Day: November 21, 2022

Hong, Seung Youn published the artcileChemoselective Primary Amination of Aryl Boronic Acids by P^III/P^V=O-Catalysis: Synthetic Capture of the Transient Nef Intermediate HNO, Computed Properties of 371766-08-4, the publication is Journal of the American Chemical Society (2022), 144(20), 8902-8907, database is CAplus and MEDLINE.

A catalytic approach to intercept the transient HNO for a chemoselective primary amination of arylboronic acids was reported. A phosphetane-based catalyst operating within P^III/P^V=O redox cycling was shown to capture HNO, generated in situ by Nef decomposition of 2-nitropropane, to selectively install the primary amino group at aryl Csp² centers. The method furnished versatile primary arylamines from arylboronic acid substrates with the preservation of otherwise reactive functional groups.

Journal of the American Chemical Society published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Computed Properties of 371766-08-4.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Zurwerra, Didier published the artcileSynthesis and Stability of Boratriazaroles, Computed Properties of 371766-08-4, the publication is Organic Letters (2015), 17(1), 74-77, database is CAplus and MEDLINE.

We describe the synthesis and stability anal. of novel boratriazaroles that can be viewed as bioisosteres of imidazoles or pyrazoles. These heterocycles could conveniently be obtained by condensing a boronic acid and amidrazone 1 in various solvents. A detailed stability anal. of selected compounds at different pH values as a function of time led to the identification of steric hindrance around the boron atom as a key element for stabilization.

Organic Letters published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C10H9ClN2O, Computed Properties of 371766-08-4.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Zhu, Lifei published the artcileNovel 2,3-dihydro-1H-imidazo[2,1-A]isoquinolin-4-ium salts: synthesis, antitumor, and antibacterial activity, Computed Properties of 46000-11-7, the publication is Acta Poloniae Pharmaceutica (2022), 79(1), 89-96, database is CAplus.

To overcome the metabolic instability brought by the highly reactive and polar iminium moiety (C=N+) of sanguinarine, a series of novel 2,3-dihydro-1H-imidazo[2,1-a]isoquinolin-4-um salts I (R = H, Me, Et) was designed and synthesized with a vital step of the cyclization between isoquinolin-1-amines II and 1,2-dibromoethane, followed by evaluation of the antitumor and antibacterial activity. The I (R = Et) presented good antitumor activity against NB4 cells (IC₅₀ = 30.00μ M), and I (R = Me) showed the best antibacterial activity in most cases among I, especially against E. coli and Salmonella, with a MIC value of 241.4μM. Despite all compounds I showed decreased bioactivity, the results might support the significance of maintaining a sufficient pos. charge on quaternary ammonium ion to exert potential bioactivity. Compared with I (R = H), the introduction of Me I (R = Me) or Et I (R = Et) could significantly enhance the bioactivity in a possible manner of stabilizing the pos. charge as electron-donating groups. This study provides guidance on the structural design of isoquinoline as an antitumor or antibacterial agent.

Acta Poloniae Pharmaceutica published new progress about 46000-11-7. 46000-11-7 belongs to isoquinoline, auxiliary class Isoquinoline,Amine, name is N-Methylisoquinolin-1-amine, and the molecular formula is C3H12Cl2N2, Computed Properties of 46000-11-7.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Li, Gen published the artcileP(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate, Name: Isoquinolin-5-ylboronic acid, the publication is Journal of the American Chemical Society (2020), 142(38), 16205-16210, database is CAplus and MEDLINE.

The direct reductive N-arylation of nitromethane by organophosphorus-catalyzed reductive C-N coupling with arylboronic acid derivatives is reported. This method operates by the action of a small ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) together with a mild terminal reductant hydrosilane to drive the selective installation of the methylamino group to (hetero)aromatic boronic acids and esters. This method also provides for a unified synthetic approach to isotopically labeled N-methylanilines from various stable isotopologues of nitromethane (i.e., CD₃NO₂, CH₃¹⁵NO₂, and ¹³CH₃NO₂), revealing this easy-to-handle compound as a versatile precursor for the direct installation of the methylamino group.

Journal of the American Chemical Society published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Name: Isoquinolin-5-ylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Tao, J. published the artcileSynthesis of tetrandrine derivatives and their anti-tumor activities, Formula: C9H8BNO2, the publication is ChemXpress (2018), 11(1), 134/1-134/15, database is CAplus.

Cancer is among the most serious diseases endangering human life and health. At present, traditional Chinese medicine has showed excellent prospects for wide application in tumor treatment. In this study, fourteen novel bisbenzylisoquinoline derivatives were designed and synthesized by Suzuki-Miyaura reaction of 5-bromotetrandrine with a variety of arylboronic acids. The anti-tumor activities of these new compounds on human lung cancer cells (A549) and murine leukemia cells (P388) were evaluated by using the CCK-8 method. Apoptosis and cell cycle were detected by flow cytometry. These compounds exhibited better activities than tetrandrine itself on A549 cells. Among them, compound 1 exhibited the most significant cytotoxic effects. Preliminary mechanistic studies indicated that the ant proliferative efficacy of compound 1 was mediated by its induction of apoptosis and cell cycle arrest at the S and G2 phases. Fourteen new tetrandrine derivatives were synthesized and tested for their anti-tumor activities in vitro. All compounds showed stronger cytotoxic effects than the parent compound tetrandrine in A549 cell lines. These findings will contribute to the future design of more effective anti-tumor agents in lung cancer therapy.

ChemXpress published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is Al2H32O28S3, Formula: C9H8BNO2.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Li, Shasha published the artcileMerging Late-Stage Diversification with Solid-Phase Peptide Synthesis Enabled by High-Throughput On-Resin Reaction Screening, Recommanded Product: Isoquinolin-5-ylboronic acid, the publication is ACS Catalysis (2022), 12(5), 3201-3210, database is CAplus.

An integrated workflow is described that combines micromole-scale high-throughput experimentation (HTE) reaction screening and solid-phase peptide synthesis (SPPS) to enable rapid synthetic method development for on-resin peptide diversification. Using this new approach, we have identified several sets of robust Suzuki-Miyaura coupling conditions with complementary scope that collectively display broad coverage with respect to both resin-bound peptide substrates containing aryl halide side chains and (hetero)arylboronic acid coupling partners. We have also demonstrated the utility of this integrated SPPS/chem. diversification method by synthesizing a multidimensional library of diverse peptides in high yields.

ACS Catalysis published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Recommanded Product: Isoquinolin-5-ylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Duncton, Matthew A. J. published the artcileArylphthalazines. Part 2: 1-(Isoquinolin-5-yl)-4-arylamino phthalazines as potent inhibitors of VEGF receptors I and II, Recommanded Product: Isoquinolin-5-ylboronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(6), 1579-1581, database is CAplus and MEDLINE.

A novel class of 1-(isoquinolin-5-yl)-4-arylamino-phthalazines is described as inhibitors of vascular endothelial growth factor receptor II (VEGFR-2). Many compounds display VEGFR-2 inhibitory activity with an IC₅₀ as low as 0.017 μM in an HTRF enzymic assay. The compounds also inhibit VEGFR-1, a related tyrosine kinase.

Bioorganic & Medicinal Chemistry Letters published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Recommanded Product: Isoquinolin-5-ylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Duncton, Matthew A. J. published the artcileArylphthalazines as potent, and orally bioavailable inhibitors of VEGFR-2, Computed Properties of 371766-08-4, the publication is Bioorganic & Medicinal Chemistry (2009), 17(2), 731-740, database is CAplus and MEDLINE.

A series of arylphthalazine derivatives were synthesized and evaluated as antagonists of VEGF receptor II (VEGFR-2). IM-094482 57, which was prepared in two steps from com. available starting materials, was found to be a potent inhibitor of VEGFR-2 in enzymic, cellular and mitogenic assays (comparable activity to ZD-6474). Addnl., 57 inhibited the related receptor, VEGF receptor I (VEGFR-1), and showed excellent exposure when dosed orally to female CD-1 mice.

Bioorganic & Medicinal Chemistry published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Computed Properties of 371766-08-4.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Niculescu-Duvaz, Dan published the artcilePotent BRAF kinase inhibitors based on 2,4,5-trisubstituted imidazole with naphthyl and benzothiophene 4-substituents, Quality Control of 1219130-56-9, the publication is Bioorganic & Medicinal Chemistry (2013), 21(5), 1284-1304, database is CAplus and MEDLINE.

The RAS-RAF-MEK-ERK pathway is hyperactivated in 30% of cancers. BRAF is a serine-threonine kinase, belonging to this pathway that is mutated with high frequency in melanoma and other cancers thus BRAF is an important therapeutic target in melanoma. We have designed inhibitors of BRAF based on 2,4,5-trisubstituted imidazoles with naphthyl and benzothiophene-4-substituents. Two compounds were discovered to be potent BRAF inhibitors: 1-(6-{2-[4-(2-dimethylamino-ethoxy)phenyl]-5-(pyridin-4-yl)-1H-imidazol-4-yl}benzo[b]thiophen-3-yl)-2,2,2-trifluoroethanol with BRAF IC₅₀ = 190 nM and with cellular GI₅₀ = 2100 nM, and 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-naphthalen-1-ol with IC₅₀ = 9 nM and GI₅₀ = 220 nM.

Bioorganic & Medicinal Chemistry published new progress about 1219130-56-9. 1219130-56-9 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Amide,Boronic Acids,Boronate Esters, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1(2H)-one, and the molecular formula is C15H18BNO3, Quality Control of 1219130-56-9.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Cheng, Yunfeng published the artcileA New Class of Fluorescent Boronic Acids That Have Extraordinarily High Affinities for Diols in Aqueous Solution at Physiological pH, Application In Synthesis of 371766-08-4, the publication is Chemistry – A European Journal (2010), 16(45), 13528-13538, S13528/1-S13528/40, database is CAplus and MEDLINE.

The boronic acid group is an important recognition moiety for sensor design. Herein, the authors report a series of isoquinolinylboronic acids that have extraordinarily high affinities for diol-containing compounds at physiol. pH. In addition, 5- and 8-isoquinolinylboronic acids also showed fairly high binding affinities towards D-glucose (K_a=42 and 46 M^-1, resp.). For the first time, weak but encouraging binding of cis-cyclohexanediol was found for these boronic acids. Such binding was coupled with significant fluorescence changes. Furthermore, 4- and 6-isoquinolinylboronic acids also showed the ability to complex Me α-D-glucopyranose (K_a=3 and 2 M^-1, resp.).

Chemistry – A European Journal published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Application In Synthesis of 371766-08-4.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem