Category: isoquinoline

Zhao, Yujun published the artcileStructure-Based Discovery of 4-(6-Methoxy-2-methyl-4-(quinolin-4-yl)-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole (CD161) as a Potent and Orally Bioavailable BET Bromodomain Inhibitor, COA of Formula: C9H8BNO2, the publication is Journal of Medicinal Chemistry (2017), 60(9), 3887-3901, database is CAplus and MEDLINE.

A series of 9H-pyrimido[4,5-b]indole-containing compounds was designed and synthesized to obtain potent and orally bioavailable BET inhibitors. By incorporation of an indole or a quinoline moiety to the 9H-pyrimido[4,5-b]indole core, we identified a series of small mols. showing high binding affinities to BET proteins and low nanomolar potencies in inhibition of cell growth in acute leukemia cell lines. One such compound, 4-(6-methoxy-2-methyl-4-(quinolin-4-yl)-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole (I) has excellent microsomal stability and good oral pharmacokinetics in rats and mice. Orally administered, I achieves significant antitumor activity in the MV4;11 leukemia and MDA-MB-231 triple-neg. breast cancer xenograft models in mice. Determination of the cocrystal structure of I with BRD4 BD2 provides a structural basis for its high binding affinity to BET proteins. Testing its binding affinities against other bromodomain-containing proteins shows that I is a highly selective inhibitor of BET proteins. These data show that I is a potent, selective, and orally active BET inhibitor.

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 C12H15ClO3, COA of Formula: C9H8BNO2.

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

Favalli, Nicholas published the artcileLarge screening of DNA-compatible reaction conditions for Suzuki and Sonogashira cross-coupling reactions and for reverse amide bond formation, Formula: C9H8BNO2, the publication is Bioorganic & Medicinal Chemistry (2021), 116206, database is CAplus and MEDLINE.

Progress in DNA-encoded chem. library synthesis and screening crucially relies on the availability of DNA-compatible reactions, which proceed with high yields and excellent purity for a large number of possible building blocks. In the past, exptl. conditions have been presented for the execution of Suzuki and Sonogashira cross-coupling reactions on-DNA. In this article, our aim was to optimize Suzuki and Sonogashira reactions, comparing our results to previously published procedures. We have tested the performance of improved conditions using 606 building blocks (including boronic acids, pinacol boranes and terminal alkynes), achieving >70% conversion for 84% of the tested mols. Moreover, we describe efficient exptl. conditions for the on-DNA synthesis of amide bonds, starting from DNA derivatives carrying a carboxylic acid moiety and 300 primary, secondary and aromatic amines, as amide bonds are frequently found in DNA-encoded chem. libraries thanks to their excellent DNA compatibility.

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, Formula: C9H8BNO2.

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

Molander, Gary A. published the artcileNickel-catalyzed C-O activation of phenol derivatives with potassium heteroaryltrifluoroborates, Synthetic Route of 371766-08-4, the publication is Organic Letters (2010), 12(18), 4022-4025, database is CAplus and MEDLINE.

A general method based on nickel-catalyzed C-O activation of various phenol derivatives with potassium (hetero)aryltrifluoroborates has been developed. A large number of heterobiaryls can be easily obtained with yields up to 99% using methanesulfonate cross-coupling partners.

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, Synthetic Route of 371766-08-4.

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

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.

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.

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

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.

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, Application of Isoquinolin-5-ylboronic acid.

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

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.

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.

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

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.

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.

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

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

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