Tag: M.W=100-150

Ceccarelli, Simona M. published the artcileRational design, synthesis, and structure-activity relationship of benzoxazolones: new potent mGlu5 receptor antagonists based on the fenobam structure, Safety of 4-Amino-2-picoline, the publication is Bioorganic & Medicinal Chemistry Letters (2007), 17(5), 1302-1306, database is CAplus and MEDLINE.

A class of potent and stable mGlu5 receptor antagonists was developed by combining information from a high-throughput screening campaign with the structure of the known anxiolytic fenobam. Representative compounds I from this class show favorable pharmacokinetic properties and are active in an in vivo model of anxiety.

Bioorganic & Medicinal Chemistry Letters 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 C6H8N2, Safety of 4-Amino-2-picoline.

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

Kolman, Viktor published the artcilePolysubstituted 4,6-bis(hetero)arylpyrimidines as dual inhibitors of nitric oxide and prostaglandin E₂ production, HPLC of Formula: 197958-29-5, the publication is Nitric Oxide (2017), 53-57, database is CAplus and MEDLINE.

As a part of our extensive structure-activity relationship study of anti-inflammatory heterocycles, a novel series of 67 polysubstituted 2-aminopyrimidines was prepared bearing one (at the C-4 position of the pyrimidine ring) or two (in the C-4 and C-6 positions) (hetero)aryl substituents attached directly through the C-C bond. The key synthetic steps involved either Suzuki-Miyaura or Stille cross-coupling reactions carried out on easily available 4,6-dichloropyrimidines. All prepared compounds, except one, were able to inhibit immune-activated production of nitric oxide (NO) significantly. Moreover, several compounds were found to be low micromolar dual inhibitors of NO and prostaglandin E₂ (PGE₂) production Although the exact mode of action of the prepared compounds remains to be elucidated, non-toxic dual inhibitors of NO and PGE₂ production may have great therapeutic benefit in treatment of various inflammation diseases and deserve further preclin. evaluation.

Nitric Oxide 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, HPLC of Formula: 197958-29-5.

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

Xin, Zhijun published the artcileStudy on N-(pyridin-4-yl) salicylamides as antimycobacterial agents, HPLC of Formula: 18437-58-6, the publication is Advanced Materials Research (Durnten-Zurich, Switzerland) (2013), 1371-1375, 6 pp., database is CAplus.

A series of N-(pyridin-4-yl) salicylamides derivatives were prepared through acylation of the corresponding acetylsalicyloyl chlorides with substituted 4-amino-pyridines. These compounds were evaluated in vitro for antimycobacterial activities against Mycobacterium tuberculosis (TB) and Mycobacterium avium (A) by the min. inhibitory concentrations (MIC) values. Eight of the compounds exhibited lower MIC against A than isoniazide (INH). Meanwhile, four of the compounds exhibited good anti-TB activity, when they were compared with INH. Antimycobacterial activities of N-(pyridin-4-yl) salicylamides were influenced by the balance between hydrophobicity and electron-withdrawing substituent effect on the Ph and pyridine ring. These studies show that these compounds might serve as prospective wide-spectrum antimycobacterial substances.

Advanced Materials Research (Durnten-Zurich, Switzerland) 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 C24H12, HPLC of Formula: 18437-58-6.

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

Allegretti, Paul A. published the artcileGeneration of highly potent DYRK1A-dependent inducers of human β-Cell replication via Multi-Dimensional compound optimization, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid, the publication is Bioorganic & Medicinal Chemistry (2020), 28(1), 115193, database is CAplus and MEDLINE.

Small mol. stimulation of β-cell regeneration has emerged as a promising therapeutic strategy for diabetes. Although chem. inhibition of dual specificity tyrosine-phosphorylation-regulated kinase 1A (DYRK1A) is sufficient to enhance β-cell replication, current lead compounds have inadequate cellular potency for in vivo application. Herein, we report the clin. stage anti-cancer kinase inhibitor OTS167 as a structurally novel, remarkably potent DYRK1A inhibitor and inducer of human β-cell replication. Unfortunately, OTS167’s target promiscuity and cytotoxicity curtails utility. To tailor kinase selectivity towards DYRK1A and reduce cytotoxicity we designed a library of fifty-one OTS167 derivatives based upon a modeled structure of the DYRK1A-OTS167 complex. Indeed, derivative characterization yielded several leads with exceptional DYRK1A inhibition and human β-cell replication promoting potencies but substantially reduced cytotoxicity. These compounds are the most potent human β-cell replication-promoting compounds yet described and exemplify the potential to purposefully leverage off-target activities of advanced stage compounds for a desired application.

Bioorganic & Medicinal Chemistry published new progress about 903899-13-8. 903899-13-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Alcohol,Boronic Acids,Boronic acid and ester, name is (6-Hydroxypyridin-3-yl)boronic acid, and the molecular formula is C5H6BNO3, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid.

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

Ju, Han published the artcileIterative Optimization and Structure-Activity Relationship Studies of Oseltamivir Amino Derivatives as Potent and Selective Neuraminidase Inhibitors via Targeting 150-Cavity, COA of Formula: C5H6BNO2, the publication is Journal of Medicinal Chemistry (2022), 65(17), 11550-11573, database is CAplus and MEDLINE.

With our continuous endeavors in seeking neuraminidase (NA) inhibitors, we reported herein three series of novel oseltamivir amino derivatives with the goal of exploring the druggable chem. space inside the 150-cavity of influenza virus NAs. Among them, around half of the compounds in series C were demonstrated to be better inhibitors against both wild-type and oseltamivir-resistant group-1 NAs than oseltamivir carboxylate (OSC). Notably, compounds 12d, 12e, 15e, and 15i showed more potent or equipotent antiviral activity against H1N1, H5N1, and H5N8 viruses compared to OSC in cellular assays. Furthermore, compounds 12e and 15e exhibited high metabolic stability in human liver microsomes (HLMs) and low inhibitory effect on main cytochrome P 450 (CYP) enzymes, as well as low acute/subacute toxicity and certain antiviral efficacy in vivo. Also, pharmacokinetic (PK) and mol. docking studies were performed. Overall, 12e (I) and 15e (II) possess great potential to serve as anti-influenza candidates and are worthy of further investigation.

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 C5H6BNO2, COA of Formula: C5H6BNO2.

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

Barnett, Kerry L. published the artcileAir-Stable [(R₃P)PdCl₂]₂ Complexes of Neopentylphosphines as Cross-Coupling Precatalysts: Catalytic Application and Mechanism of Catalyst Activation and Deactivation, Recommanded Product: 2-Pyridinylboronic acid, the publication is Organometallics (2018), 37(9), 1410-1424, database is CAplus.

Air-stable [(R₃P)PdCl₂]₂ complexes with di-tert-butylneopentylphosphine (DTBNpP, 1a) or trineopentylphosphine (TNpP, 1b) ligands were applied to Suzuki cross-coupling reactions, and the mechanism of their conversion to the active LPd(0) catalyst species was studied. Precatalysts 1a,b provide effective catalysts for Suzuki cross-coupling of aryl bromides at room temperature, even when the reactions were performed in air. The precatalyst systems provided much higher activity catalysts in toluene/H₂O in comparison to MeCN/H₂O. Precatalyst loadings could be decreased by a factor of 50 in toluene in comparison to MeCN, while achieving equal or better yields. In MeCN/H₂O, ligand metalation to form a [(κ²-P,C-DTBNpP)PdX]₂ palladacycle was found to compete with formation of the active Pd(0) species. The palladacycle shows low catalytic activity; thus, its formation represents a catalyst deactivation pathway. In toluene, clean formation of the active Pd(0) species occurs without competitive palladacycle formation. The improved selectivity to form the active Pd(0) species in toluene appears to account for the higher activity of the precatalysts in toluene/H₂O.

Organometallics 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, Recommanded Product: 2-Pyridinylboronic acid.

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

Wu, Zhibing published the artcileSynthesis and antifungal activity of N-(substituted pyridinyl)-1-methyl(phenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives, Computed Properties of 18437-58-6, the publication is Molecules (2012), 14205-14218, database is CAplus and MEDLINE.

A series of 1-methyl- and 1-phenyl-N-pyridinyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamides was synthesized. All target compounds were bioassayed in vitro against of phytopathogenic fungi (Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica). Some of the compounds exhibited moderate antifungal activities, among which three of the compounds displayed >50% inhibition against G. zeae at 100 μg/mL, which was better than that of the com. fungicides carboxin and boscalid.

Molecules 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 C9H6N2O2, Computed Properties of 18437-58-6.

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

Aoki, Toshihiro published the artcileOptimizing the Physicochemical Properties of Raf/MEK Inhibitors by Nitrogen Scanning, Synthetic Route of 18437-58-6, the publication is ACS Medicinal Chemistry Letters (2014), 5(4), 309-314, database is CAplus and MEDLINE.

Substituting a carbon atom with a nitrogen atom (nitrogen substitution) on an aromatic ring in our leads I and II (X⁸ = X⁹ = CH) by applying nitrogen scanning afforded a set of compounds that improved not only the solubility but also the metabolic stability. The impact after nitrogen substitution on interactions between a derivative and its on- and off-target proteins (Raf/MEK, CYPs, and hERG channel) was also detected with most of them contributing to weaker interactions. After identifying the positions that kept inhibitory activity on HCT116 cell growth and Raf/MEK, compound II (X⁸ = X⁹ = N) (CH5126766/RO5126766) was selected as a clin. compound A phase I clin. trial is ongoing for solid cancers.

ACS Medicinal Chemistry Letters 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 C6H8N2, Synthetic Route of 18437-58-6.

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

Lee, Li-Chen published the artcileFunctionalized polymer-supported pyridine ligands for palladium-catalyzed C(sp³)-H arylation, Application In Synthesis of 18437-58-6, the publication is ACS Catalysis (2016), 6(8), 5245-5250, database is CAplus.

Palladium trifluoroacetate, ligated to polymer-anchored 2-methylpyridine ligands, catalyzed C(sp³)-H bond activation and arylation of N-phthalimido-L-alaninamide with iodoarenes ArI, giving monoarylated products, ArCH₂CH(NPhth)CONHAr^F (2, Phth = 1,2-(CO)₂C₆H₄, Ar^F = 4-CF₃C₆H₄). The use of ligands to tune the reactivity and selectivity of transition-metal catalysts for C(sp³)-H bond activation is a current central challenge. One of us previously developed an uncommon example of a homogeneous catalyst that performs controlled C(sp³)-H arylation using pyridine derivatives as ligands, along with Pd [Science, 2014, 343, 1216-1220]. In this work, we report a functionalizable and tunable polymer support used in the immobilization of pyridine derivatives that yields a soluble, polymeric ligand platform facilitating C(sp³)-H activation reactions with good yields, selectivities differing from the homogeneous catalyst, and recovery of Pd. Unlike the homogeneous system, the supported catalysts in Pd-catalyzed C-H monoarylation reactions respond sensitively to the steric hindrance of the coupling partners.

ACS Catalysis 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 C6H8N2, Application In Synthesis of 18437-58-6.

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

Shaw, Arthur Y. published the artcileCharacterization of novel diaryl oxazole-based compounds as potential agents to treat pancreatic cancer, Synthetic Route of 197958-29-5, the publication is Journal of Pharmacology and Experimental Therapeutics (2009), 331(2), 636-647, database is CAplus and MEDLINE.

A series of diaryl- and fluorenone-based analogs of the lead compound UA-62784 [4-(5-(4-methoxyphenyl)oxazol-2-yl)-9H-fluoren-9-one] was synthesized with the intention of improving upon the selective cytotoxicity of UA-62784 against human pancreatic cancer cell lines with a deletion of the tumor suppressor gene deleted in pancreas cancer locus 4 (DPC-4, SMAD-4). Over 80 analogs were synthesized and tested for antitumor activity against pancreatic cancer (PC) cell lines (the PC series). Despite a structural relationship to UA-62784, which inhibits the mitotic kinesin centromere protein E (CENP-E), none of the analogs was selective for DPC-4-deleted pancreatic cancer cell lines. Furthermore, none of the analogs was a potent or selective inhibitor of four different mitotic kinesins (mitotic kinesin-5, CENP-E, mitotic kinesin-like protein-1, and mitotic centromere-associated kinesin). Therefore, other potential mechanisms of action were evaluated. A diaryl oxazole lead analog from this series, PC-046 [5-(4-methoxyphenyl)-2-(3-(3-methoxyphenyl)pyridin-4-yl) oxazole], was shown to potently inhibit several protein kinases that are overexpressed in human pancreatic cancers, including tyrosine receptor kinase B, interleukin-1 receptor-associated kinase-4, and proto-oncogene Pim-1. Cells exposed to PC-046 exhibit a cell cycle block in the S-phase followed by apoptotic death and necrosis. PC-046 effectively reduced MiaPaca-2 tumor growth in severe combined immunodeficiency mice by 80% compared with untreated controls. The plasma half-life was 7.5 h, and cytotoxic drug concentrations of >3 μM were achieved in vivo in mice. The diaryl oxazole series of compounds represent a new chem. class of anticancer agents that inhibit several types of cancer-relevant protein kinases.

Journal of Pharmacology and Experimental Therapeutics 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 C19H14N2, Synthetic Route of 197958-29-5.

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