Day: October 11, 2022

Alamudun, Sophya F.; Tanovitz, Kyle; Fajardo, April; Johnson, Kaitlind; Pham, Andy; Jamshidi Araghi, Tina; Petit, Andrew S. published the artcile< Structure-Photochemical Function Relationships in Nitrogen-Containing Heterocyclic Aromatic Photobases Derived from Quinoline>, Name: 5-Methoxyisoquinoline, the main research area is nitrogen containing heterocyclic aromatic photobasicity structure photochem function relationship.

Photobases are compounds that become strong bases after electronic excitation. Recent exptl. studies have highlighted the photobasicity of the 5-R quinoline compounds, demonstrating a strong substituent dependence to the pKa*. In this paper, we describe our systematic study of how the thermodn. driving force for photobasicity is tuned through substituents in four families of nitrogen-containing heterocyclic aromatics We show that substituent position and identity both significantly impact the pKa*. We demonstrate that the substituent effects are additive and identify many disubstituted compounds with substantially greater photobasicity than the most photobasic 5-R quinoline compound identified previously. We show that the addition of a second fused benzene ring to quinoline, along with two electron-donating substituents, lowers the S0 → SPBS vertical excitation energy into the visible region while still maintaining a pKa* > 14. Overall, the structure-function relationships developed in this study provide new insights to guide the development of new photocatalysts that employ photobasicity.

Journal of Physical Chemistry A published new progress about Aromatic nitrogen heterocycles Role: PRP (Properties). 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Name: 5-Methoxyisoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Wu, Yue; Guo, Peng; Chen, Long; Duan, Weijie; Yang, Zengzhuan; Wang, Tao; Chen, Ting; Xiong, Fei published the artcile< Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines>, Safety of 5-Methoxyisoquinoline, the main research area is azole dioxolone iron tandem Minisci type oxidative coupling hydrolysis; carbonyl azole preparation green chem; isoquinoline dioxolone iron tandem Minisci type oxidative coupling hydrolysis; formylisoquinoline preparation green chem.

The direct formylation of benzothiazoles and isoquinolines was reported. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using com. available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction was performed under exceedingly mild reaction conditions and exhibited broad functional group tolerance.

Chemical Communications (Cambridge, United Kingdom) published new progress about Alkyl aryl ketones Role: SPN (Synthetic Preparation), PREP (Preparation). 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Safety of 5-Methoxyisoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Montgomery, Deanna; Anand, Jessica P.; Baber, Mason A.; Twarozynski, Jack J.; Hartman, Joshua G.; Delong, Lennon J.; Traynor, John R.; Mosberg, Henry I. published the artcile< Structure-activity relationships of 7-substituted dimethyltyrosine-tetrahydroisoquinoline opioid peptidomimetics>, Reference of 721401-43-0, the main research area is dimethyltyrosine tetrahydroisoquinoline opioid peptidomimetic structure activity; multifunctional ligands; opioids; peptidomimetic; structure-activity.

The opioid receptors modulate a variety of biol. functions, including pain, mood, and reward. As a result, opioid ligands are being explored as potential therapeutics for a variety of indications. Multifunctional opioid ligands, which act simultaneously at more than one type of opioid receptor, show promise for use in the treatment of addiction, pain, and other conditions. Previously, we reported the creation of bifunctional kappa opioid receptor (KOR) agonist/mu opioid receptor (MOR) partial agonist ligands from the classically delta opioid receptor (DOR) antagonist selective dimethyltyrosine-tetrahydroisoquinoline (Dmt-Tiq) scaffold through the addition of a 7-benzyl pendant on the tetrahydroisoquinoline ring. This study further explores the structure-activity relationships surrounding 7-position pendants on the Dmt-Tiq scaffold. Some analogs maintain a KOR agonist/MOR partial agonist profile, which is being explored in the development of a treatment for cocaine addiction. Others display a MOR agonist/DOR antagonist profile, which has potential to be used in the creation of a less addictive pain medication. Ultimately, we report the synthesis and in vitro evaluation of novel opioid ligands with a variety of multifunctional profiles.

Molecules published new progress about Cell membrane. 721401-43-0 belongs to class isoquinoline, and the molecular formula is C9H8BNO2, Reference of 721401-43-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Mansour, Oula C.; Evison, Benny J.; Sleebs, Brad E.; Watson, Keith G.; Nudelman, Abraham; Rephaeli, Ada; Buck, Damian P.; Collins, J. Grant; Bilardi, Rebecca A.; Phillips, Don R.; Cutts, Suzanne M. published the artcile< New Anthracenedione Derivatives with Improved Biological Activity by Virtue of Stable Drug-DNA Adduct Formation>, Category: isoquinoline, the main research area is anthracenedione amino derivative DNA adduct formation.

Mitoxantrone is an anticancer agent that acts as a topoisomerase II poison, however, it can also be activated by formaldehyde to form DNA adducts. Pixantrone, a 2-aza-anthracenedione with terminal primary amino groups in its side chains, forms formaldehyde-mediated adducts with DNA more efficiently than mitoxantrone. Mol. modeling studies indicated that extension of the “”linker”” region of anthracenedione side arms would allow the terminal primary amino greater flexibility and thus access to the guanine residues on the opposite DNA strand. New derivatives based on the pixantrone and mitoxantrone backbones were synthesized, and these incorporated primary amino groups as well as extended side chains. The stability of DNA adducts increased with increasing side chain length of the derivatives A mitoxantrone derivative bearing extended side chains (I) formed the most stable adducts with ∼100-fold enhanced stability compared to mitoxantrone. This finding is of great interest because long-lived drug-DNA adducts are expected to perturb DNA-dependent functions at all stages of the cell cycle.

Journal of Medicinal Chemistry published new progress about Acute promyelocytic leukemia. 144511-13-7 belongs to class isoquinoline, and the molecular formula is C13H5F2NO2, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Guo, Ya-Ru; Wu, Peng-Xiang; Xu, Han-Mei; Qi, Wei-Yan published the artcile< A new 1,5-dihydroxy-4-methoxyisoquinoline from Scolopendra subspinipes mutilans>, Application In Synthesis of 3336-49-0, the main research area is dihydroxymethoxyisoquinoline Scolopendra; Scolopendra subspinipes mutilans ; Cancer; Cytotoxic activities; Isoquinoline alkaloid; Migration.

A new isoquinoline, 1,5-dihydroxy-4-methoxyisoquinoline (1), was obtained from Scolopendra subspinipes mutilans. Compound 1 showed moderate cytotoxicity on tumor cells with IC50 values ranging from 13 to 26 μM against five esophageal squamous cancer cells whereas low cytotoxicity against normal human esophageal epithelial cells. Isoquinoline ring oxidized at C(1), C(4), and C(5) can enhance its cytotoxicity. In addition, compound 1 showed potent inhibitory effect (inhibition rate > 50% at 13 μM) on cell migration in human umbilical vein endothelial cells. This article mainly studies the structure and activity of 1, and more modification of 1 as a potential anticancer agent.

Chemistry & Biodiversity published new progress about Antitumor agents. 3336-49-0 belongs to class isoquinoline, and the molecular formula is C9H7NO, Application In Synthesis of 3336-49-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kazmi, M. Zain H.; Rygus, Jason P. G.; Ang, Hwee Ting; Paladino, Marco; Johnson, Matthew A.; Ferguson, Michael J.; Hall, Dennis G. published the artcile< Lewis or Bronsted? A Rectification of the Acidic and Aromatic Nature of Boranol-Containing Naphthoid Heterocycles>, Category: isoquinoline, the main research area is aromatic nature Boranol Containing naphthoid heterocycles Lewis Bronsted.

Boron-containing heterocycles are important in a variety of applications from drug discovery to materials science; therefore a clear understanding of their structure and reactivity is desirable to optimize these functions. Although the boranol (B-OH) unit of boronic acids behaves as a Lewis acid to form a tetravalent trihydroxyborate conjugate base, it has been proposed that pseudoarom. hemiboronic acids may possess sufficient aromatic character to act as Bronsted acids and form a boron oxy conjugate base, thereby avoiding the disruption of ring aromaticity that would occur with a tetravalent boronate anion. Until now no firm evidence existed to ascertain the structure of the conjugate base and the aromatic character of the boron-containing ring of hemiboronic “”naphthoid”” isosteres. Here, these questions are addressed with a combination of exptl., spectroscopic, X-ray crystallog., and computational studies of a series of model benzoxazaborine and benzodiazaborine naphthoids. Although these hemiboronic heterocycles are unambiguously shown to behave as Lewis acids in aqueous solutions, boraza derivatives possess partial aromaticity provided their nitrogen lone electron pair is sufficiently available to participate in extended delocalization. As demonstrated by dynamic exchange and crossover experiments, these heterocycles are stable in neutral aqueous medium, and their measured pKa values are consistent with the ability of the endocyclic heteroatom substituent to stabilize a partial neg. charge in the conjugate base. Altogether, this study corrects previous inaccuracies and provides conclusions regarding the properties of these compounds that are important toward the methodical application of hemiboronic and other boron heterocycles in catalysis, bioconjugation, and medicinal chem.

Journal of the American Chemical Society published new progress about Aromaticity. 3336-49-0 belongs to class isoquinoline, and the molecular formula is C9H7NO, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Jiang, Xingjun; He, Jianbo; Chen, Hongli; Yang, Weiqing; Zhang, yuanyuan; Ma, Menglin published the artcile< Copper-catalyzed hydrolysis of bromoisoquinolines: preparation of hydroxyisoquinolines>, HPLC of Formula: 3336-49-0, the main research area is hydroxyisoquinoline preparation; bromoisoquinoline copper catalyst hydrolysis.

A complex phenomenon was observed in the process of preparing hydroxyisoquinoline through copper-catalyzed hydrolysis of bromoisoquinoline. The copper (II) complexes of hydroxyisoquinoline (L2Cu.5H2O) were characterized by high resolution mass spectra, thermogravimetric anal., IR, 1H NMR (NMR), and 2D-NMR. The Cu (II) complexes were mononuclear and coordinated with oxygen and nitrogen atom of two hydroxyisoquinoline and five water mols. in which a strong hydrogen bond was present. Two optimized methods were studied to prevent the formation of copper (II) complexes. The isoquinoline with 4, 5, 6, 7, and 8 hydroxyl substitutions were successfully prepared by copper-catalyzed hydrolysis of corresponding bromoisoquinoline and then workup by sodium sulfide or adjusted pH by dry ice or carbon dioxide gas.

Indian Journal of Heterocyclic Chemistry published new progress about Hydrolysis. 3336-49-0 belongs to class isoquinoline, and the molecular formula is C9H7NO, HPLC of Formula: 3336-49-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Chopard, Claude; Bertho, Gildas; Prange, Thierry published the artcile< Naphthalene dioxygenase catalyzed cis-dihydroxylation of bicyclic aza arenes>, Related Products of 3336-49-0, the main research area is quinoline isoquinoline phthalazine naphthalene dioxygenase catalyst dihydroxylation biocatalyst enzyme; naphthyridine quinoxaline quinazoline cinnoline naphthalene dioxygenase catalyst dihydroxylation.

The scope of the biotransformation of a series of aza arene compounds by recombinant whole-cells of Escherichia coli JM109(DE3)(pDTG141) expressing the naphthalene dioxygenase system (NDOS) from Pseudomonas sp. NCIB 9616-4 was explored. The present study establishes that several bicyclic aza arenes are good substrates in the NDO-catalyzed reaction, giving cis-dihydrodiol derivatives Monohydroxylated products were also observed (quinolinemethanol, quinolinol, isoquinolinol, isoquinolinemethanol, phthalazinol, cinnolinol, quinazolinol).

RSC Advances published new progress about Aromatic alcohols Role: BPN (Biosynthetic Preparation), BIOL (Biological Study), PREP (Preparation) (aza arene alc. derivatives). 3336-49-0 belongs to class isoquinoline, and the molecular formula is C9H7NO, Related Products of 3336-49-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Wu, Wei; Wang, Yan; Guo, Jing; Cai, Liu; Chen, Yuan; Huang, Yanmin; Peng, Yungui published the artcile< Asymmetric acyl-Mannich reaction of isoquinolines with α-(diazomethyl)phosphonate and diazoacetate catalyzed by chiral Bronsted acids>, SDS of cas: 90806-58-9, the main research area is diazo isoquinoline phosphonate acetate asym synthesis; isoquinoline enantioselective acyl Mannich diazomethyl phosphonate diazoacetate.

An efficient asym. acyl-Mannich reaction of isoquinolines with di-Et pyrocarbonate and α-(diazomethyl)phosphonate or diazoacetate has been developed using chiral spiro phosphoric acids as catalysts. This reaction allowed the construction of a series of chiral α-diazo-β-isoquinoline phosphonates and acetates I [R1 = H, 5-Cl, 7-MeO, 4-Ph, etc.; X = (MeO)2P(O), MeO2C, EtO2C, i-PrO2C, t-BuO2C] bearing a tertiary stereocenter at the C1 position with up to 98% yield and 99% ee.

Chemical Communications (Cambridge, United Kingdom) published new progress about Bronsted acids Role: CAT (Catalyst Use), USES (Uses). 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, SDS of cas: 90806-58-9.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zeng, Jia; Lytle, Anna K.; Gage, David; Johnson, Sean J.; Zhan, Jixun published the artcile< Specific chlorination of isoquinolines by a fungal flavin-dependent halogenase>, Category: isoquinoline, the main research area is halogenase Rdc1 Pochonia isoquinoline specific chlorination; chloroisoquinoline biosynthesis halogenase Rdc1 Pochonia.

Rdc2 of Pochonia chlamydosporia is the 1st flavin-dependent halogenase identified from fungi. Based on the reported structure of the bacterial halogenase CmlS, the authors built a homol. model for Rdc2. The model suggested an open substrate binding site that was capable of binding the natural substrate, monocillin II, and possibly other mols. such as 4-hydroxyisoquinoline (I) and 6-hydroxyisoquinoline (II). In vitro and in vivo halogenation experiments confirmed that I and II could be halogenated at the position ortho to the OH group, leading to the synthesis of the chlorinated isoquinolines, 3-chloro-4-hydroxyisoquinoline and 5-chloro-6-hydroxyisoquinoline, resp., which further expanded the spectrum of identified substrates of Rdc2. This work revealed that Rdc2 is a useful biocatalyst for the synthesis of various halogenated compounds

Bioorganic & Medicinal Chemistry Letters published new progress about Pochonia chlamydosporia. 3336-49-0 belongs to class isoquinoline, and the molecular formula is C9H7NO, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem