technique was used to protect the mass spectrometer. The six-way valve was set to divert the eluent of 7.5-11.6 min to waste and the rest of the eluent into the mass spectrometer. The Orbitrap mass spectrometer was coupled with the UHPLC system by an electrospray ion (ESI) source. The sheath gas and auxiliary gas flow rates were 60 and 20 arb (arbitrary units), respectively. The spray voltage was 3.5 kV, while the capillary temperature and auxiliary gas heater temperature were set as 350 â„?and 400 â„? respectively. The positive ion parallel reaction monitoring (PRM) scanning mode was adopted, and the mass spectral resolution was set to 35000 FWHM. The accurate masses of the [M+H]⁺ precursor ions of impurities 2, 6, and 12 were m/z 347.1230, 361.1026, and 347.1230, respectively. The accurate masses of the extracted [M+H]⁺ fragment ions of impurities 2, 6, and 12 were m/z 315.0968, 298.1069, and 315.0968, respectively. The normalized collision energies (NCEs) were optimized to 10%, 42%, and 10% for impurities 2, 6, and 12, respectively. The external standard method was utilized for quantitative analysis. The established method was validated in detail by investigating the specificity, linear range, limit of detection (LOD), limit of quantification (LOQ), recovery, precision, and stability. This method had good specificity, and the solvent did not interfere with the determination of impurities. The peak areas of impurities 2, 6, and 12 as well as their concentrations showed good linear relationships in the ranges of 0.2-100 ng/mL, with all correlation coefficients (r)â‰?.9998. The recoveries of impurities 2, 6, and 12 at three levels (low, medium, and high) were in the range of 96.9%-105.0%, while the RSDs were between 1.21% and 5.12%. The LODs were 0.05 ng/mL and the LOQs were 0.2 ng/mL for all three impurities. This analytical method was used to determine impurities 2, 6, and 12 in three batches of nifedipine samples. Impurity 6 was not detected in the three batches, but impurities 2 and 12 were detected in all the three samples, and the detection amount was within the limit. The developed method is sensitive, fast, accurate, and easy to operate. It can provide a reference for the quality control of nifedipine by pharmaceutical companies and extend strong technical support for the supervision by drug regulatory authorities.

Se pu = Chinese journal of chromatography 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, Recommanded Product: Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

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