M.W=150-200| Page 39 of 107 | Heterocyclic Building Blocks-Isoquinoline

Gleave, Robert J.’s team published research in Bioorganic & Medicinal Chemistry Letters in 20 | CAS: 371766-08-4

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, Product Details of C9H8BNO2.

Gleave, Robert J. published the artcileSynthesis and evaluation of 3-amino-6-aryl-pyridazines as selective CB₂ agonists for the treatment of inflammatory pain, Product Details of C9H8BNO2, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(2), 465-468, database is CAplus and MEDLINE.

A series of 3-amino-6-aryl-pyridazines have been identified as CB₂ agonists with high efficacy and selectivity against the CB₁ receptor. Details of the investigation of structure-activity relationships (SAR) are disclosed, which led to the identification of pyridazine analog I, a compound with high potency in an in vivo model of inflammatory pain.

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

Desage-El Murr, Marine’s team published research in Bioorganic & Medicinal Chemistry Letters in 18 | CAS: 371766-08-4

Desage-El Murr, Marine published the artcile8-Biarylchromen-4-one inhibitors of the DNA-dependent protein kinase (DNA-PK), Application of Isoquinolin-5-ylboronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2008), 18(17), 4885-4890, database is CAplus and MEDLINE.

The synthesis and biol. evaluation of libraries of 8-biarylchromen-4-ones enabled the elucidation of structure-activity relationships for inhibition of the DNA-dependent protein kinase (DNA-PK), with 8-(3-(thiophen-2-yl)phenyl)chromen-4-one and 8-(3-(thiophen-3-yl)phenyl)chromen-4-one being especially potent inhibitors.

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

Ruelas-Alvarez, Glenda Y.’s team published research in European Journal of Inorganic Chemistry in 2019 | CAS: 371766-08-4

European Journal of Inorganic 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, Formula: C9H8BNO2.

Ruelas-Alvarez, Glenda Y. published the artcileExploration of the Luminescence Properties of Organic Phosphate Salts of 3-Quinoline- and 5-Isoquinolineboronic Acid, Formula: C9H8BNO2, the publication is European Journal of Inorganic Chemistry (2019), 2019(22), 2707-2724, database is CAplus.

3-Quinoline- and 5-isoquinolineboronic acids (3QBA and 5IQBA) were combined with 1-naphthyl and di-Ph phosphate (1NP and DPP) to give three crystalline mol. salts of 1:1 stoichiometric composition, viz., 3QBA–1NP, 5IQBA–1NP and 3QBA–DPP. The products were characterized by elemental anal., single-crystal x-ray diffraction studies, IR spectroscopy, luminescence spectroscopy and TG-DSC measurements. The anal. of the solid-state structures revealed that the mol. components are linked by strong charge-assisted hydrogen bonds forming heterodimeric synthons of the type B(OH)₂···^–O₂P and N⁺-H···O(P). In addition, the hydrogen phosphate salts derived from 1NP exhibit the homodimeric P(O)OH···O(HO)P synthon. The aggregates formed through the above-mentioned hydrogen bonding motifs are further connected through π···π interactions, which involve mainly the aromatic rings of the quinolinium/isoquinolinium cations. The crystal structure analyses were accomplished by Hirshfeld surface analyses and the associated 2D fingerprint plots, illustrating the similarities and differences of the three salts more concisely. Solid-state photoluminescence spectroscopy of the title compounds showed emission in the blue region with an extraordinary high quantum yield (Φ_f = 98 %) for compound 3QBA–DPP.

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

Storch, Jan’s team published research in Journal of Organic Chemistry in 75 | CAS: 371766-08-4

Journal of Organic 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 C3H8N2S, Computed Properties of 371766-08-4.

Storch, Jan published the artcileSynthesis of 2-Aza[6]helicene and Attempts To Synthesize 2,14-Diaza[6]helicene Utilizing Metal-Catalyzed Cycloisomerization, Computed Properties of 371766-08-4, the publication is Journal of Organic Chemistry (2010), 75(9), 3137-3140, database is CAplus and MEDLINE.

