Tag: M.W=150-200

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, 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

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

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

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

Berlot, Jean published the artcileAminoquinolines. XI. Decomposition of tertiary 4-aminoquinolines and of related amines by hydrobromic acid in aqueous solution. Influence of the nature of the ring and of the hydrocarbon chain, Formula: C10H10N2, the publication is Bulletin de la Societe Chimique de France (1973), 3175-8, database is CAplus.

Tertiary 4-aminoquinolines I [R = R1 = Me, Pr, allyl, Ph, CH2Ph, (CH2)2Ph, (CH2)3Ph; R2 = Me, R3 = H; R-R3 = Me; R = R1 = Pr, R2 = R3 = Me; R = R1 = Me, CH2Ph, R2 = R3 = H] were completely dealkylated to the corresponding secondary amines by boiling dilute HBr. When R �R1 the shorter radical was eliminated preferentially. The reaction was general for N-heterocyclic amines in which the amine was ortho or para to the ring N. Other amines R4NR5R6 (R4 = 2-quinolyl, 3-quinolyl, 5-quinolyl, 4-pyridyl, 1-naphthyl, 2-naphthyl, CH2Ph, Ph) were not dealkylated when R5 = Me and R6 = Me or Ph, but underwent partial dealkylation when R5 = R6 = CH2Ph.

Bulletin de la Societe Chimique de France 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 C10H10N2, Formula: C10H10N2.

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

Gesmundo, Nathan J. published the artcileNanoscale synthesis and affinity ranking, Product Details of C9H8BNO2, the publication is Nature (London, United Kingdom) (2018), 557(7704), 228-232, database is CAplus and MEDLINE.

Most drugs are developed through iterative rounds of chem. synthesis and biochem. testing to optimize the affinity of a particular compound for a protein target of therapeutic interest. This process is challenging because candidate mols. must be selected from a chem. space of more than 10⁶⁰ drug-like possibilities¹, and a single reaction used to synthesize each mol. has more than 10⁷ plausible permutations of catalysts, ligands, additives and other parameters². The merger of a method for high-throughput chem. synthesis with a biochem. assay would facilitate the exploration of this enormous search space and streamline the hunt for new drugs and chem. probes. Miniaturized high-throughput chem. synthesis^3-7 has enabled rapid evaluation of reaction space, but so far the merger of such syntheses with bioassays has been achieved with only low-d. reaction arrays, which analyze only a handful of analogs prepared under a single reaction condition^8-13. High-d. chem. synthesis approaches that have been coupled to bioassays, including on-bead¹⁴, on-surface¹⁵, on-DNA¹⁶ and mass-encoding technologies¹⁷, greatly reduce material requirements, but they require the covalent linkage of substrates to a potentially reactive support, must be performed under high dilution and must operate in a mixture format. These reaction attributes limit the application of transition-metal catalysts, which are easily poisoned by the many functional groups present in a complex mixture, and of transformations for which the kinetics require a high concentration of reactant. Here the authors couple high-throughput nanomole-scale synthesis with a label-free affinity-selection mass spectrometry bioassay. Each reaction is performed at a 0.1-M concentration in a discrete well to enable transition-metal catalysis while consuming less than 0.05 mg of substrate per reaction. The affinity-selection mass spectrometry bioassay is then used to rank the affinity of the reaction products to target proteins, removing the need for time-intensive reaction purification This method enables the primary synthesis and testing steps that are critical to the invention of protein inhibitors to be performed rapidly and with minimal consumption of starting materials.

Nature (London, United Kingdom) 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, Product Details of C9H8BNO2.

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

Kekesi, Laszlo published the artcileSynthesis and biological evaluation of novel pyrido[2,3-b]pyrazines inhibiting both erlotinib-sensitive and erlotinib-resistant cell lines, SDS of cas: 371766-08-4, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(22), 6152-6155, database is CAplus and MEDLINE.

A series of novel pyrido[2,3-b]pyrazines I [R¹ = H, Ph, 4-MeC₆H₄, etc.; R² = H, Ph, 2-thienyl, etc.; R³ = pyridin-3-yl, quinolin-3-yl; indol-4-yl, etc.] were synthesized as potential antitumor agents for erlotinib-resistant tumors. Known signal inhibitor compounds from the Nested Chem. Library were tested in phenotypic assays on erlotinib-sensitive PC9 and erlotinib-resistant PC9-ER cell lines to find a compound class to be active on erlotinib resistant cell lines. Based on the screening data, novel pyrido[2,3-b]pyrazines were designed and synthesized. The effect of the substituent position of the heteroaromatic moiety in position 7 and the importance of unsubstituted position 2 of the pyridopyrazine core were explored. Compound I [R¹R² = 1,4-benzodioxan-6-yl; R³ = indol-5-yl] had an IC₅₀ value of 0.09 μM for the inhibition of PC9 and 0.15 μM for the inhibition of PC9-ER. The authors found that some lead compounds of these structures overcome erlotinib-resistance which might become promising drug candidates to fight against NSCLC with EGFR T790M mutation. The signaling network(s) involved in the mechanism(s) of action of these novel compounds in overcoming erlotinib resistance remain to be elucidated.

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, SDS of cas: 371766-08-4.

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

Wiles, Jason A. published the artcileBiological evaluation of isothiazoloquinolones containing aromatic heterocycles at the 7-position: In vitro activity of a series of potent antibacterial agents that are effective against methicillin-resistant Staphylococcus aureus, Recommanded Product: Isoquinolin-5-ylboronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(5), 1277-1281, database is CAplus and MEDLINE.

A diverse series of 9H-isothiazolo[5,4-b]quinoline-3,4-diones containing heteroaromatic groups at the 7-position was prepared via palladium-catalyzed cross-coupling. Many of these compounds demonstrated potent antistaphylococcal activity (MICs â‰? μg/mL) against a multi-drug-resistant strain (ATCC 700699) and low cytotoxic activity (CC₅₀ > 100 μM) against the human cell line Hep2 (laryngeal carcinoma).

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 C16H18O4, Recommanded Product: Isoquinolin-5-ylboronic acid.

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

Hennessy, Edward J. published the artcilePreparation of highly functionalized 1,5-disubstituted tetrazoles via palladium-catalyzed Suzuki coupling, Category: isoquinoline, the publication is Tetrahedron Letters (2017), 58(17), 1709-1713, database is CAplus.

The preparation of a range of 1,5-disubstituted tetrazoles has been achieved through palladium-catalyzed Suzuki coupling. Using appropriately substituted 5-p-toluenesulfonyltetrazoles as substrates (obtained by cycloaddition of a substituted azide with p-toluenesulfonyl cyanide), this methodol. provides access to a variety of highly substituted tetrazoles that would be difficult to access otherwise [e.g., 1-phenethyl-5-tosyltetrazole + (4-fluorophenyl)boronic acid �I (94%) in presence of potassium carbonate, RuPhos and palladium(II) acetate in 1,4-dioxane/water]. The procedure is compatible with functional groups commonly found in drug-like mols., and has been used to generate a number of compounds of potential biol. interest.

Tetrahedron 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, Category: isoquinoline.

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