Day: December 5, 2022

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

Kloek, Susan M. published the artcileC-H bond activation by rhodium(I) hydroxide and phenoxide complexes, Related Products of pyridine-derivatives, the publication is Angewandte Chemie, International Edition (2007), 46(25), 4736-4738, database is CAplus and MEDLINE.

Rhodium(I) complexes of the form [(PNP)Rh(OR)](R = H, CH₂CF₃, C₆H₅; PNP = 2,6-bis[(di-tert-butylphosphino)-methyl]pyridine) have been prepared Upon thermolysis in [D₆]benzene, the hydroxide and trifluoroethoxide complexes undergo benzene activation. [(PNP)Rh(OC₆H₅)] is an active catalyst for the H/D exchange between D₂O and benzene and between H₂O and [D₈]toluene, for which exchange occurs selectively at the meta and para positions.

Angewandte Chemie, International Edition 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, Related Products of pyridine-derivatives.

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

Hanson, Susan Kloek published the artcileC-H Bond Activation by Rhodium(I) Phenoxide and Acetate Complexes: Mechanism of H-D Exchange between Arenes and Water, HPLC of Formula: 338800-13-8, the publication is Organometallics (2008), 27(7), 1454-1463, database is CAplus.

New rhodium(I) complexes (PNP)Rh(X) (PNP = 2,6-bis(di-tert-butylphosphinomethyl)pyridine) (X = OTf (1), OAc (3), OH (8), OCH₂CF₃ (9), OC₆H₅ (10), OC₆H₄NO₂ (11)) have been prepared Hydroxide complex 8 and trifluoroethoxide complex 9 undergo stoichiometric activation of benzene-d₆ to form the Ph complex (PNP)Rh(C₆D₅). Acetate and aryloxide complexes 3, 10, and 11 are active catalysts for H-D exchange between arenes and water. Control experiments indicate that the rhodium complexes are the active catalysts and that the observed exchange is not catalyzed by adventitious acid. Mechanistic studies of the H-D exchange reaction support a pathway involving dissociation of aryloxide or acetate ligand. The reaction is accelerated by added alc. and, for the acetate complex, inhibited by added sodium acetate.

Organometallics 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, HPLC of Formula: 338800-13-8.

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

Murayama, Hiroaki published the artcileIridium-Catalyzed Enantioselective Transfer Hydrogenation of Ketones Controlled by Alcohol Hydrogen-Bonding and sp³-C-H Noncovalent Interactions, Application of Phenyl(pyridin-2-yl)methanone, the publication is Advanced Synthesis & Catalysis (2020), 362(21), 4655-4661, database is CAplus.

Iridium-catalyzed enantioselective transfer hydrogenation of ketones with formic acid was developed using a prolinol-phosphine chiral ligand. Cooperative action of the iridium atom and the ligand through alc.-alkoxide interconversion was crucial to facilitate the transfer hydrogenation. Various ketones including alkyl aryl ketones, ketoesters, and an aryl heteroaryl ketone were competent substrates. An attractive feature of this catalysis was efficient discrimination between the alkyl and aryl substituents of the ketones, promoting hydrogenation with the identical sense of enantioselection regardless of steric demand of the alkyl substituent and thus resulting in a rare case of highly enantioselective transfer hydrogenation of tert-alkyl aryl ketones. Quantum chem. calculations revealed that the sp³-C-H/π interaction between an sp³-C-H bond of the prolinol-phosphine ligand and the aryl substituent of the ketone was crucial for the enantioselection in combination with O-H···O/sp³-C-H···O two-point hydrogen-bonding between the chiral ligand and carbonyl group.

Advanced Synthesis & 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, Application of Phenyl(pyridin-2-yl)methanone.

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

Doyle, Laurence R. published the artcileA Convenient Synthetic Protocol to 1,2-Bis(dialkylphosphino)ethanes, COA of Formula: C23H43NP2, the publication is Advanced Synthesis & Catalysis (2014), 356(2-3), 603-608, database is CAplus and MEDLINE.

1,2-Bis(dialkylphosphino)ethanes are readily prepared from the parent phosphine oxides, via a novel NaAlH₄/NaH reduction protocol of intermediate chlorophosphonium chlorides. This approach is amenable to multi-gram syntheses, uses readily available and inexpensive reagents, and benefits from a facile nonaqueous work-up in the final reductive step.

Advanced Synthesis & Catalysis 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, COA of Formula: C23H43NP2.

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

Zhang, Han published the artcileDesign, synthesis and biological activities of piperidine-spirooxadiazole derivatives as α7 nicotinic receptor antagonists, Product Details of C6H8BNO3, the publication is European Journal of Medicinal Chemistry (2020), 112774, database is CAplus and MEDLINE.

7 Nicotinic acetylcholine receptors (nAChRs) expressed in the nervous and immune systems was suggested to play important roles in the control of inflammation. However, the lack of antagonist tools specifically inhibiting α7 nAChR impedes the validation of the channel as therapeutic target. To discover a selective α7 antagonist, a pharmacophore-based virtual screening and identified a piperidine-spirooxadiazole derivative T761-0184 that acts as a α7 antagonist. A series of novel piperidine-spirooxadiazole derivatives were subsequently synthesized and evaluated using two-electrode voltage clamp (TEVC) assay in Xenopus oocytes. Lead compounds from two series inhibited α7 with their IC₅₀ values ranging from 3.3μM to 13.7μM. Compound 3-(4-Bromophenyl)-8-methyl-1-oxa-2,4,8-triazaspiro[4.5]dec-2-ene exhibited α7 selectivity over other α4β2 and α3β4 nAChR subtypes. The anal. of structure-activity relationship (SAR) provides valuable insights for further development of selective α7 nAChR antagonists.

European Journal of Medicinal Chemistry 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 C13H10F2, Product Details of C6H8BNO3.

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

Jafarpour, Farnaz published the artcilePalladium-catalyzed chelation-assisted C-H bond halogenation: selective chlorination of 2-arylpyridines with acid chlorides, SDS of cas: 85237-71-4, the publication is Synthesis (2014), 46(9), 1224-1228, 5 pp., database is CAplus.

Palladium-catalyzed chelation-assisted C-H bond halogenation of arenes using acid chlorides as chlorinating agents is reported. E.g., in presence of PdCl₂ and CuCl₂ in 1,4-dioxane at 140 °C, regioselective chlorination of 2-phenylpyridine by PhCOCl gave 92% I. This method provides a monoselective, straightforward, and clean route for the construction of aryl chlorides as privileged motifs in organic transformations.

Synthesis published new progress about 85237-71-4. 85237-71-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is 5-Methyl-2-(p-tolyl)pyridine, and the molecular formula is C13H13N, SDS of cas: 85237-71-4.

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

Hoque, Emdadul Md published the artcileRemarkably Efficient Iridium Catalysts for Directed C(sp²)-H and C(sp³)-H Borylation of Diverse Classes of Substrates, Recommanded Product: 5-Methyl-2-(p-tolyl)pyridine, the publication is Journal of the American Chemical Society (2021), 143(13), 5022-5037, database is CAplus and MEDLINE.

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp³)-H bond borylations. Heterocyclic mols. are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp²)-H and C(sp³)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chem.

Journal of the American Chemical Society published new progress about 85237-71-4. 85237-71-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is 5-Methyl-2-(p-tolyl)pyridine, and the molecular formula is C13H13N, Recommanded Product: 5-Methyl-2-(p-tolyl)pyridine.

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