A modular synthetic approach leading to 2-aza[6]helicene (I) is reported. It involves assembly of key hetero biphenylylnaphthalenes from functionalized building blocks and study of their metal catalyzed cycloisomerization.

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

Sun, Bin’s team published research in ChemistrySelect in 4 | CAS: 371766-08-4

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.

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.

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

Kelly, Aidan M.’s team published research in Organic Letters in 22 | CAS: 371766-08-4

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.

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.

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

Solum, Eirik Johansson’s team published research in RSC Advances in 5 | CAS: 371766-08-4

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.

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.

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

Solum, Eirik Johansson’s team published research in European Journal of Medicinal Chemistry in 85 | CAS: 371766-08-4

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.

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

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

Takenouchi, Osamu’s team published research in Journal of Toxicological Sciences in 2013-08-31 | CAS: 21834-92-4

Journal of Toxicological Sciences published new progress about Allergic contact dermatitis. 21834-92-4 belongs to class isoquinoline, name is 5-Methyl-2-phenylhex-2-enal, and the molecular formula is C13H16O, Name: 5-Methyl-2-phenylhex-2-enal.

Takenouchi, Osamu published the artcilePredictive performance of the human Cell Line Activation Test (h-CLAT) for lipophilic chemicals with high octanol-water partition coefficients, Name: 5-Methyl-2-phenylhex-2-enal, the main research area is lipophilic chem skin sensitization hCLAT toxicity allergic contact dermatitis; octanol water partition coefficient.

To meet the urgent need for a reliable alternative test for predicting skin sensitizing potential of many chems., we have developed a cell-based in vitro test, human Cell Line Activation Test (h-CLAT). However, the predictive performance for lipophilic chems. in the h-CLAT still remains relatively unknown. Moreover, it’s suggested that low water solubility of chems. might induce false neg. outcomes. Thus, in this study, we tested relatively low water soluble 37 chems. with log Kow values above and below 3.5 in the h-CLAT. The small-scale assessment resulted in nine false neg. outcomes for chems. with log Kow values greater than 3.5. We then created a dataset of 143 chems. by combining the existing dataset of 106 chems. and examined the predictive performance of the h-CLAT for chems. with a log Kow of less than 3.5; a total of 112 chems. from the 143 chems. in the dataset. The sensitivity and overall accuracy for the 143 chems. were 83% and 80%, resp. In contrast, sensitivity and overall accuracy for the 112 chems. with log Kow values below 3.5 improved to 94% and 88%, resp. These data suggested that the h-CLAT could successfully detect sensitizers with log Kow values up to 3.5. When chems. with log Kow values greater than 3.5 that were deemed pos. by h-CLAT were included with the 112 chems., the sensitivity and accuracy in terms of the resulting applicable 128 chems. out of the 143 chems. became 95% and 88%, resp. The use of log Kow values gave the h-CLAT a higher predictive performance. Our results demonstrated that the h-CLAT could predict sensitizing potential of various chems., which contain lipophilic chems. using a large-scale chem. dataset.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Tang, Hai-Jun’s team published research in Angewandte Chemie, International Edition in 2020 | CAS: 104-01-8

Angewandte Chemie, International Edition published new progress about Arylation (fluoroarylation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Name: 4-Methoxyphenylacetic acid.

Tang, Hai-Jun published the artcileVisible-Light-Assisted Gold-Catalyzed Fluoroarylation of Allenoates, Name: 4-Methoxyphenylacetic acid, the main research area is gold catalyst fluoroarylation allenoate; allenoates; arylation; fluorination; gold; redox catalysis.

A strategically novel synthetic method for the fluoroarylation of allenic ester was developed that enables the expedient construction of a host of β-fluoroalkyl-containing cinnamate derivatives The reaction proceeds through visible-light-promoted gold redox catalysis, occurs smoothly under very mild reaction conditions, accommodates a large variety of functional groups, and more importantly allows the incorporation of fluorine and aryl groups with excellent regio- and stereoselectivity. The concomitant activation mode for both the allene motif and the hydrogen fluoride is key for the success of the reaction.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem