Day: November 21, 2022

Serafim, Ricardo A. M. published the artcileDevelopment of Pyridine-based Inhibitors for the Human Vaccinia-related Kinases 1 and 2, HPLC of Formula: 371766-08-4, the publication is ACS Medicinal Chemistry Letters (2019), 10(9), 1266-1271, database is CAplus and MEDLINE.

Vaccinia-related kinases 1 and 2 (VRK1 and VRK2) are human Ser/Thr protein kinases associated with increased cell division and neurol. disorders. Nevertheless, the cellular functions of these proteins are not fully understood. Despite their therapeutic potential, there are no potent and specific inhibitors available for VRK1 or VRK2. The authors report here the discovery and elaboration of an aminopyridine scaffold as a basis for VRK1 and VRK2 inhibitors. The most potent compound for VRK1 (26) displayed an IC₅₀ value of 150 nM and was fairly selective in a panel of 48 human kinases (selectivity score S(50%) of 0.04). Differences in compound binding mode and substituent preferences between the two VRKs were identified by the structure-activity relationship combined with the crystallog. anal. of key compounds The authors expect the results to serve as a starting point for the design of more specific and potent inhibitors against each of the two VRKs.

ACS 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 C9H9BN2O3, HPLC of Formula: 371766-08-4.

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

Beaumard, Floriane published the artcileSynthesis of nonsymmetrical 5-aryl-2-indolopyrrole derivatives via controlled mono Suzuki-Miyaura cross-coupling on N-Boc-2,5-dibromopyrrole, SDS of cas: 371766-08-4, the publication is Synthesis (2010), 4033-4042, database is CAplus.

The first example of mono Suzuki-Miyaura cross-coupling of N-Boc-2,5-dibromopyrrole with a boronic acid (indol-2-yl-boronic acid) is reported. The coupling of the resulting 2-indolyl-5-bromopyrrole I (R¹ = Boc) with boronic acids R²B(OH₂) (R² = Ph, 4-biphenyl, 3-pyridinyl, etc.) gave 2,5-disubstituted pyrroles II in good to excellent yields. The tert-butoxycarbonyl (Boc) groups could be easily removed to give the completely deprotected products.

Synthesis 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

Mydock-McGrane, Laurel published the artcileAntivirulence C-Mannosides as Antibiotic-Sparing, Oral Therapeutics for Urinary Tract Infections, HPLC of Formula: 371766-08-4, the publication is Journal of Medicinal Chemistry (2016), 59(20), 9390-9408, database is CAplus and MEDLINE.

Gram-neg. uropathogenic Escherichia coli (UPEC) bacteria are a causative pathogen of urinary tract infections (UTIs). Previously developed antivirulence inhibitors of the type 1 pilus adhesin, FimH, demonstrated oral activity in animal models of UTI but were found to have limited compound exposure due to the metabolic instability of the O-glycosidic bond (O-mannosides). Herein, we disclose that compounds having the O-glycosidic bond replaced with carbon linkages had improved stability and inhibitory activity against FimH. We report on the design, synthesis, and in vivo evaluation of this promising new class of carbon-linked C-mannosides that show improved pharmacokinetic (PK) properties relative to O-mannosides. Interestingly, we found that FimH binding is stereospecifically modulated by hydroxyl substitution on the methylene linker, where the R-hydroxy isomer has a 60-fold increase in potency. This new class of C-mannoside antagonists have significantly increased compound exposure and, as a result, enhanced efficacy in mouse models of acute and chronic UTI.

Journal of 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, HPLC of Formula: 371766-08-4.

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

Salazar-Mendoza, Domingo published the artcileMacrocycles and Coordination Polymers Derived from Self-Complementary Tectons Based on N-Containing Boronic Acids, Application of Isoquinolin-5-ylboronic acid, the publication is Crystal Growth & Design (2013), 13(6), 2441-2454, database is CAplus.

A series of N-containing boronic esters have been prepared by combination of 3-pyridineboronic acid (3-pyba), 4-pyridineboronic acid (4-pyba), and 5-isoquinolineboronic acid (5-iqba) with ethanol, 1,2-ethanediol, and 1,3-propanediol. The resulting self-complementary tectons (SCTs) assembled further through N â†?B bond formation to give one tetranuclear macrocyclic and four one-dimensional polymeric boron complexes: [(3-py)B(OEt)₂]₄ (2), [(3-py)B(OCH₂CH₂O)]_n (3), [(4-py)B(OEt)₂]_n (4), [(5-iq)B(OCH₂CH₂O)]_n (6), and [(5-iq)B(OCH₂CH₂CH₂O)]_n (7). In conjunction with the previously reported pentadecanuclear boroxine cage (1) and high-dimensional assemblies derived from pentaerythritol, [(4-py)B(OCH₂)₂C(CH₂O)₂B(4-py)]_n·4nEtOH·nH₂O·nC₇H₈ (5), and [(5-iq)B(OCH₂)₂C(CH₂O)₂B(5-iq)]_n·nEtOH (8), it was shown that a single class of self-complementary boron-based tectons can give a varied series of finite and infinite supramol. aggregates. A comparative structural characterization of boron complexes 2–4 and 6–7 by single-crystal x-ray diffraction anal. and quantum-chem. calculations revealed that the corresponding SCTs could have been organized in all cases in the form of tetrameric macrocycles, as it occurred for 2, indicating that intermol. noncovalent interactions during crystallization probably play a significant role in the output of the assembly process and influence the formation of supramol. isomers. This observation was supported by a comparison of the mol. geometries of a series of tetranuclear macrocyclic and related linear oligomeric boronic esters derived from 3-pyba, 4-pyba, and 5-iqba, whose structures have been optimized by quantum-chem. calculations at the (B3LYP/cc-pVDZ) level of theory. The calculated structure of [(3-py)B(OEt)₂]₄ was in good agreement with the structure obtained exptl. by single-crystal x-ray diffraction anal. For the cyclo-tetramers derived from 3-pyba and 5-iqba, all common conformers known from calixarene chem. have been analyzed (cone, 1,3-alternate, 1,2-alternate, and partial cone), showing that the boronic ester group has a significant influence on their relative stability.

