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Journal articles on the topic 'Isoquinoline'

Author: Grafiati

Published: 4 June 2021

Last updated: 30 July 2024

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1

Mandrekar, Ketan S., and Santosh G. Tilve. "P₄O₁₀/TfOH mediated domino condensation–cyclization of amines with diacids: a route to indolizidine alkaloids under catalyst- and solvent-free conditions." RSC Advances 12, no. 28 (2022): 17701–5. http://dx.doi.org/10.1039/d2ra02534e.

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A highly efficient and direct methodology for the construction of pyrrolo[2,1-a]isoquinoline, pyrido[2,1-a]isoquinoline, and 12b-H and 12b-OH isoindolo[2,1-a]isoquinolinone alkaloids from commercially available synthons is devised.

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2

Yang, Chunmei, Guoqing Zhang, Senling Tang, Yang Pan, Huawu Shao, and Wei Jiao. "Dess–Martin Periodinane-Mediated Oxidative Coupling Reaction of Isoquinoline with Benzyl Bromide." Molecules 28, no. 3 (January 17, 2023): 923. http://dx.doi.org/10.3390/molecules28030923.

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Dess–Martin periodinane (DMP) is a broadly applicable oxidant in chemical synthesis. In this work, an efficient and convenient synthesis of N-substituted isoquinolinone derivatives mediated by DMP was achieved through the oxidative coupling reaction of functionalized isoquinoline with readily available benzyl bromide, which is a metal-free, mild, and practical method for synthesizing isoquinoline-1,3-dione or isoquinoline-1,3,4-trione derivatives in excellent yields. The H2O18-labeling experiment was performed to gain insight into the possible mechanism for this reaction.

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3

Koketsu, Mamoru, Amol Sonawane, Yunnus Shaikh, and Dinesh Garud. "Synthesis of Isoquinoline-Fused Quinazolinones through Ag(I)-Catalyzed Cascade Annulation of 2-Aminobenzamides and 2-Alkynylbenzaldehydes." Synthesis 51, no. 02 (September 21, 2018): 500–507. http://dx.doi.org/10.1055/s-0037-1610910.

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A new route for the expedient synthesis of a specific regioisomer of isoquinoline-fused quinazolinones is reported. Silver(I)-catalyzed cascade cyclization of 2-aminobenzamides and 2-alkynylbenzaldehydes followed by in situ oxidation gives 12-butyl- or 12-aryl-6H-isoquinolino[2,1-a]quinazolin-6-ones in 69–91% yields. The structure of the isoquinoline-fused quinazolinone was confirmed by X-ray crystallography analysis.

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4

Murtagh, Kevin, Brian A. Sweetman, and Patrick J. Guiry. "New chiral tridentate ligands for asymmetric catalysis." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 311–20. http://dx.doi.org/10.1351/pac200678020311.

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The synthesis of new tridentate, isoquinoline-derived ligands, involving successive Suzuki cross-coupling reactions, is described. We were able to resolve 1-[3-(2-hydroxy-phenyl)-isoquinolin-1-yl]-naphthalen-2-ol via molecular complexation with N-benzylcinchonidinium chloride, whereas 1,3-bis(2-hydroxy-naphthalen-1-yl)-isoquinoline was resolved by chromatographic separation of its epimeric camphorsulfonates. Their barrier to rotation about the central biaryl axis was evaluated via racemization studies. Application of enantiopure 1,3-bis(2-hydroxynaphthalen-1-yl)-isoquinoline in the addition of diethylzinc to aldehydes proceeded in moderate yield but without asymmetric induction. A new tridentate ligand, 4-tert-butyl-2-chloro-6-[1-(2-hydroxymethyl-naphthalen-1-yl)-isoquinolin-3-yl]-phenol, was prepared in good yield and resolved by semipreparative high-performance liquid chromatography (HPLC). Its application in the addition of diethylzinc to a range of aromatic aldehydes proceeded in near perfect enantioselectivities at low ligand loadings of 1 mol %.

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5

Zhang, Lujun, Wenfang Xiong, Biao Yao, Haitao Liu, Meng Li, Yu Qin, Yujian Yu, et al. "Facile synthesis of isoquinolines and isoquinoline N-oxides via a copper-catalyzed intramolecular cyclization in water." RSC Advances 12, no. 47 (2022): 30248–52. http://dx.doi.org/10.1039/d2ra06097c.

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6

Wu, Wei, Yan Wang, Jing Guo, Liu Cai, Yuan Chen, Yanmin Huang, and Yungui Peng. "Asymmetric acyl-Mannich reaction of isoquinolines with α-(diazomethyl)phosphonate and diazoacetate catalyzed by chiral Brønsted acids." Chemical Communications 56, no. 76 (2020): 11235–38. http://dx.doi.org/10.1039/d0cc03201h.

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7

Sloop, Joseph C. "Advances in the Preparation of Fluorinated Isoquinolines: A Decade of Progress." Journal of Chemistry 2017 (2017): 1–15. http://dx.doi.org/10.1155/2017/2860123.

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Heterocyclic molecules incorporating fluorinated isoquinoline components are found in many medicinally and agriculturally important bioactive products as well as industrially impactful materials. Within the past decade, a variety of isoquinolinic ring assembly techniques has enabled the introduction of diverse fluorine-containing functionalities which can enhance potential bioactivity and industrial utility. This review examines recent noncatalyzed and transition metal catalyzed synthetic approaches to the assembly of isoquinoline derivatives that are ring-fluorinated and/or result in the incorporation of fluorine-containing functional groups. Specifically, efficient synthetic methods and regioselectivity in the incorporation of functional groups into isoquinoline ring systems are examined.

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8

Li, Jiu-ling, Wei-ze Li, Ying-chun Wang, Qiu Ren, Heng-shan Wang, and Ying-ming Pan. "Palladium(ii)-catalyzed C–C and C–O bond formation for the synthesis of C1-benzoyl isoquinolines from isoquinoline N-oxides and nitroalkenes." Chemical Communications 52, no. 65 (2016): 10028–31. http://dx.doi.org/10.1039/c6cc03530b.

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9

An, Yuanyuan, Hongguang Xia, and Jie Wu. "Base-controlled [3+3] cycloaddition of isoquinoline N-oxides with azaoxyallyl cations." Chemical Communications 52, no. 68 (2016): 10415–18. http://dx.doi.org/10.1039/c6cc03650c.

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A base-controlled [3+3] cycloaddition reaction of isoquinoline N-oxides with azaoxyallyl cations is developed, leading to 1,11b-dihydro-[1,2,4]oxadiazino[3,2-a]isoquinolin-2(3H)-ones and 2-(isoquinolin-1-yloxy)acetamides, respectively. This transformation proceeds through an azaoxyallyl cation generated in situ from α-bromohydroxamate.

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10

Clark, Robin D., Jahangir, and James A. Langston. "Heteroatom-directed lateral lithiation: synthesis of isoquinoline derivatives from N-(tert-butoxycarbonyl)-2-methylbenzylamines." Canadian Journal of Chemistry 72, no. 1 (January 1, 1994): 23–30. http://dx.doi.org/10.1139/v94-005.

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Methodology for the preparation of isoquinoline derivatives from N-(tert-butoxycarbonyl)-2-methylbenzylamines (1) was developed. Conversion of 1 to the dilithio species followed by condensation with DMF afforded Boc-3-hydroxy-1,2,3,4-tetrahydroisoquinolines 3, which could be dehydrated to 1,2-dihydroisoquinolines 4. Hydrogenation of dihydro compounds 4 afforded the corresponding tetrahydroisoquinolines 5. Treatment of the dilithio species from 1 with N-methoxy-N-methylamides afforded ketones 14, which were converted to 3-substituted dihydro-isoquinoline 15, tetrahydroisoquinolines (16, 17), or isoquinolines (20).

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11

Solongo, A., R. Istatkova, S. Philipov, S. Javzan, and D. Selenge. "Phytochemical study on Berberis sibirica Pall." Mongolian Journal of Chemistry 12 (September 24, 2014): 117–22. http://dx.doi.org/10.5564/mjc.v12i0.185.

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From the aerial parts (700g) of berberis sibirica pall. 6 isoquinoline alkaloids of protoberberine, protopine, benzophenantridine and proaporphine type were isolated. The known alkaloids (-)-tetrahydropseudocoptisine, pseudoprotopine, (+)-chelidonine and (+)-glaziovine are new for the family berberidaceae. from the aerial part ii (3.9 kg) 14 isoquinoline alkaloids of aporphine, proaporphine, protoberberine, protopine, benzylisoquinoline, bisbenzylisoquinoline,proaporphine-benzylisoquinoline and simple isoquinolin type were isolated and identified. The aporphine alkaloid 1-o-methylisotebaidine and simple isoquinoline dehydrocorypalline have been found for the first time in the family of berberidaceae. From the roots of b. sibirica 10 isoquinoline alkaloids of protoberberine, benzylisoquinoline, bisbenzylisoquinoline, aporphine-benzylisoquinoline and proaporphine-benzylisoquinoline type were isolated. 1,10-di-omethylpakistanine has been reported for the first time as a natural alkaloid. The known alkaloids (-) -isothalidezine and (+)-armepavine have been found for the first time in the family berberidaceae. All structures were determined by physical and spectral data.DOI: http://dx.doi.org/10.5564/mjc.v12i0.185 Mongolian Journal of Chemistry Vol.12 2011: 117-122

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12

Hussain, S. Fazal, M. Tariq Siddiqui, and Maurice Shamma. "Berbidine: A Simple Isoquinoline-Isoquinolone Dimer." Journal of Natural Products 52, no. 2 (March 1989): 317–19. http://dx.doi.org/10.1021/np50062a016.

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13

Hošt'álková, Anna, Zdeněk Novák, Milan Pour, Anna Jirošová, Lubomír Opletal, Jiří Kuneš, and Lucie Cahlíková. "Berbanine: A New Isoquinoline-Isoquinolone Alkaloid from Berberis Vulgaris (Berberidaceae)." Natural Product Communications 8, no. 4 (April 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800407.

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14

Laha, Joydev K., Ummehani Tinwala, and Mandeep Kaur Hunjan. "Minisci aroylation of N-heterocycles using choline persulfate in water under mild conditions." New Journal of Chemistry 45, no. 48 (2021): 22853–59. http://dx.doi.org/10.1039/d1nj05068k.

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A modified Minisci aroylation of isoquinoline using arylglyoxylic acids in the presence of choline persulfate or pre-composition (choline acetate and K2S2O8) in water at ambient temperature affording aroylated isoquinolines is reported.

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15

Nanaji, Yerramsetti, Seema Kirar, Sandip V. Pawar, and Ashok Kumar Yadav. "A mild and metal-free synthesis of 2- and 1-alkyl/aryl/dialkyl-aminoquinolines and isoquinolines." RSC Advances 10, no. 13 (2020): 7628–34. http://dx.doi.org/10.1039/c9ra10397j.

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A synthetic strategy has been developed for synthesis of 2 and 1-aminoquinolines and isoquinolines from quinoline and isoquinoline-N-oxides, amines and triflic anhydride in acetonitrile at 0 °C to room temperature.

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16

Yang, Xiaobo, Jiyang Jie, Haoyi Li, and Meihui Piao. "Ir(iii)-catalyzed synthesis of isoquinolines from benzimidates and α-diazocarbonyl compounds." RSC Advances 6, no. 62 (2016): 57371–74. http://dx.doi.org/10.1039/c6ra10045g.

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We report herein a tandem Ir(iii)-catalyzed C–H activation and annulation reactions for the synthesis of isoquinolines. This novel method affords an alternative strategy for the construction of diverse and useful isoquinoline derivatives.

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17

Pearson, Stuart, Shaun Fillery, Kristin Goldberg, Julie Demeritt, Jonathan Eden, Jonathan Finlayson, and Anil Patel. "Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions." Synthesis 50, no. 24 (August 20, 2018): 4963–81. http://dx.doi.org/10.1055/s-0037-1610223.

