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Journal articles on the topic 'Quinoxaline'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

El-Telbani, Emad M., Ibrahim Radini, and Sameh R. Elgogary. "Syntheses of tricyclic fused quinoxaline ring systems: Pyrazoloquinoxalines (a-review)." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 35, no. 02 (2025): 279. https://doi.org/10.59467/ijhc.2025.35.279.

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Quinoxaline derivatives have gained significant interest due to their diverse pharmacological activity and have been included in numerous marketed drugs used to treat of various diseases. Examples include glecaprevir (Mavyret), voxilaprevir (Vosevi), Balversa (L01EX16) (erdafitinib), carbadox, XK469R (NSC698215), and becampanel (AMP397). Among the five-membered fused tricyclic quinoxalines ring systems, the pyrazoloquinolines belong to the azaheterocyclic group as derivatives of quinoxalines and pyrazoles and have characterized by many biological and pharmaceutical properties. There are three

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2

Elgogary, Sameh R., Emad M. El-Telbani, and Ibrahim Radini. "Syntheses and Biological Activities of Tricyclic-fused Quinoxaline Ring Systems (A Review). Part I: Thienoquinoxalines." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 34, no. 02 (2024): 173. http://dx.doi.org/10.59467/ijhc.2024.34.173.

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Quinoxaline derivatives are an interesting class of heterocyclic compounds in drug discovery. It is rare in natural state, but their synthesis is easy to perform coupling between benzene and pyrazine rings. In addition, quinoxaline nucleus has received notable attention as an important pharmacophore that has broad-spectrum applications, especially in the fields of pharmaceutics and medicine. This review spotlights the biological activities and the different methods of preparation of three isomers of thienoquinoxalines, namely thieno[2,3-b]quinoxaline, thieno[3,4-b]quinoxaline, and thieno[2,3-g

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3

Soleymani, Mousa, and Mahdieh Chegeni. "The Chemistry and Applications of the Quinoxaline Compounds." Current Organic Chemistry 23, no. 17 (2019): 1789–827. http://dx.doi.org/10.2174/1385272823666190926094348.

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The quinoxaline derivatives are beneficial compounds because of their various medicinal and industrial applications. They are well-known for application in organic light emitting devices, polymers and pharmaceutical agents. The quinoxaline-containing polymers are applicable in optical devices due to their thermal stability and low band gap. There are many reported procedures for the synthesis of bis- and polyquinoxalines and quinoxaline-containing macrocycles. The quinoxaline-based compounds as fascinating structures are important subjects of interest in either basic or applied sciences. This

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4

El-Sawy, Eslam, Fatma Bassyouni, Sherifa Abu-Bakr, Hanaa Rady, and Mohamed Abdlla. "Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives." Acta Pharmaceutica 60, no. 1 (2010): 55–71. http://dx.doi.org/10.2478/v10007-010-0004-0.

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Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivativesStarting from 1-benzyl- (2a) and 1-benzoyl-3-bromoacetyl indoles (2b) new heterocyclic, 2-thioxoimidazolidine (4a, b), imidazolidine-2,4-dione (5a, b), pyrano(2,3-d)imida-zole (8a, band9a, b), 2-substituted quinoxaline (11a, b-17a, b) and triazolo(4,3-a)quinoxaline derivatives (18a, band19a, b) were synthesized and evaluated for their antimicrobial and anticancer activities. Antimicrobial activity screening performed with concentrations of 0.88, 0.44 and 0.22 μg mm-2showed that 3-(1-substitute

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5

Wu, Degui, Jian Zhang, Jianhai Cui, Wei Zhang, and Yunkui Liu. "AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C–H bond and direct conversion of 2-methyl quinoxalines into related nitriles." Chem. Commun. 50, no. 74 (2014): 10857–60. http://dx.doi.org/10.1039/c4cc01327a.

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A unique method for AgNO<sub>2</sub>-mediated direct nitration of the quinoxaline tertiary C–H bond and direct conversion of 2-methyl quinoxalines into 2-quinoxaline nitriles under oxidative conditions has been developed.

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6

Kasatkina, Svetlana O., Ekaterina E. Stepanova, Maksim V. Dmitriev, Ivan G. Mokrushin, and Andrey N. Maslivets. "Synthesis of pyrimido[1,6-a]quinoxalines via intermolecular trapping of thermally generated acyl(quinoxalin-2-yl)ketenes by Schiff bases." Beilstein Journal of Organic Chemistry 14 (July 11, 2018): 1734–42. http://dx.doi.org/10.3762/bjoc.14.147.

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Acyl(quinoxalin-2-yl)ketenes generated by thermal decarbonylation of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones react regioselectively with Schiff bases under solvent-free conditions to form pyrimido[1,6-a]quinoxaline derivatives in good yields.

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7

Chaouiki, Abdelkarim, Maryam Chafiq, Mohamed Rbaa, et al. "New 8-Hydroxyquinoline-Bearing Quinoxaline Derivatives as Effective Corrosion Inhibitors for Mild Steel in HCl: Electrochemical and Computational Investigations." Coatings 10, no. 9 (2020): 811. http://dx.doi.org/10.3390/coatings10090811.

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There has been substantial research undertaken on the role of green synthesized corrosion inhibitors as a substantial approach to inhibit the corrosion of metals and their alloys in acidic environments. Herein, electrochemical studies, surface characterization, and theoretical modeling were adopted to investigate the corrosion inhibition proprieties of novel synthesized quinoxaline derivatives bearing 8-Hydroxyquinoline, namely 1-((8-hydroxyquinolin-5-yl) methyl)-3,6-dimethylquinoxalin-2(1H)-one (Q1) and 1-((8-hydroxyquinolin-5-yl)methyl) quinoxalin-2(1H)-one (Q2) on mild steel corrosion in 1

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8

Ridhima, Chauhan, S. Chundawat N., and Pal Singh Girdhar. "Quinoxaline Derivatives: Synthesis and Biological Significance." Pharmaceutical and Chemical Journal 10, no. 3 (2023): 137–47. https://doi.org/10.5281/zenodo.13995628.

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Quinoxaline is a well-known and important nitrogen-containing heterocyclic compound with a complex ring consisting of a benzene ring and a pyrazine ring. Different modified quinoxalines and their derivatives with various functional groups are an important part of biological science, and important research projects are introduced in this course. Many methods have been developed to combine them. The demonstration that many quinoxaline derivatives have many biological activities encourages research in this field. There are many useful drugs such as antibiotics, antibiotics, antibiotics, antibioti

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9

Ruiz, Diego M., Juan C. Autino, Nancy Quaranta, Patricia G. Vázquez, and Gustavo P. Romanelli. "An Efficient Protocol for the Synthesis of Quinoxaline Derivatives at Room Temperature Using Recyclable Alumina-Supported Heteropolyoxometalates." Scientific World Journal 2012 (2012): 1–8. http://dx.doi.org/10.1100/2012/174784.

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We report a suitable quinoxaline synthesis using molybdophosphovanadates supported on commercial alumina cylinders as catalysts. These catalysts were prepared by incipient wetness impregnation. The catalytic test was performed under different reaction conditions in order to know the performance of the synthesized catalysts. The method shows high yields of quinoxaline derivatives under heterogeneous conditions. Quinoxaline formation was obtained using benzyl,o-phenylenediamine, and toluene as reaction solvent at room temperature. The CuH2PMo11VO40supported on alumina showed higher activity in t

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10

Yadav, Deepika, Surendra Nath Pandeya, Sachin Kumar, and Shewta Sinha. "Biological Activity of Quinoxaline Derivatives." International Journal of Current Pharmaceutical Review and Research 2, no. 1 (2011): 34–46. https://doi.org/10.5281/zenodo.12699293.

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Quinoxaline derivatives constitute an important class of heterocycles in drug discovery. They areclinically effective as antibacterial, antifungal, anti-inflammatory, anticancer, anti-tubercular andantineoplastic agents. Interestingly, it also shows hypoglycemic and antiglaucoma activity.Modification in their structure has offered a high degree of diversity that has proven useful for thedevelopment of new therapeutic agents having improved potency and lesser toxicity. Consideringthe extensive research on quinoxaline in the past, it was essential to review the wide spectrum ofbiological activit

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11

Goyal, Rakesh, Mukesh Sharma, Dharmendra Ahuja, and Anurekha Jain. "Synthesis and Evaluation of Phenol Derivatives of Sulfonyl Chloride Quinoxaline." Journal of Drug Delivery and Therapeutics 9, no. 4 (2019): 774–82. http://dx.doi.org/10.22270/jddt.v9i4.3016.

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The objective of the present study was to synthesize some new 7-sulfonate of 2, 3- Diphenyl quinoxaline which are more potential as antibacterial than parent quinoxalines. The present study was synthesis of derivatives of sulfonyl chloride quinoxaline and physicochemical and spectral characterization, in vitro antimicrobial screening against gram positive and gram negative bacteria.The concentration of derivatives used as 200 and 400 microgram initially. When 200 µg concentrations was used R6 shows sensitivity towards S. aureus and R6 shows sensitivity towards gram negative E. coli organism. W

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12

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000550.

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Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety

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13

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000550/jcsp/43.01.2021.

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Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety

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14

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000009.

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Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety

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15

Zayed, Mohamed F. "Chemistry, Synthesis, and Structure Activity Relationship of Anticancer Quinoxalines." Chemistry 5, no. 4 (2023): 2566–87. http://dx.doi.org/10.3390/chemistry5040166.

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Quinoxaline is a fused heterocycle system of a benzene ring and pyrazine ring. It has earned considerable attention due to its importance in the field of medicinal chemistry. The system is of extensive importance due to its comprehensive array of biological activities. Quinoxaline derivatives have been used as anticancer, anticonvulsant, anti-inflammatory, antidiabetic, antioxidant, antibacterial, anti-TB, antimalarial, antiviral, anti-HIV, and many other uses. Variously substituted quinoxalines are significant therapeutic agents in the pharmaceutical industry. This review spotlights on the ch

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16

Irfan, Ali, Sajjad Ahmad, Saddam Hussain, et al. "Recent Updates on the Synthesis of Bioactive Quinoxaline-Containing Sulfonamides." Applied Sciences 11, no. 12 (2021): 5702. http://dx.doi.org/10.3390/app11125702.

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Quinoxaline is a privileged pharmacophore that has broad-spectrum applications in the fields of medicine, pharmacology and pharmaceutics. Similarly, the sulfonamide moiety is of considerable interest in medicinal chemistry, as it exhibits a wide range of pharmacological activities. Therefore, the therapeutic potential and biomedical applications of quinoxalines have been enhanced by incorporation of the sulfonamide group into their chemical framework. The present review surveyed the literature on the preparation, biological activities and structure-activity relationship (SAR) of quinoxaline su

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17

Viji, Mayavan, Manjunatha Vishwanath, Jaeuk Sim та ін. "α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction". RSC Advances 10, № 61 (2020): 37202–8. http://dx.doi.org/10.1039/d0ra07093a.

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18

Rodriguez-Afanado, Michael Daniela, Fabian Lopez-Vallejo, Cristian Ochoa-Puentes, Luz M. Salazar, and Carlos Yesid Soto. "Pyrrolo[1,2-a]quinoxalinic Core-Derived Compounds Targeting the Mycobacterium tuberculosis P-type ATPase Plasma Membrane Ca2+ Transporter, CtpF, as Potential Antituberculous Drugs." International Journal of Mycobacteriology 14, no. 1 (2025): 10–23. https://doi.org/10.4103/ijmy.ijmy_197_24.

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Background: The resistance of Mycobacterium tuberculosis (Mtb) on first- and second-line anti-tuberculosis (TB) drugs is an issue for TB control; therefore, developing new anti-TB drugs is a priority in TB research. In this sense, the Ca2+ P-type ATPase plasma membrane transporter CtpF is an interesting anti-TB drug target. Methods: In this work, the activity of 4C-substituted pyrrolo[1,2-a]quinoxalinic compounds on Mtb viability and Ca2+ ATPase activity mediated by the plasma membrane transporter, CtpF, was assessed. The pyrrolo[1,2-a]quinoxalines compounds were initially in silico and analyz

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19

Khatoon, Hena, and Emilia Abdulmalek. "Novel Synthetic Routes to Prepare Biologically Active Quinoxalines and Their Derivatives: A Synthetic Review for the Last Two Decades." Molecules 26, no. 4 (2021): 1055. http://dx.doi.org/10.3390/molecules26041055.

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Quinoxalines, a class of N-heterocyclic compounds, are important biological agents, and a significant amount of research activity has been directed towards this class. They have several prominent pharmacological effects like antifungal, antibacterial, antiviral, and antimicrobial. Quinoxaline derivatives have diverse therapeutic uses and have become the crucial component in drugs used to treat cancerous cells, AIDS, plant viruses, schizophrenia, certifying them a great future in medicinal chemistry. Due to the current pandemic situation caused by SARS-COVID 19, it has become essential to synth

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20

Montana, Marc, Vincent Montero, Omar Khoumeri, and Patrice Vanelle. "Quinoxaline Derivatives as Antiviral Agents: A Systematic Review." Molecules 25, no. 12 (2020): 2784. http://dx.doi.org/10.3390/molecules25122784.

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Background: In recent decades, several viruses have jumped from animals to humans, triggering sizable outbreaks. The current unprecedent outbreak SARS-COV-2 is prompting a search for new cost-effective therapies to combat this deadly pathogen. Suitably functionalized polysubstituted quinoxalines show very interesting biological properties (antiviral, anticancer, and antileishmanial), ensuring them a bright future in medicinal chemistry. Objectives: Focusing on the promising development of new quinoxaline derivatives as antiviral drugs, this review forms part of our program on the anti-infectio

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21

Ou, Zhongping, Wenbo E, Jianguo Shao, et al. "Electrochemical and spectroelectrochemical properties of building blocks for molecular arrays: reactions of quinoxalino[2,3-b]porphyrins containing metal(II) ions." Journal of Porphyrins and Phthalocyanines 09, no. 02 (2005): 142–51. http://dx.doi.org/10.1142/s1088424605000216.

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Quinoxalino[2,3-b]porphyrins are laterally-extended porphyrins with aromatic ring systems fused to the β,β'-positions of a pyrrolic ring of the macrocycle. They are building blocks for coplanar laterally-extended oligoporphyrins with applications in molecular electronics. The electrochemistry and spectroelectrochemistry of four such quinoxalinoporphyrins containing metal(II) ions and one free-base quinoxalinoporphyrin dissolved in nonaqueous media have been investigated and the data are compared to that seen for the same derivatives of the parent macrocycle lacking the fused quinoxaline ring.

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22

Liu, Yali, Yu Wei, Zhen Yang, Yang Li, Yan Liu, and Ping Liu. "Highly selective C3–H iodination of pyrrolo[1,2-a]quinoxalines." Organic & Biomolecular Chemistry 19, no. 23 (2021): 5191–96. http://dx.doi.org/10.1039/d1ob00759a.

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23

Goswami, Shyamaprosad, Shampa Chakraborty, Avijit Kumar Das, et al. "Selective colorimetric and ratiometric probe for Ni(ii) in quinoxaline matrix with the single crystal X-ray structure." RSC Adv. 4, no. 40 (2014): 20922–26. http://dx.doi.org/10.1039/c4ra00594e.

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A quinoxaline based colorimetric nickel sensor,HQAP[2-(quinoxalin-2-ylmethyleneamine)phenol] with high selectivity and sensitivity toward Ni<sup>2+</sup>ions is shown to have potential for practical use.

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24

EI-Bendary, E. R., F. E. Goda, A. R. Maarouf, and F. A. Badria. "Synthesis and antimicrobial evaluation of 3-hydrazino-quinoxaline derivatives and their cyclic analoaues." Scientia Pharmaceutica 72, no. 2 (2004): 175–85. http://dx.doi.org/10.3797/scipharm.aut-04-15.

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A series of quinoxaline derivatives has been synthesized by reacting 3-hydrazinoquinoxalines 1a,b with many bifunctional reagents. Reaction of 1a,b with chloroacetyl chloride and ethyl chloroacetate afforded 1-chloromethyl[1,2,4]tnazoIo[4,3-a]quinoxalines 2a,b and dihydro[1,2,4]triazino[4,3-a]quinoxalin-2-ones 3a,b respectively. Condensation of 1a,b with ethyl acetoacetate and acetylacetone yielded 2-quinoxalinylhydrazonobutanoates 4a,b and 2-quinoxalinylhydrazono-2-pentanones 5a,b respectively. Cyclization of 5a,b gave 3,5-dimethylpyrazolylquinoxalines 6a,b. Moreover, reaction of compounds 2a

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25

Kamal, Ahmed, Korrapati Suresh Babu, Shaikh Faazil, S. M. Ali Hussaini, and Anver Basha Shaik. "l-Proline mediated synthesis of quinoxalines; evaluation of cytotoxic and antimicrobial activity." RSC Adv. 4, no. 86 (2014): 46369–77. http://dx.doi.org/10.1039/c4ra08615e.

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A simple, greener and highly efficient method for the synthesis of functionalized quinoxalines has been developed employing l-proline as a catalyst in water. The newly synthesized quinoxaline–sulphonamide conjugates exhibited significant cytotoxic and antimicrobial activities.

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26

Li, Yuwen, Mei Qiu, Yubin Bai, Shaoqi Qu, and Zhihui Hao. "Improved synthesis of quinocetone and its two desoxymetabolites." Journal of the Serbian Chemical Society 83, no. 3 (2018): 265–70. http://dx.doi.org/10.2298/jsc170614118l.

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Oxidation of o-nitroaniline with sodium hypochlorite afforded benzofurazan oxide in 96 % yield, and treatment of benzofurazan oxide with acetylacetone in the presence of triethylamine gave 2-acetyl-3-methyl-quinoxaline- -1,4-dioxide in 94 % yield. Finally, condensation of 2-acetyl-3-methyl-quinoxaline- 1,4-dioxide with benzaldehyde using 4-(dimethylamino)pyridinium acetate as a catalyst led to quinocetone in 95 % yield. Subsequently, reduction of the synthesized quinocetone with sodium dithionite resulted in two deoxy derivatives, 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one and

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27

Kovrizhina, Anastasia R., Elizaveta I. Samorodova, and Andrei I. Khlebnikov. "11H-Indeno[1,2-b]quinoxalin-11-one 2-(4-ethylbenzylidene)hydrazone." Molbank 2021, no. 4 (2021): M1299. http://dx.doi.org/10.3390/m1299.

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11H-Indeno[1,2-b]quinoxaline derivatives present an important type of nitrogen-containing heterocyclic compound that are useful intermediate products in organic synthesis and have potential pharmaceutical applications. A new 11H-indeno[1,2-b]quinoxalin-11-one-2-(4-ethylbenzylidene)hydrazone (compound 3) was synthesized. Compound 3 is the first example of an azine derivative based on the 11H-indeno[1,2-b]quinoxaline system. The Z,E-isomerism of compound 3 was investigated by DFT calculations. Bioavailability was evaluated in silico using ADME predictions. According to the ADME results, compound

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28

Mamedov, Vakhid A. "Recent advances in the synthesis of benzimidazol(on)es via rearrangements of quinoxalin(on)es." RSC Advances 6, no. 48 (2016): 42132–72. http://dx.doi.org/10.1039/c6ra03907c.

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The review describes all the quinoxaline-benzimidazole rearrangements as a whole and the new quinoxalinone-benzimidazol(on)e rearrangements in particular when exposed to nucleophilic rearrangements which can be used for the synthesis of various biheterocyclic motifs.

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29

M., Z. A. BADR, A. MAHGOUB S., M. ATTA F., S. MOUSTAFA O., and M. ABO EL-LATIF F. "Synthesis and Chemistry of 3-Amino- and 3-Hydrazocarbonylquinoxalinone Derivatives." Journal of Indian Chemical Society Vol. 71, Oct 1994 (1994): 617–19. https://doi.org/10.5281/zenodo.5896678.

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Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt <em>Manuscript received 4 June 1993, accepted 18 August 1993</em> 3-Ethoxycarbonyl-2(1<em>H</em>)-quinoxalinone (1) reacts with nucleophiles, namely, dimethylamine, diethylamine, <em>o</em>- phenylenediamine and/or p-phenylenediamine to produce the corresponding 3-<em>N</em>-substituted-aminocarbonyl-2(1<em>H)</em>-quinoxalinones (3-6). Treatment of 1 with hydrazine hydrate produces the 2(1<em>H</em>)-quinoxalinone-3-carbohydrazide (2) with acylating reagents, namely, acetic anhydride, acetic acid or acetyl chloride/pyr

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30

M., A. El-Sekily, H. Mancy S., and Kh. El-Sekely M. "Synthesis and characterisation of triazolo- and pyrazol-3-yl quinoxaline derivatives from dehydro-L-ascorbic acid hydrazone and their antimicrobial activity." Journal of India Chemical Society Vol. 95, Jun 2018 (2018): 641–49. https://doi.org/10.5281/zenodo.5642875.

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Department of Chemistry, Faculty of Science, University of Alexandria, Ibrahimia, P.O.Box 426, 21321 Alexandria, Egypt E-mail: prof_dr_m_a_elsekily@yahoo.com Department of Physics and Chemistry, Faculty of Education, University of Alexandria, El-Chatby, Alexandria, Egypt Department of Chemistry, Faculty of Science, Alexandria University, Egypt <em>Manuscript received 08 February 2018, revised 14 February 2018, accepted 29 May 2018</em> The 4-(pyrazol-3-yl)[1,2,4]triazolo[4,3-a]quinoxaline derivatives 4a-c were prepared by the reaction of 2-chloro-3-[5- (acetoxymethyl)-1-phenylpyrazol-3-yl]quin

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31

Gavernet, Luciana, Pablo Hernan Palestro, and Luis Bruno-Blanch. "Docking Applied to the Study of Inhibitors of c-Met Kinase." ISRN Physical Chemistry 2012 (December 13, 2012): 1–5. http://dx.doi.org/10.5402/2012/391897.

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Quinoxaline derivatives were studied as inhibitors of c-Met kinase, a receptor associated with high tumor grade and poor prognosis in a number of human cancers. In this paper we used docking methodologies to predict the binding conformation of a set of quinoxalines and to explain the differences of biological activities previously reported.

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32

Patinote, Cindy, Sandy Raevens, Amélie Baumann, Eloise Pellegrin, Pierre-Antoine Bonnet, and Carine Deleuze-Masquéfa. "[1,2,4]triazolo[4,3-a]quinoxaline as Novel Scaffold in the Imiqualines Family: Candidates with Cytotoxic Activities on Melanoma Cell Lines." Molecules 28, no. 14 (2023): 5478. http://dx.doi.org/10.3390/molecules28145478.

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Cutaneous melanoma is one of the most aggressive human cancers and is the deadliest form of skin cancer, essentially due to metastases. Novel therapies are always required, since cutaneous melanoma develop resistance to oncogenic pathway inhibition treatment. The Imiqualine family is composed of heterocycles diversely substituted around imidazo[1,2-a]quinoxaline, imidazo[1,2-a]pyrazine, imidazo[1,5-a]quinoxaline, and pyrazolo[1,5-a]quinoxaline scaffolds, which display interesting activities on a panel of cancer cell lines, especially melanoma cell lines. We have designed and prepared novel com

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33

Bowroju, Suresh Kuarm, Hanumaiah Marumamula, and Rajitha Bavanthula. "One-pot protocol for the synthesis of quinoxalines from styrenes, o-phenylenediamine and benzo[c][1,2,5]thiadiazole-4,5-diamine using triiodoisocyanuric acid." Organic Communications 14, no. 1 (2021): 48–57. http://dx.doi.org/10.25135/acg.oc.93.2009.1800.

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Triiodoisocyanuric acid (TICA) controlled one-pot and easy-operational protocol has been developed for the synthesis of substituted phenylquinoxalines (3a-3i) and phenyl-[1,2,5]thiadiazolo[3,4-f]quinoxaline (5a-5f) from styrenes with o-phenylenediamine and benzo[c][1,2,5]thiadiazole-4,5-diamine respectively. The reaction involves co-bromination and oxidation for the formation of an a-bromo ketone as an intermediate in the presence of triiodoisocyanuric acid, followed by condensation with the o-phenylenediamine and benzo[c][1,2,5]thiadiazole-4,5-diamine for the formation of phenylquinoxalines (

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34

Piltan, Mohammad. "One-Pot Synthesis of Thiazolo[3,4-a]Quinoxalines from 1,2-Diamines, Aryl Isothiocyanates and Ethyl Bromopyruvate." Journal of Chemical Research 41, no. 12 (2017): 712–14. http://dx.doi.org/10.3184/174751917x15127369231305.

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Some hitherto unreported thiazolo[3,4- a]quinoxaline derivatives have been synthesised in excellent yields via a one-pot, three-component reaction of benzene-1,2-diamines, ethyl bromopyruvate and aryl isothiocyanates in MeCN, for the first time. The protocol avoids the use of any catalysts or chromatographic separations and provides a wide range of novel thiazolo[3,4- a]quinoxalines.

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35

Lima, Rafaely N., Jaqueline R. Gonçalves, Valdenizia R. Silva, et al. "Antioxidant, Antitumor and Bactericidal Activities of Ethyl Gallate Quinoxalines." Current Bioactive Compounds 16, no. 6 (2020): 900–910. http://dx.doi.org/10.2174/1573407215666190318144105.

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Background: Quinoxaline, a fused heterocycle of benzene and pyrazine rings are becoming recognized as a potent class of anti-cancer compounds, such as, in a wide array of pharmacological activities. Methods: We evaluate the three gallate quinoxalines (G-A1, G-A2, and G-A3) as c-Met kinase inhibitors using a docking study, in vitro anticancer potential measurements, antioxidant and bactericidal activities. Results: The docking study showed hydrogen bond linkage of quinoxalines with amino acids at active site of c-Met kinase structures, indicating a possible cancer inhibition cell proliferation.

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36

Hossain, MM, MM Hossain, MH Muhib, MR Mia, S. Kumar, and SA Wadud. "In vitro antioxidant potential study of some synthetic quinoxalines." Bangladesh Medical Research Council Bulletin 38, no. 2 (2012): 47–50. http://dx.doi.org/10.3329/bmrcb.v38i2.12880.

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In continuation of our study the in vitro antioxidant activity of some novel quinoxaline derivatives was investigated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method with respect to ascorbic acid. To determine the antioxidant activity, a number of substituted indoxyls (3A-G), cyclic ketones (2A-G), and quinoxalines (1A-G) were synthesized by both microwave and conventional heating methods. The present findings revealed that some quinoxalines and their precursors (1D, 1F, 1G and 2E) exhibited a marked scavenging effect on DPPH radical. DOI: http://dx.doi.org/10.3329/bmrcb.v38i2.12880 Bangladesh

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37

Yan, Rulong, and Xin Guan. "Copper-Catalyzed Synthesis of Alkyl-Substituted Pyrrolo[1,2-a]quinoxalines from 2-(1H-Pyrrol-1-yl)anilines and Alkylboronic Acids." Synlett 31, no. 04 (2020): 359–62. http://dx.doi.org/10.1055/s-0037-1610743.

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A radical pathway for the construction of pyrrolo[1,2-a]quinoxalines by using 2-(1H-pyrrol-1-yl)anilines and alkylboronic acids has been developed. Features of this process include Cu catalysis, readily accessible starting materials, and simple operations. Alkylboronic acids are used for the construction of pyrrolo[1,2-a]quinoxaline derivatives, and the desired products are obtained in moderate yields.

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38

Ho, Tuan Hoang. "Iron(III) promoted oxidative annulation of benzylic C-H bonds in (α-amino)arylacetic acids for synthesis of 4-aryl pyrrolo[1,2-a]quinoxalines". Ministry of Science and Technology, Vietnam 65, № 4 (2023): 11–13. http://dx.doi.org/10.31276/vjste.65(4).11-13.

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Using amino acids for synthesis of heterocycles is a synthetically promising field. However, developing the practical methods for transformations of amino acids into heterocycles is still challenging. Given that alpha amino acids are abundant or easily prepared, herein we report a method for annulation of benzylic C-H bonds in derivatives of 2-phenylglycine with 1-(2-nitroaryl)pyrroles. The reactions proceeded well in the presence of iron(III) acetylacetonate catalyst and potassium carbonate base. Scope of pyrrolo[1,2-a]quinoxalines was studied. Regardless of electronic properties of substitue

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39

Azizian, Javad, Shahab Zomorodbakhsh, Mahdieh Entezari, and Hossein Anaraki-Ardakani. "Functionalization of Carboxylated Multi-Wall Nanotubes with Derivatives ofN1-(11H-Indeno[1,2-b]quinoxalin-11-ylidene)benzene-1,4-diamine." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/917970.

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Quinoxaline derivatives are compounds with pharmaceutical applications. In this study, derivatives ofN1-(11H-indeno[1,2-b]quinoxalin-11-ylidene)benzene-1,4-diamine were synthesized and attached to carboxylated multi-wall nanotubes (MWNT–COOH). Functionalized carbon nanotubes were characterized by scanning electron microscopy (SEM) to study the shape of structures, transmission electron microscopy (TEM), fast Fourier transform infrared (FT-IR), Raman spectroscopy, and elemental analysis.

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40

Tang, Xiang-Ying, Yue-fa Gong, and Heng-rui Huo. "Metal-Free Synthesis of Pyrrolo[1,2-a]quinoxalines Mediated by TEMPO Oxoammonium Salts." Synthesis 50, no. 14 (2018): 2727–40. http://dx.doi.org/10.1055/s-0037-1610131.

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We herein describe a novel TEMPO oxoammonium salt initiated Pictet–Spengler reaction of imines, generated in situ from carbonyl compounds and pyrrole- or indole-containing substrates, to afford 4,5-dihydropyrrolo[1,2-a]quinoxalines or 5,6-dihydroindolo[1,2-a]quinoxalines in good to excellent yields. Moreover, a one-pot synthesis of a biologically important quinoxaline is achieved via a cyclization–dehydrogenation process using one equivalent of the oxoammonium salt.

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41

Yao, Hua, Sen Lin, Xiaoyang Zhong, Bingqing Wang, Zhaohua Yan, and Feng Xiong. "H2O2-Promoted Alkylation of Quinoxalin-2(1H)-ones with Styrenes and Dimethyl Sulfoxide." Synlett 32, no. 12 (2021): 1213–18. http://dx.doi.org/10.1055/a-1507-6499.

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AbstractA hydrogen peroxide (H2O2)-mediated quinoxaline-2(1H)-ones hydrocarbylation reaction has been reported. The reaction is achieved through the difunctionalization of styrene. In this transformation, methyl radical resulting from dimethyl sulfoxide firstly attacks styrenes to provide alkyl radicals which then undergo alkylation at the C3 position of quinoxalin-2(1H)-one. A green, convenient, and simple protocol for the synthesis of 3-alkylquinoxalin-2(1H)-ones was provided.

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42

Nhari, Laila M., Elham N. Bifari, Aisha R. Al-Marhabi, et al. "Synthesis of Novel Key Chromophoric Intermediates via C-C Coupling Reactions." Catalysts 12, no. 10 (2022): 1292. http://dx.doi.org/10.3390/catal12101292.

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The fundamentals of Pd-catalyzed Csp2−Csp2 Miyaura borylation, Suzuki cross-coupling, and Stille cross-coupling reactions for a variety of borylated precursors based on phenothiazine (PTZ), phenoxazine (POZ), carbazole (Cz), and quinoxaline (QX) units have been explored. Three palladium-based catalysts were chosen for this study: Pd(PPh3)4, Pd(PPh3)2Cl2, and Pd(dppf)Cl2, applying different reaction conditions. Around 16 desired chromophores were successfully designed and synthesized using C-C cross-coupling reactions in moderate to excellent yields, including PTZ, POZ, and Cz units coupled wit

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43

Montero, Vincent, Marc Montana, Omar Khoumeri, Florian Correard, Marie-Anne Estève, and Patrice Vanelle. "Synthesis, In Vitro Antiproliferative Activity, and In Silico Evaluation of Novel Oxiranyl-Quinoxaline Derivatives." Pharmaceuticals 15, no. 7 (2022): 781. http://dx.doi.org/10.3390/ph15070781.

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The quinoxaline core is a promising scaffold in medicinal chemistry. Multiple quinoxaline derivatives, such as the topoisomerase IIβ inhibitor XK-469 and the tissue transglutaminase 2 inhibitor GK-13, have been evaluated for their antiproliferative activity. Previous work reported that quinoxaline derivatives bearing an oxirane ring present antiproliferative properties against neuroblastoma cell lines SK-N-SH and IMR-32. Likewise, quinoxalines with an arylethynyl group displayed promising antineoplastic properties against glioblastoma and lung cancer cell lines, U87-MG and A549 respectively. H

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44

Nicolescu, Alina, Emilian Georgescu, Florea Dumitrascu, et al. "Exocyclic Enamines of Pyrrolo[1,2-a]quinoxalines Generated by 1,3-dipolar Cycloaddition Reactions of Benzimidazolium Ylides to Activated Alkynes." Revista de Chimie 71, no. 3 (2001): 197–209. http://dx.doi.org/10.37358/rc.20.3.7989.

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The reactions of N-acetonylbenzimidazolium chlorides with various activated alkynes, in the presence of bases, led under mild conditions to a mixture of pyrrolo[1,2-a]benzimidazoles (3), 4-methylene-pyrrolo[1,2-a]quinoxaline derivatives (4) and pyrrolo[1,2-a]quinoxalin-4-one derivatives (5). The exocyclic enamine derivatives 4 have been fully characterized by multinuclear NMR spectroscopy and X-ray crystallography. A mechanism rationalizing the formation of the enamine derivatives is proposed.

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45

Guillon, Jean, Solène Savrimoutou, Sandra Rubio, et al. "1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one: Synthesis, Crystal Structure and Anti-Leukemic Activity." Molbank 2020, no. 1 (2020): M1113. http://dx.doi.org/10.3390/m1113.

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1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential against several human leukemia cell lines (K562, HL60, and U937 cells).

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46

Rahman, Faiz-Ur, Yong-sheng Li, Ioannis D. Petsalakis, Giannoula Theodorakopoulos, Julius Rebek, and Yang Yu. "Recognition with metallo cavitands." Proceedings of the National Academy of Sciences 116, no. 36 (2019): 17648–53. http://dx.doi.org/10.1073/pnas.1909154116.

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We describe here the effects of metal complexation on the molecular recognition behavior of cavitands with quinoxaline walls. The nitrogen atoms of the quinoxalines are near the upper rim of the vase-like shape and treatment with Pd(II) gave 2:1 metal:cavitand derivatives. Characterization by 1H, 13C NMR spectroscopy, HR ESI-MS, and computations showed that the metals bridged adjacent quinoxaline panels and gave cavitands with C2v symmetry. Both water-soluble and organic-soluble versions were prepared and their host/guest complexes with alkanes, alcohols, acids, and diols (up to C12) were stud

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47

Y., A. AMMAR, M. ISMAIL I., M. SH. EL-SHARIEF A., A. MOHAMED Y., and M. AMER R. "Synthesis of some Newer Thiazolo and Thiadiazino Derivatives from 6-Methyl- or 6-Nitro-2,3-dichloroquinoxalines." Journal of Indian Chemical Society Vol. 66, Feb 1989 (1989): 124–27. https://doi.org/10.5281/zenodo.6303632.

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Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt <em>Manuscript received 23 October 1987, revised 18 August 1988, accepted 18 November 1988</em> lnteraction or 6-methyl or 6-nitro-2,3-dichloroquinoxaline (1a, b) with thiourea in ethanol led to the formation or diquinoxalino[2,3-<em>b</em>: 2',3'-<em>e</em>]-1,4-dithiien derivatives (2a, b) with 2-imino-2,3-dihydrothiazolol [4,5-<em>b</em> ]quinoxalines (3a, b). 7-Methyl- or 7- nitro-3-amino-2-imino-2,3-dihydrothiazolo[4,5-<em>b</em>]quinoxaline (6a, b) were prepared and reacted with acid

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48

Kathrotiya, Haresh G., Sagar P. Gami, and Yogesh T. Naliapara. "An Efficient and Clean Synthesis of Thiophenyl Thiazole Depended Novel Triazolo[4,3-a]Quinoxaline Derivatives." International Letters of Chemistry, Physics and Astronomy 51 (May 2015): 125–34. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.51.125.

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A simple and efficient approach for the synthesis of thiophenyl thiazole based triazolo [4,3-a] quinoxaline derivatives is described. In this methodology, 3-hydrazinyl-N-(4-(thiophen-2-yl) thiazol-2-yl) quinoxalin-2-amine derivatives treated with various aromatic aldehyde to form Schiff base which on treatment with iodobenzene diacetate in dichloromethane at room temperature to furnish title compounds. The synthesized compounds were characterized by 1H NMR, 13C NMR, FT-IR, elemental analysis, and mass spectral data

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49

Kathrotiya, Haresh G., Sagar P. Gami, and Yogesh T. Naliapara. "An Efficient and Clean Synthesis of Thiophenyl Thiazole Depended Novel Triazolo[4,3-<i>a</i>]Quinoxaline Derivatives." International Letters of Chemistry, Physics and Astronomy 51 (May 15, 2015): 125–34. http://dx.doi.org/10.56431/p-flw9zc.

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A simple and efficient approach for the synthesis of thiophenyl thiazole based triazolo [4,3-a] quinoxaline derivatives is described. In this methodology, 3-hydrazinyl-N-(4-(thiophen-2-yl) thiazol-2-yl) quinoxalin-2-amine derivatives treated with various aromatic aldehyde to form Schiff base which on treatment with iodobenzene diacetate in dichloromethane at room temperature to furnish title compounds. The synthesized compounds were characterized by 1H NMR, 13C NMR, FT-IR, elemental analysis, and mass spectral data

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50

Guillon, Jean, Solène Savrimoutou, Sandra Albenque-Rubio, et al. "Synthesis, Crystal Structure and Anti-Leukemic Activity of (E)-Pyrrolo[1,2-a]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one." Molbank 2023, no. 3 (2023): M1691. http://dx.doi.org/10.3390/m1691.

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(E)-Pyrrolo[1,2-a]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one was designed then synthesized using a multi-step pathway starting from commercially available 2-nitroaniline. Structure characterization of this original substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline shows interesting cytotoxic potential against different human leukemia cell lines (MV4-11, K562, MOLM14 and Jurkat cells).

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