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Journal articles on the topic 'Isoquinoline derivatives'

Author: Grafiati

Published: 4 June 2021

Last updated: 27 July 2025

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1

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 (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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2

Wu, Wei, Yan Wang, Jing Guo та ін. "Asymmetric acyl-Mannich reaction of isoquinolines with α-(diazomethyl)phosphonate and diazoacetate catalyzed by chiral Brønsted acids". Chemical Communications 56, № 76 (2020): 11235–38. http://dx.doi.org/10.1039/d0cc03201h.

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3

Yang, Xiaobo, Jiyang Jie, Haoyi Li та Meihui Piao. "Ir(iii)-catalyzed synthesis of isoquinolines from benzimidates and α-diazocarbonyl compounds". RSC Advances 6, № 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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4

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 (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 resea

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5

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 (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

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6

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 inco

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7

Bremner, JB, CL Raston, GL Rowbottom, AH White, and KN Winzenberg. "A Ring Destruction Approach to Some Benzo-Fused Medium-Sized Heterocycles by Means of Cyanogen-Bromide Under Solvolytic Conditions - X-Ray Structure of a '1h-2,6-Benzoxazecine-6-Carbonitrile and a '2h-3,6-Benzoxazecine-6-Carbonitrile Derivative." Australian Journal of Chemistry 39, no. 6 (1986): 893. http://dx.doi.org/10.1071/ch9860893.

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Reaction of the reduced pyrrolo [2,1-a] isoquinoline amine (1a) with cyanogen bromide in the presence of methanol gave the medium-ring cyanamide derivative 7,9,10-trimethoxy-2,3,4,5,6,7-hexahydro-1H-3- benzazonine-3-carbonitrile (2a). Analogous products were also obtained from reaction of the reduced 5H-oxazolo[2,3-a] isoquinoline , 2H- benzo [a] quinolizine , 2H,6H-[1,3] oxazino [2,3-a] isoquinoline and [1,4] oxazino [3,4-a] isoquinoline derivatives (1b-e), whereas the reduced 3H-oxazolo[4,3-a] isoquinoline and 5H-oxazolo[2,3-a] isoquinoline derivatives (1f) and (8) gave 1-(2,4-dioxapentyl)-6

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8

Gouda, Moustafa A., Hanan I. Althagbi, Nourah A. Al Zahrani, Ameen A. Abu-Hashem, Tahah A. Ameen, and Alshymaa Z. Al-Mokadem. "Synthesis, reactions and applications of pyrimido[2,1-a]isoquinolines derived from 1, 2-difunctionalized pyrimidine derivatives (Part V)." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 35, no. 01 (2025): 1. https://doi.org/10.59467/ijhc.2025.35.1.

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Pyrimido[2,1-a]isoquinolines (Py-[2,1-a]isoQs) are a class of heterocyclic compounds that have gained significant attention in the fields of organic chemistry, medicinal chemistry, and materials science. (Py-[2,1-a]isoQs) consist of a pyrimidine ring fused to an isoquinoline ring. This unique structure imparts distinct electronic and steric properties, making them attractive for various applications. They have been explored as potential therapeutic agents for treating cancer, and infectious diseases; their planar structure and conjugation make them suitable for applications in organic electron

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9

Pearson, Stuart, Shaun Fillery, Kristin Goldberg, et al. "Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions." Synthesis 50, no. 24 (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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10

Hammouda, M., A. S. El-Ahl, Y. M. El-Toukhee, and M. A. Metwally. "Reactions of Ketonic Mannich Bases with Malononitrile and Malononitrile dimer." Journal of Chemical Research 2002, no. 2 (2002): 89–94. http://dx.doi.org/10.3184/030823402103171258.

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The reaction of malononitrile with the tertiary Mannich base hydrochloride derived from acetophenone and some related compounds 1, 3, 5 and 7, in piperidine at 50°C afforded the pyrido[1,2-a]pyrimidine derivatives 2, tetrahydronaphthalene derivative 4 substituted quinolines 6 and benzopyran derivatives 8. While the condensation of malononitrile dimer with acetophenone, cyclohexanone and/ or α-tetralone Mannich bases hydrochloride 1, 3 and 9 gave the pyridine, isoquinoline and benzo[f]isoquinoline derivatives 10–12 in moderate to good yield.

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11

Vorobyeva, Daria V., Dmitry A. Petropavlovskikh, Ivan A. Godovikov, Fedor M. Dolgushin та 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, № 23 (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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12

Mosiagin, Ivan P., Olesya A. Tomashenko, Dar’ya V. Spiridonova, Mikhail S. Novikov, Sergey P. Tunik, and Alexander F. Khlebnikov. "Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings." Beilstein Journal of Organic Chemistry 17 (June 23, 2021): 1490–98. http://dx.doi.org/10.3762/bjoc.17.105.

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A wide range of derivatives with new pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline skeleton was synthesized by free-radical intramolecular cyclization of o-bromophenyl-substituted pyrrolylpyridinium salts using the (TMS)3SiH/AIBN system. The cyclization provides generally good yields of pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline hydrobromides having no additional radical-sensitive substituents. The free bases can be obtained from the synthesized hydrobromides in quantitative yield by basification at room temperature. The selectivity control of intramolecular arylation was achieved by replacing the halo

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13

NITYA, G. KUNDU, NANDI BIDISHA, CHANG JIH, and H. BOFHME PHILLIP. "DNA-Interacting Agents in Cancer Chemotherapy and Cyclopenta[f]isoquinoline Derivatives." Journal of Indian Chemical Society Vol. 74, Nov-Dec 1997 (1997): 877–83. https://doi.org/10.5281/zenodo.5900423.

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Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta-700 032 6 LAC-USC Cancer Research Laboratory, University of Southern California, Los Angeles, California 90033, U S A <em>Manuscript received 3 September 1997</em> Cancer chemotherapeutic agents have been briefly reviewed with an emphasis on DNA-binders. Cyclopenta[<em>f</em>]isoquinoline derivatives which we developed on CPK-molecular model studies, have been discussed. The synthesis of a few new cyclopenta[<em>f</em>]isoquinolines is also described.

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14

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 (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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15

Susanta, Kr. Borthakur, and N. Goswami Birendra. "Synthesis of 3,4,5,6,7,8-hexahydro-1-substituted phenyl isoquinoline and 3,4,5,6,7,8-hexahydro-1-substituted benzyl isoquinoline." Journal of Indian Chemical Society Vol. 84, Oct 2007 (2007): 1045–47. https://doi.org/10.5281/zenodo.5827264.

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Department of Chemistry, Handique Girls' College, Panbazar, Guwahati-781 001, Assam, India Formerly of the Synthetic Organic Chemistry Division, Regional Research Laboratory, Jorhat-785 006, Assam, India <em>E-mail</em>: drbngoswami@yahoo.com <em>Manuscript received 1 December 2006, accepted 20 July 2007</em> Isoquinoline derivatives arc obtained from amidcs using AICl<sub>3</sub>-KI in acetonitrile solvent. This eyclo dehydrating Lewis acid produced no side product and yield is above 95% isoquinoline derivative at room temperature.

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16

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 (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 tripheny

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17

Mao, Yanna, Kunjal Soni, Chetan Sangani, and Yongfang Yao. "An Overview of Privileged Scaffold: Quinolines and Isoquinolines in Medicinal Chemistry as Anticancer Agents." Current Topics in Medicinal Chemistry 20, no. 28 (2020): 2599–633. http://dx.doi.org/10.2174/1568026620999200917154225.

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: Cancer is one of the most difficult diseases and causes of death for many decades. Many pieces of research are continuously going on to get a solution for cancer. Quinoline and isoquinoline derivatives have shown their possibilities to work as an antitumor agent in anticancer treatment. The members of this privileged scaffold quinoline and isoquinoline have shown their controlling impacts on cancer treatment through various modes. In particular, this review suggests the current scenario of quinoline and isoquinoline derivatives as antitumor agents and refine the path of these derivatives to

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18

Balog, József, Zsuzsanna Riedl, György Hajós, Zsombor Miskolczy, and László Biczók. "New fluorescent isoquinoline derivatives." Tetrahedron Letters 52, no. 41 (2011): 5264–66. http://dx.doi.org/10.1016/j.tetlet.2011.07.143.

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19

Mohareb, Rafat Milad, Rehab Ali Ibrahim, Amira Mohamed Elmetwally, and Marwa Soliman Gamaan. "Synthesis of Fused Quinoline Derivatives with Antiproliferative Activities and Tyrosine Kinases, Pim-1 Kinase Inhibitions." Acta Chimica Slovenica 69, no. 1 (2022): 13–29. https://doi.org/10.17344/acsi.2021.6733.

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Cyclohexan-1,3-dione (1) reacted with either 2-aminoprop-1-ene-1,1,3-tricarbonitrile (2a) or diethyl 3-amino-2-cyanopent-2-enedioate (2b) to give the 5,6,7,8-tetrahydronaphthalene derivatives 3a and 3b, respectively. The latter compounds underwent further heterocyclization reactions to give the thieno[2’,3’:5,6]benzo[1,2-e][1,3]oxazine derivatives. On the other hand, the reaction of compound 1 with trichloroacetonitrile afforded the (2,2,2-trichloroethylidene)cyclohexane derivative 14. The latter underwent a series of reactions to produce 2,3,6,7-tetrahydroquinazoline, dihydrothieno[2,3-h]isoq

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20

Obydennik, Arina Y., Alexander A. Titov, Anna V. Listratova, et al. "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 (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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21

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 (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 tetrahydroisoqu

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22

S, Priyanka. "Recent advances in Synthesis & Pharmacotherapeutic potential of Benzothiazoles." Der Pharma Chemica 14, no. 1 (2022): 2. https://doi.org/10.5281/zenodo.13353756.

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Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in naturally occurring alkaloids including papaverine. The isoquinoline ring in these natural compounds derives from the aromatic amino acid tyrosine.

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23

Phillips, Matthew J. A., Alison T. Ung, Elizabeth J. Harry, Jason Ashmore, and Andrew M. McDonagh. "Synthesis and Investigation of Tricyclic Isoquinoline Derivatives as Antibacterial Agents." BioChem 5, no. 1 (2024): 1. https://doi.org/10.3390/biochem5010001.

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Isoquinoline derivatives exhibit a range of biological properties, including antibacterial activity, and are thus attractive as a scaffold for developing broad-spectrum antibacterial compounds. A series of six isoquinoline-based compounds were synthesized using the reaction of 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline with dimethyl acetylenedicarboxylate (DMAD) to provide the tricyclic (2Z)-[2-oxo-5,6-dihydropyrrolo[2,1,a]isoquinolin-3-ylidene]-2-ethanoate. The [2 + 3] cycloaddition of DMAD with C-6 and C-7 substituted 1-methyl-3,4-dihydroisoquinolines proceeded using aryl ethers or unsub

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24

Belguedj, Roumaissa, Sofiane Bouacida, Hocine Merazig, Ali Belfaitah, Aissa Chibani, and Abdelmalek Bouraiou. "Synthesis and crystal structures of three novel benzimidazole/benzoindolizine hybrids." Zeitschrift für Naturforschung B 71, no. 3 (2016): 231–39. http://dx.doi.org/10.1515/znb-2015-0164.

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AbstractThree benzoindolizine derivatives, 1, 2, and 3, were obtained via 1,3-dipolar cycloaddition. The reaction of 1-(2′-benzimidazolylmethyl)isoquinolinium ylides with dimethyl acetylenedicarboxylate gave a mixture of pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (1) and 1,10b-dihydropyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (2) derivatives containing a benzimidazole moiety. The reaction of this isoquinolinium N-ylide with dimethyl maleate gave an unexpected 2,3-dihydropyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (3). The structures of all reported compounds have been examined by X-ray cr

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25

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 (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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26

Defois, Mathilde, Chloé Rémondin, Béatrice Josselin, et al. "Synthesis and Kinase Inhibitory Potencies of Pyrazolo[3,4-g]isoquinolines." Molecules 27, no. 17 (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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27

Ma, Xue-Qin, Hua-Jie Zhang, Ya-Hui Zhang та ін. "Novel irreversible caspase-1 inhibitor attenuates the maturation of intracellular interleukin-1β". Biochemistry and Cell Biology 85, № 1 (2007): 56–65. http://dx.doi.org/10.1139/o06-149.

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. Caspase-1, the most efficient enzyme in processing the proinflammatory cytokines interleukin 1β and interleukin 18 in humans, is associated with inflammatory diseases such as rheumatoid arthritis, osteoarthritis, and some neuronal diseases. We previously reported that isoquinoline-1,3,4-trione and its derivatives are novel caspase-3 inhibitors that could attenuate apoptosis in vitro and in vivo. Here we report a novel derivative of isoquinoline-1,3,4-trione that is highly potent in inhibiting caspase-1 activity in an irreversible and slow-binding manner, thus inhibiting cellular caspase-1 ac

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28

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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29

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 effe

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30

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 (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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31

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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Mahmoud, Mahmoud R., Manal M. El-Shahawi, and Samira E. Farahat. "Novel isocoumarin and isoquinoline derivatives." Journal of Chemical Research 2008, no. 2 (2008): 86–88. http://dx.doi.org/10.3184/030823408x296212.

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Gzella, Andrzej, Danuta Brózda, Łukasz Koroniak, and Maria D. Rozwadowska. "Two optically active isoquinoline derivatives." Acta Crystallographica Section C Crystal Structure Communications 58, no. 8 (2002): o503—o506. http://dx.doi.org/10.1107/s0108270102011915.

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Milata, Viktor, Alexandra Svedova, Zuzana Barbierikova, et al. "Synthesis and Anticancer Activity of Novel 9-O-Substituted Berberine Derivatives." International Journal of Molecular Sciences 20, no. 9 (2019): 2169. http://dx.doi.org/10.3390/ijms20092169.

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Berberine is a bioactive isoquinoline alkaloid derived from many plants. Although berberine has been shown to inhibit growth and induce apoptosis of several tumor cell lines, its poor absorption and moderate activity hamper its full therapeutic potential. Here, we describe the synthesis of a series of 9-O-substituted berberine derivatives with improved antiproliferative and apoptosis-inducing activities. An analysis of novel berberine derivatives by EPR spectroscopy confirmed their similar photosensitivity and analogous behavior upon UVA irradiation as berberine, supporting their potential to

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Ohba, Shigeru, Noriaki Gomi, Tadaaki Ohgiya, and Kimiyuki Shibuya. "Three derivatives of 4-fluoro-5-sulfonylisoquinoline." Acta Crystallographica Section C Crystal Structure Communications 68, no. 10 (2012): o427—o430. http://dx.doi.org/10.1107/s0108270112039388.

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In 4-fluoroisoquinoline-5-sulfonyl chloride, C9H5ClFNO2S, (I), one of the two sulfonyl O atoms lies approximately on the isoquinoline plane as a result of minimizing the steric repulsion between the chlorosulfonyl group and the neighbouring F atom. In (S)-(−)-4-fluoro-N-(1-hydroxypropan-2-yl)isoquinoline-5-sulfonamide, C12H13FN2O3S, (II), there are two crystallographically independent molecules (Z′ = 2). The molecular conformations of these two molecules differ in that the amine group of one forms an intramolecular bifurcated hydrogen bond with the F and OH groups, whilst the other forms only

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Tantawy, Mohamed A., Farid M. Sroor, Magda F. Mohamed, et al. "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 (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 co

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Rao, Nalla Krishna, Tentu Nageswara Rao, Botsa Parvatamma, Y. Prashanthi, and Ravi Kumar Cheedarala. "Novel Synthesis of 4-Benzylidene-2-((1-phenyl-3,4-dihydroisoquinoline-2(1H)-yl)methyl) oxazol-5(4H)-one Derivatives Using 1,2,3,Tetrahydroisoquinoline and their Antimicrobial Activity." Current Organic Synthesis 17, no. 5 (2020): 396–403. http://dx.doi.org/10.2174/1570179417666200415151228.

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Aims: A series of six 4-benzylidene-2-((1-phenyl-3,4-dihydro isoquinoline-2(1H)-yl)methyloxazol- 5(4H)-one derivatives were synthesized by condensation of substituted aryl aldehydes with 2-(2-(1-phenyl-3,4- dihydro isoquinoline-2(1H)-acetamido)acetic acid in the presence of sodium acetate, acetic anhydride and zinc oxide as catalysts. Background: Novel Synthesis of 4-Benzylidene-2-((1-phenyl-3,4-dihy droisoquinoline-2(1H)-yl)methyl)oxazol- 5(4H)-one derivatives using 1,2,3,Tetrahydroisoquinoline and their antimicrobial activity. Objective: The title compounds can be synthesized from 1,2,3,4-te

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Khan, Taj-Malook, Noor Shad Gul, Xing Lu, et al. "Rhodium(iii) complexes with isoquinoline derivatives as potential anticancer agents: in vitro and in vivo activity studies." Dalton Transactions 48, no. 30 (2019): 11469–79. http://dx.doi.org/10.1039/c9dt01951k.

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Markmee, Sutthatip, Somsak Ruchirawat, Vilailak Prachyawarakorn, Kornkanok Ingkaninan, and Nantaka Khorana. "Isoquinoline derivatives as potential acetylcholinesterase inhibitors." Bioorganic & Medicinal Chemistry Letters 16, no. 8 (2006): 2170–72. http://dx.doi.org/10.1016/j.bmcl.2006.01.067.

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Galán, Abraham, Laura Moreno, Javier Párraga, et al. "Novel isoquinoline derivatives as antimicrobial agents." Bioorganic & Medicinal Chemistry 21, no. 11 (2013): 3221–30. http://dx.doi.org/10.1016/j.bmc.2013.03.042.

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Balasubramanian, Marudai, and Eric F. V. Scriven. "ChemInform Abstract: Isoquinoline and Its Derivatives." ChemInform 30, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199938240.

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Balog, József, Zsuzsanna Riedl, György Hajós, Zsombor Miskolczy, and László Biczók. "Novel fluorescent isoquinoline derivatives obtained via Buchwald-Hartwig coupling of isoquinolin-3-amines." Arkivoc 2012, no. 5 (2012): 109–19. http://dx.doi.org/10.3998/ark.5550190.0013.511.

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Abbasi, Maryam, Fariba Zamani Hargalani, Siavash Afrashteh, and Rezvaneh Rostamian. "Bio-Fe3O4-MNPs catalyzed green synthesis of pyrrolo[2,1-a]isoquinoline derivatives using isoquinolium bromide salts: study of antioxidant activity." Canadian Journal of Chemistry 97, no. 12 (2019): 848–55. http://dx.doi.org/10.1139/cjc-2019-0167.

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In this research, a novel, one-pot, efficient procedure with high yield for the synthesis of pyrrolo[2,1-a]isoquinoline derivatives using multi-component reaction of isoquinoline, alkyl bromides, and triphenylphosphine in the presence of Fe3O4-MNPs as catalyst under solvent-free conditions at room temperature is investigated. This study highlights an easy, simple, rapid, and clean method for the preparation of pyrrolo[2,1-a]isoquinoline derivatives. The Fe3O4-MNPs in these reactions were produced employing a green procedure by reduction of ferric chloride solution with pomegranate peel water e

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Undeela, Sridhar, Rajesh Chandra, Jagadeesh Babu Nanubolu, and Rajeev S. Menon. "Gold-catalysed regioselective cascade cycloisomerisation reactions of aza-enediynes for the synthesis of substituted benzoisoquinoline derivatives." Organic & Biomolecular Chemistry 17, no. 2 (2019): 369–73. http://dx.doi.org/10.1039/c8ob02544d.

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Xiao, Pu, Frédéric Dumur, Jing Zhang, et al. "Amino and nitro substituted 2-amino-1H-benzo[de]isoquinoline-1,3(2H)-diones: as versatile photoinitiators of polymerization from violet-blue LED absorption to a panchromatic behavior." Polymer Chemistry 6, no. 7 (2015): 1171–79. http://dx.doi.org/10.1039/c4py01409j.

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Bubnov, Yu N., E. V. Klimkina, I. V. Zhun', F. V. Pastukhov, and I. V. Yampolsky. "Allylic boron and zinc derivatives in synthesis and transformations of nitrogen heterocycles." Pure and Applied Chemistry 72, no. 9 (2000): 1641–44. http://dx.doi.org/10.1351/pac200072091641.

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Zhao, Wannian, Ping Xie, Min Zhang, et al. "Synthesis of isoquinoline-1,3(2H,4H)-dione derivatives via cascade reactions of N-alkyl-N-methacryloyl benzamide with aryl aldehydes." Org. Biomol. Chem. 12, no. 39 (2014): 7690–93. http://dx.doi.org/10.1039/c4ob01442a.

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Therkelsen, M., M. T. Rasmussen, and A. T. Lindhardt. "Decarboxylative Reissert type trifluoro- and trichloro-methylation of (iso)quinoline derivatives in batch and continuous flow." Chemical Communications 51, no. 47 (2015): 9651–54. http://dx.doi.org/10.1039/c5cc02807h.

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You, Yong, Wen-Ya Lu, Ke-Xin Xie, Jian-Qiang Zhao, Zhen-Hua Wang, and Wei-Cheng Yuan. "Enantioselective synthesis of isoquinoline-1,3(2H,4H)-dione derivatives via a chiral phosphoric acid catalyzed aza-Friedel–Crafts reaction." Chemical Communications 55, no. 58 (2019): 8478–81. http://dx.doi.org/10.1039/c9cc04057a.

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50

Huang, Sheng-Han, Wan-Yu Huang, Guo-Lun Zhang та Te-Fang Yang. "Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines". Molecules 26, № 20 (2021): 6126. http://dx.doi.org/10.3390/molecules26206126.

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It was found that 4-hydroxy-2-butenoic ester (11) could not react with 3,4-dihydro-isoquinoline (4a). Individual addition reactions of γ-mercapto-α,β-unsaturated esters (18) and -unsaturated amide (19) with 3,4-dihydroisoquinolines (4) were carried out under appropriate conditions to provide the corresponding thiazolo[2,3-α]isoquinoline derivatives with good yields (up to 87%) and significant diastereomeric selectivity. The mechanism of the crucial reaction was discussed.

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