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Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described.

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18

Wang, Xiao-Ling. "Tetrahydroepiberberine." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (March 8, 2006): o1271—o1272. http://dx.doi.org/10.1107/s1600536806007471.

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The title compound [systematic name: 6,6a,11,12-tetrahydro-8,9-dimethoxy-14H-dioxolo[4′,5′:7,8]isoquinolino[3,2-a]isoquinoline], also known as sinactine, C20H21NO4, a protoberberine-type alkaloid, was isolated from the roots of the plant Sinomenium acutum. Both piperidine rings adopt half-chair conformations.

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19

Zhu, Di, Wen-Kun Luo, Luo Yang, and Da-You Ma. "Iodine-catalyzed oxidative multiple C–H bond functionalization of isoquinolines with methylarenes: an efficient synthesis of isoquinoline-1,3,4(2H)-triones." Organic & Biomolecular Chemistry 15, no. 34 (2017): 7112–16. http://dx.doi.org/10.1039/c7ob01539a.

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An iodine-catalyzed multiple C–H bond functionalization of isoquinolines with methylarenes via a successive benzylic sp³ C–H iodination/N-benzylation/amidation/double sp² C–H oxidation sequence to yield isoquinoline-1,3,4(2H)-triones is developed for the first time.

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20

Balewski, Łukasz, Franciszek Sączewski, Maria Gdaniec, Anita Kornicka, Karolina Cicha, and Aleksandra Jalińska. "Synthesis and Fluorescent Properties of Novel Isoquinoline Derivatives." Molecules 24, no. 22 (November 10, 2019): 4070. http://dx.doi.org/10.3390/molecules24224070.

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Isoquinoline derivatives have attracted great interest for their wide biological and fluorescent properties. In the current study, we focused on the synthesis of a series of novel isoquinoline derivatives substituted at position 3 of the heteroaromatic ring. Compounds were obtained in a Goldberg–Ullmann-type coupling reaction with appropriate amides in the presence of copper(I) iodide, N,N-dimethylethylenediamine (DMEDA), and potassium carbonate. The structures of novel isoquinolines were confirmed by IR, NMR, and elemental analysis, as well as X-ray crystallography. In the course of our research work, the visible fluorescence of this class of compounds was observed. The above findings prompted us to investigate the optical properties of the selected compounds.

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21

Hassaneen, Hamdi M., Wagnat W. Wardkhan, and Yasmin Sh Mohammed. "A Novel Route to Isoquinoline[2,1-g][1,6]naphthyridine, Pyrazolo[5,1-a] isoquinoline and Pyridazino[4´,5´:3,4]pyrazolo[5,1-a]isoquinoline Derivatives With Evaluation of Antitumor Activities." Zeitschrift für Naturforschung B 68, no. 8 (August 1, 2013): 895–904. http://dx.doi.org/10.5560/znb.2013-3101.

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(E)-2-Chloro-3-(2-cyanovinyl)-9,10-dimethoxy-4-oxo-6,7-dihydro-4H-pyrido[2,1-a] isoquinoline- 1-carbonitrile (5) was obtained by treatment of the 2-chloro-3-formylpyrido[2,1-a]isoquinoline derivative 3 with 2-(triphenylphosphoranylidene)acetonitrile (4). Treatment of 5 with sodium azide afforded the corresponding azido compound 6 which could be reduced by sodium dithionite to compound 7. A novel isoquinolino[2,1-g][1,6]naphthyridine derivative 11 was obtained by the reaction of phenyl isothiocyanate with the phosphorane compound 8, which was prepared by the reaction of compound 6 with triphenylphosphine. Treatment of 5 with amines 12a-c and thiophenols 14a-c in refluxing ethanol afforded the corresponding substitution products 13a-c and 15a-c, respectively. Also, the reaction of 1 with a-oxo hydroxamoyl chlorides 16 was reinvestigated, and the synthesized pyrazoloisoquinolines 19a-f and pyridazinopyrazoloisoquinolines 20a, e were screened for their in vitro antitumor activities.

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22

Liu, Cheng-Mei, Fei-Hua Yao, Xin-Hua Lu, Xue-Xia Zhang, Lian-Xiang Luo, Xiao Liang, and Shu-Hua Qi. "Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus Aspergillus puniceus." Marine Drugs 20, no. 1 (January 17, 2022): 78. http://dx.doi.org/10.3390/md20010078.

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Puniceusines A–N (1–14), 14 new isoquinoline alkaloids, were isolated from the extracts of a deep-sea-derived fungus, Aspergillus puniceus SCSIO z021. Their structures were elucidated by spectroscopic analyses. The absolute configuration of 9 was determined by ECD calculations, and the structures of 6 and 12 were further confirmed by a single-crystal X-ray diffraction analysis. Compounds 3–5 and 8–13 unprecedentedly contained an isoquinolinyl, a polysubstituted benzyl or a pyronyl at position C-7 of isoquinoline nucleus. Compounds 3 and 4 showed selective inhibitory activity against protein tyrosine phosphatase CD45 with IC50 values of 8.4 and 5.6 µM, respectively, 4 also had a moderate cytotoxicity towards human lung adenocarcinoma cell line H1975 with an IC50 value of 11.0 µM, and 14, which contained an active center, -C=N+, exhibited antibacterial activity. An analysis of the relationship between the structures, enzyme inhibitory activity and cytotoxicity of 1–14 revealed that the substituents at C-7 of the isoquinoline nucleus could greatly affect their bioactivity.

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23

Hua, Ruimao. "Isoquinolone Syntheses by Annulation Protocols." Catalysts 11, no. 5 (May 11, 2021): 620. http://dx.doi.org/10.3390/catal11050620.

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Isoquinolones (isoquinolin-1(2H)-ones) are one of the important nitrogen-heterocyclic compounds having versatile biological and physiological activities, and their synthetic methods have been recently developed greatly. This short review illustrates the significant advances in the construction of isoquinolone ring with atom- and step-economy, focusing on the intermolecular annulation protocols and intramolecular cyclization in the presence of a variety of catalyst systems. The syntheses of isoquinolone-fused rings are also included.

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24

Azad, Leila, Maryam Ghazvini, Haleh Sanaeishoar, and Issa Yavari. "Synthesis of functionalized 1,2-dihydroisoquinolines via one-pot reactions of isoquinoline, alkyl propiolate, and thiazolidin-2,4-dione." Journal of Chemical Research 43, no. 11-12 (August 30, 2019): 457–60. http://dx.doi.org/10.1177/1747519819871028.

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The reactive zwitterionic intermediates, generated from addition of isoquinoline to alkyl propiolates, react with thiazolidin-2,4-dione to afford 3-[1-(2,4-dioxothiazolidin-3-yl)isoquinolin-2(1 H)-yl]acrylates in good yields. Using (Z)-5-arylidenethiazolidine-2,4-diones as the NH-acidic component leads to 3-{1-[( Z)-5-benzylidene-2,4-dioxothiazolidin-3-yl] isoquinolin-2(1 H)-yl}acrylates in moderate to good yields in the absence of any catalysts under mild reaction conditions. The reaction between quinoline, ethyl propiolate, and thiazolidin-2,4-dione leads to ethyl 3-[2-(2,4-dioxothiazolidin-3-yl) quinolin-1(2 H)-yl]acrylate.

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25

Vorobyeva, Daria V., Dmitry A. Petropavlovskikh, Ivan A. Godovikov, Fedor M. Dolgushin, and Sergey N. Osipov. "Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF3-α-Amino Carboxylates." Molecules 27, no. 23 (December 2, 2022): 8488. http://dx.doi.org/10.3390/molecules27238488.

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A convenient pathway to a new series of α-CF3-substituted α-amino acid derivatives bearing pharmacophore isoquinolone core in their backbone has been developed. The method is based on [4+2]-annulation of N-(pivaloyloxy) aryl amides with orthogonally protected internal acetylene-containing α-amino carboxylates under Rh(III)-catalysis. The target annulation products can be easily transformed into valuable isoquinoline derivatives via a successive aromatization/cross-coupling operation.

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26

Kmieciak, Anna, Marta Ćwiklińska, Karolina Jeżak, Afef Shili, and Marek P. Krzemiński. "Searching for New Biologically Active Compounds Derived from Isoquinoline Alkaloids." Chemistry Proceedings 3, no. 1 (November 14, 2020): 97. http://dx.doi.org/10.3390/ecsoc-24-08417.

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Many isoquinoline alkaloids are biologically active compounds and successfully used as pharmaceuticals. Compounds belonging to the isoquinolines and tetrahydroisoquinolines (TIQs) can be used as anesthetics, antihypertensive drugs, antiviral agents, and vasodilators. In the presented studies, the search for new compounds and synthesis of tetrahydroisoquinoline alkaloid derivatives was undertaken. Several dihydroisoquinolines were synthesized by Bishler–Napieralski reaction from the corresponding amides. Dihydroisoquinolines were reduced with sodium borohydride to obtain racemic tetrahydroisoquinolines. Asymmetric reduction of selected 3,4-dihydroisoquinolines was attempted with borane in the presence of chiral terpene spiroboranes.

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27

Hensen, K., R. Mayr-Stein, and M. Bolte. "Isoquinoline." Acta Crystallographica Section C Crystal Structure Communications 55, no. 9 (September 15, 1999): 1565–67. http://dx.doi.org/10.1107/s0108270199006320.

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28

Shih, Tzenge-Lien, Min-Chen Tsai, Pei Huang, and Liang Syu. "Synthesis of Novel Isoquinolino[5,4-ab]phenanthridine Derivatives via Pictet–Spengler Reaction." Synthesis 51, no. 06 (November 21, 2018): 1377–82. http://dx.doi.org/10.1055/s-0037-1610670.

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The reaction of 5-amino-2-[2-(dimethylamino)ethyl]-6-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione with a series of aldehydes in acidic media (phosphoric acid, trifluoromethanesulfonic acid, and trifluoroacetic acid) is described. This key step is based on the Pictet–Spengler reaction to synthesize ten novel isoquinolino[5,4-ab]phenanthridine derivatives. The most effective acid is phosphoric acid and optimized yields were obtained. The frameworks of target compounds are unique and have never been reported.

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29

Obydennik, Arina Y., Alexander A. Titov, Anna V. Listratova, Tatiana N. Borisova, Victor B. Rybakov, Leonid G. Voskressensky, and Alexey V. Varlamov. "Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-a]isoquinoline Derivatives via a 1,2-Rearrangement Step." International Journal of Molecular Sciences 25, no. 2 (January 16, 2024): 1085. http://dx.doi.org/10.3390/ijms25021085.

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Here, An efficient approach to obtaining previously unknown furo[2′,3′:2,3]pyrrolo[2,1-a]isoquinoline derivatives from readily available 1-R-1-ethynyl-2-vinylisoquinolines is described. The reaction features a simple procedure, occurs in hexaflouroisopropanol and does not require elevated temperatures. It has been found that the addition of glacial acetic acid significantly increases the yields of the target spirolactone products. Using trifluoroethanol instead of hexaflouroisopropanol results in the formation of pyrido[2,1-a]isoquinolines.

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30

Kratzer, Philipp, Susanne Steinhauser, and Gerhard Maas. "Propyne Iminium Salts and Isoquinoline – 1 : 1 and 2 : 1 Adducts." Zeitschrift für Naturforschung B 69, no. 5 (May 1, 2014): 567–79. http://dx.doi.org/10.5560/znb.2014-4032.

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The reaction of equimolar amounts of propyne iminium trifluoromethanesulfonates 1a, b and isoquinoline yielded, after hydrolytic work-up, the N-(3-oxoprop-1-en-1-yl)isoquinolinium salts 4a, b in modest yields. Monitoring of the reaction by 1H NMR spectroscopy indicated the formation of salts 4, 3-isoquinolinio-substituted propene iminium salts 3, and N,N,N',N'-tetramethylvinamidinium salts 5 as the major components. The expected aminoallenes (2-(3-(dimethylamino)allen-1- yl)isoquinolinium triflates) 2 could not be detected in the reaction solutions. It is possible, however, to trap the aminoallene intermediates in a polar [4+2] cycloaddition reaction, as shown by the isolation of 2 : 1 adducts 7c, d in good yield from cyclopropyl-substituted propyne iminium triflates 1c, d and isoquinoline. Hydride abstraction from 7c, d yielded the 2,4-dicyclopropyl-1,3- bis((dimethyliminio)(aryl)methyl)pyrido[2,1-a]isoquinolinium tris(triflates) 8c, d.

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31

Hajinasiri, Rahimeh, and Sobhan Rezayati. "Solvent-free Synthesis of 1,2-Disubstituted Derivatives of 1,2- Dihydroisoquinoline, 1,2-Dihydroquinoline and 1,2-Dihydropyridine." Zeitschrift für Naturforschung B 68, no. 7 (July 1, 2013): 818–22. http://dx.doi.org/10.5560/znb.2013-3095.

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A one-pot and efficient approach to the synthesis of dialkyl 2-[1-[(alkoxycarbonyl)anilino]-2(1H)- (isoquinolin-2-yl) (or -quinolin-1-yl or -pyridin-1-yl)]-2-butenedioates is described. This method involves a three-component reaction between isoquinoline, quinoline or pyridine, dialkyl acetylenedicarboxylates and N-phenylcarbamates under solvent-free conditions, without using any catalyst and at room temperature. The mild reaction conditions and good yields of the products exhibit the synthetic advantage of this method.

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32

Potikha, Lyudmyla, Volodymyr Brovarets, and Victor Zhirnov. "Biological Evaluation of 3-Aminoisoquinolin-1(2H)-one Derivatives as Potential Anticancer Agents Authors Lyudmyla Potikha." French-Ukrainian Journal of Chemistry 9, no. 2 (2021): 52–63. http://dx.doi.org/10.17721/fujcv9i2p52-63.

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Anticancer activity of a series of 3-(hetaryl/aryl)amino substituted isoquinolin-1(2H)-ones has been studied within the international scientific program “NCI-60 Human Tumor Cell Lines Screen”. Screening was performed in vitro on 60 cell lines of lungs, kidneys, CNS, ovaries, prostate, and breast cancer, epithelial cancer, leukemia, and melanoma. The most effective compounds were those with thiazolyl or pyrazolyl substituent at 3-amino group and had no substituents at C(4) of the isoquinoline cycle. We identified a new lead compound, 3-(1,3-thiazol-2-ylamino)isoquinolin-1(2H)-one 12, which effectively prevents tumor cell growth (average lg GI50 = -5.18, lg TGI = -4.1, lg LC50 > -4.0) with good selectivity.

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Lantos, Ivan, and Haralambos E. Katerinopoulos. "Synthetic transformations of cyclopropyl annulated dihydroisoquinolines." Canadian Journal of Chemistry 69, no. 6 (June 1, 1991): 1033–37. http://dx.doi.org/10.1139/v91-152.

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Isomeric 3-cyano-3-methyl-2-acetyl-cycloprop[c]isoquinolines, 5 and 6, were prepared by alkylation and cyclopropanation of Reissert compounds and their reactions under basic conditions were examined. Both compounds, under the influence of methoxide, yielded isoquinoline derived products resulting from cleavage of the peripheral C—C bond. The results are postulated to derive from attack of the methoxide on the acyl carbonyl, forming a tetrahedral adduct that undergoes ring opening. Key words: cyclopropanation, ring opening, tetrahedral complex, pyramidalization.

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Altshuler, Heinrich N., Galina Yu Shkurenko, and Sergey Yu Lyrschikov. "Encapsulation of isoquinoline in a polymer nanocontainer based on the CU-2-4 sulfocationite." Butlerov Communications 61, no. 2 (February 29, 2020): 97–102. http://dx.doi.org/10.37952/roi-jbc-01/20-61-2-97.

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The possibility of the encapsulation of isoquinoline in the nanocontainer on the matrix of the sulfonated copolymer based on styrene and divinylbenzene (CU-2-4 sulfocationite) has been researched. The encapsulation of isoquinoline in the nanocontainer on polymer matrix was performed by ion-exchange sorption from aqueous solutions. CU-2-4 sulfocationite in hydrogen and isoquinoline forms was studied by NMR and Fourier IR spectroscopy. In the 13C NMR spectra of solid-state samples of the CU-2-4 cation exchanger in the isoquinoline form is observed additional resonance absorption band of 13C in the range of chemical shift 136 ppm, corresponding to the nodal carbon atom of the pyridine ring. The IR spectrum of the polymer containing the encapsulated isoquinoline be observed bands characteristic for skeletal vibrations in the area of isoquinoline fingerprints (1300-1600 cm-1) and the band of 938 cm-1 that corresponds to the deformation vibrations of the CH-group of pyridine ring, which is not in the spectrum of the H-form sulfocationite. The ion-exchange capacity of the nanocontainer based on СU-2-4 sulfocationite for isoquinoline was 5.5 meq/g. This corresponds to the content of ionogenic groups in the polymer. The dynamic ion-exchange capacity of sulfonated CU-2-4 cation exchanger during encapsulation of isoquinoline coincides with the ion-exchange capacity of sulfonated cation exchanger upon the release of isoquinoline from the polymer nanocontainer. The content of immobilized isoquinoline in the nanocontainer on the СU-2-4 matrix reaches 71 % by weight of the polymer. It is shown that isoquinoline is encapsulated and desorbed with the solution of hydrochloric acid at the same rate. Encapsulated isoquinoline is completely released from the polymer by desorption with the aqueous hydrochloric acid solution. The half-life during sorption and desorption (release) of isoquinoline is approximately 400 seconds. It is shown that the encapsulated isoquinoline to be completely released from the polymer by desorption with an aqueous hydrochloric acid solution. The kinetics of the encapsulation and release of isoquinoline from the nanocontainer based on CU-2-4 sulfocationite is determined by its diffusion in the polymer phase.

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35

Defois, Mathilde, Chloé Rémondin, Béatrice Josselin, Lionel Nauton, Vincent Théry, Fabrice Anizon, Sandrine Ruchaud, Francis Giraud, and Pascale Moreau. "Synthesis and Kinase Inhibitory Potencies of Pyrazolo[3,4-g]isoquinolines." Molecules 27, no. 17 (August 30, 2022): 5578. http://dx.doi.org/10.3390/molecules27175578.

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A new series of pyrazolo[3,4-g]isoquinoline derivatives, diversely substituted at the 4- or 8-position, were synthesized. The results of the kinase inhibitory potency study demonstrated that the introduction of a bromine atom at the 8-position was detrimental to Haspin inhibition, while the introduction of an alkyl group at the 4-position led to a modification of the kinase inhibition profiles. Altogether, the results obtained demonstrated that new pyrazolo[3,4-g]isoquinolines represent a novel family of kinase inhibitors with various selectivity profiles.

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36

Liu, Yi Bin, Yu Zhen Li, and Xue Ding. "Adsorption Simulation of Basic Nitrogen Compounds in ZSM-5 and USY Zeolites by Grand Canonical Monte Carlo Method." Advanced Materials Research 1096 (April 2015): 189–93. http://dx.doi.org/10.4028/www.scientific.net/amr.1096.189.

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Adsorption behaviors of pyridine, quinoline and isoquinoline in ZSM-5 and USY zeolites at 773 K were studied by Grand Canonical Monte Carlo simulations. Interaction energy, adsorption isothermal and localization for each adsorbate were obtained. The results show that pyridine and quinoline/isoquinoline molecules have different adsorption behaviors in the zeolite, while quinoline and isoquinoline molecules have similar adsorption behaviors. The maximum interaction energy between quinoline/isoquinoline and zeolite is more negative than that of pyridine and zeolite, which indicates that the quinoline/isoquinoline can be adsorbed more stable than pyridine. But the loadings of pyridine are significantly larger than that of quinoline/isoquinoline at the same pressure. Otherwise, pyridine can be adsorbed on most sites while quinoline/isoquinoline can only enter the large channels or cages. And the adsorption quantities in USY zeolite are much more than the adsorption quantities in ZSM-5 zeolite for each adsorbate.

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Zhang, Yangyang, Yun Kang, Hui Xie, Yaqin Wang, Yaoting Li, and Jianming Huang. "Comparative Transcriptome Analysis Reveals Candidate Genes Involved in Isoquinoline Alkaloid Biosynthesis in Stephania tetrandra." Planta Medica 86, no. 17 (August 5, 2020): 1258–68. http://dx.doi.org/10.1055/a-1209-3407.

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AbstractThe roots of Stephania tetrandra are used as a traditional Chinese medicine. Isoquinoline alkaloids are considered to be the most important and effective components in this herb, but little is known about the molecular mechanism underlying their biosynthesis. In this context, this study aimed to reveal candidate genes related to isoquinoline alkaloid biosynthesis in S. tetrandra. Determination of tetrandrine and fangchinoline in the roots and leaves of S. tetrandra by HPLC showed that the roots had much higher contents of the two isoquinoline alkaloids than the leaves. Thus, a comparative transcriptome analysis of the two tissues was performed to uncover candidate genes involved in isoquinoline alkaloid biosynthesis. A total of 71 674 unigenes was obtained and 31 994 of these were assigned putative functions based on BLAST searches against 6 annotation databases. Among the 79 isoquinoline alkaloid-related unigenes, 51 were differentially expressed, with 42 and 9 genes upregulated and downregulated, respectively, when the roots were compared with the leaves. The upregulated differentially expressed genes were consistent with isoquinoline alkaloid accumulation in roots and thus were deemed key candidate genes for isoquinoline alkaloid biosynthesis in the roots. Moreover, the expression profiles of 10 isoquinoline alkaloid-related differentially expressed genes between roots and leaves were validated by quantitative real-time polymerase chain reaction, which indicated that our transcriptome and gene expression profiles were reliable. This study not only provides a valuable genomic resource for S. tetrandra but also proposes candidate genes involved in isoquinoline alkaloid biosynthesis and transcription factors related to the regulation of isoquinoline alkaloid biosynthesis. The results lay a foundation for further studies on isoquinoline alkaloid biosynthesis in this medicinal plant.

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E, Yong Sheng. "Extraction and Purification of Isoquinoline from Wash Oil." Advanced Materials Research 791-793 (September 2013): 93–96. http://dx.doi.org/10.4028/www.scientific.net/amr.791-793.93.

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Isoquinoline is a basic chemical raw material, which has wide applications.This paper introduces the current isoquinoline technology of extration and purification from wash oil. I use the residual oil after producting quinoline as raw material, get isoquinoline by distillation twice. The content of isoquinoline is higher than 98%.The total yield is 76.9%, which is higher than current domestic production levels.

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39

Zhao, Yun-Hui, Zhihua Zhou, Yong-Cheng Ma, Yueyang Luo, Yingli Zhu, Hang Wang, Hangbin Zhou, Hailong Tan, Wenlin Xie, and Zilong Tang. "Synthesis of Potential Anticancer 1-(1H-Indol-3-yl)isoquinolines by Silver Nitrate Mediated Tandem Reactions of 2-Alkynylbenzaldehyde Azines and Indoles." Synlett 29, no. 06 (January 2, 2018): 773–78. http://dx.doi.org/10.1055/s-0036-1591743.

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Novel antitumor compounds featuring isoquinoline and indole moieties were synthesized by a silver nitrate promoted domino reaction involving intramolecular cyclization, nucleophilic addition of indole, and subsequent N–N bond cleavage. The transformation from readily available starting materials into an interesting class of indole-substituted isoquinolines was completed under mild conditions and by simple operations in moderate to good yields. The antitumor activity of these compounds in vitro was significantly greater than that of a reference compound, 5-fluorouracil. The products might serve as new lead compounds for drugs for the treatment of cancer.

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40

Aislabie, J., N. K. Richards, and T. C. Lyttle. "Description of bacteria able to degrade isoquinoline in pure culture." Canadian Journal of Microbiology 40, no. 7 (July 1, 1994): 555–60. http://dx.doi.org/10.1139/m94-089.

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Isoquinoline is a nitrogen heterocyclic compound that is associated with coal- and oil-derived wastes. Four strains of bacteria able to degrade isoquinoline in pure culture were isolated from sites known to be contaminated with oil. Isoquinoline was used as the sole source of carbon and nitrogen by these isolates. Isoquinoline was initially transformed to 1-hydroxyisoquinoline, which accumulated in the broth culture, and then disappeared. The four strains isolated were Gram negative, aerobic, rod-shaped bacteria with polar flagella. The strains have been presumptively identified as members of the family Comamonadaceae.Key words: isoquinoline degradation, Comamonadaceae.not available

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41

Min, Xinyi, Ting Zhu, Xinyi Hu, Cong Hou, Jianing He, and Xia Liu. "Transcriptome and Metabolome Analysis of Isoquinoline Alkaloid Biosynthesis of Coptis chinensis in Different Years." Genes 14, no. 12 (December 18, 2023): 2232. http://dx.doi.org/10.3390/genes14122232.

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Coptis chinensis is a perennial herb of the Ranunculaceae family. The isoquinoline alkaloid is the main active component of C. chinensis, mainly exists in its rhizomes and has high clinical application potential. The in vitro synthesis of isoquinoline alkaloids is difficult because their structures are complex; hence, plants are still the main source of them. In this study, two-year and four-year rhizomes of C. chinensis were selected to investigate the effect of growth years on the accumulation of isoquinoline alkaloids. Two-year and four-year C. chinensis were selected for metabolomics detection and transcriptomic analysis. A total of 413 alkaloids were detected by metabolomics analysis, of which 92 were isoquinoline alkaloids. (S)-reticuline was a significantly different accumulated metabolite of the isoquinoline alkaloids biosynthetic pathway in C. chinensis between the two groups. The results of transcriptome analysis showed that a total of 464 differential genes were identified, 36 of which were associated with the isoquinoline alkaloid biosynthesis pathway of C. chinensis. Among them, 18 genes were correlated with the content of important isoquinoline alkaloids. Overall, this study provided a comprehensive metabolomic and transcriptomic analysis of the rapid growth stage of C. chinensis rhizome from the perspective of growth years. It brought new insights into the biosynthetic pathway of isoquinoline alkaloids and provided information for utilizing biotechnology to improve their contents in C. chinensis.

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42

Possner, Sven T., Frank C. Schroeder, Hans Tore Rapp, Volker Sinnwell, Stefan Franke, and Wittko Francke. "3,7-Isoquinoline quinones from the ascidian tunicate Ascidia virginea." Zeitschrift für Naturforschung C 72, no. 7-8 (July 14, 2017): 259–64. http://dx.doi.org/10.1515/znc-2017-0012.

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AbstractA new isoquinoline quinone system and its iodinated derivatives were isolated from the ascidian tunicateAscidia virgineaMüller 1776 (Phlebobranchia: Ascidiidae). Structures were elucidated by spectroscopic methods and derivatization reactions. Ascidine A (3,7-dihydro-1,8-dihydroxy-4-(4′-hydroxyphenyl)isoquinoline-3,7-dione (1), ascidine B (3,7-dihydro-1,8-dihydroxy-4-(4′-hydroxy-3′-iodophenyl)isoquinoline-3,7-dione (2), and ascidine C (3,7-dihydro-1,8-dihydroxy-4-(4′-hydroxy-3′,5′-diiodophenyl)isoquinoline-3,7-dione (3) represent a novel type of tyrosine-derived alkaloids.

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43

Niopas, Ioannis, and Gordon A. Smail. "N-substituted tricyclic isoquinoline hydantoins." Collection of Czechoslovak Chemical Communications 55, no. 2 (1990): 540–45. http://dx.doi.org/10.1135/cccc19900540.

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Mannich condensation of the 1,3-dioxo-5H-10,10a-dihydroimidazo[1,5-b]isoquinoline (Ia) and 5-ethoxy-10-bromo-1,3-dioxo-5H-imidazo[1,5-b]isoquinoline (IVa) with secondary amines gave a series of N-2-aminomethyl isoquinoline hydantoins IIa-IIg and IVb, respectively. Alkylation of Ia with N,N-dialkylaminoethyl chlorides and ethyl chloroacetate afforded the N-dialkylaminoethyl and N-ethoxycarbonylmethyl derivatives Va, Vb and IIh. The N-2-hydroxymethyl and N-2-amino isoquinoline hydantoins IIj and If were also prepared.

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44

Kostova, Nadezhda, and Tsvetelina Doncheva. "Hypecoum spp.—Chemistry and Biological Activity of Alkaloids." Diversity 15, no. 9 (September 19, 2023): 1023. http://dx.doi.org/10.3390/d15091023.

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Genus Hypecoum Tourn. ex L. belongs to the poppy family Papaveraceae and comprises about 19 species occurring in Europe, Northern Africa and Asia. Hypecoum species have been widely used in traditional medicine as antipyretic, analgesic and anti-inflammatory remedies. Their effects are associated with the biologically and pharmacologically active isoquinoline alkaloids in them, such as protopines, protoberberines, benzophenanthridines, aporphines, simple isoquinolines, secoberbines, spirobenzylisoquinolines and others. In this study, we aimed to review and organize information on ethnomedicinal, phytochemical, chemotaxonomical and pharmacological studies of alkaloids and extracts obtained from Hypecoum plants, and to suggest opportunities for further research.

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45

Donati, C., TV Hung, and RH Prager. "The Chemistry of Phthalide-3-carboxylic Acid. VII. Reaction With Isoquinoline Derivatives." Australian Journal of Chemistry 43, no. 2 (1990): 375. http://dx.doi.org/10.1071/ch9900375.

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Phthalide-3-carboxylic acid has been decarboxylated in the presence of isoquinoline, 1-chloroisoquinoline and isoquinoline N-oxides to give low yields of compounds resulting from alkylation of the isoquinoline heterocycle at C1 with a phthalidyl group. Attempted Barton decarboxylation-alkylation in the presence of isoquinolinium salts was unsuccessful.

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46

Richards, N. K., H. K. Mahanty, and J. Aislabie. "Construction of a DNA probe to detect isoquinoline-degrading bacteria." Canadian Journal of Microbiology 40, no. 7 (July 1, 1994): 561–66. http://dx.doi.org/10.1139/m94-090.

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To facilitate the cloning of DNA encoding isoquinoline degradation an assay was developed that allowed the rapid visual scoring of the isoquinoline degradation phenotype of single colonies. Transposon mutagenesis of one of the isolates, Comamonas acidovorans IQ3, was performed using Tn 5, and nine Isq− mutants deficient in the ability to utilise isoquinoline as the sole nitrogen source were isolated. These mutants were also incapable of utilising the first metabolite of the isoquinoline degradation pathway, 1-hydroxyisoquinoline, as the sole carbon source. For each Isq− mutant, the EcoRI fragment containing the Tn5 insertion was cloned into pBR322. Restriction and Southern analyses of the cloned DNA revealed that of the nine Isq− mutants, six contained Tn5 insertions in a common 8.9-kb EcoRI fragment derived from the wild type, C. acidovorans IQ3. The cloned DNA thought to be involved in the degradation of isoquinoline proved to be specific when used as a probe in colony hybridization to some bacteria possessing the ability to degrade isoquinoline.Key words: DNA probe, isoquinoline degradation, transposon mutagenesis, Comamonas acidovorans.

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47

Jankowski, Christopher K., Gaëtan LeClair, Jacqueline MR Bélanger, Jocelyn RJ Paré, and Marie-Rose VanCalsteren. "Microwave-assisted Diels-Alder synthesis." Canadian Journal of Chemistry 79, no. 12 (December 1, 2001): 1906–9. http://dx.doi.org/10.1139/v01-183.

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The synthesis of isoquinolinone carboxylates was performed using arecoline or its isomer N-methyl tetrahydro pyridine carboxylate with Danishefsky's diene via thermal or microwave assisted Diels-Alder reaction. The comparison of both condensation modes showed that the microwave method not only afforded higher yields of the adducts, but also lead to the formation of a new α,β-unsaturated pyridyl ketone. All structures were identified with the help of high resolution 2D NMR.Key words: Diels-Alder microwave assisted reaction, microwave synthesis, Michael, diene, isoquinoline carboxylate synthesis, Danishefsky diene synthesis, MAP Diels-Alder2.

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48

Tantawy, Mohamed A., Farid M. Sroor, Magda F. Mohamed, Mostafa E. El-Naggar, Fatma M. Saleh, Hamdi M. Hassaneen, and Ismail A. Abdelhamid. "Molecular Docking Study, Cytotoxicity, Cell Cycle Arrest and Apoptotic Induction of Novel Chalcones Incorporating Thiadiazolyl Isoquinoline in Cervical Cancer." Anti-Cancer Agents in Medicinal Chemistry 20, no. 1 (April 10, 2020): 70–83. http://dx.doi.org/10.2174/1871520619666191024121116.

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Background: Chalcones are naturally occurring compounds found in various plant species which are widely used for the traditional popular treatments. Chalcones are distinguished secondary metabolites that are reported to display diverse biological activities such as antiviral, antiplatelet, anti-inflammatory, anticancer, antibacterial and antioxidant agents. The presence of a,ß-unsaturated carbonyl group in chalcones is assumed to be responsible for their bioactivity. In addition, heterocyclic compounds having nitrogen such as isoquinolines are of considerable interest as they constitute the core structural element of many alkaloids that have enormous pharmacological activities. Objective: The objective of this study is the synthesis and biological activity of novel chalcones incorporating thiadiazolyl isoquinoline as potential anticancer candidates. Different genetic tools were used in an attempt to know the mechanism of action of this compound against breast cancer. Methods: An efficient one pot synthesis of novel chalcones incorporating thiadiazolyl isoquinoline has been developed. The cytotoxic activity of the novel synthesized compounds was performed against four different kinds of cancer cell lines. Results: Among all the tested derivatives, chalcone 3 has the best cytotoxic profile against A549, MCF7, and HeLa cell lines, with IC50s (66.1, 51.3, and 85.1μM, respectively). Molecular docking studies for chalcone 3 revealed that CDK2, and EGFRTK domains have strong binding affinities toward the novel chalcone 3, while tubulin-colchicine-ustiloxin, and VEGFRTK domains illustrated moderate mode of binding. Conclusion: We have developed an efficient method for the synthesis of novel chalcones incorporating thiadiazolyl isoquinoline. All compounds showed better cytotoxicity results against four kinds of cancer cell lines (A549, MCF7, HCT116, and HELA cells). The results depicted that chalcone 3 has a high and promising cytotoxic effect against HELA cell line and the mechanism of cytotoxicity was widely studied through different theoretical and experimental tools. Thus, the newly synthesized derivative 3 can be utilized as a novel chemotherapeutic compound for cervical carcinoma.

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Young, Steven D., J. Mark Wiggins, and Joel R. Huff. "3,4-Dihydrobenz[f]isoquinoline and 3,4-dihydrobenz[g]isoquinoline." Journal of Organic Chemistry 53, no. 5 (March 1988): 1114–16. http://dx.doi.org/10.1021/jo00240a042.

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Yao, Bo, Chen-Liang Deng, Yan Liu, Ri-Yuan Tang, Xing-Guo Zhang, and Jin-Heng Li. "Palladium-catalyzed oxidative carbamoylation of isoquinoline N-oxides with formylamides by means of dual C–H oxidative coupling." Chemical Communications 51, no. 19 (2015): 4097–100. http://dx.doi.org/10.1039/c4cc10140e.

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