Month: December 2022

Butler, Richard N. published the artcileDetection of a metalo intermediate and geometrical isomerizations in an oxidative cyclization of a heterocyclic hydrazone with mercury(II) acetate, Name: 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, the publication is Journal of the Chemical Society, Chemical Communications (1981), 376-7, database is CAplus.

Oxidative cyclization of the (E)-hydrazone I on treatment with Hg(OAc)₂ (AcOH, 70°, 16 h) gave 37% II, via the (Z)-intermediate III. The reaction mechanism, which involves a series of cis-trans isomerizations, is discussed.

Journal of the Chemical Society, Chemical Communications published new progress about 2215-33-0. 2215-33-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, and the molecular formula is C11H10N4, Name: 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine.

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

Butler, Richard N. published the artcileStereoisomerization in heterocyclic hydrazones derived from 2-acylpyridines and their oxidative cyclization with mercury(II) acetate and lead tetraacetate to fused 1,2,4-triazoles and 1,2,3-triazolium systems, Recommanded Product: 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1984), 2109-16, database is CAplus.

Fourteen hydrazones I (R = H, Me, Ph; R¹ = 2-pyridyl, 4-O₂NC₆H₄, Ph, 4-BrC₆H₄, 4-MeOC₆H₄, 4-MeC₆H₄), prepared by coupling 2-formyl-, -benzoyl-, or -acetylpyridine with H₂NNHR¹ (R¹ as before), were isolated predominantly as E isomers, when the acyl substituent R was small (H = Me). When R = Ph, significant yield of Z isomers containing an intramol. H bond were also obtained. The structure of E-I (R = R¹ = Ph) was determined by x-ray crystallog. Oxidation reactions of I were not configuration dependent contrary to the report of R. Kuhn and W. Munzig (1952). A common metallo intermediate II, was obtained by oxidation of E– and Z–I (R = H, R¹ = 2-pyridyl) with Hg(OAc)₂. In Pb(OAc)₄ oxidation of the hydrazones, the product controlling factor was the nature of the methine substituent R. For the ketone derivatives I (R â‰?H), oxidation to fused 1,2,3-triazolium systems occurred via a 5-exo–tet cyclization with E- and Z-hydrazones, whereas for aldehyde systems, I (R = H), the oxidation involved dehydration to a nitrilimine and gave products by solvent addition or a 5-endo–dig cyclization to fused 1,2,4-triazolo systems. Thus, Pb(OAc)₄ oxidation of E– or Z–I (R = Ph, R¹ = 4-O₂NC₆H₄) gave 80% triazolopyridinium III, whereas similar oxidation of E– or Z–I (R = H, R¹ = 2-pyridyl) gave 73-86% triazolopyridine IV.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 2215-33-0. 2215-33-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, and the molecular formula is C11H10N4, Recommanded Product: 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine.

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

Shaffer, David W. published the artcileReactivity of a Series of Isostructural Cobalt Pincer Complexes with CO₂, CO, and H⁺, Product Details of C23H43NP2, the publication is Inorganic Chemistry (2014), 53(24), 13031-13041, database is CAplus and MEDLINE.

The preparation and characterization of a series of isostructural cobalt complexes [Co(t-Bu)₂P^EPy^EP(t-Bu)₂(MeCN)₂][BF₄]₂ (Py = pyridine, E = CH₂, NH, O, and X = BF₄ (1a–c)) and the corresponding one-electron reduced analogs [Co(t-Bu)₂P^EPy^EP(t-Bu)₂(MeCN)][BF₄] (2a–c) are reported. The reactivity of the reduced cobalt complexes with CO₂, CO, and H⁺ to generate intermediates in a CO₂ reduction to CO and H₂O cycle are described. The reduction of 1a–c and subsequent reactivity with CO₂ was investigated by cyclic voltammetry, and for 1a also by IR spectroelectrochem. The corresponding CO complexes of (2a–c) were prepared, and the Co-CO bond strengths were characterized by IR spectroscopy. Quantum mech. methods (B3LYP-d3 with solvation) were used to characterize the competitive reactivity of the reduced cobalt centers with H⁺ vs. CO₂. By investigating a series of isostructural complexes, correlations in reactivity with ligand electron withdrawing effects are made.

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 C9H10O4, Product Details of C23H43NP2.

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

Shah, Sonya C. published the artcileCovalent modification of cytochrome c with a hydrazone complex of platinum(II), COA of Formula: C11H10N4, the publication is Journal of the Serbian Chemical Society (1988), 53(3), 139-48, database is CAplus.

The complex Pt(sbpaphy)Cl^– (where sbpaphy is 2-(3-sulfobenzoyl)-pyridine-2-aldehyde 2′-pyridylhydrazone) modifies selectively the histidine (His) 33 residue in horse heart cytochrome c at pH 7.0. The reaction takes place under mild conditions and the Pt(sbpaphy)His label is stable at pH 7.0. The binding site is identified by UV-vis spectrophotometry and by studies of model complexes. The labeled protein is purified readily by cation-exchange chromatog. and the inorganic chromophore in it is quantitated easily owing to its strong UV absorption bands. Cyclic voltammetry, differential-pulse voltammetry, and UV-vis spectrophotometry show that labeling does not perturb the protein.

Journal of the Serbian Chemical Society published new progress about 2215-33-0. 2215-33-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, and the molecular formula is C6H17NO3Si, COA of Formula: C11H10N4.

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

Griswold, Jessica A. published the artcileStereoconvergent Conjugate Addition of Arylboronic Acids to α-Angelica Lactone Derivatives: Synthesis of Stereochemically Complex γ-Butyrolactones, Category: pyridine-derivatives, the publication is ACS Catalysis (2019), 9(12), 11614-11618, database is CAplus and MEDLINE.

Catalyzed stereoconvergent 1,4-additions to unsaturated carbonyls are rare but of high potential value. This letter details the development of enantioselective arylation reactions of boronic acids and β,γ-butenolides. These reactions are catalyzed by com. available hydroxy[(S)-BINAP]-rhodium(I) dimer to afford stereochem. complex γ-butyrolactone derivatives The reaction products provide functionality amenable to further manipulation and can lead to products with up to three contiguous stereocenters. The reaction proceeds under a dynamic kinetic resolution manifold by isomerizing the achiral starting material into an interconverting mixture of enantiomeric conjugate acceptors, followed by catalyst-controlled, enantiomer-selective 1,4-additionBase-promoted racemization of the intermediate α,β-butenolide is possible due to the high kinetic and thermodn. acidity of the γ-proton.

ACS Catalysis 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, Category: pyridine-derivatives.

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

Nara, Susheel J. published the artcileDiscovery of BMS-986339, a Pharmacologically Differentiated Farnesoid X Receptor Agonist for the Treatment of Nonalcoholic Steatohepatitis, Recommanded Product: (6-Ethoxypyridin-3-yl)boronic acid, the publication is Journal of Medicinal Chemistry (2022), 65(13), 8948-8960, database is CAplus and MEDLINE.

While several farnesoid X receptor (FXR) agonists under clin. investigation for the treatment of nonalcoholic steatohepatitis (NASH) have shown beneficial effects, adverse effects such as pruritus and elevation of plasma lipids have limited their clin. efficacy and approvability. Herein, we report the discovery and preclin. evaluation of compound 32 (BMS-986339), a nonbile acid FXR agonist with a pharmacol. distinct profile relative to our previously reported agonist BMS-986318. Compound 32 exhibited potent in vitro and in vivo activation of FXR, albeit with a context-dependent profile that resulted in tissue-selective effects in vivo. To our knowledge, this is the first report that demonstrates differential induction of Fgf15 in the liver and ileum by FXR agonists in vivo. Compound 32 demonstrated robust antifibrotic efficacy despite reduced activation of certain genes in the liver, suggesting that the addnl. pharmacol. of BMS-986318 does not further benefit efficacy, possibly presenting an opportunity for reduced adverse effects. Further evaluation in humans is warranted to validate this hypothesis.

Journal of Medicinal Chemistry 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, Recommanded Product: (6-Ethoxypyridin-3-yl)boronic acid.

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

Quan, Zheng-Jun published the artcilePalladium(II) catalyzed Suzuki/Sonogashira cross-coupling reactions of sulfonates: an efficient approach to C2-functionalized pyrimidines and pyridines, Synthetic Route of 89076-64-2, the publication is European Journal of Organic Chemistry (2013), 2013(31), 7175-7183, database is CAplus.

Pyrimidin-2-yl sulfonates, as a reaction partner, can be easily prepared from inexpensive com. materials and are efficiently cross-coupled with arylboronic acids and terminal alkynes by using Pd(OAc)₂-catalyzed Suzuki and Sonogashira reactions. A wide array of C2-functionalized pyrimidines have been prepared in good to excellent yields. 2-Arylpyridines and 2-(oct-1-ynyl)pyridine were also synthesized.

European Journal of 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, Synthetic Route of 89076-64-2.

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

Gui, Yue published the artcileCrystal Energy Landscape of Nifedipine by Experiment and Computer Prediction, Name: Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, the publication is Crystal Growth & Design (2022), 22(2), 1365-1370, database is CAplus.

The six polymorphs of nifedipine (NIF) known at present have been discovered over the past 50 years, and the most recent one (δ), discovered in 2020, came from an unusual route. This polymorph is ranked second in thermodn. stability but evaded all previous workers until its melt was seeded with the crystal of a foreign substance, felodipine, in which the mol. has a different conformation from all other NIF polymorphs known at that time. Given this unusual discovery in the lab, we investigated whether crystal structure prediction (CSP) can find this and other polymorphs in a “routine” search. We show that our CSP finds all ordered polymorphs of NIF known at present as low-energy structures (Ranks 1, 3, 4, and 43), including the most recent one unveiled by pseudoseeding (Rank 4). NIF being a flexible mol., it is of interest to learn which of its many conformers provides the best building block for crystals. An exptl. investigation of this question is limited by survival; i.e., information exists on the structures that are observed but not on those that are difficult to observe or not yet discovered. In this regard, our “computer experiments” access the full range of possibilities. We find that the synperiplanar (sp) conformer with respect to Ph torsion produces lower-energy crystals than the antiperiplanar (ap) conformer, with the most stable ap crystal being 4 kJ/mol higher in energy than the most stable sp structure. Exptl., the sp conformer dominates the ap in solution and is the only conformer observed in crystals. With respect to the ester torsions, the cis/trans conformer produces the lowest-energy crystals, followed by the cis/cis conformer and by the trans/trans conformer. Exptl., five of the six known polymorphs contain the cis/trans conformer, one contains the cis/cis conformer, and none contain the trans/trans conformer. Overall, the CSP is remarkably successful in predicting the polymorphs of NIF in spite of its complex conformational space and provides a quant. assessment of the relative costs of employing different conformers as units of crystal building.

Crystal Growth & Design 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, Name: Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

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

Niu, Nana published the artcileDesign and Synthesis of Tetrandrine Derivatives as Potential Anti-tumor Agents Against A549 Cell Lines, Category: pyridine-derivatives, the publication is ChemistrySelect (2019), 4(1), 196-201, database is CAplus.

Tetrandrine was converted to 5-bromotetrandrine using a mild oxidative system (DMSO/HBr). Suzuki-Miyaura and Sonogashira cross-coupling reactions were then employed to yield a set of 5-substituted tetrandrine derivatives I (R = 5-formylfuran-2-yl, pyrimidin-5-yl, 2-cyclopropylethynyl, etc.). Their antiproliferative activities against A549 cell lines in vitro were evaluated using the MTT assay. Most of the compounds were found to possess significant inhibitory activities and compound I (R = 2-methoxypyrimidin-5-yl) (A) had the highest (IC₅₀ = 3.04 μM). Further studies on the mechanism demonstrated by (A) showed that it promotes apoptosis of A549 cells in a dose-dependent manner and reduces the mitochondrial membrane potential. Western blot results showed that the compound up-regulated the levels of Bax protein and down-regulated the level of Bcl-2 protein. Compared to the control group, the expression of cleaved-caspase 3 and cleaved-PARP in cells was significantly increased.

ChemistrySelect published new progress about 1008506-24-8. 1008506-24-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Ether,Pyridine,Boronic Acids,Boronic acid and ester, name is 3-Methoxypyridine-4-boronic acid, and the molecular formula is C6H8BNO3, Category: pyridine-derivatives.

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

Gu, Lijun published the artcileSynthesis and antitumor activity of α-aminophosphonates containing thiazole[5,4-b]pyridine moiety, Related Products of pyridine-derivatives, the publication is Organic & Biomolecular Chemistry (2012), 10(35), 7098-7102, database is CAplus and MEDLINE.

A new procedure is developed for the synthesis of α-aminophosphonates containing thiazole[5,4-b]pyridine moiety from conveniently available starting materials. The target compounds were characterized by IR, ¹H NMR, ¹³C NMR, ³¹P NMR, mass spectrometry and elemental anal. The newly synthesized compounds were evaluated for their anticancer activities against PC-3, Bcap-37, H460 cells in vitro by the MTT method. Two compounds are highly effective against PC-3, Bcap-37 cells and good to H460 cells. Further study is necessary to find out the potential antitumor activities.

Organic & Biomolecular 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, Related Products of pyridine-derivatives.

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