Category: isoquinoline

Xiong, Qian; Dong, Shunxi; Chen, Yushuang; Liu, Xiaohua; Feng, Xiaoming published the artcile< Asymmetric synthesis of tetrazole and dihydroisoquinoline derivatives by isocyanide-based multicomponent reactions>, Formula: C10H9NO, the main research area is alkylidene malonate diastereoselective enantioselective annulation isoquinoline isocyanide; imino dihydro pyrroloisoquinoline dicarboxylate enantioselective diastereoselective preparation; isocyanide trimethylsilyl azide alkylidene malonate enantioselective heterocyclization; tetrazole diester enantioselective preparation.

Herein, several isocyanide-based multicomponent reactions based on enantioselective addition of simple isocyanides to C=C bonds were realized in the presence of a chiral Mg(II)-N,N’-dioxide catalyst. Three- or four-component reactions of an isocyanide, TMSN3, and an (alkylidene)malonate could be precisely controlled by modulating reaction conditions to afford two types of enantioenriched tetrazole derivatives in moderate to high yields. Possible catalytic cycles via a key zwitterionic intermediate, and the vital roles of H2O or excess ligand are provided based on control experiments Moreover, taking advantage of this zwitterionic intermediate as a 1,3-dipole, an enantioselective dearomative [3+2] annulation reaction of nonactivated isoquinolines is achieved, furnishing chiral dihydropyrrolo[2,1-a]isoquinolines in good to excellent results.

Nature Communications published new progress about Diastereoselective synthesis. 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Formula: C10H9NO.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Hartung, Ryan E.; Wall, Mark C.; Lebreton, Sylvain; Smrcina, Martin; Patek, Marcel published the artcile< Selectivity of N- versus O-alkylation in Mitsunobu reactions with various quinolinols and isoquinolinols>, Quality Control of 3336-49-0, the main research area is quinolinol alc chemoselective Mitsunobu alkylation; isoquinolinol alc chemoselective Mitsunobu alkylation.

Reacting quinolinols and isoquinolinols under Mitsunobu conditions could give rise to N-alkylated products in addition to the normally desired O-alkylated structures. An in-depth study of how the solvent, reagent equivalent, position of the quinoline/isoquinoline nitrogen and type of reacting aliphatic alc. employed affected the ratio of N- vs. O-alkylation was described.

Heterocycles published new progress about Aliphatic alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 3336-49-0 belongs to class isoquinoline, and the molecular formula is C9H7NO, Quality Control of 3336-49-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Fuse, Hiromu; Irie, Yu; Fuki, Masaaki; Kobori, Yasuhiro; Kato, Kosaku; Yamakata, Akira; Higashi, Masahiro; Mitsunuma, Harunobu; Kanai, Motomu published the artcile< Identification of a Self-Photosensitizing Hydrogen Atom Transfer Organocatalyst System>, Product Details of C10H9NO, the main research area is aldehyde isoquinoline organocatalyst photochem hydroxyalkylation C H activation; isoquinolylmethanol preparation; alc isoquinoline organocatalyst photochem alkylation C H activation; alkylisoquinoline preparation.

Organocatalyst systems to promote the cleavage of stable C-H bonds, such as formyl, α-hydroxy and benzylic C-H bonds, through a hydrogen atom transfer (HAT) process without the use of exogenous photosensitizers have been developed. An electronically tuned thiophosphoric acid, 7,7′-OMe-TPA, were assembled with substrate or co-catalyst N-heteroaromatics through hydrogen bonding and π-π interactions to form electron donor-acceptor (EDA) complexes. Photoirradiation of the EDA complex induced stepwise, sequential single-electron transfer (SET) processes to generate a HAT-active thiyl radical. The first SET were from the electron-rich naphthyl group of 7,7′-OMe-TPA to the protonated N-heteroaromatics and the second proton-coupled SET (PCET) from the thiophosphoric acid moiety of 7,7′-OMe-TPA to the resulting naphthyl radical cation. Spectroscopic studies and theor. calculations characterized the stepwise SET process mediated by short-lived intermediates. This organocatalytic HAT system were applied to four different carbon-hydrogen (C-H) functionalization reactions, hydroxyalkylation and alkylation of N-heteroaromatics, acceptorless dehydrogenation of alcs. and benzylation of imines, with high functional group tolerance.

Journal of the American Chemical Society published new progress about 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, Product Details of C10H9NO.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Krapcho, A. Paul; Menta, Ernesto; Oliva, Ambrogio; Di Domenico, Roberto; Fiocchi, Luigi; Maresch, Martin E.; Gallagher, Cynthia E.; Hacker, Miles P.; Beggiolin, Gino; Giuliani, Fernando C.; Pezzoni, Gabriella; Spinelli, Silvano published the artcile< Synthesis and Antitumor Evaluation of 2,5-Disubstituted-Indazolo[4,3-gh]isoquinolin-6(2H)-ones (9-Aza-anthrapyrazoles)>, Recommanded Product: 6,9-Difluorobenzo[g]isoquinoline-5,10-dione, the main research area is indazoloisoquinolinone antitumor preparation; azaanthrapyrazole antitumor preparation; anthrapyrazole aza antitumor preparation.

The synthesis and antitumor evaluation of 2,5-disubstituted-indazolo[4,3-gh]isoquinolin-6(2H)-ones (9-aza-APs) are described. The key intermediates in the synthesis are benz[g]isoquinoline-5,10-diones which are substituted at positions 6 and 9 with groups of different nucleofugacity for SNAr displacements. The initial displacement of fluoride by a substituted hydrazine leads to the pyrazole analogs. Substitution of the remaining leaving group by an amine or BOC-protected amines leads to the 9-aza-APs. These analogs were converted into their maleate or hydrochloride salts. In 2 cases, sidearm buildup was also employed in the synthetic pathway. In vitro evaluation of 9-aza-APs against the human colon tumor cell line LoVo uncovered for most of the compounds a cytotoxic potency lower than that of DuP-941 or mitoxantrone and comparable to that of doxorubicin. Only 3 analogs were as cytotoxic as DuP-941. Interestingly, while DuP-941 was highly cross-resistant in the LoVo cell line resistant to doxorubicin (LoVo/Dx), the 9-aza-APs carrying a distal lipophilic tertiary amine moiety in both chains were capable of overcoming the MDR resistance induced in this cell line. The 9-aza-APs have outstanding in vivo antitumor activity against both systemic P388 murine leukemia and MX-1 human mammary carcinoma transplanted in nude mice. At their optimal dosages, these were highly effective against P388 leukemia with T/C% of 200-381, while the T/C% value of DuP-941 was 147. In the MX-1 tumor model, 24 compounds elicited percentages of tumor weight inhibitions (TWI) ranging from 50% to 99%. Some of theses compounds emerged as the most effective ones, with TWI% 96, similar to that of DuP-941 (TWI% = 95). On the basis of their efficacy profile in addnl. exptl. tumors and lack of cardiotoxicity in preclin. models, 2 congeners have surfaced as potential clin. candidates.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 144511-13-7 belongs to class isoquinoline, and the molecular formula is C13H5F2NO2, Recommanded Product: 6,9-Difluorobenzo[g]isoquinoline-5,10-dione.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Teng, Min; Hilgers, Mark T.; Cunningham, Mark L.; Borchardt, Allen; Locke, Jeffrey B.; Abraham, Sunny; Haley, Gregory; Kwan, Bryan P.; Hall, Courtney; Hough, Grayson W.; Shaw, Karen J.; Finn, John published the artcile< Identification of Bacteria-Selective Threonyl-tRNA Synthetase Substrate Inhibitors by Structure-Based Design>, Synthetic Route of 552331-06-3, the main research area is bacteria threonyl tRNA synthetase substrate design crystal structure.

A series of potent and bacteria-selective threonyl-tRNA synthetase (ThrRS) inhibitors have been identified using structure-based drug design. These compounds occupied the substrate binding site of ThrRS and showed excellent binding affinities for all of the bacterial orthologs tested. Some of the compounds displayed greatly improved bacterial selectivity. Key residues responsible for potency and bacteria/human ThrRS selectivity have been identified. Antimicrobial activity has been achieved against wild-type Haemophilus influenzae and efflux-deficient mutants of Escherichia coli and Burkholderia thailandensis.

Journal of Medicinal Chemistry published new progress about Antimicrobial agents. 552331-06-3 belongs to class isoquinoline, and the molecular formula is C9H5BrClN, Synthetic Route of 552331-06-3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Shi, Jianyi; Chen, Zhichao; Lu, Yantong; Xu, Shengting; Wen, Tingting; Luo, Yuehua; Zhu, Zhongzhi; Chen, Xiuwen published the artcile< Nucleophilic Dearomatization Strategy to Synthesize Disubstituted 3-Isoquinolinones under Transition Metal-Free Conditions>, Synthetic Route of 552331-06-3, the main research area is haloisoquinoline alkyl halide indole three component reaction green chem; benzyl indolyl dihydroisoquinolinone preparation.

Herein, a one-pot protocol for constructing the disubstituted isoquinolinone derivatives via the three-component reactions of 3-haloisoquinolines, alkyl halides, and indoles under transition-metal-free conditions was described. The reaction realized the trifunctionalization of isoquinoline via a dearomatization strategy, which displayed high chem. selectivity, excellent functional group tolerance, and a wide range of substrates, and was environmentally friendly. The three-component coupling involves the construction of new C-N, C=O, and C-C bonds in one step.

Journal of Organic Chemistry published new progress about Aralkyl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 552331-06-3 belongs to class isoquinoline, and the molecular formula is C9H5BrClN, Synthetic Route of 552331-06-3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Li, Hong-Liang; Yang, Deng-Feng; Jing, Hua-Qing; Antilla, Jon C.; Kuninobu, Yoichiro published the artcile< Palladium-Catalyzed Enantioselective C(sp3)-H Arylation of 2-Propyl Azaaryls Enabled by an Amino Acid Ligand>, Related Products of 90806-58-9, the main research area is propyl azaaryl enantioselective arylation amino acid ligand palladium catalyst.

A palladium(II)-catalyzed enantioselective arylation of unbiased secondary C(sp3)-H bonds was developed. The enantioselectivity was controlled by the combination of a pyridyl or isoquinolinyl directing group and an amino acid, N-Boc-2-pentyl proline. A variety of 2-Pr azaaryls and biaryl iodides were employed to provide arylated products in moderate to good yields (up to 82%) with high enantioselectivities (up to 93:7 er). This reaction is a rare example of an amino-acid-enabled enantioselective acyclic methylene C(sp3)-H arylation. Furthermore, the reaction proceeded with high enantioselectivity even on a gram scale, and the product was transformed to a 5,6,7,8-tetrahydroisoquinoline bioactive mol. Kinetic isotope effect (KIE) experiments indicated that C-H activation is the rate-determining step for the enantioselective C(sp3)-H arylation.

Organic Letters published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Related Products of 90806-58-9.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Mackman, Richard L.; Steadman, Victoria A.; Dean, David K.; Jansa, Petr; Poullennec, Karine G.; Appleby, Todd; Austin, Carol; Blakemore, Caroline A.; Cai, Ruby; Cannizzaro, Carina; Chin, Gregory; Chiva, Jean-Yves C.; Dunbar, Neil A.; Fliri, Hans; Highton, Adrian J.; Hui, Hon; Ji, Mingzhe; Jin, Haolun; Karki, Kapil; Keats, Andrew J.; Lazarides, Linos; Lee, Yu-Jen; Liclican, Albert; Mish, Michael; Murray, Bernard; Pettit, Simon B.; Pyun, Peter; Sangi, Michael; Santos, Rex; Sanvoisin, Jonathan; Schmitz, Uli; Schrier, Adam; Siegel, Dustin; Sperandio, David; Stepan, George; Tian, Yang; Watt, Gregory M.; Yang, Hai; Schultz, Brian E. published the artcile< Discovery of a potent and orally bioavailable cyclophilin inhibitor derived from the sanglifehrin macrocycle>, Synthetic Route of 552331-06-3, the main research area is cyclic peptidomimetic total synthesis orally bioavailable cyclophilin inhibitor; drug discovery antihepatitis C virus agent structure activity; isoquinoline peptide Stille coupling hydrolysis reduction vinylation RCM macrolactamization; mol docking crystal structure.

Cyclophilins are a family of peptidyl-prolyl isomerases that are implicated in a wide range of diseases including hepatitis C. Our aim was to discover through total synthesis an orally bioavailable, non-immunosuppressive cyclophilin (Cyp) inhibitor with potent anti-hepatitis C virus (HCV) activity that could serve as part of an all oral antiviral combination therapy. An initial lead (I) derived from the sanglifehrin A macrocycle was optimized using structure based design to produce a potent and orally bioavailable inhibitor (II). The macrocycle ring size was reduced by one atom, and an internal hydrogen bond drove improved permeability and drug-like properties. II demonstrates potent Cyp inhibition (Kd = 5 nM), potent anti-HCV 2a activity (EC50 = 98 nM), and high oral bioavailability in rat (100%) and dog (55%). The synthetic accessibility and properties of II support its potential as an anti-HCV agent and for interrogating the role of Cyp inhibition in a variety of diseases.

Journal of Medicinal Chemistry published new progress about Anti-hepatitis C virus agents. 552331-06-3 belongs to class isoquinoline, and the molecular formula is C9H5BrClN, Synthetic Route of 552331-06-3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Miao, Hongjie; Bai, Xuguan; Wang, Lele; Yu, Junhui; Bu, Zhanwei; Wang, Qilin published the artcile< Diastereoselective construction of cage-like and bridged azaheterocycles through dearomative maximization of the reactive sites of azaarenes>, Product Details of C10H9NO, the main research area is cage like bridged azaheterocycle preparation diastereoselective; pyridinium quinolinium isoquinolinium diazapentadienium salt dearomatization.

A highly diastereoselective multicomponent dearomative multifunctionalization of N-alkyl activated azaarenes with 1,5-diazapentadienium salts has been developed, which not only represented a significant advance in maximum utilization of the reactive sites of azaarenes, but also provided a convenient and robust approach to access structurally rigid and synthetically challenging cage-like and bridged azaheterocycles. As an important complement, author also realized the dearomative multi-functionalization of N-aryl azaarenes through an in situ activation strategy. Moreover, the workup-directed selective tri- and bi-functionalization of isoquinolinium salts have been accomplished.

Organic Chemistry Frontiers published new progress about Bridged heterocyclic compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Product Details of C10H9NO.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zhang, Dong; Cai, Jinlin; Du, Jinze; Wang, Qingdong; Yang, Jinming; Geng, Rongqing; Fang, Zheng; Guo, Kai published the artcile< Electrochemical-Oxidation-Promoted Direct N-ortho-Selective Difluoromethylation of Heterocyclic N-Oxides>, Computed Properties of 90806-58-9, the main research area is difluoromethyl quinoline isoquinoline oxide preparation green chem; isoquinoline quinoline oxide electrochem oxidation ortho selective difluoromethylation.

An efficient and green electrochem. N-ortho-selective difluoromethylation method of various quinoline and isoquinoline N-oxides has been developed. In this method sodium difluoromethanesulfinate (HCF2SO2Na) was used as the source of difluoromethyl moiety and various N-ortho-selective difluoromethylation quinolines and isoquinolines N-oxides were obtained in good to excellent yield under constant current. In addition, the reaction was easy to scale up and maintains good yields. Preliminary mechanism studies suggested that the reaction has underwent a free radical addition and hydrogen elimination pathway.

Organic Letters published new progress about Difluoromethylation. 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Computed Properties of 90806-58-9.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem