Category: isoquinoline

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

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

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

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

Xie, Hongling; Yang, Zhenkun; Tang, Luning; Han, Zhengyu; Sun, Jianwei; Huang, Hai published the artcile< Construction of nine-membered N,N,O-heterocycles via Pd-catalyzed [6+3] dipolar cycloaddition>, Synthetic Route of 90806-58-9, the main research area is vinyl oxetane iminoisoquinolinium ylide palladium catalyst dipolar cycloaddition; tetrahydrooxadiazoninoisoquinoline preparation.

A new approach for the synthesis of 9-membered N,N,O-heterocycles by Pd-catalyzed [6+3] dipolar cycloaddition of N-iminoisoquinolinium ylides and 2-vinyl oxetanes was developed. The scope of this cycloaddition was demonstrated with 28 examples. This was another important synthetic strategy for medium-sized rings by employing N-iminoisoquinolinium ylides as ternary synthons.

Chemical Communications (Cambridge, United Kingdom)published new progress about Allylic alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Synthetic Route of 90806-58-9.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Li, Tao; Liang, Kangjiang; Zhang, Yang; Hu, Dongyan; Ma, Zhixian; Xia, Chengfeng published the artcile< Three-Component Minisci Reaction with 1,3-Dicarbonyl Compounds Induced by Visible Light>, Product Details of C10H9NO, the main research area is quinoline preparation visible light Minisci dicarbonyl vinyl ether heterocycle; isoquinoline preparation visible light Minisci dicarbonyl vinyl ether heterocycle.

A three-component Minisci reaction coupling of 1,3-dicarbonyl compounds with vinyl ethers and quinolines or isoquinolines under visible light is developed. The 1,3-dicarbonyl compound undergoes single-electron oxidation to afford an electrophilic 1,3-dicarbonyl radical under visible light irradiation Due to the polarity of the free radical, the electrophilic radical adds to the electron-rich olefin to afford the nucleophilic radical. It coupled with the heteroarene to afford the three-component coupling products.

Organic Letterspublished new progress about 1,3-Dicarbonyl compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Product Details of C10H9NO.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Dong, Jianyang; Yue, Fuyang; Liu, Jianhua; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin published the artcile< Visible-light-mediated three-component Minisci reaction for heteroarylethyl alcohols synthesis>, Quality Control of 90806-58-9, the main research area is heteroarylethyl alc green diastereoselective preparation; heteroaryl alkene three component Minisci visible light iridium catalyst.

Herein, a mild, modular, practical Minisci reaction for catalytic synthesis of heteroarylethyl alcs. such as ArCH(R1)CHR2OH [Ar = quinol-2-yl, isoquinolin-1-yl, 2-benzothiazolyl, etc.; R1R2 = CH2(CH2)2CH2, CH2CH2CH2; R1 = On-Bu, Me; R2 = H, Me] via sequential addition of H2O and N-heteroarenes across olefinic double bonds was reported. This scalable protocol was used for direct hydroxy-heteroarylation of olefins with a wide range of N-heteroarenes and could be expected to permit rapid conversion of abundant feedstock materials into medically relevant mols.

Green Chemistrypublished new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation) (heteroarylethyl). 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Quality Control of 90806-58-9.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Bai, Xu-Guan; Miao, Hong-Jie; Zhao, Yang; Wang, Qi-Lin; Bu, Zhan-Wei published the artcile< Regioselective and Diastereoselective Dearomative Multifunctionalization of In-Situ-Activated Azaarenes: An Access to Bridged Azaheterocycles>, Name: 5-Methoxyisoquinoline, the main research area is polycyclic bridged azaheterocycle regioselective diastereoselective synthesis; dearomative ring opening closure sequence polycyclic bridged azaheterocycle preparation.

Reported herein is an unprecedented multicomponent one-pot dearomative multifunctionalization of com. available azaarenes through an in situ activation strategy, which not only achieved the first full exploitation of the reactive sites of the azaarenes, but also accomplished the efficient synthesis of bridged hydrogenated pyridines and (iso)quinolines in a highly regioselective and diastereoselective manner. In addition, we could successfully realize the step-controlled dearomative trifunctionalization and bifunctionalization of quinolines.

Organic Letterspublished new progress about Addition reaction. 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Name: 5-Methoxyisoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Pan, Guihua; He, Changli; Chen, Min; Xiong, Qian; Cao, Weidi; Feng, Xiaoming published the artcile< Synthesis of dihydroisoquinoline and dihydropyridine derivatives via asymmetric dearomative three-component reaction>, SDS of cas: 90806-58-9, the main research area is dihydroisoquinoline dihydropyridine diastereoselective enantioselective; heteroarene allenoate methyleneindolinone asym dearomative three component reaction.

Authors report the first asym. three-component nucleophilic addition/dearomative [4+2] cycloaddition/isomerization cascade of transient dipoles generated from N-heteroarenes and allenoates with methyleneindolinones in the presence of chiral N,N’-dioxide/metal complexes. This tandem reaction enabled rapid access to versatile chiral polycyclic N-heterocycles with good to excellent enantioselectivities under mild reaction conditions in spite of the strong background reaction, including 1,2-dihydroisoquinoline, 1,2-dihydropyridine derivatives, and others. Meanwhile, a series of control experiments were conducted to elucidate the reaction mechanism and the roles of additives.

CCS Chemistrypublished new progress about [4+2] Cycloaddition reaction. 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

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>, Name: 5-Methoxyisoquinoline, 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, Name: 5-Methoxyisoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem