Day: December 2, 2022

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

Midya, Siba Prasad published the artcileSynthesis of fused cyanopyrroles and spirocyclopropanes via addition of N-ylides to chalconimines, Computed Properties of 17281-59-3, the publication is Organic & Biomolecular Chemistry (2017), 15(17), 3616-3627, database is CAplus and MEDLINE.

Addition of N-ylides derived from DABCO to chalconimines takes place through a Michael addition-cyclization pathway to afford fused cyanopyrroles I (R = C₆H₅, 4-CH₃OC₆H₄, 4-FC₆H₄, 4-H₃CC₆H₄, 1,3-benzodioxol-5-yl) and/or spirocyclopropanes II (R = C₆H₅, 4-BrC₆H₄, 3-CH₃OC₆H₄, etc.; n = 1, 2, 3). The product profile depends heavily on the nature of chalconimines. While 6-membered cyclic chalconimines provide a mixture of pyrrole and spirocyclopropane, 5-membered chalconimines furnish exclusively spirocyclopropane. Cyclopropane was the only product in the case of a representative open chain chalconimine as well. On the other hand, chalcones provide only spirocyclopropanes which is in contrast to the previously reported reactivity of enones. The complementary nature of the reactivity of the tetralone derived chalcone and its corresponding imine in providing spirocyclopropane and pyrrole, resp., has also been demonstrated.

Organic & Biomolecular Chemistry published new progress about 17281-59-3. 17281-59-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitrile,Salt, name is 1-(Cyanomethyl)pyridin-1-ium chloride, and the molecular formula is C7H7ClN2, Computed Properties of 17281-59-3.

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

Pickart, Loren published the artcileInhibition of the growth of cultured cells and an implanted fibrosarcoma by aroylhydrazone analogs of the Gly-His-Lys-copper(II) complex, Category: pyridine-derivatives, the publication is Biochemical Pharmacology (1983), 32(24), 3868-71, database is CAplus and MEDLINE.

Both salicylaldehydebenzoylhydrazonato-Cu(II) chloride hydrate (I) [83614-45-3] and pyridine-2-carboxaldehyde-2-pyridylhydrazonato-Cu(II) dichloride (II) [46847-77-2] inhibited DNA formation in 6 types of human and mouse cultured cells (normal and neoplastic). The degree of inhibition by I or II was comparable to that obtained with cisplatin, bleomycin, and thiotepa. In vivo, I or II injection into the tumor area of mice implanted s.c. with MCA1511 fibrosarcoma resulted in marked tumor-size regression. I.p. treatment of the transplanted tumors was less effective in controlling tumor growth. The Cu-free ligands were inactive as antitumor agents. Thus, I and II, both analogs of Gly-His-Lys-Cu(II), are potent antimitotic and antineoplastic agents.

Biochemical Pharmacology published new progress about 2215-33-0. 2215-33-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, and the molecular formula is C11H10N4, Category: pyridine-derivatives.

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

Green, R. W. published the artcileThermodynamics of chelation. I. Iron (II) and zinc (II) complexes of pyridine-2-carboxaldehyde 2′-pyridylhydrazone, Computed Properties of 2215-33-0, the publication is Australian Journal of Chemistry (1968), 21(5), 1165-73, database is CAplus.

In dilute solution, pyridine-2-carboxaldehyde 2′-pyridylhydrazone can behave as a diacid base or as a tridentate chelating agent. Its cationic bis complexes further undergo 2 stages of deprotonation. Equilibrium constants were measured at 7 temperatures from 5° to 60° and over a range of ionic strength. They have been used to derive values of enthalpies and entropies of reaction with H+, Fe2+, and Zn2+.

Australian Journal of Chemistry published new progress about 2215-33-0. 2215-33-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, and the molecular formula is C11H10N4, Computed Properties of 2215-33-0.

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

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

Korthals, Brigitte published the artcileNickel(II)-Methyl Complexes with Water-Soluble Ligands L [(salicylaldiminato-κ²N,O)NiMe(L)] and Their Catalytic Properties in Disperse Aqueous Systems, Application of Pyridine-3-sulfonic acid, the publication is Organometallics (2007), 26(6), 1311-1316, database is CAplus.

Neutral (salicylaldiminato)nickel(II) Me complexes [{6-C(H):NAr-2,4-I₂C₆H₂O-κ²N,O}NiMe(L)] (Ar = 2,6-{3,5-(F₃C)₂C₆H₃}₂C₆H₃) with different water-soluble ligands L (2a, L = 1,3,5-triaza-7-phosphaadamantane; 2b, L = hexamethylenetetramine (urotropine); 2c, L = tetraethylammonium pyridine-3-sulfonate; 2d, L = amino-terminated poly(ethylene glycol) monomethoxy ether) were prepared 2A–d are potentially water-soluble catalyst precursors for ethylene polymerization, which form a water-insoluble active site [{κ²-N,O}NiR(ethylene)] (R = growing chain). Only complex 2d was water-soluble (>2 mmol L^-1); 2c is soluble in water/2-propanol mixtures In toluene as a reaction medium, only the relatively weakly coordinated tertiary amine complex 2b is polymerization active (1.7 × 10⁴ TO). In aqueous systems 2c,d are also active due to compartmentalization of the active site in the polymer particles and of L in the aqueous phase. Polyethylene particle sizes vary from 18 nm (dispersions formed with 2d) to over 0.5 μm (2c) to suspensions (2b) depending on the initial state of the reaction mixture, correlated with catalyst solubility

Organometallics 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, Application of Pyridine-3-sulfonic acid.

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

Wu, Zhao published the artcileAnti-Markovnikov hydro(amino)alkylation of vinylarenes via photoredox catalysis, Quality Control of 91-02-1, the publication is Nature Communications (2021), 12(1), 5956, database is CAplus and MEDLINE.

Herein, the application of this powerful catalytic manifold to address the hydroalkylation and hydroaminoalkylation of electronically diverse vinylarenes e.g., 1,1-diphenylethylene was presented. This reaction allows for generalized alkene hydroalkylation leveraging common alkyl radical precursors, such as organotrifluoroborate salts and carboxylic acids. Furthermore, utilizing easily accessible α-silyl amine reagents or tertiary amines directly, secondary and tertiary amine moieties can be installed onto monoaryl and diaryl alkenes to access valuable products. Thus, under a unified system, both hydroalkylation and hydroaminoalkylation of alkenes are achieved. The substrate scope is evaluated through 57 examples, the synthetic utility of the method is demonstrated, and preliminary mechanistic insights are presented.

Nature Communications 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 C16H24BF4Ir, Quality Control of 91-02-1.

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

de Boer, Sandra Y. published the artcileCu^I click catalysis with cooperative noninnocent pyridylphosphine ligands, Related Products of pyridine-derivatives, the publication is Inorganica Chimica Acta (2012), 336-342, database is CAplus.

The authors describe the synthesis and characterization of compound L1H, 2-di(tert-butyl)phosphinomethyl-6-methylpyridine (NP^tBu), and the 1st dimeric Cu^I complex, [Cu(μ-Br)(L1H)]₂ (3), with this novel bidentate ligand. The mol. structure of 3 was determined by x-ray crystallog. The ligand scaffold exhibits noninnocent reactivity through dearomatization behavior, similar to its well-studied tridentate analog L2H, 2,6-bis((di-tert-butylphosphino)methyl)pyridine (PNP^tBu). The mol. structure of [Cu(CCPh)(L2H)]₂ (4) is reported, which is a rare case of a crystallog. characterized Cu-acetylide dimer. Cu(I) complexes with either ligand L1H or L2H or their dearomatized counterparts act as active, cooperative catalysts for the [2+3] polar cycloaddition of azides and acetylenes. These results represent the 1st indications of selective Cu-based cooperative catalysis, using noninnocent lutidine-based PNP backbone. Catalysts [Cu(PN-P^tBu)] (2, PN-P^tBu = de-aromatized L2H (C₆H₃P(:CHP^tBu₂)-2-(CH₂P^tBu₂)-6)) and [Cu(CCPh)(L2H)] (5) could thus be termed all-inclusive systems for this reaction.

Inorganica Chimica Acta 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

Toure, B. Barry published the artcileToward the Validation of Maternal Embryonic Leucine Zipper Kinase: Discovery, Optimization of Highly Potent and Selective Inhibitors, and Preliminary Biology Insight, Product Details of C6H8BNO3, the publication is Journal of Medicinal Chemistry (2016), 59(10), 4711-4723, database is CAplus and MEDLINE.

MELK kinase has been implicated in playing an important role in tumorigenesis. Our previous studies suggested that MELK is involved in the regulation of cell cycle and its genetic depletion leads to growth inhibition in a subset of high MELK-expressing basal-like breast cancer cell lines. Herein we describe the discovery and optimization of novel MELK inhibitors 8a and 8b that recapitulate the cellular effects observed by short hairpin RNA (shRNA)-mediated MELK knockdown in cellular models. We also discovered a novel fluorine-induced hydrophobic collapse that locked the ligand in its bioactive conformation and led to a 20-fold gain in potency. These novel pharmacol. inhibitors achieved high exposure in vivo and were well tolerated, which may allow further in vivo evaluation.

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 C10H9NO4S, Product Details of C6H8BNO3.

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