Heterocyclic Building Blocks-Isoquinoline

Synthesis and research of benzylamides of some isocyclic and heterocyclic acids as potential anticonvulsants was written by Strupinska, Marzanna;Rostafinska-Suchar, Grazyna;Pirianowicz-Chaber, Elzbieta;Stables, James P.;Jiang, Jeff;Paruszewski, Ryszard. And the article was included in Acta Poloniae Pharmaceutica in 2013.Synthetic Route of C10H7NO2 This article mentions the following:

A series of benzylamides of isocyclic and heterocyclic acids was synthesized and tested in anticonvulsant screening project (ASP) of antiepileptic drug development program of NIH. Near all synthesized derivatives of heterocyclic acids showed activity. All obtained derivatives of mono- and bicyclic isocyclic acids were inactive. The power of action of heterocyclic acids derivatives seems does not depend upon kind of heteroatom (N, O or S). One of the compounds (2-furoic acid benzylamide) appeared most promising. It showed in minimal clonic seizure (6Hz) test (ASP) in rats after i. p. administration: MES ED₅₀ = 36.5 mg/kg, TOX TD₅₀ = 269.75 mg/kg, and PI = 7.39. In the experiment, the researchers used many compounds, for example, Isoquinoline-1-carboxylic acid (cas: 486-73-7Synthetic Route of C10H7NO2).

Isoquinoline-1-carboxylic acid (cas: 486-73-7) belongs to isoquinoline derivatives. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.Synthetic Route of C10H7NO2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Two asymmetrical perylene diimide derivatives: Synthesis, optical-electrochemical properties and morphologies of self-assembly was written by Tao, Jiayu;Zhang, Jiuxuan;Song, Yuting;Liu, Jian;Xu, Hai-Jun. And the article was included in Journal of Solid State Chemistry in 2022.Synthetic Route of C50H62N2O4 This article mentions the following:

In this manuscript, two PDI derivatives I [X = N] and I [X = O] with unsym. N-substitution of amine and ester-bridge were designed and synthesized. These two compounds were characterized by NMR, Fourier transform IR (FT-IR), and high-resolution mass spectrometry (HRMS). The photophys. properties were studied by UV-Vis absorption and fluorescence spectroscopy. Cyclic voltammograms of I [X = N] and I [X = O] were investigated and HOMO and LUMO energy levels of both two PDIs were estimated as -6.2 and -3.9 eV, resp. Thermal properties were also studied by thermogravimetric anal. (TGA) and differential scanning calorimetry (DSC). I [X = N] was assembled into nanotubes while I [X = O] was assembled into nanobelts resp., via a reprecipitation method. I [X = N] and I [X = O] show good potential application in organic devices such as solar cells, organic field-effect transistors (OFETs) and so on. 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: 110590-84-6Synthetic Route 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. 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.Synthetic Route of C50H62N2O4

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions was written by Sarmah, Bikash Kumar;Konwar, Monuranjan;Bhattacharyya, Dipanjan;Adhikari, Priyanka;Das, Animesh. And the article was included in Advanced Synthesis & Catalysis in 2019.Recommanded Product: 607-32-9 This article mentions the following:

A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide was developed to obtain 2-substituted N-heteroaromatic nitriles without the requirement of any external activator-, metal-, base- and solvent. The present protocol was a straightforward, one-pot heteroaromatic C-H cyanation process and proceeded smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allowed access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biol. important mols. Based on the exptl. observations, a plausible mechanism was also proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. In the experiment, the researchers used many compounds, for example, 5-Nitroisoquinoline (cas: 607-32-9Recommanded Product: 607-32-9).

5-Nitroisoquinoline (cas: 607-32-9) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Recommanded Product: 607-32-9

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Discovery of the oncogenic MDM2, a direct binding target of berberine and a potential therapeutic, in multiple myeloma was written by Li, Chuting;Su, Ru;Wang, Xiuyuan;Huang, Guiping;Liu, Yanjun;Yang, Juhua;Yin, Zhao;Gu, Chunming;Fei, Jia. And the article was included in Functional & Integrative Genomics in 2022.Related Products of 2086-83-1 This article mentions the following:

Recent studies have suggested the potency of berberine (BBR) for multiple cancer treatments, including multiple myeloma (MM). However, the direct target and underlying mechanism of BBR remain largely understood in MM. Here, we demonstrated that BBR inhibited cell proliferation and acted synergistically with bortezomib in MM.1S cells. BBR treatment induced MM cell cycle arrest by downregulating several cell cycle-related proteins. Murine double minute 2 (MDM2) as a BBR-binding protein was identified by surface plasmon resonance image (SPRi) anal. and mol. docking. Overexpression of MDM2 is associated with MM progression and a poor prognosis. Knockdown MDM2 by siRNA transfection can repress MM malignant progression and attenuate the BBR sensitivity to MM.1S cells. BBR treatment induced the degradation of MDM2 through the ubiquitin-proteasome system and reactivated P53/P21 in MM cells. Overall, our data has illustrated that MDM2, as a binding protein of BBR for the first time, may serve as a potential therapeutic option for MM. 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: 2086-83-1Related Products of 2086-83-1).

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. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. 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 2086-83-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Synthesis and structure-activity data of some new epibatidine analoges was written by Seerden, Jean-Paul G.;Tulp, Martin Th. M.;Scheeren, Hans W.;Kruse, Chris G.. And the article was included in Bioorganic & Medicinal Chemistry in 1998.HPLC of Formula: 55270-33-2 This article mentions the following:

The high-pressure Diels-Alder reaction of N-carbomethoxypyrroles and Ph vinyl sulfone affords versatile intermediates for the palladium-catalyzed preparation of new epibatidine analogs. Structure-activity relationships of new epibatidine analogs are presented. High affinities of K_i = 0.81 and 2.6 nM for the [³H]-cytisine rat brain nicotinic acetylcholine binding sites were found for the 5-pyrimidinyl and the 5-(2-amino)pyrimidinyl epibatidine analogs I (R = H, NH₂), resp. In the experiment, the researchers used many compounds, for example, 4-Iodoisoquinoline (cas: 55270-33-2HPLC of Formula: 55270-33-2).

4-Iodoisoquinoline (cas: 55270-33-2) belongs to isoquinoline derivatives. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. 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: 55270-33-2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Synthesis, cytotoxicity and docking simulation of bioactive [1,2,4]triazolo[3,4-a]dihydroisoquinoline chalcone derivatives was written by Teleb, Mohamed A. M.;Hassan, Nourhan;Hassaneen, Hamdi M.;Hassaneen, Huwaida M. E.;Laboud, Yara N.;Saleh, Fatma M.. And the article was included in Heterocycles in 2022.Synthetic Route of C11H13NO2 This article mentions the following:

1-(1-Aryl-8,9-dimethoxy-1,5,6,10b-tetrahydro-[1,2,4]triazolo[3,4-a]isoquinolin-3-yl)ethan-1-ones were prepared via reaction of C-acetylmethanohydrazonoyl chlorides with 6,7-dimethoxy-3,4-dihydroisoquinoline. Treatment of the latter products with 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehyde derivatives in ethanol in the presence of sodium hydroxide solution at room temperature afforded chalcones I (X = Me, OMe; Y = H, Me, OMe, Cl). Cytotoxic assay was performed for in vitro antitumor screening against caucasian breast adenocarcinoma (MCF7) and hepatocellular carcinoma (HepG2) cell lines. Chalcones I (X = Y = Me) and I (X = OMe, Y = H) have promising cytotoxic effects against MCF7 with IC50 values 8.0 and 7.5渭g/mL, resp. Mol. docking using Mcule.com was carried out, for the most potent compounds I (X = Y = Me) and I (X = OMe, Y = H) against two protiens which are EGFR and DHFR. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-3,4-dihydroisoquinoline (cas: 3382-18-1Synthetic Route of C11H13NO2).

6,7-Dimethoxy-3,4-dihydroisoquinoline (cas: 3382-18-1) belongs to isoquinoline derivatives. Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Synthetic Route of C11H13NO2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Identification and removal of polycyclic aromatic hydrocarbons in wastewater treatment processes from coke production plants was written by Zhang, Wanhui;Wei, Chaohai;Yan, Bo;Feng, Chunhua;Zhao, Guobao;Lin, Chong;Yuan, Mengyang;Wu, Chaofei;Ren, Yuan;Hu, Yun. And the article was included in Environmental Science and Pollution Research in 2013.Related Products of 607-32-9 This article mentions the following:

Identification and removal of polycyclic aromatic hydrocarbons (PAHs) were investigated at two coke plants located in Shaoguan, Guangdong Province of China. Samples of raw coking wastewaters and wastewaters from subunits of a coke production plant were analyzed using gas chromatog.-mass spectrometry (GC/MS) to provide a detailed chem. characterization of PAHs. The identification and characterization of PAH isomers was based on a pos. match of mass spectral data of sample peaks with those for PAH isomers in mass spectra databases with electron impact ionization mass spectra and retention times of internal reference compounds In total, 270 PAH compounds including numerous nitrogen, oxygen, and sulfur heteroat. derivatives were pos. identified for the first time. Quant. anal. of target PAHs revealed that total PAH concentrations in coking wastewaters were in the range of 98.5卤8.9 to 216卤20.2 渭g/L, with 3-4-ring PAHs as dominant compounds Calculation of daily PAH output from four plant subunits indicated that PAHs in the coking wastewater came mainly from ammonia stripping wastewater. Coking wastewater treatment processes played an important role in removing PAHs in coking wastewater, successfully removing 92 % of the target compounds However, 69 weakly polar compounds, including PAH isomers, were still discharged in the final effluent, producing 8.8卤2.7 to 31.9卤6.8 g/day of PAHs with potential toxicity to environmental waters. The study of coking wastewater herein proposed can be used to better predict improvement of coke production facilities and treatment conditions according to the identification and removal of PAHs in the coke plant as well as to assess risks associated with continuous discharge of these contaminants to receiving waters. In the experiment, the researchers used many compounds, for example, 5-Nitroisoquinoline (cas: 607-32-9Related Products of 607-32-9).

