Tag: M.W=150-200

Vrijdag, Johannes L. published the artcileTowards New Tricyclic Motifs: Intramolecular C-H Arylation as the Key Step in a Formal [3+3] Cyclocondensation Strategy, Category: pyridine-derivatives, the publication is European Journal of Organic Chemistry (2017), 2017(11), 1465-1474, database is CAplus.

Tricyclic scaffolds structurally related to the well-known benzodiazepine class of drugs show diverse biol. activities strikingly different from those of their benzodiazepine counterparts. Interested by this scaffold-hopping perspective, we previously developed a continuous-flow method for the conversion of benzodiazepinediones into oxazoloquinolinones. Attempted extension of this synthetic route to the corresponding oxazolonaphthyridinone scaffolds met with limited success, however. This encouraged us to develop a different approach to pyridine-based tricyclic motifs. In line with our interest in scaffold hopping, in this paper authors describe a general, convergent [3+3] cyclocondensation approach to [1,3]oxazolo[4,5-c]-1-naphthyridin-4(5H)-ones. The key synthetic steps in this approach are: (1) the construction of an amide linkage connecting two peripheral heterocycles; and (2) a palladium-catalyzed intramol. C-H arylation to complete the tricyclic scaffold.

European 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 C8H10O2, Category: pyridine-derivatives.

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

Guo, Beibei published the artcileSelective α-Deuteration of Cinnamonitriles using D₂O as Deuterium Source, Quality Control of 91-02-1, the publication is Advanced Synthesis & Catalysis (2022), 364(1), 179-186, database is CAplus.

The selective α-deuteration of α,β-unsaturated nitriles using the strong base t-BuOK or a metal-ligand cooperative Ru pincer catalyst was described. With D₂O as deuterium source and glyme as solvent at 70°C, t-BuOK is an efficient catalyst for deuteration at the α-C(sp²) position of cinnamonitriles, providing access to a broad range of deuterated derivatives in good to excellent yields and with very high levels of deuterium incorporation. While the t-BuOK-catalyzed protocol does not tolerate base-sensitive functional groups, cinnamonitrile derivatives containing a benzylic bromide or ester moiety were deuterated in excellent yields using Milstein’s ruthenium PNN pincer catalyst. Moreover, the activity for H/D exchange of the metal-ligand cooperative Ru catalyst was found to be significantly higher than that of t-BuOK, allowing reactions to proceed well even at room temperature A mechanistic proposal is put forward that involves deprotonation of the cinnamonitrile α-CH position when using t-BuOK as catalyst, whereas H/D exchange catalysis with the Ru PNN pincer likely proceeds via (reversible) oxa-Michael addition of D₂O.

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, Quality Control of 91-02-1.

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

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

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

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

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

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

Mori-Quiroz, Luis M. published the artcileExploiting Iminoquinones as Electrophilic at Nitrogen “N+” Synthons for C-N Bond Construction, HPLC of Formula: 39856-58-1, the publication is Organic Letters (2021), 23(18), 7008-7013, database is CAplus and MEDLINE.

New methods for C-N bond construction exploiting the N-centered electrophilic character of iminoquinones were reported. Iminoquinones, generated in situ via the condensation of o-vinylanilines with benzoquinones, underwent acid-catalyzed cyclization to afford N-arylindoles I [R = H, F; R¹ = H, Me, Ph, etc.; R² = H, Me; R³ = H, Cl, CO₂Me, etc.; Ar = 3,5-di-(t-Bu)-4-OHC₆H₂, 3,5-di-Me-4-OHC₆H₂, 3,5-di-(t-Bu)-2-OHC₆H₂, 10-hydroxy-9-phenanthryl] in excellent yields. Under similar reaction conditions, homoallylic amines reacted analogously to afford N-arylpyrroles II [R⁴ = Ph, 3-MeOC₆H₄, 4-FC₆H₄, 2,6-di-FC₆H₃, 2,3-dihydrobenzofuran-5-yl; R⁵ = H, 4-MeC₆H₄; Ar = 3,5-di-(t-Bu)-4-OHC₆H₂]. Addnl., organometallic nucleophiles were shown to add to the nitrogen atom of N-alkyliminoquinones to provide amine products. Finally, iminoquinones were shown to be competent electrophiles for copper-catalyzed hydroamination.

Organic Letters 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, HPLC of Formula: 39856-58-1.

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

Egbertson, Melissa S. published the artcileNon-Peptide GPIIb/IIIa Inhibitors. 20. Centrally Constrained Thienothiophene α-Sulfonamides Are Potent, Long Acting in Vivo Inhibitors of Platelet Aggregation, Recommanded Product: Pyridine-3-sulfonic acid, the publication is Journal of Medicinal Chemistry (1999), 42(13), 2409-2421, database is CAplus and MEDLINE.

The synthesis and pharmacol. of a potent thienothiophene non-peptide fibrinogen receptor antagonist (I) are reported. Compound I inhibited the aggregation of human gel-filtered platelets with an IC₅₀ of 8 nM and demonstrated an 8-fold improvement in affinity for isolated GPIIb/IIIa receptors over analogs possessing an isoindolinone backbone. Flow cytometry studies revealed that the binding of I to resting platelets is a diffusion-controlled process (k_on = 3.3 × 10⁶ M^-1 s^-1) and that I binds to dog and human platelets with comparable affinity (K_d = 0.04 and 0.07 nM, resp.). Ex vivo platelet aggregation in dogs was completely inhibited by an i.v. dose of 5 mg/kg, and an oral dose of 50-90 mg/kg followed by low daily doses of 10 mg/kg was sufficient to maintain ∼80% inhibition of ex vivo platelet aggregation over several days. Inhibition of ADP-induced platelet aggregation in anesthetized dogs at 77 ± 7% resulted in a moderate 2.5-fold increase in bleeding time, while complete inhibition (100%) resulted in an approx. 10-min bleeding time. Addnl. doses were required to increase the bleeding time to the maximum time allowed in the protocol (15 min), thus indicating a potentially useful and safe separation of efficacy and bleeding time.

Journal of Medicinal Chemistry 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