Heterocyclic Building Blocks-Isoquinoline

Effects of neutral sulfate berberine on LPS-induced cardiomyocyte TNF-α secretion, abnormal calcium cycling, and cardiac dysfunction in rats was written by Yang, Jing;Wang, Hua-dong;Lu, Da-xiang;Wang, Yan-ping;Qi, Ren-bin;Li, Jing;Li, Fei;Li, Chu-jie. And the article was included in Acta Pharmacologica Sinica in 2006.Recommanded Product: 316-41-6 This article mentions the following:

Aim: To evaluate the effect of neutral sulfate berberine on cardiac function, tumor necrosis factor α (TNF-α) release, and intracellular calcium concentration ([Ca²⁺]_i) in cardiomyocytes exposed to lipopolysaccharide (LPS). Methods: Primary cultured rat cardiomyocytes were prepared from ventricles of 3 – 4-day old Sprague-Dawley rats. TNF-α concentrations in cell-conditioned media were measured by using a Quantikine ELISA kit, and cardiomyocyte [Ca²⁺]_i was measured by using Fura-2/AM. The isolated rat hearts were perfused in the Langendorff mode. Results: LPS at doses of 1, 5, 10, and 20 μg/mL markedly stimulated TNF-α secretion from cardiomyocytes, and neutral sulfate berberine inhibited LPS-induced TNF-α production Intracellular calcium concentration was significantly decreased after LPS stimulation for 1 h, and increased 2 h after LPS treatment. Pretreatment with neutral sulfate berberine reversed the LPS-induced [Ca²⁺]_i alterations, although neutral sulfate berberine did not inhibit a rapid increase in cardiomyocyte [Ca²⁺]_i induced by LPS. Perfusion of isolated hearts with LPS (100 μg/mL) for 20 min resulted in significantly impaired cardiac performance at 120 min after LPS challenge: the maximal rate of left ventricular pressure rise and fall (±dp/dt_max) decreased compared with the control. In contrast, ±dp/dt_max at 120 min in hearts perfused with neutral sulfate berberine (1 μmol/L) for 10 min followed by 20 min LPS (100 μg/mL) was greater than the corresponding value in the LPS group. Conclusion: Neutral sulfate berberine inhibits LPS-stimulated myocardial TNF-α production, impairs calcium cycling, and improves LPS-induced contractile dysfunction in intact heart. 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 sulfate(2:1) (cas: 316-41-6Recommanded Product: 316-41-6).

9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium sulfate(2:1) (cas: 316-41-6) 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. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.Recommanded Product: 316-41-6

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Catalysis by palladium salts. XIII. The reductive carbonylation of nitroaromatic compounds to isocyanates with Pd^II and Pd⁰ complexes as homogeneous catalysts was written by Ugo, R.;Psaro, R.;Pizzotti, M.;Nardi, P.;Dossi, C.;Andreetta, A.;Capparella, G.. And the article was included in Journal of Organometallic Chemistry in 1991.Computed Properties of C18H14Cl2N2Pd This article mentions the following:

A study was made of the reductive carbonylation of 2,4-dinitrotoluene (2,4-DNT) to 2,4-diisocyanatotoluene (2,4-TDI) with catalysis either by [Pd(isoquinoline)₂Cl₂], in the presence of Fe₂O₃ and MoO₃ or of Fe₂(MoO₄)₃ as cocatalysts, or by Pd⁰ complexes without cocatalysts. In the case of catalytic systems based upon [Pd(isoquinoline)₂Cl₂] the reaction was carried out at about 200 °C and under 200 atm of CO to produce 2,4-TDI with high conversions and acceptable selectivities. With Pd⁰ complexes as catalysts good conversions were achieved at much lower temperatures (100-120 °C) but with a low selectivity when a higher pressure of CO was used (300 atm or more). An investigation of the reductive carbonylation of PhNO₂ to PhNCO as a model system, together with a study of the thermal stability of [Pd(isoquinoline)₂Cl₂] in the presence of CO, provided evidence that the actual active catalyst was a reduced (probably zerovalent) form of palladium stabilized by the nitroarom. substrate or by some of the products from it as ligands. In the experiment, the researchers used many compounds, for example, Dichlorobis(isoquinoline)-Palladium (cas: 23807-51-4Computed Properties of C18H14Cl2N2Pd).

Dichlorobis(isoquinoline)-Palladium (cas: 23807-51-4) belongs to isoquinoline derivatives. Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. Most traditional methods of generating isoquinoline do so via oxidative aromatization of dihydro- or tetrahydro-isoquinolines, usually offering some environmental or economic advantage.Computed Properties of C18H14Cl2N2Pd

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Experimental and Computational Studies on the Formation of Three para-Benzyne Analogues in the Gas Phase was written by Kirkpatrick, Lindsey M.;Vinueza, Nelson R.;Jankiewicz, Bartlomiej J.;Gallardo, Vanessa A.;Archibold, Enada F.;Nash, John J.;Kenttaemaa, Hilkka I.. And the article was included in Chemistry – A European Journal in 2013.Electric Literature of C9H6IN This article mentions the following:

Exptl. and computational studies on the formation of three gaseous, pos.-charged para-benzyne analogs in a Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer are reported. The structures of the cations were examined by isolating them and allowing them to react with various neutral reagents whose reactions with aromatic carbon-centered σ-type mono- and biradicals are well understood. Cleavage of two iodine-carbon bonds in N-deuterated 1,4-diiodoisoquinolinium cation by collision-activated dissociation (CAD) produced a long-lived cation that showed nonradical reactivity, which was unexpected for a para-benzyne. However, the reactivity closely resembles that of an isomeric enediyne, N-deuterated 2-ethynylbenzonitrilium cation. A theor. study on possible rearrangement reactions occurring during CAD revealed that the cation formed upon the first iodine atom loss undergoes ring-opening before the second iodine atom loss to form an enediyne instead of a para-benzyne. Similar results were obtained for the 5,8-didehydroisoquinolinium cation and the 2,5-didehydropyridinium cation. The findings for the 5,8-didehydroisoquinolinium cation are in contradiction with an earlier report on this cation. The cation described in the literature was regenerated by using the literature method and demonstrated to be the isomeric 5,7-didehydro-isoquinolinium cation and not the expected 5,8-isomer. In the experiment, the researchers used many compounds, for example, 4-Iodoisoquinoline (cas: 55270-33-2Electric Literature of C9H6IN).

4-Iodoisoquinoline (cas: 55270-33-2) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. Other industrial applications include their use as corrosion inhibitors, preservatives, and as solvents for resins and terpenes.Electric Literature of C9H6IN

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

On the synthesis of arylpropiolic acids and investigations towards the formation of vinyl chlorides by HCl addition during esterification reactions was written by Hapke, Marko;Kral, Karolin;Spannenberg, Anke. And the article was included in Synthesis in 2011.Related Products of 55270-33-2 This article mentions the following:

The synthesis protocol for the preparation of different arylpropiolic acids using the Negishi reaction and the addition of HCl to the alkyne moiety of these acids in subsequent esterification reactions using SOCl₂ was examined In the experiment, the researchers used many compounds, for example, 4-Iodoisoquinoline (cas: 55270-33-2Related Products of 55270-33-2).

4-Iodoisoquinoline (cas: 55270-33-2) 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.Related Products of 55270-33-2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Structural Refinement of Ladder-Type Perylenediimide Dimers: A Classical Tale of Conformational Dynamics was written by Myahkostupov, Mykhaylo;Prusakova, Valentina;Oblinsky, Daniel G.;Scholes, Gregory D.;Castellano, Felix N.. And the article was included in Journal of Organic Chemistry in 2013.Quality Control of 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 This article mentions the following:

The authors synthesized and thoroughly characterized two representative ladder-type acetylene-bridged perylenediimide dimers bearing long alkyl chain solubilizing groups, bis[1-ethynyl-N,N’-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide] ([PDICC]₂, 1) and 1,1′-ethynyl-bis[N,N’-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide] ([PDI]₂CC, 2). In these dimeric PDI mols., NMR-based structural characterization became nontrivial because severe ¹H spectral broadening and greater than expected numbers of observed ¹³C resonances substantially complicated the interpretation of traditional 1-dimensional spectra. However, rational two-dimensional NMR approaches based on both homo- and heteronuclear couplings (¹H-¹H COSY; ¹H-¹³C HSQC), in conjunction with high-level structural DFT calculations (GIAO/B3LYP/6-31G(d,p)/PCM, chloroform), were readily applied to these structures, producing well-defined anal. characterization, and the associated methodol. is described. Also, from dynamic NMR experiments, both 1 and 2 exist in a perylene-centered conformational dynamic equilibrium (ΔG‡ = 13-17 kcal/mol), which primarily caused the observed ambiguities in conventional 1-dimensional spectra. 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: 110590-84-6Quality Control of 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).

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. 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. Most traditional methods of generating isoquinoline do so via oxidative aromatization of dihydro- or tetrahydro-isoquinolines, usually offering some environmental or economic advantage.Quality Control of 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

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Synthesis and study of substituted amides of isoquinoline-3- and isoquinoline-1-carboxylic acids as potential anticonvulsants was written by Strupinska, Marzanna;Rostafinska-Suchar, Grazyna;Jakubowicz, Bartlomiej;Klimkiewicz, Paulina;Lal, Ewelina;Oczkowski, Mateusz;Prochniak, Ewa;Pirianowicz-Chaber, Elzbieta;Mazurek, Aleksander P.. And the article was included in Acta Poloniae Pharmaceutica in 2017.Reference of 486-73-7 This article mentions the following:

Previously obtained benzylamides of isoquinoline-3-carboxylic acids and isoquinoline-1-carboxylic acids exhibited anticonvulsant activity. In search for more effective anticonvulsants, a series of amides of isoquinoline- 3- and isoquinoline-1-carboxylic acids have been synthesized (1-9). The obtained compounds were evaluated qual. for their anticonvulsant activity in the maximal electroshock seizure test (MES test), minimal clonic seizure test (6Hz test) and s.c. metrazol seizure threshold test (s.c. MET test) as well as in the rotorod neurotoxicity test (Tox test). One selected compound was tested quant. in 6Hz-test in mice after i.p. administration and showed activity ED50 = 385.69 mg/kg and TD50 > 600 mg/kg (1). In the experiment, the researchers used many compounds, for example, Isoquinoline-1-carboxylic acid (cas: 486-73-7Reference of 486-73-7).

Isoquinoline-1-carboxylic acid (cas: 486-73-7) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.Reference of 486-73-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Photophysical properties of solutions of 6,7-dimethoxy-3,4-dihydroisoquinoline was written by Dubouski, V. L.;Gulyakevich, O. V.;Mikhal’chuk, A. L.;Raichenok, T. F.;Tikhomirov, S. A.;Tolstorozhev, G. B.. And the article was included in Optics and Spectroscopy in 2006.Formula: C11H13NO2 This article mentions the following:

The effect of acid-base interactions on the photophys. properties of 6,7-dimethoxy-3,4-dihydroisoquinoline in protic solvents is studied by the methods of steady-state and picosecond spectroscopy. The specific features of the spectral and luminescent properties of solutions of 6,7-dimethoxy-3,4-dihydroisoquinoline are connected with the presence of emission centers of 2 types-solvated initial mols. and their protonated cationic forms. Considerable long-wavelength shifts observed in the electronic absorption and fluorescence spectra of the cationic form of the mol. as compared to the spectra of its initial form are caused by the elongation of a conjugated chain present in the fragment of the mol. that separates the N atom and the O atoms of the methoxy groups. The transition of the cationic form of the mol. to an excited electronic state is not accompanied by a change in its dipole moment. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-3,4-dihydroisoquinoline (cas: 3382-18-1Formula: C11H13NO2).

6,7-Dimethoxy-3,4-dihydroisoquinoline (cas: 3382-18-1) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. Most traditional methods of generating isoquinoline do so via oxidative aromatization of dihydro- or tetrahydro-isoquinolines, usually offering some environmental or economic advantage.Formula: C11H13NO2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Glycosylation-induced asymmetric synthesis of 1-substituted tetrahydroisoquinolines was written by Allef, Petra;Kunz, Horst. And the article was included in Heterocycles in 2007.Recommanded Product: 3382-18-1 This article mentions the following:

Activation of imines by N-glycosylation and simultaneous diastereodifferentiation in reactions of the formed N-glycosyl iminium ions provide new stereoselective routes to 1-substituted tetrahydroisoquinolines. Pictet-Spengler reactions induced by N-galactosylation of β-arylethyl imines of aromatic aldehydes give 1-aryl tetrahydroisoquinolines with high stereoselectivity. Glycosylation-induced addition of dialkylzinc reagents to 3,4-dihydroisoquinoline furnish 1-alkyl-tetrahydroisoquinolines with excellent diastereoselectivity. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-3,4-dihydroisoquinoline (cas: 3382-18-1Recommanded Product: 3382-18-1).

6,7-Dimethoxy-3,4-dihydroisoquinoline (cas: 3382-18-1) 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.Recommanded Product: 3382-18-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Syntheses of nitrogen-containing heterocyclic compounds. XXVII. Isoquinoline, cyclization by the Bischler-Napieralski method was written by Sugasawa, Shigehiko;Shigehara, Hajime. And the article was included in Yakugaku Zasshi in 1942.HPLC of Formula: 394-67-2 This article mentions the following:

3,4-(MeO)₂C₆H₃(CH₂)₂NH₂, 3,4-(MeO)₂C₆H₃(CH₂)₃NH₂, and 3,4-(MeO)₂C₆H₃CH(OH)(CH₂)₂NH₂ are acylated with BzOH, veratric acid, 2,3,4-(MeO)₃C₆H₂CO₂H, etc., and the amides are heated in toluene with POCl₃ to effect ring closure to 1-substituted 3,4-dihydroisoquinolines. These are converted to methine bases by the Hofmann decomposition The neutral substances are obtained by the Emde decomposition and oxidized to benzophenonecarboxylic acid derivatives which are the same as products formed by the Friedel-Crafts condensation of m-hemipic anhydride and C₆H₆, veratrole, or pyrogallol tri-Me ether. This indicates that the isoquinoline ring closure always occurs at the para-position with reference to a MeO group at the 3-position of the acid amide and not at the ortho-position as stated by Pfeiffer, et al. (C.A. 34, 2383.3). In the experiment, the researchers used many compounds, for example, 4-Fluoroisoquinoline (cas: 394-67-2HPLC of Formula: 394-67-2).

4-Fluoroisoquinoline (cas: 394-67-2) belongs to isoquinoline derivatives. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. Most traditional methods of generating isoquinoline do so via oxidative aromatization of dihydro- or tetrahydro-isoquinolines, usually offering some environmental or economic advantage.HPLC of Formula: 394-67-2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Determination of homopiperazine in fasudil hydrochloride by ion chromatography was written by Chen, Mei-lan;Zhang, Ting-ting;Ye, Ming-li;Huang, Qiao-qiao;Hu, Zhong-yang;Pan, Guang-wen. And the article was included in Yaowu Fenxi Zazhi in 2013.Recommanded Product: 105628-07-7 This article mentions the following:

A new method for the determination of homopiperazine in fasudil hydrochloride based on high-performance ion chromatog. was established. Fasudil hydrochloride was first dissolved in methane sulfonic acid, and then the solution was filtered through a 0.45 μm syringe membrane filter and Guard RP cleanup column before injection. The IC separation was performed on an IonPac CS17 (4 mm × 250 mm) column with 17 mmol · L^-1 methanesulfonic acid and acetonitrile (85:15) as the elution and a Cation MicroMembrane Suppressor (CMMS 300, 4 mm) as the suppression. The background was much reduced and the sensitivities of homopiperazine were greatly improved. Calibration curves of peak area vs. concentration showed a linear correlation coefficient of 0.9996 for homopiperazine in the range of 0.05-10 μg · mL^-1. Average recoveries were between 98.0%-102.0%. The established Ion chromatog. method has the advantages of high sensitivity, specificity and reproductivity, which can be applied to the limit amount determination of drug homopiperazine. In the experiment, the researchers used many compounds, for example, 5-((1,4-Diazepan-1-yl)sulfonyl)isoquinoline hydrochloride (cas: 105628-07-7Recommanded Product: 105628-07-7).

5-((1,4-Diazepan-1-yl)sulfonyl)isoquinoline hydrochloride (cas: 105628-07-7) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Recommanded Product: 105628-07-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem