Tag: M.W=150-200

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

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

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

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

Visseq, Alexia published the artcilePyridin-2(1H)one derivatives: A possible new class of therapeutics for mechanical allodynia, Synthetic Route of 371766-08-4, the publication is European Journal of Medicinal Chemistry (2020), 111917, database is CAplus and MEDLINE.

A series of 3,5-disubstituted pyridin-2(1H)-ones I [R = 1H-indol-4-yl, (1,1-biphenyl)-4-yl, 3-chlorophenyl, etc.] was designed, synthesized and evaluated in vivo toward a rat model of inflammatory mech. allodynia. The series rapidly and strongly prevented the development of mech. allodynia. The compound I (R = 2-bromophenyl (A)), a most active compound of the series, which was also able to quickly reverse neuropathic MA in rats, was founded. Next, when compound (A) was evaluated toward a panel of 50 protein kinases (PK) in order to identify its potential biol. target(s), it was found that compound (A) is a p38α MAPK inhibitor, a PK known to contribute to pain and hypersensitivity in animal models. 3,5-Disubstituted pyridin-2(1H)-ones I thus could represent a novel class of analgesic for the treatment of mech. allodynia.

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 C12H10O4S, Synthetic Route of 371766-08-4.

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

Engers, Darren W. published the artcileSynthesis and structure-activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of Dorsomorphin: The discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe, Computed Properties of 371766-08-4, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(11), 3248-3252, database is CAplus and MEDLINE.

A structure-activity relation of the 3- and 6-positions of the pyrazolo[1,5-a]pyrimidine scaffold of the known BMP inhibitors dorsomorphin, 1, LDN-193189, 2, and DMH1, 3, led to the identification of a potent and selective compound for ALK2 vs. ALK3. The potency contributions of several 3-position substituents were evaluated with subtle structural changes leading to significant changes in potency. From these studies, a novel 5-quinoline mol. was identified and designated an MLPCN probe mol., ML347, which shows >300-fold selectivity for ALK2 and presents the community with a selective mol. probe for further biol. evaluation.

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, Computed Properties of 371766-08-4.

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

Beveridge, Ramsay E. published the artcileA direct copper-catalyzed route to pyrrolo-fused heterocycles from boronic acids, Application of Isoquinolin-5-ylboronic acid, the publication is Tetrahedron Letters (2012), 53(5), 564-569, database is CAplus.

A convenient route to prepare azaindoles and related pyrrolo-fused heterocycles from boronic acids, DBAD (di-tert-Bu diazodicarboxylate), and enolizable aldehydes and ketones is presented. E.g., reaction of 6-methoxy-3-pyridineboronic acid, DMAD, and PhCH₂CHO, catalyzed by Cu(OAc)₂, gave 70% azaindole derivative I. The reaction proceeds via a one-pot four-step cascade sequence with key steps involving a copper-catalyzed boronic acid coupling to DBAD and a Fischer indolization providing access to a variety of pharmaceutically interesting heterocycles including pyrrolopyridines, -pyrimidines, -quinolines, and -isoquinolines from readily available aza-aryl boronic acid precursors.

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, Application of Isoquinolin-5-ylboronic acid.

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

Le Manach, Claire published the artcileMedicinal Chemistry Optimization of Antiplasmodial Imidazopyridazine Hits from High Throughput Screening of a SoftFocus Kinase Library: Part 1, Safety of Isoquinolin-5-ylboronic acid, the publication is Journal of Medicinal Chemistry (2014), 57(6), 2789-2798, database is CAplus and MEDLINE.

A novel class of imidazopyridazines identified from whole cell screening of a SoftFocus kinase library was synthesized and evaluated for antiplasmodial activity against K1 (multidrug resistant strain) and NF54 (sensitive strain). Structure-activity relationship studies led to the identification of highly potent compounds against both strains. Compound I was highly active (IC₅₀: K1 = 6.3 nM, NF54 = 7.3 nM) and comparable in potency to artesunate, and I exhibited 98% activity in the in vivo P. berghei mouse model (4-day test by Peters) at 4 × 50 mg/kg po. Compound I was also assessed against P. falciparum in the in vivo SCID mouse model where the efficacy was found to be more consistent with the in vitro activity. Furthermore, I displayed high (78%) rat oral bioavailability with good oral exposure and plasma half-life. Mice exposure at the same dose was 10-fold lower than in rat, suggesting lower oral absorption and/or higher metabolic clearance in mice.

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, Safety of Isoquinolin-5-ylboronic acid.

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

Coombs, John R. published the artcileAdvances in Base-Metal Catalysis: Development of a Screening Platform for Nickel-Catalyzed Borylations of Aryl (Pseudo)halides with B₂(OH)₄, Recommanded Product: Isoquinolin-5-ylboronic acid, the publication is Organometallics (2019), 38(1), 157-166, database is CAplus.

Investigations into nickel-catalyzed borylation reactions have led to the development of an exptl. design of 24 reaction conditions for rapid lead identification. A case study on the borylation of a model aryl bromide with B₂(OH)₄ prompted a series of mechanistic and stability studies to better understand the catalytic cycle and factors that affect robustness. HTEx was employed to study the effect of a series of scavengers on the remediation of nickel from the reaction stream. These combined results have generated an increased understanding of nickel-catalyzed borylation reactions and set the stage for their expanded use in process chem.

Organometallics 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

Bensch, Lisa published the artcile5-(Hetero)aryl-Substituted 9-Hydroxyphenalenones: Synthesis and Electronic Properties of Multifunctional Donor-Acceptor Conjugates, Category: isoquinoline, the publication is Chemistry – A European Journal (2017), 23(44), 10551-10558, database is CAplus and MEDLINE.

5-(Hetero)aryl-substituted 9-hydroxyphenalenones (9-HP) can be readily synthesized by Suzuki coupling of 5-bromo 9-HP with (hetero)aryl boronic acid (derivatives) without protection of the hydroxyl functionality in moderate to excellent yields (57-94 %). A library of 5-(hetero)aryl substituted 9-HP with broad substituent variation was studied with respect to their electronic properties (absorption and emission spectroscopies and cyclic voltammetry) and their computed electronic structures. All compounds show reversible reductive potentials between -1230 and -1110 mV and the donor-substituted representatives possess irreversible oxidation potentials around 600 mV. Compounds with electron-rich donors even show reversible oxidation potentials. Especially the donor-substituted 9-HPs display emission bands between 466 and 567 nm with quite large Stokes shifts (up to 4100 cm^-1). TD-DFT calculations nicely reproduce the spectroscopic data and Hammett correlations underline a pronounced resonance substituent influence on the photophys. properties.

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, Category: isoquinoline.

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