5-Nitroisoquinoline (cas: 607-32-9) belongs to isoquinoline derivatives. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. The Pomeranz鈥揊ritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Related Products of 607-32-9

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Optimizing Pt Electronic States through Formation of a Schottky Junction on Non-reducible Metal-Organic Frameworks for Enhanced Photocatalysis was written by Sun, Zi-Xuan;Sun, Kang;Gao, Ming-Liang;Metin, Onder;Jiang, Hai-Long. And the article was included in Angewandte Chemie, International Edition in 2022.SDS of cas: 52250-50-7 This article mentions the following:

Charge transfer between metal sites and supports is crucial for catalysis. Redox-inert supports are usually unfavorable due to their less electronic interaction with metal sites, which, we demonstrate, is not always correct. Herein, three metal-organic frameworks (MOFs) are chosen to mimic inert or active supports for Pt nanoparticles (NPs) and the photocatalysis is studied. Results demonstrate the formation of a Schottky junction between Pt and the MOFs, leading to the electron-donation effect of the MOFs. Under light irradiation, both the MOF electron-donation effect and Pt interband excitation dominate the Pt electron d. Compared with the “active” UiO-66 and MIL-125 supports, Pt NPs on the “inert” ZIF-8 exhibit higher electron d. due to the higher Schottky barrier, resulting in superior photocatalytic activity. This work optimizes metal catalysts with non-reducible supports, and promotes the understanding of the relationship between the metal-support interaction and photocatalysis. In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7SDS of cas: 52250-50-7).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.SDS of cas: 52250-50-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Metal-free decarboxylative acylation of isoquinolines using 伪-keto acids in water was written by Chaubey, Narendra R.;Singh, Krishna Nand. And the article was included in Tetrahedron Letters in 2017.Quality Control of 5-Nitroisoquinoline This article mentions the following:

An efficient method for acylation of isoquinolines such as isoquinoline, 4-bromoisoquinoline, 4-phenylisoquinoline, etc. has been developed using 伪-ketoacids RC(O)C(O)₂H (R = Me, thiophen-2-yl, naphthalene-2-yl, etc.) under metal- and additive-free conditions in water. The protocol involves C(sp²)-H functionalization of isoquinolines providing an easy access to C1-benzoylated isoquinolines RC(O)R¹ (R¹ = 4-bromoisoquinolin-1-yl, 4-phenylisoquinolin-1-yl, 5-nitroisoquinolin-1-yl, etc.), which constitute the core structure of a number of biol. active compounds and serve as key intermediate in the synthesis of many alkaloids. In the experiment, the researchers used many compounds, for example, 5-Nitroisoquinoline (cas: 607-32-9Quality Control of 5-Nitroisoquinoline).

5-Nitroisoquinoline (cas: 607-32-9) belongs to isoquinoline derivatives. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Quality Control of 5-Nitroisoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Syntheses and antifilarial profile of 5-amino and 5,8-diaminoisoquinoline derivatives: a new class of antifilarial agents. [Erratum to document cited in CA126:84084] was written by Srivastava, Sanjay K.;Chauhan, P. M. S.;Agarwal, S. K.;Bhaduri, A. P.;Singh, S. N.;Fatma, Nigar;Chatterjee, R. K.;Bose, Chhanda;Srivastava, V. M. L.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1997.COA of Formula: C9H5BrN2O2 This article mentions the following:

Structures 4 and 7 are corrected The structures and other materials of 10, 11 and 12 are omitted. Reagent (III) is corrected to propylene oxide. The spectroscopic data for 4 and 7 are corrected In the experiment, the researchers used many compounds, for example, 5-Bromo-8-nitroisoquinoline (cas: 63927-23-1COA of Formula: C9H5BrN2O2).

5-Bromo-8-nitroisoquinoline (cas: 63927-23-1) 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. The Pomeranz鈥揊ritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.COA of Formula: C9H5BrN2O2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem