Month: December 2022

Dick, Benjamin L. published the artcileMetal-Binding Isosteres as New Scaffolds for Metalloenzyme Inhibitors, SDS of cas: 197958-29-5, the publication is Inorganic Chemistry (2018), 57(15), 9538-9543, database is CAplus and MEDLINE.

The principle of isosteres or bioisosteres in medicinal chem. is a central and essential concept in modern drug discovery. For example, carboxylic acids are often replaced by bioisosteres to mitigate issues related to lipophilicity or acidity while retaining acidic characteristics in addition to hydrogen bond donor/acceptor abilities. Sep., the development of metal-binding pharmacophores (MBPs) for binding to the active site metal ion in metalloenzymes of therapeutic interest is an emerging area in the realm of fragment-based drug discovery (FBDD). The direct application of the bioisostere concept to MBPs has not been well-described or systematically investigated. Herein, the picolinic acid MBP is used as a case study for the development of MBP isosteres (so-called MBIs). Many of these isosteres are novel compounds, and data on their physicochem. properties, metal binding capacity, and metalloenzyme inhibition characteristics are presented. The results show that MBIs of picolinic acid generally retain metal coordinating properties and exhibit predictable metalloenzyme inhibitory activity while possessing a broad range of physicochem. properties (e.g., pK_a, logP). These findings demonstrate the use of bioisosteres results in an untapped source of metal binding functional groups suitable for metalloenzyme FBDD. These MBIs provide a previously unexplored route for modulating the physicochem. properties of metalloenzyme inhibitors and improving their drug-likeness.

Inorganic 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, SDS of cas: 197958-29-5.

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

Dau, Phuong V. published the artcileCyclometalated metal-organic frameworks as stable and reusable heterogeneous catalysts for allylic N-alkylation of amines, Related Products of pyridine-derivatives, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(55), 6128-6130, database is CAplus and MEDLINE.

Metal-organic frameworks (MOFs) functionalized via Ir(I) cyclometalation are shown to be effective as heterogeneous catalysts for the allylic N-alkylation of various amines. The MOF catalysts are one of the first and most effective MOF-based heterogeneous organometallic catalysts for the direct formation of C-N bonds. In addition, these MOFs represent a rare, stable and reusable, class of reactive Ir catalysts.

Chemical Communications (Cambridge, United Kingdom) 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, Related Products of pyridine-derivatives.

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

Ben-Ari, Eyal published the artcileOrtho C-H activation of haloarenes and anisole by an electron-rich iridium(I) complex: mechanism and origin of regio- and chemoselectivity. An experimental and theoretical study, Name: 2,6-Bis((di-tert-butylphosphino)methyl)pyridine, the publication is Organometallics (2006), 25(13), 3190-3210, database is CAplus.

Iridium(I) pincer PNP-complex undergoes facile C-H-activation with benzene, haloarenes and anisole, forming stable hydrido-aryl Ir(III) complexes; the origin of ortho-chemoselectivity of the reaction was explored exptl. and by quantum-chem. calculations Reaction of (PNP)Ir(COE)⁺PF₆^– (1; PNP = 2,6-bis(di-tert-butylphosphinomethyl)pyridine; COE = cyclooctene) with benzene yields a stable unsaturated square pyramidal Ir(III) hydrido-aryl complex, [(PNP)Ir(H)(Ph)] (2), which undergoes arene exchange upon reaction with other arenes at 50°. Upon reaction of 1 with haloarenes (chlorobenzene and bromobenzene) and anisole at 50°, selective ortho C-H activation takes place. No C-halogen bond activation was observed, even in the case of the normally reactive bromobenzene and despite the steric hindrance imposed by the halo substituent. The ortho-activated complexes [(PNP)Ir(H)(Ar)](8a, 9a, 10a; Ar = 2-ClC₆H₄, 2-BrC₆H₄, 2-MeOC₆H₄) exhibited a higher barrier to arene exchange; i.e., no exchange took place when heating at a temperature as high as 60°. These complexes were more stable, both thermodynamically and kinetically, than the corresponding meta- and para-isomers. The observed selectivity is a result of coordination of the heteroatom to the metal center, which kinetically directs the metal to the ortho C-H bond and stabilizes the resulting complex thermodynamically. Upon reaction of complex 1 with fluorobenzene under the same conditions, no such selectivity was observed, due to low coordination ability of the fluorine substituent. Competition experiments showed that the ortho-activated complexes 8a, 9a, and 10a have similar kinetic stability, while thermodynamically the chloro and methoxy complexes 8a and 10a are more stable than the bromo complex 9a. Computational studies, using the DFT mPW1K exchange-correlation functional and a variety of basis sets for PNP-based systems, provide mechanistic insight. The rate-determining step for the overall C-H activation process of benzene is COE dissociation to form a reactive 14e complex, followed by formation of a η²_C-C intermediate, which is converted into an η²_C-H complex, both being important intermediates in the C-H activation process. In the case of chlorobenzene, bromobenzene, and anisole, η¹-coordination via the heteroatom to the 14e species followed by formation of the ortho η²_C-H complex leads to selective activation. The unobserved C-halide activation process was shown computationally in the case of chlorobenzene to involve the same Cl-coordinated intermediate as in the C-H activation process, but it experiences a higher activation barrier. The ortho C-H activation product is also thermodynamically more stable than the C-Cl oxidative addition complex.

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, Name: 2,6-Bis((di-tert-butylphosphino)methyl)pyridine.

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

Lee, Norizan A. published the artcileA natural isolate of Pseudomonas maltophila which degrades aromatic sulfonic acids, Recommanded Product: Pyridine-3-sulfonic acid, the publication is FEMS Microbiology Letters (1993), 107(2-3), 151-5, database is CAplus and MEDLINE.

A natural isolate, designated BSA56, which was originally selected for growth with benzenesulfonic acid as sole carbon and energy source, was identified as a strain of P. maltophila. Strain BSA56 grew on a wide range of aromatic sulfonic acids and was shown to release sulfite from benzenesulfonic acid and 2-naphthalenesulfonic acid. Although it also grew on toluenesulfonic acid and pyridinesulfonic acid, no significant sulfite release was observed with these substrates. Release of sulfite from benzenesulfonic acid was greatly promoted by the presence of glycerol. The ability to release sulfite was induced by growth in the presence of benzenesulfonic acid and was repressed almost entirely by substrates allowing rapid growth such as acetate. Strain BSA56 grew better at 30° than 37° on most aromatic substrates, but the reverse was true for most aromatic sulfonates. Several mutants of BSA56 were isolated with defects in benzoate, salicylate, or gentisate metabolism However, all these mutants retained the ability to degrade the aromatic sulfonates.

FEMS Microbiology Letters published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C5H5NO3S, Recommanded Product: Pyridine-3-sulfonic acid.

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

Schroeder, Tenna Juul published the artcileThe identification of AF38469: An orally bioavailable inhibitor of the VPS10P family sorting receptor Sortilin, Recommanded Product: 4-Amino-2-picoline, the publication is Bioorganic & Medicinal Chemistry Letters (2014), 24(1), 177-180, database is CAplus and MEDLINE.

The identification of the novel, selective, orally bioavailable sortilin inhibitor AF38469 [5-(trifluoromethyl)-2- [(6-methylpyridin-2-ylamino)carbonyl]]benzoic acid is described. Structure-activity relationships and syntheses are reported, along with an X-ray crystal structure of the sortilin-AF38469 protein-inhibitor complex.

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, Recommanded Product: 4-Amino-2-picoline.

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

Babak, Maria V. published the artcileInterfering with Metabolic Profile of Triple-Negative Breast Cancers Using Rationally Designed Metformin Prodrugs, Synthetic Route of 91-02-1, the publication is Angewandte Chemie, International Edition (2021), 60(24), 13405-13413, database is CAplus and MEDLINE.

Triple-neg. breast cancer (TNBC) is the most aggressive subtype of breast cancer, characterized by an aberrant metabolic phenotype with high metastatic capacity, resulting in poor patient prognoses and low survival rates. We designed a series of novel AuIII cyclometalated prodrugs of energy-disrupting Type II antidiabetic drugs namely, metformin and phenformin. Prodrug activation and release of the metformin ligand was achieved by tuning the cyclometalated AuIII fragment. The lead complex 3met was 6000-fold more cytotoxic compared to uncoordinated metformin and significantly reduced tumor burden in mice with aggressive breast cancers with lymphocytic infiltration into tumor tissues. These effects was ascribed to 3met interfering with energy production in TNBCs and inhibiting associated pro-survival responses to induce deadly metabolic catastrophe.

Angewandte Chemie, International Edition 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, Synthetic Route of 91-02-1.

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

Chatterjee, Tanmay published the artcileVisible-light-induced regioselective synthesis of polyheteroaromatic compounds, SDS of cas: 39856-58-1, the publication is Chemical Communications (Cambridge, United Kingdom) (2016), 52(22), 4203-4206, database is CAplus and MEDLINE.

A method for visible-light-induced synthesis of polyheteroaroms. e.g., I, from 2-heteroaryl-substituted anilines and heteroarylalkynes was developed. The process, which uses fac-Ir(ppy)₃ as the photocatalyst and tBuONO as the diazotization reagent, is highly regioselective.

Chemical Communications (Cambridge, United Kingdom) 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, SDS of cas: 39856-58-1.

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

Lim, Chae Jo published the artcileSynthesis and structure-activity relationship of naphtho[1,2-b]furan-2-carboxamide derivatives as melanin concentrating hormone receptor 1 antagonists, SDS of cas: 197958-29-5, the publication is Chemical & Pharmaceutical Bulletin (2013), 61(12), 1239-1247, database is CAplus and MEDLINE.

Synthesis and structure-activity relationship of naphtho[1,2-b]furan-2-carboxamides I (n = 2-5; R = H, Br, Ph, 4-MeC₆H₄, 3-ClC₆H₄, 2-pyridyl, 3-furyl, 3-thienyl, etc.) containing linked piperidinylphenylacetamide groups as melanin concentrating hormone receptor 1 (MCH-R1) antagonists are described. The structure activity relationship (SAR) study, probing members of this family that contain a variety of aryl and heteroaryl groups at C-5 of I skeleton and having different chain linker lengths, led to the identification of the 5-(4-pyridinyl)-substituted analog I (n = 2; R = pyridin-4-yl) as a highly potent MCH-R1 antagonist with an IC₅₀ value of 3nM. This compound also displayed excellent metabolic stability and did not significantly inhibit cytochrome P 450 (CYP450) enzymes.

Chemical & Pharmaceutical Bulletin 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

Iqbal, Naeem published the artcileVisible-Light-Mediated Synthesis of Amides from Aldehydes and Amines via in Situ Acid Chloride Formation, Name: 2-Bromopyridin-3-amine, the publication is Journal of Organic Chemistry (2016), 81(5), 1905-1911, database is CAplus and MEDLINE.

An efficient visible-light photocatalysis-based one-pot amide synthesis method was developed; visible-light irradiation of a mixture of an aldehyde, tert-Bu hydrogen peroxide, and N-chlorosuccinimide using a Ru(bpy)₃Cl₂ photocatalyst afforded an acid chloride, which subsequently reacted with amine to yield the corresponding amide. The reaction was used to synthesize moclobemide and a D3 receptor intermediate.

Journal of Organic 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, Name: 2-Bromopyridin-3-amine.

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

Kumar, Pardeep published the artcileAziridination of olefins mediated by a [Cu^I(L1)₂]⁺ complex via nitrene transfer reaction, COA of Formula: C12H9NO, the publication is Inorganica Chimica Acta (2022), 120858, database is CAplus.

Copper-catalyzed aziridination of alkenes is dominated in the literature compared to any other metal catalysts. This catalytic reaction is believed to be mediated by the elusive Cu-nitrene intermediate. However, anal. characterization of this intermediate is extremely scarce in the literature. In this article, we intend to shed the light on the electronic structure of the Cu-nitrene intermediate. The reaction of Cu(I) salt in the presence of the redox-active bidentate Schiff base ligand (C₂₁H₂₀N₂; L1) led us to isolate a monomeric copper(I) complex with the mol. formula of [Cu(L1)₂]ClO₄. 2C₆H₆ (1), which was structurally characterized. Complex 1 behaves as an excellent catalyst that promotes the nitrene group transfer to the variety of alkenes in the presence of (N-(p-tolylsulfonyl)imino)phenyliodinane (PhINTs). The intermediate generated from 1 by the addition of PhINTs shows an m/z peak at 832.3079 g/mol which corresponds to an M+ ion peak of the intermediate with the mol. formula of [(L1)₂Cu^II-NTs]⁺ (where Ts = Tosyl). Further, based on the detailed exptl. studies (in-situ UV-Vis measurement and X-band EPR measurements) we propose that the active catalyst that possesses the copper ion in its +2 oxidation state under our exptl. condition, whose electronic structure can be best described as [(L1)₂Cu^II-NTs]⁺ nitrene radicals. The optimized structure of the Cu-nitrene intermediate suggests that the triplet state was found to be the ground state. Besides, we propose a mechanism for this catalytic reaction.

Inorganica Chimica Acta 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, COA of Formula: C12H9NO.

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