Category: 197958-29-5

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

Olson, Kirk L. published the artcileNovel amide and imidazole compounds as potent hematopoietic prostaglandin D₂ synthase inhibitors, COA of Formula: C5H6BNO2, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 127759, database is CAplus and MEDLINE.

In seeking novel and potent small mol. hematopoietic prostaglandin D₂ synthase (H-PGDS) inhibitors as potential therapies for PGD₂-mediated diseases and conditions, we explored a series comprising multiple aryl/heteroaryl rings attached in a linear arrangement. Each compound incorporates an amide or imidazole “linker” between the pyrimidine or pyridine “core” ring and the “tail” ring system. We synthesized and screened twenty analogs by fluorescence polarization binding assay, thermal shift assay, glutathione S-transferase inhibition assay, and a cell-based assay measuring suppression of LPS-induced PGD₂ stimulation. Amide analogs show ten-fold greater shift in the thermal shift assay in the presence of glutathione (GSH) vs. the same assay run in the absence of GSH. The imidazole analogs did not produce a significant change in thermal shift between the two assay conditions, suggesting a possible stabilization effect of the amide linker in the synthase-GSH-inhibitor complex. Imidazole analog 23, (KMN-010034) demonstrates superior potency across the in vitro assays and good in vitro metabolic stability in both human and guinea pig liver microsomes.

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, COA of Formula: C5H6BNO2.

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

Lei, Tao published the artcileDiscovery of the Potent Phosphoinositide 3-Kinase d (PI3 K d) Inhibitors, SDS of cas: 197958-29-5, the publication is ChemistrySelect (2020), 5(1), 196-200, database is CAplus.

The PI3Kd plays a pivotal role in regulating immune cell function and has recently emerged as a promising therapeutic target in treating various diseases, which draw more and more attention to discover potent PI3Kd inhibitors in recent years. Starting from structure-based drug design, a series of derivatives were designed and synthesized as new chemotypes of PI3Kd inhibitors. The potential compounds were structurally optimized by interaction showed in docking study. In cell-free kinase activity assays, Homogeneous Time-Resolved Fluorescence Assay (HTRF) method was performed for evaluating the inhibitory activities against PI3Kd. Interestingly, the representative compound 4 exhibited potent PI3Kd activity (IC₅₀=72 nM), which is comparable to that of pos. compound TGR1202. Furthermore, compound 4 showed 15-fold water solubility than TGR1202. In addition, the tests of compound 4 on anti-cancer activity against jeko-1 cancer cell line and cytotoxicity against peripheral blood mononuclear cell (PBMC) suggested high inhibition activity and low toxicity resp. A series of experiments indicated that compound 4 possessed novel chem. structure and high-efficiency PI3Kd inhibition activity, deserving further structural optimization to develop highly potent PI3Kd inhibitors.

ChemistrySelect 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

Yang, Yang published the artcileSynthetic versatility of 2-substituted-6-methyl 2,3-dihydropyridinones in the synthesis of polyfunctional piperidine-based compounds and related β amino acid derivatives, Recommanded Product: 2-Pyridinylboronic acid, the publication is Organic & Biomolecular Chemistry (2017), 15(40), 8576-8593, database is CAplus and MEDLINE.

Chiral 2-substituted-6-Me 2,3-dihydropyidinones (I) (R¹ = cyclohexyl, n-pentyl, CH₂TBSO, n-butyl), which can be facilely obtained from an asym. vinylogous Mannich reaction (VMR) with 1,3-bis-trimethylsilyl enol ether, were used as versatile intermediates in constructing chiral polyfunctional piperidine-based compounds The 6-Me group of such compounds can be conveniently functionalized via alkylation and acylation reactions to provide efficient entries to the synthesis of a variety of chiral multi-substituted piperidine-based compounds Further elaboration of the corresponding intermediates also provided access to polyfunctional indolizidine-based compounds These methods were showcased in an asym. synthesis of 2,6-di-substituted piperidine compound (II), reported as the key intermediate in the synthesis of (+)-calvine and a natural alkaloid (-)-indolizidine 209D. Furthermore, selective C5 iodination of compound I enabled the installation of addnl. functional groups at this position. Finally, we demonstrated that the oxidative cleavage of 2-substituted-6-methyl-2,3-dihydropyidinones is a practical and efficient method for the enantioselective synthesis of β-amino acids, which can undergo further intra-mol. cyclization to give the corresponding chiral four-membered β-lactam derivatives

Organic & Biomolecular 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 C13H18BNO3, Recommanded Product: 2-Pyridinylboronic acid.

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

Zhao, Zhijian published the artcileSynthesis and optimization of N-heterocyclic pyridinones as catechol-O-methyltransferase (COMT) inhibitors, COA of Formula: C5H6BNO2, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(12), 2952-2956, database is CAplus and MEDLINE.

A series of N-heterocyclic pyridinone catechol-O-methyltransferase (COMT) inhibitors were synthesized. Physicochem. properties, including ligand lipophilic efficiency (LLE) and clog P, were used to guide compound design and attempt to improve inhibitor pharmacokinetics. Incorporation of heterocyclic central rings provided improvements in physicochem. parameters but did not significantly reduce in vitro or in vivo clearance. Nevertheless, compound I was identified as a potent inhibitor with sufficient in vivo exposure to significantly affect the dopamine metabolites homovanillic acid (HVA) and dihydroxyphenylacetic acid (DOPAC), and indicate central COMT inhibition.

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 C18H24N6O6S4, COA of Formula: C5H6BNO2.

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

Lee, Jongkook published the artcileSynthesis and structure-activity relationship of aminopyridines with substituted benzoxazoles as c-Met kinase inhibitors, Recommanded Product: 2-Pyridinylboronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(12), 4044-4048, database is CAplus and MEDLINE.

A series of hydroxybenzoxazole derivatives, e.g., I [R² = H, Cl, MeNH, MeCONH, R³ = H, MeCO, Me(OH)CH, 3-pyrazolyl, etc., R⁴ = H, 2-pyridinyl, 4-MeOC₆H₄, Me₂CHNH], was synthesized, and their c-Met kinase inhibitory activity was evaluated. Described herein is a potent c-Met inhibitor by structural modification of the parent benzoxazole scaffold, with particular focus on the hydroxyl substituent of the benzoxazole moiety.

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, Recommanded Product: 2-Pyridinylboronic acid.

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

Mahmoudi, Malek published the artcileOrnamenting of Blue Thermally Activated Delayed Fluorescence Emitters by Anchor Groups for the Minimization of Solid-State Solvation and Conformation Disorder Corollaries in Non-Doped and Doped Organic Light-Emitting Diodes, Name: 2-Pyridinylboronic acid, the publication is ACS Applied Materials & Interfaces (2022), 14(35), 40158-40172, database is CAplus and MEDLINE.

Motivated to minimize the effects of solid-state solvation and conformation disorder on emission properties of donor-acceptor-type emitters, we developed five new asym. multiple donor-acceptor type derivatives of tert-Bu carbazole and trifluoromethyl benzene exploiting different electron-accepting anchoring groups. Using this design strategy, for a compound containing four di-tert-Bu carbazole units as donors as well as 5-Me pyrimidine and trifluoromethyl acceptor moieties, small singlet-triplet splitting of ca. 0.03 eV, reverse intersystem crossing rate of 1 x 10⁶ s^-1, and high photoluminescence quantum yield of neat film of ca. 75% were achieved. This compound was also characterized by the high value of hole and electron mobilities of 8.9 x 10^-4 and 5.8 x 10^-4 cm² V^-1 s^-1 at an elec. field of 4.7 x 10⁵ V/cm, showing relatively good hole/electron balance, resp. Due to the lowest conformational disorder and solid-state solvation effects, this compound demonstrated very similar emission properties (emission colors) in non-doped and differently doped organic light-emitting diodes (OLEDs). The lowest conformational disorder was observed for the compound with the addnl. accepting moiety inducing steric hindrance, limiting donor-acceptor dihedral rotational freedom. It can be exploited in the multi-donor-acceptor approach, increasing the efficiency. Using an emitter exhibiting the minimized solid-state solvation and conformation disorder effects, the sky blue OLED with the emitting layer of this compound dispersed in host 1,3-bis(N-carbazolyl)benzene displayed an emission peak at 477 nm, high brightness over 39 000 cd/m², and external quantum efficiency up to 15.9% along with a maximum current efficiency of 42.6 cd/A and a maximum power efficiency of 24.1 lm/W.

ACS Applied Materials & Interfaces 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, Name: 2-Pyridinylboronic acid.

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

Han, Sang Hoon published the artcileStructure-based optimization of ML300-derived, noncovalent inhibitors targeting the severe acute respiratory syndrome coronavirus 3CL protease (SARS-CoV-2 3CL^pro), Quality Control of 197958-29-5, the publication is Journal of Medicinal Chemistry (2022), 65(4), 2880-2904, database is CAplus and MEDLINE.

Starting from the MLPCN probe compound ML300, a structure-based optimization campaign was initiated against the recent severe acute respiratory syndrome coronavirus (SARS-CoV-2) main protease (3CL^pro). X-ray structures of SARS-CoV-1 and SARS-CoV-2 3CL^pro enzymes in complex with multiple ML300-based inhibitors, including the original probe ML300, were obtained and proved instrumental in guiding chem. toward probe compound 41 (I)(CCF0058981). The disclosed inhibitors utilize a noncovalent mode of action and complex in a noncanonical binding mode not observed by peptidic 3CL^pro inhibitors. In vitro DMPK profiling highlights key areas where further optimization in the series is required to obtain useful in vivo probes. Antiviral activity was established using a SARS-CoV-2-infected Vero E6 cell viability assay and a plaque formation assay. I demonstrates nanomolar activity in these resp. assays, comparable in potency to remdesivir. These findings have implications for antiviral development to combat current and future SARS-like zoonotic coronavirus outbreaks.

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, Quality Control of 197958-29-5.

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

Eastwood, Paul published the artcileDiscovery of N-(5,6-diarylpyridin-2-yl)amide derivatives as potent and selective A_2B adenosine receptor antagonists, HPLC of Formula: 197958-29-5, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(5), 1697-1700, database is CAplus and MEDLINE.

The synthesis and SAR of a series of N-(5,6-diarylpyridin-2-yl)amide derivatives as potent A_2B adenosine receptor antagonists is described. Several compounds showed good selectivity vs. other adenosine receptors. The potent and selective analog I was shown to have good oral bioavailability in the rat.

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, HPLC of Formula: 197958-29-5.

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

Chatterjee, Nachiketa published the artcileMetal and base free synthesis of primary amines via ipso amination of organoboronic acids mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA), Safety of 2-Pyridinylboronic acid, the publication is Organic & Biomolecular Chemistry (2015), 13(29), 7940-7945, database is CAplus and MEDLINE.

A metal and base free synthesis of primary amines has been developed at ambient temperature through ipso amination of diversely functionalized organoboronic acids, employing a combination of [bis(trifluoroacetoxy)iodo]benzene (PIFA)-N-bromosuccinimide (NBS) and methoxyamine hydrochloride as the aminating reagent. The amines were primarily obtained as their trifluoroacetate salts which on subsequent aqueous alk. work up provided the corresponding free amines. The combination of PIFA-NBS is found to be the mildest choice compared to the commonly used strong bases (e.g. n-BuLi, Cs₂CO₃) for activating the aminating agent. The reaction is expected to proceed via activation of the aminating reagent followed by B-N 1,2-aryl migration.

Organic & Biomolecular 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, Safety of 2-Pyridinylboronic acid.

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