Crystal Growth & Design 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 of 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

Solum, Eirik Johansson published the artcileSynthesis and biological evaluations of new analogs of 2-methoxyestradiol: Inhibitors of tubulin and angiogenesis, Category: isoquinoline, the publication is European Journal of Medicinal Chemistry (2014), 391-398, database is CAplus and MEDLINE.

The synthesis, cytotoxicity, inhibition of tubulin polymerization and anti-angiogenic effects of 15 analogs of 2-methoxyestradiol are reported. The biol. studies revealed that the position of nitrogen atom in the heterocyclic ring is important for inhibition of both tubulin polymerization and angiogenesis. The most potent inhibitors were compounds I and II, with a 6-substituted isoquinoline ring in the 17-position of the steroid skeleton. Moreover, low estrogen activity was observed for the analogs tested at 10 μM concentrations

European Journal of 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 C5H5F3O2, Category: isoquinoline.

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

Solum, Eirik Johansson published the artcileSynthesis, biological evaluation and molecular modeling of new analogs of the anti-cancer agent 2-methoxyestradiol: potent inhibitors of angiogenesis, Category: isoquinoline, the publication is RSC Advances (2015), 5(41), 32497-32504, database is CAplus.

The synthesis, cytotoxicity, inhibition of tubulin polymerization and anti-angiogenic effects of 10 analogs of 2-methoxyestradiol are reported. These efforts revealed that the analog with a 4-pyridine ring in the 17-position, in combination with 2-ethyl- and 3-sulfamate substituents on the steroid A-ring, is the most interesting anti-cancer agent. This compound showed potent inhibitory effects against angiogenesis (IC₅₀ = 0.1 ± 0.02 μM) and selective cytotoxic effects towards the CEM, H460 and HT-29 cancer cell lines, with no cytotoxicity observed against the healthy VERO cell line. The most interesting analog also displayed inhibition of tubulin polymerization (IC₅₀ = 4.3 μM) almost as potent as 2-methoxyestradiol (IC₅₀ = 3.5 μM). Mol. modeling experiments showed that this analog interacts within the colchicine-binding site of β-tubulin via multiple bonding with several amino acids. These observations provide support that the cytotoxic and anti-angiogenic effects observed for this novel analog are, at least in part, mediated by binding to tubulin.

RSC Advances 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 C48H47FeP, Category: isoquinoline.

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

Kelly, Aidan M. published the artcileA Mild Method for Making MIDA Boronates, Category: isoquinoline, the publication is Organic Letters (2020), 22(24), 9408-9414, database is CAplus and MEDLINE.

It is disclosed that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride (I), acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, it was developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in laboratories that do not specialize in organic synthesis.

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 C9H8BNO2, Category: isoquinoline.

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

Sun, Bin published the artcileSynthesis and In Vitro Antibacterial Activity of Novel Naphthyridinone Derivatives, Synthetic Route of 371766-08-4, the publication is ChemistrySelect (2019), 4(21), 6552-6556, database is CAplus.

This study describes a series of novel hydrochloride salts of 5,6,7,8-tetrahydro-1,6-naphthyridin-2-(1H)-one derivatives I (R = C₆H₅, 2-FC₆H₄, isoquinolin-5-yl, etc.) as potential antibacterial agents and corresponding synthetic routes. The majority of analogs exhibit antibacterial activity against Gram-neg. bacteria (E. coli) and Gram-pos. bacteria (S. aureus). Several of them I (R = 3-F₃CC₆H₄, 3-Cl-2-MeC₆H₃, 3-NCC₆H₄, 2,3-F₂C₆H₃) showed potent antibacterial activity towards E. coli. Compound I (R = 2-methylquinolin-6-yl) is also the first reported compound to exhibit quorum sensing inhibitory activity against C. violaceum ATCC 12472. The presence of quorum sensing inhibitory compound indicates its potential use in the treatment of bacterial infections.

ChemistrySelect 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 C10H15NO, Synthetic Route of 371766-08-4.

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