October 2022 | Page 7 of 19 | Heterocyclic Building Blocks-Isoquinoline

St. Laurent, Denis R. et al. published their research in Journal of Medicinal Chemistry in 2014 |CAS: 1367744-24-8

The Article related to stilbene acylprolinamide preparation inhibition ns5a replication complex hepatitis c, structure bisacylprolinamide inhibition selectivity hepatitis c toxicity, hepatitis c genotype 1a replication inhibition stilbene acylprolinamide and other aspects.Related Products of 1367744-24-8

On March 13, 2014, St. Laurent, Denis R.; Serrano-Wu, Michael H.; Belema, Makonen; Ding, Min; Fang, Hua; Gao, Min; Goodrich, Jason T.; Krause, Rudolph G.; Lemm, Julie A.; Liu, Mengping; Lopez, Omar D.; Nguyen, Van N.; Nower, Peter T.; O’Boyle, Donald R. II; Pearce, Bradley C.; Romine, Jeffrey L.; Valera, Lourdes; Sun, Jin-Hua; Wang, Ying-Kai; Yang, Fukang; Yang, Xuejie; Meanwell, Nicholas A.; Snyder, Lawrence B. published an article.Related Products of 1367744-24-8 The title of the article was HCV NS5A Replication Complex Inhibitors. Part 4. Optimization for Genotype 1a Replicon Inhibitory Activity. And the article contained the following:

Sym. stilbene bis(acylprolinamides) such as I (R = PhCH2, 2-EtC6H4, Ph, 2-vinylphenyl, 1-naphthyl, 3-ethyl-2-pyridinyl, 4-ethyl-2-pyridinyl, 3-vinyl-2-pyridinyl, 3-phenyl-2-pyridinyl, 1-isoquinolyl, 3-isoquinolinyl, 2-quinolinyl, 4-isoquinolinyl, 4-quinazolinyl, 1-phthalazinyl, 3-chloro-1-isoquinolinyl, 4-chloro-1-isoquinolinyl, 5-chloro-1-isoquinolinyl, 6-chloro-1-isoquinolinyl, 7-chloro-1-isoquinolinyl, 3-fluoro-1-isoquinolinyl, 5-fluoro-1-isoquinolinyl, 3-methyl-1-isoquinolinyl, 5-methyl-1-isoquinolinyl, 3-methoxy-5-isoquinolinyl, 5-methoxy-1-isoquinolinyl, 3-chloro-1-naphthyl, 3-chloro-5-fluoro-1-isoquinolinyl, 3-chloro-5-methoxy-1-isoquinolinyl, 5-methoxy-2-quinolinyl, 7-methoxy-2-quinolinyl) derived from the library-synthesized lead I (R = PhCH2) were prepared as HCV genotype 1a (G-1a) and genotype 1b (G-1b) replicon inhibitors; their selectivities for inhibition of HCV over general viral inhibition and their cytotoxicities to human Huh-7 cells were determined The structure-activity relationships for inhibition of HCV replication by sym. bis(prolinamide) HCV inhibitors were determined I (R = 1-isoquinolinyl) was a selective HCV NS5A inhibitor exhibiting submicromolar potency against both G-1a and G-1b replicons; further optimization identified I (R = 3-chloro-5-methoxy-1-isoquinolinyl) as a potent, dual G-1a/1b HCV NS5A inhibitor. The structure-activity relations derived from I were used in the discovery of the NS5A replication complex inhibitor daclatasvir II. The experimental process involved the reaction of 5-Methylisoquinoline-1-carbonitrile(cas: 1367744-24-8).Related Products of 1367744-24-8

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Yamada, Rintaro et al. published their patent in 2004 |CAS: 58142-46-4

The Article related to diazaphenalene preparation myosin regulatory light chain phosphorylation inhibitor, antiglaucoma diazaphenalene preparation myosin regulatory light chain phosphorylation inhibition, antiasthmatic diazaphenalene preparation myosin regulatory light chain phosphorylation inhibition and other aspects.HPLC of Formula: 58142-46-4

On December 16, 2004, Yamada, Rintaro; Seto, Minoru published a patent.HPLC of Formula: 58142-46-4 The title of the patent was Preparation of diazaphenalene compounds as myosin-control light chains phosphorylation inhibitors. And the patent contained the following:

Title compounds I [R1 = H, chloro, OH; X1···X2 represents CH(R2)-CH(R3), etc.; R2, R3 = H, alkyl; A1, A11, A2, A21 = H, alkyl; Y = CH(A3), etc.; A3 = H, alkyl; Z = OH, etc.] were prepared For example, cyclization of compound II using potassium tert-butoxide followed by deprotection of tert-butoxycarbonyl group with HCl afforded compound III hydrochloride. In myosin regulatory light chains phosphorylation inhibition assays, the IC50 value of compound III·HCl was ≤10 μM. Compounds I are claimed to be useful for the treatment of glaucoma, bronchial asthma, etc. The experimental process involved the reaction of 4-Bromo-5-nitroisoquinoline(cas: 58142-46-4).HPLC of Formula: 58142-46-4

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Taveras, Arthur G. et al. published their patent in 2004 |CAS: 74904-29-3

The Article related to aminocyclobutenedione preparation cxc chemokine receptor ligand, inflammation treatment aminocyclobutenedione preparation, inflammatory pain treatment aminocyclobutenedione preparation, cancer treatment aminocyclobutenedione preparation, psoriasis treatment aminocyclobutenedione preparation, atopic dermatitis treatment aminocyclobutenedione preparation and other aspects.Product Details of 74904-29-3

On February 5, 2004, Taveras, Arthur G.; Aki, Cynthia J.; Chao, Jianping; Dwyer, Michael; Chao, Jianhua; Yu, Younong; Merritt, J. Robert; Biju, Purakkattle; Jakway, James; Lai, Gaifa; Wu, Minglang; Hecker, Evan A.; Lundell, Daniel; Fine, Jay S. published a patent.Product Details of 74904-29-3 The title of the patent was Preparation of 3,4-di(substituted amino)cyclobutene-1,2-diones as CXC-chemokine receptor ligands. And the patent contained the following:

Disclosed are novel compounds of the formula (I) or pharmaceutically acceptable salts or solvates thereof [A = Q, Q1; B = substituted Ph, (un)substituted 1H-pyrazol-3-yl, 1H-pyrazol-5-yl, 2- or 3-thienyl, 1H-pyrrol-3-yl, 1H-pyrrol-2-yl, isothiazol-3-yl, 1,2-dihydro-4-hydroxy-2-oxo-pyridin-3-yl, 4-hydroxypyrimidin-4-yl, or 4-hydroxypyridin-3-yl, 1,2-dihydro-4-hydroxy-2-oxo-pyridin-5-yl, 1,4-dihydro-1-hydroxy-4-oxopyridin-2-yl, 1H-benzotriazol-7-yl, 1H-benzimidazol-7-yl, 1H-indol-7-yl, or benzo[c]pyrazol-7-yl; R7, R8 = H, each (un)substituted alkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, CO2H, CONH2, alkynyl, alkenyl, cycloalkenyl; R12 = H,each (un)substituted CO2H, aryl, heteroaryl, arylalkyl, cycloalkyl, alkyl, cycloalkylalkyl, or heteroarylalkyl group]. Also disclosed is the treatment of chemokine-mediated diseases, where the chemokine binds to CXCR2 and/or CXCR1 receptor, using compounds of the formula I. The diseases include chronic inflammation, acute inflammatory pain, chronic inflammatory pain, acute neuropathic pain, chronic neuropathic pain, psoriasis, atopic dermatitis, asthma, COPD, adult respiratory disease, arthritis, inflammatory bowel disease, Crohn’s disease, ulcerative colitis, septic shock, endotoxic shock, gram neg. sepsis, toxic shock syndrome, stroke, cardiac and renal reperfusion injury, glomerulonephritis, thrombosis, Alzheimer’s disease, graft vs. host reaction, allograft rejections, malaria, acute respiratory distress syndrome, delayed type hypersensitivity reaction, atherosclerosis, cerebral and cardiac ischemia, osteoarthritis, multiple sclerosis, restenosis, angiogenesis, osteoporosis, gingivitis, respiratory viruses, herpes viruses, hepatitis viruses, HIV, Kaposi’s sarcoma associated virus, meningitis, cystic fibrosis, preterm labor, cough, pruritis, multiorgan dysfunction, trauma, strains, sprains, contusions, psoriatic arthritis, herpes, encephalitis, CNS vasculitis, traumatic brain injury, CNS tumors, and subarachnoid hemorrhage. They also include post surgical trauma, interstitial pneumonitis, hypersensitivity, crystal induced arthritis, acute and chronic pancreatitis, acute alc. hepatitis, necrotizing enterocolitis, chronic sinusitis, angiogenic ocular disease, ocular inflammation, retinopathy of prematurity, diabetic retinopathy, macular degeneration with the wet type preferred and corneal neovascularization, polymyositis, vasculitis, acne, gastric and duodenal ulcers, celiac disease, esophagitis, glossitis, airflow obstruction, airway hyperresponsiveness, bronchiectasis, bronchiolitis, bronchiolitis obliterans, chronic bronchitis, cor pulmonae, cough, dyspnea, emphysema, hypercapnea, hyperinflation, hypoxemia, hyperoxia-induced inflammations, hypoxia, surgical lung volume reduction, pulmonary fibrosis, pulmonary hypertension, right ventricular hypertrophy, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), granulocytic ehrlichiosis, sarcoidosis, small airway disease, ventilation-perfusion mismatching, wheeze, colds, gout, alc. liver disease, lupus, burn therapy, periodontitis, transplant reperfusion injury and early transplantation rejection, acute inflammation, and rheumatoid arthritis as well as cancer. The compounds I had IC50 of <10 μM for inhibiting the binding of [125I]-IL-8 to human chemokine receptor CXCR1. The experimental process involved the reaction of 8-Methoxy-3,4-dihydroisoquinolin-1(2H)-one(cas: 74904-29-3).Product Details of 74904-29-3

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Abate, Carmen et al. published their research in European Journal of Medicinal Chemistry in 2013 |CAS: 74904-29-3

The Article related to brain, homo sapiens, human, positron emission tomography, tomography imaging agents, tumor imaging, σ1-non-opioid intracellular receptors role: bsu (biological study, unclassified), biol (biological study), σ2-non-opioid intracellular receptors role: bsu (biological study, unclassified), biol (biological study) and other aspects.Related Products of 74904-29-3

On November 30, 2013, Abate, Carmen; Selivanova, Svetlana V.; Muller, Adrienne; Kramer, Stefanie D.; Schibli, Roger; Marottoli, Roberta; Perrone, Roberto; Berardi, Francesco; Niso, Mauro; Ametamey, Simon M. published an article.Related Products of 74904-29-3 The title of the article was Development of 3,4-dihydroisoquinolin-1(2H)-one derivatives for the Positron Emission Tomography (PET) imaging of σ2 receptors. And the article contained the following:

σ2 Receptors are promising biomarkers for cancer diagnosis given the relationship between the proliferative status of tumors and their d. With the aim of contributing to the research of σ2 receptor Positron Emission Tomog. (PET) probes, we developed 2-[3-[6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl]propyl]-3,4-dihydroisoquinolin-1(2H)-one (3), with optimal σ2 pharmacol. properties and appropriate lipophilicity. Hence, 3 served as the lead compound for the development of a series of dihydroisoquinolinones amenable to radiolabeling. Radiosynthesis for compound 26, which displayed the most appropriate σ2 profile, was developed and σ2 specific binding for the corresponding [18F]-26 was confirmed by in vitro autoradiog. on rat brain slices. Despite the excellent in vitro properties, [18F]-26 could not successfully image σ2 receptors in the rat brain in vivo, maybe because of its interaction with P-gp. Nevertheless, [18F]-26 may still be worthy of further investigation for the imaging of σ2 receptors in peripheral tumors devoid of P-gp overexpression. The experimental process involved the reaction of 8-Methoxy-3,4-dihydroisoquinolin-1(2H)-one(cas: 74904-29-3).Related Products of 74904-29-3

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Dong, Jianyang’s team published research in Advanced Synthesis & Catalysis in 2020-06-03 | 90806-58-9

Advanced Synthesis & Catalysis published new progress about Aromatic nitrogen heterocycles 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, Recommanded Product: 5-Methoxyisoquinoline.

Dong, Jianyang; Wang, Xiaochen; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin published the artcile< Photoredox-Catalyzed Redox-Neutral Minisci C-H Formylation of N-Heteroarenes>, Recommanded Product: 5-Methoxyisoquinoline, the main research area is heteroarene dioxoisoindolinyl diethoxyacetate iridium photocatalyst regioselective Minisci formylation; formyl heteroarene preparation.

A protocol for redox-neutral Minisci C-H formylation of N-heteroarenes using 1,3-dioxoisoindolin-2-yl 2,2-diethoxyacetate as a formyl equivalent at room temp was reported. This scalable benchtop protocol offered a distinct advantage over traditional reductive carbonylation and Minisci C-H formylation methods in not requiring the use of carbon monoxide, pressurized gas, a stoichiometric reductant, or a stoichiometric oxidant.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Khanapure, Subash P’s team published research in Journal of Fluorine Chemistry in 1994-08-31 | 144511-13-7

Journal of Fluorine Chemistry published new progress about 1,3-Dipolar cycloaddition reaction. 144511-13-7 belongs to class isoquinoline, and the molecular formula is C13H5F2NO2, Name: 6,9-Difluorobenzo[g]isoquinoline-5,10-dione.

Khanapure, Subash P.; Han, Wei; Swartling, Dan J.; Biehl, Edward R. published the artcile< Synthesis of fluorine-substituted anthraquinones and aza-anthraquinones>, Name: 6,9-Difluorobenzo[g]isoquinoline-5,10-dione, the main research area is fluoro anthraquinone azaanthraquinone; anthraquinone fluoro; benzquinolinone fluoro; mitoxantrone fluoroanthraquinone intermediate; ametantrone fluoroanthraquinone intermediate; aza anthraquinone fluoro.

Using 1,4-dipolar-aryne cycloaddition methodol., a convenient, short synthesis of several fluoroanthraquinones I (R1 = H, methoxy, methoxymethoxy; n = integer) is presented which involves the reaction of haloarenes and 3-cyanophthalides in the presence of lithium diisopropylamide (LDA) in THF. The fluorine substituent(s) can be introduced by using fluorine-substituted haloarenes and/or 3-cyanophthalides. Similarly, fluorine-substituted pyridines, i.e. (fluoro)benz[g]isoquinoline-5,10-diones, II (R1 = H, methoxy, methoxymethoxy; n = integer) can be prepared by treating fluorine-substituted cyanophthalides and halopyridines in the presence of lithium diisopropylamide.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Liu, Shihui’s team published research in Chemical Science in 2019 | 90806-58-9

Chemical Science published new progress about Green chemistry. 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Safety of 5-Methoxyisoquinoline.

Liu, Shihui; Pan, Peng; Fan, Huaqiang; Li, Hao; Wang, Wei; Zhang, Yongqiang published the artcile< Photocatalytic C-H silylation of heteroarenes by using trialkylhydrosilanes>, Safety of 5-Methoxyisoquinoline, the main research area is photocatalytic silylation heteroarene hydrosilane green chem.

The efficient and selective C-H silylation of heteroarenes, especially the pharmaceutically relevant electron-deficient heteroarenes, represents a great challenge in organic synthesis. Herein we wish to report a distinctive visible light-promoted photocatalytic C-H silylation approach that enables the direct coupling of trialkylhydrosilanes with both electron-deficient and -rich heteroarenes as well as with cyano-substituted arenes in moderate to high yields and with good regioselectivity. The protocol features operational simplicity, mild reaction conditions, and the use of safe and readily available Na2S2O8, bis(trimethylsilyl) peroxide (BTMSPO) or iPr3SiSH as the radical initiators. Notably, the challenging bulky and inert trialkylhydrosilanes, such as (t-butyldimethyl)silane (tBuMe2SiH) and (triisopropyl)silane (iPr3SiH), work smoothly with the protocol. Moreover, despite the higher stability of tBuMe2Si silylation products, our studies revealed their great reactivity and versatility in diverse C-Si-based chem. transformations, providing an operationally simple, low-cost, and environmentally benign synthetic technol. for mol. construction and elaboration.

Chemical Science published new progress about Green chemistry. 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Safety of 5-Methoxyisoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Huang, Cheng’s team published research in Chem in 2021-05-13 | 90806-58-9

Chem published new progress about Alkenes 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, Category: isoquinoline.

Huang, Cheng; Qiao, Jia; Ci, Rui-Nan; Wang, Xu-Zhe; Wang, Yang; Wang, Jing-Hao; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu published the artcile< Quantum dots enable direct alkylation and arylation of allylic C(sp3)-H bonds with hydrogen evolution by solar energy>, Category: isoquinoline, the main research area is alkene amine preparation quantum dot photocatalyst cross coupling alkylation; heteroarene alkene quantum dot photocatalyst arylation; cadmium sulfide quantam dot preparation; quantum dot cadmium selenide preparation.

A general and mild strategy using semiconductor quantum dots (QDs) as photocatalysts for coupling a broad range of available allylic C(sp3)-H bonds with α-amino C-H bonds or heteroarenes, resp., under sunlight irradiation (> 85 examples) was reported. The protocol bypasses stoichiometric oxidant or reductant and pre-functionalization of both the coupling partners and produces hydrogen (H2) as the byproduct. The outstanding efficiency and selectivity and step- and atom-economy represents the first direct alkylation and arylation of allylic C(sp3)-H bonds with hydrogen evolution powered by solar energy.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Pan, Yang’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2020 | 90806-58-9

Chemical Communications (Cambridge, United Kingdom) published new progress about Density functional theory, B3LYP. 90806-58-9 belongs to class isoquinoline, and the molecular formula is C10H9NO, Product Details of C10H9NO.

Pan, Yang; Li, Jiangtao; Li, Zhefeng; Huang, Feng; Ma, Xiaofeng; Jiao, Wei; Shao, Huawu published the artcile< An efficient and facile strategy for trifluoromethylation and perfluoroalkylation of isoquinolines and heteroarenes>, Product Details of C10H9NO, the main research area is trifluoromethyl heteroarene preparation regioselective; heteroarene trimethyltrifluoromethylsilane trifluoromethylation; perfluoroalkyl heteroarene preparation regioselective; trimethyltrifluoroalkylsilane heteroarene perfluoroalkylation.

An effective and regioselective strategy for trifluoromethylation and perfluoroalkylation of isoquinolines I (R1 = OMe, Ph, Br, etc.; R2 = H, formyl, OMe, NO2; R3 = Me, 2-phenylethynyl, Cl, etc.; R4 = H, OMe; R5 = H, Ph, Br) and heteroarenes R6H (R6 = phenanthridin-6-yl, thieno[2,3-c]pyridin-7-yl, quinazolin-2-yl, etc.) was developed. By combination of TMSCnF2n+1 (n = 1, 2, 3) with PIFA, the method achieved the corresponding perfluoroalkylated products R6CnF2n+1 (n = 1, 2, 3) with broad functional group tolerance.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Fier, Patrick S’s team published research in Organic Letters in 2017-06-02 | 3336-49-0

Organic Letters published new progress about Amides Role: CAT (Catalyst Use), SPN (Synthetic Preparation), USES (Uses), PREP (Preparation) (di-). 3336-49-0 belongs to class isoquinoline, and the molecular formula is C9H7NO, Application In Synthesis of 3336-49-0.

Fier, Patrick S.; Maloney, Kevin M. published the artcile< Reagent Design and Ligand Evolution for the Development of a Mild Copper-Catalyzed Hydroxylation Reaction>, Application In Synthesis of 3336-49-0, the main research area is aryl halide oxime copper dicarboxamide hydroxylation catalyst; phenol preparation; dicarboxamide preparation hydroxylation ligand.

Parallel synthesis and mass-directed purification of a modular ligand library, high-throughput experimentation, and rational ligand evolution have led to a novel copper catalyst for the synthesis of phenols with a traceless hydroxide surrogate. The mild reaction conditions reported here enable the late-stage synthesis of numerous complex, druglike phenols.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem