Day: December 8, 2022

Zhang, Yongda published the artcileAn Enantioselective Synthesis of an 11-β-HSD-1 Inhibitor via an Asymmetric Methallylation Catalyzed by (S)-3,3′-F₂-BINOL, Name: (1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)boronic acid, the publication is Journal of Organic Chemistry (2016), 81(6), 2665-2669, database is CAplus and MEDLINE.

An efficient asym. synthesis of 11-β-HSD inhibitor I has been accomplished in five linear steps and 53% overall yield, starting from the readily available 3-chloro-1-phenylpropan-1-one. The key feature of the synthesis includes an asym. methallylation of 3-chloro-1-phenylpropan-1-one catalyzed by the highly effective organocatalyst (S)-3,3′-F₂-BINOL under solvent-free and metal-free conditions.

Journal of Organic Chemistry published new progress about 1351413-50-7. 1351413-50-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Amide,Pyridine,Boronic Acids,Boronic acid and ester, name is (1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)boronic acid, and the molecular formula is C11H8ClN3, Name: (1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)boronic acid.

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

Luo, Zhongfeng published the artcileCesium Fluoride and Copper-Catalyzed One-Pot Synthesis of Benzoxazoles via a Site-Selective Amide C-N Bond Cleavage, Safety of 2-Bromopyridin-3-amine, the publication is Advanced Synthesis & Catalysis (2019), 361(17), 4117-4125, database is CAplus.

We report herein a two-step one-pot strategy for the synthesis of benzoxazoles from amides by using cesium fluoride/copper as catalysts. This approach involves the in situ generation of acyl fluorides from the corresponding amides, and the acyl fluorides undergo transamidation and cyclization to give benzoxazoles in good yields. In this work, the amide C-N bonds are activated by CsF to form the acyl fluoride intermediates, which further react with o-bromoanilines to efficiently yield benzoxazoles. Notably, this methodol. demonstrates a broad substrate scope, as primary/secondary benzamides are well tolerated, and this process might facilitate the development of one-pot transformations of amides.

Advanced Synthesis & Catalysis 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, Safety of 2-Bromopyridin-3-amine.

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

Hynes, John Jr. published the artcileDiscovery of potent and efficacious pyrrolopyridazines as dual JAK1/3 inhibitors, Recommanded Product: (6-Ethoxypyridin-3-yl)boronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(14), 3101-3106, database is CAplus and MEDLINE.

A series of potent dual JAK1/3 inhibitors have been developed from a moderately selective JAK3 inhibitor. Substitution at the C6 position of the pyrrolopyridazine core with aryl groups provided exceptional biochem. potency against JAK1 and JAK3 while maintaining good selectivity against JAK2 and Tyk2. Translation to in vivo efficacy was observed in a murine model of chronic inflammation. X-ray co-crystal structure determination confirmed the presumed inhibitor binding orientation in JAK3. Efforts to reduce hERG channel inhibition will be described.

Bioorganic & Medicinal Chemistry Letters 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

Yuan, Xinrui published the artcileDesign, synthesis and biological evaluation of pyridone-aminal derivatives as MNK1/2 inhibitors, Computed Properties of 18437-58-6, the publication is Bioorganic & Medicinal Chemistry (2019), 27(7), 1211-1225, database is CAplus and MEDLINE.

Excessive phosphorylation of eukaryotic translation initiation factor 4E (eIF4E) plays a major role in the dysregulation of mRNA translation and the activation of tumor cell signaling. eIF4E is exclusively phosphorylated by mitogen-activated protein kinase interacting kinases 1 and 2 (MNK1/2) on Ser209. So, MNK1/2 inhibitors could decrease the level of p-eIF4E and regulate tumor-associated signaling pathways. A series of pyridone-aminal derivatives were synthesized and evaluated as MNK1/2 inhibitors. Several compounds exhibited great inhibitory activity against MNK1/2 and selected compounds showed moderate to excellent anti-proliferative potency against hematol. cancer cell lines. In particular, compound 42i (MNK1 IC₅₀ = 7.0 nM; MNK2 IC₅₀ = 6.1 nM) proved to be the most potent compound against TMD-8 cell line with IC₅₀ value of 0.91 μM. Furthermore, 42i could block the phosphorylation level of eIF4E in CT-26 cell line, and 42i inhibited the tumor growth of CT-26 allograft model significantly. These results indicated that compound 42i was a promising MNK1/2 inhibitor for the potent treatment of colon cancer.

Bioorganic & Medicinal Chemistry 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 C8H6BrClO, Computed Properties of 18437-58-6.

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

Lin, Shuqun published the artcileUtilization of a nitrogen-sulfur nonbonding interaction in the design of new 2-aminothiazol-5-yl-pyrimidines as p38α MAP kinase inhibitors, Synthetic Route of 197958-29-5, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(19), 5864-5868, database is CAplus and MEDLINE.

The design, synthesis, and structure-activity relationships (SAR) of a series of 2-aminothiazol-5-yl-pyrimidines as novel p38α MAP kinase inhibitors are described. These efforts led to the identification of I as a potent p38α inhibitor that utilizes a unique nitrogen-sulfur intramol. nonbonding interaction to stabilize the conformation required for binding to the p38α active site. X-ray crystallog. studies that confirm the proposed binding mode of this class of inhibitors in p38α and provide evidence for the proposed intramol. nitrogen-sulfur interaction are discussed.

Bioorganic & Medicinal Chemistry Letters 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 C5H6BNO2, Synthetic Route of 197958-29-5.

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

Melancon, Bruce J. published the artcileOptimization of M₄ pos. allosteric modulators (PAMs): The discovery of VU0476406, a non-human primate in vivo tool compound for translational pharmacol., Synthetic Route of 197958-29-5, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(11), 2296-2301, database is CAplus and MEDLINE.

Optimization of M₄ pos. allosteric modulators (PAMs): The discovery of VU0476406, a non-human primate in vivo tool compound for translational pharmacol. This letter describes the further chem. optimization of the 5-amino-thieno[2,3-c]pyridazine series (VU0467154/VU0467485) of M₄ pos. allosteric modulators (PAMs), developed via iterative parallel synthesis, culminating in the discovery of the non-human primate (NHP) in vivo tool compound, VU0476406 (8p). VU0476406 is an important in vivo tool compound to enable translation of pharmacodynamics from rodent to NHP, and while data related to a Parkinson’s disease model has been reported with 8p, this is the first disclosure of the optimization and discovery of VU0476406, as well as detailed pharmacol. and DMPK properties.

Bioorganic & Medicinal Chemistry Letters 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 C5H6BNO2, Synthetic Route of 197958-29-5.

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

Pereira, Raul published the artcileSynthesis and characterization of a novel N-F reagent derived from the ethano-Tröger’s base: ¹J_FN coupling constants as a signature for the N-F bond, Application In Synthesis of 107263-95-6, the publication is Chemical Communications (Cambridge, United Kingdom) (2016), 52(8), 1606-1609, database is CAplus and MEDLINE.

Methylation of 2,8-dimethyl-6H,12H-5,11-ethanodibenzo[b,f][1,5]-diazocine (ethano-Troddoger’s base) with Me iodide followed by ion metathesis and fluorination with N-fluoro-2,3,4,5,6-pentachloropyridinium triflate affords a new electrophilic N-F reagent, that is more reactive than Selectfluor. 2D ¹⁹F-¹⁵N HMQC experiments provide ¹J_NF coupling constants which are diagnostic for the N-F functional group.

Chemical Communications (Cambridge, United Kingdom) published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Application In Synthesis of 107263-95-6.

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

Balaraman, Kaluvu published the artcilePalladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides, SDS of cas: 197958-29-5, the publication is Organic Letters (2021), 23(22), 8994-8999, database is CAplus and MEDLINE.

Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides RF (R = octyl, cyclohexyl, (4-nitrophenyl)methyl, etc.) with aryl- and alkenylboronic acids R¹B(OH)₂ (R¹ = Ph, 2-phenylethenyl, pyridin-2-yl, etc.) has been achieved via mechanistically distinct Pd and Ni catalyzed pathways that outperform competing protodeboronation, β-hydride elimination, and homocoupling processes. The utility is demonstrated with more than 20 examples e.g., 1-benzyl-4-nitrobenzene.

Organic Letters 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 C5H6BNO2, SDS of cas: 197958-29-5.

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

Prechtl, Martin H. G. published the artcileDirect coupling of alcohols to form esters and amides with evolution of H₂ using in situ formed ruthenium catalysts, Recommanded Product: 2,6-Bis((di-tert-butylphosphino)methyl)pyridine, the publication is Catalysis Science & Technology (2012), 2(10), 2039-2042, database is CAplus.

A simple approach for the catalytic conversion of primary alcs. into their corresponding esters and amides, with evolution of H₂ gas using in situ formed ruthenium PNP- and PNN-pincer catalysts (I; X = NEt₂,P-tert-Bu₂), is presented. The evaluation showed conversions for the esterification with turnover numbers as high as 4300, and >400 for the amidation.

Catalysis Science & Technology 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, Recommanded Product: 2,6-Bis((di-tert-butylphosphino)methyl)pyridine.

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

Schwertz, Geoffrey published the artcileAntimalarial Inhibitors Targeting Serine Hydroxymethyltransferase (SHMT) with in Vivo Efficacy and Analysis of their Binding Mode Based on X-ray Cocrystal Structures, Name: 2-Pyridinylboronic acid, the publication is Journal of Medicinal Chemistry (2017), 60(12), 4840-4860, database is CAplus and MEDLINE.

Target-based approaches towards new antimalarial treatments are highly valuable to prevent resistance development. The authors report several series of pyrazolopyran-based inhibitors targeting the enzyme serine hydroxymethyltransferase (SHMT), designed to improve microsomal metabolic stability and to identify suitable candidates for in vivo efficacy evaluation. The best ligands inhibited Plasmodium falciparum (Pf) and Arabidopsis thaliana (At) SHMT in target assays and PfNF54 strains in cell-based assays with values in the low nanomolar range (3.2-55 nM). A set of carboxylate derivatives demonstrated markedly improved in vitro metabolic stability (t_1/2 > 2 h). A selected ligand showed significant in vivo efficacy with 73% of parasitemia reduction in a mouse model. Five new cocrystal structures with PvSHMT were solved at 2.3-2.6 Å resolution, revealing a unique water-mediated interaction with Tyr63 at the end of the para-aminobenzoate channel. They also displayed the high degree of conformational flexibility of the Cys364-loop lining this channel.

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 C10H16Br3N, Name: 2-Pyridinylboronic acid.

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