Category: isoquinoline

Amidines. XVI. A new synthesis of 1-alkyl- and 1-aryl-3, 4-dihydroisoquinolines was written by Brodrick, C. I.;Short, W. F.. And the article was included in Journal of the Chemical Society in 1951.COA of Formula: C15H13N This article mentions the following:

PhCN (10.3 g.) and 12.1 g. PhCH₂CH₂NH₂ (I), treated with 13.4 g. AlCl₃ (20-30 s.) (temperature rise to 220°), heated 30 min. at 165-75°, cooled to 130°, poured into 500 cc. H₂O, the unchanged PhCN (0.2 g.) extracted with ether, the solution made alk. (pH 11), and extracted with C₆H₆, give 55% N-(2-phenylethyl)benzamidinium chloride (II), m. 182-3°; picrate (IIA), lemon yellow, m. 173-4°; the mother liquors yield N, N’-bis(2-phenylethyl)benzamidinium picrate (III), yellow, m. 170-1°; a poor quality of AlCl₃ gave 3.5% III, 74% unchanged PhCN, and 60% I. The low yield of II (47% by the Pinner method) may have been the result of the presence of moisture. PhCH₂CN (23.4 g.), 24.2 g. I, and 26.8 g. AlCl₃ (240°) give 28% of the α-Ph derivative (IV), of III, m. 173.5-4.5°; picrate, m. 113-14°; if the melt is heated 45 min. at 185°, the yield of IV is 21% and 13% PhCH₂CN is recovered. p-NCC₆H₄SO₂Me (18.1 g.), 12.1 g. I, and 13.4 g. AlCl₃(190°) give 2.6% unchanged cyanide and 55% of the p-methylsulfonyl derivative (V) of III, m. 264-5°; picrate, m. 168-8.5°. p-MeOC₆H₄CN (13.3 g.), 12.1 g. I, and 13.4 g. AlCl₃ (140°) give 22% unchanged cyanide, and 52.5% of the p-methoxyphenyl analog (VI) of I, m. 223-3.5°; 3, 4-dimethoxyphenyl analog of I, m. 200.5-1.5° (13%); picrate, orange yellow, m. 165-6°. 3-Cyanopyridine (10.4 g.), 12.1 g. I, and 13.4 g. AlCl₃ (210°) yield 36% (crude) N-2-phenylethylnicotineamidine, m. 131-1.5°; dipicrate, m. 174-5°. AmCN (8 g.), 10 g. I, and 11 g. AlCl₃ (170°) give N-2-phenylethylhexanamidine, as the benzenesulfonate, m. 74-5°. II (7.8 g.) in 81 cc. PhNO₂ and 27 cc. POCl₃, refluxed 2.5 h., gives 43% 3, 4-dihydro-1-phenylisoquinoline, b_1.2 145-54°; V yields 9.7% of the 1-(p-methylsulfonylphenyl) analog as the picrate, yellow, m. 192-2.5°; HCl salt, m. 267-8°. VI gives 3,4-dihydro-1-(p-methoxyphenyl)isoquinoline-HCl, with 1 mol. MeOH, m. 199-200°; it also seps. with 2 mols. H₂O, anhydrous, m. 212-14°; picrate, m. 161.5°. 3,4-Dihydro-1-(3-pyridyl)isoquinoline, b_0.5 155°; dipicrate, m. 196-7°; 1-amyl-3,4-dihydroisoquinoline picrate, m. 112.5-13°. In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7COA of Formula: C15H13N).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.COA of Formula: C15H13N

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Berberine treats atherosclerosis via a vitamin-like effect down-regulating Choline-TMA-TMAO production pathway in gut microbiota was written by Ma, Shu-Rong;Tong, Qian;Lin, Yuan;Pan, Li-Bin;Fu, Jie;Peng, Ran;Zhang, Xian-Feng;Zhao, Zhen-Xiong;Li, Yang;Yu, Jin-Bo;Cong, Lin;Han, Pei;Zhang, Zheng-Wei;Yu, Hang;Wang, Yan;Jiang, Jian-Dong. And the article was included in Signal Transduction and Targeted Therapy in 2022.Application In Synthesis of 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium This article mentions the following:

Trimethylamine-N-oxide (TMAO) derived from the gut microbiota is an atherogenic metabolite. This study investigates whether or not berberine (BBR) could reduce TMAO production in the gut microbiota and treat atherosclerosis. Effects of BBR on TMAO production in the gut microbiota, as well as on plaque development in atherosclerosis were investigated in the culture of animal intestinal bacterial, HFD-fed animals and atherosclerotic patients, resp. We found that oral BBR in animals lowers TMAO biosynthesis in intestine through interacting with the enzyme/co-enzyme of choline-trimethylamine lyase (CutC) and flavin-containing monooxygenase (FMO) in the gut microbiota. This action was performed by BBR’s metabolite dihydroberberine (a reductive BBR by nitroreductase in the gut microbiota), via a vitamin-like effect down-regulating Choline-TMA-TMAO production pathway. Oral BBR decreased TMAO production in animal intestine, lowered blood TMAO and interrupted plaque formation in blood vessels in the HFD-fed hamsters. Moreover, 21 patients with atherosclerosis exhibited the average decrease of plaque score by 3.2% after oral BBR (0.5 g, bid) for 4 mo (*P < 0.05, n = 21); whereas the plaque score in patients treated with rosuvastatin plus aspirin, or clopidogrel sulfate or ticagrelor (4 mo, n = 12) increased by 1.9%. TMA and TMAO in patients decreased by 38 and 29% in faeces (*P < 0.05; *P < 0.05), and 37 and 35% in plasma (***P < 0.001; *P < 0.05), after 4 mo on BBR. BBR might treat atherosclerotic plaque at least partially through decreasing TMAO in a mode of action similar to that of vitamins. In the experiment, the researchers used many compounds, for example, 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium (cas: 2086-83-1Application In Synthesis of 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium).

9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium (cas: 2086-83-1) belongs to isoquinoline derivatives. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Application In Synthesis of 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Regioselective peri-C-H selenylation of aromatic compounds with weakly coordinating ketone groups was written by Duan, Bingbing;Wu, Yao;Gao, Yi;Ying, Linkun;Tang, Jielin;Hu, Shiyu;Zhao, Qiuhua;Song, Zengqiang. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Safety of 1-Hydroxyisoquinoline This article mentions the following:

A novel and versatile method for peri-C-H selenylation of aromatic compounds bearing ketone groups, including chromones, xanthones, acridinones, quinolinones and naphthoquinones with diselenides under Ru(II) catalysis was presented. Various chromones and diselenides were applicable for this transformation, affording 5-selenyl chromones I [R¹ = H, 8-Cl, 2-Ph, etc.; R² = Ph, 3-FC₆H₄, 4-ClC₆H₄, etc.] in a highly regioselective manner in good to excellent yields. This transformation was easy to scale up and the desired products can be further modified. Most importantly, this transformation allowed the late-stage selenylation of bioactive compounds Mechanistic studies showed that radicals may be involved in this novel transformation. In the experiment, the researchers used many compounds, for example, 1-Hydroxyisoquinoline (cas: 491-30-5Safety of 1-Hydroxyisoquinoline).

1-Hydroxyisoquinoline (cas: 491-30-5) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Safety of 1-Hydroxyisoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

A Palladium(0)-Catalyzed C4 Site-Selective C-H Difluoroalkylation of Isoquinolin-1(2H)-Ones was written by Zhu, You-Quan;Hui, Li-Wen;Zhang, Shi-Bo. And the article was included in Advanced Synthesis & Catalysis in 2021.HPLC of Formula: 491-30-5 This article mentions the following:

A palladium(0)-catalyzed C4 site-selective C-H difluoroalkylation of isoquinolin-1(2H)-ones with 2-bromo-2,2-difluoroacetate or 2-bromo-2,2-difluoroacetamides through a radical pathway afforded 2,2-difluoro-2-(1-oxo-1,2-dihydroisoquinolin-4-yl)acetates/acetamides I [R = Me, Et, Ph, etc.; R¹ = H, CF₂CO₂Et, CF₂C(O)-morpholin-4-yl, CF₂C(O)NHCH₂CO₂Me; R² = H, CF₂CO₂Et; R³ = H, 6-OMe, 7-Cl, etc.]. This method provided an efficient and convenient approach to install a difluoroacetate or a difluoroacetamide moiety into bioactive mols. Bioassay results showed that introduction of these difluorinated groups at C4 position was beneficial to improve their antiviral activity and compound I [R = 3,4-MeC₆H₃; R¹ = H; R² = CF₂CO₂Et; R³ = H] was found to exhibit similar antiviral activity with com. Ningnanmycin. In the experiment, the researchers used many compounds, for example, 1-Hydroxyisoquinoline (cas: 491-30-5HPLC of Formula: 491-30-5).

1-Hydroxyisoquinoline (cas: 491-30-5) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. Other industrial applications include their use as corrosion inhibitors, preservatives, and as solvents for resins and terpenes.HPLC of Formula: 491-30-5

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Ratiometric porphyrin-based layers and nanoparticles for measuring oxygen in biosamples was written by Cywinski, Piotr J.;Moro, Artur J.;Stanca, Sarmiza E.;Biskup, Christoph;Mohr, Gerhard J.. And the article was included in Sensors and Actuators, B: Chemical in 2009.Electric Literature of C50H62N2O4 This article mentions the following:

Oxygen-sensitive polystyrene layers and nanoparticles were developed for measuring oxygen in biosamples. Polymer layers were prepared via spin-coating on glass plates while the nanoparticles were synthesized by microemulsion polymerization Platinum(II)meso-tetra(pentafluorophenyl)porphine (PtTFPP) was used as an oxygen sensor whereas N,N’-bis(1-hexylheptyl)perylene-3,4:9,10-bis-(dicarboximide) (S13) was used as a reference dye. For both, layers and nanoparticles, the sensor response was assessed in aqueous solution as well as in yeast culture. Quenching of porphyrin phosphorescence by oxygen was observed whereas fluorescence of the reference dye remained essentially unaffected. By using the signal of the reference dye fluctuations in the intensity of the excitation light or the nanosensor concentration can be easily corrected Both sensor systems were compared with respect to their spectral response and their sensitivity. In the experiment, the researchers used many compounds, for example, 2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone (cas: 110590-84-6Electric Literature of C50H62N2O4).

2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone (cas: 110590-84-6) belongs to isoquinoline derivatives. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. The discovery of chloroquine, the most well-known drug containing this stent, has helped bring about decades of malaria control and treatment.Electric Literature of C50H62N2O4

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem