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Journal articles on the topic 'Phenoxazine derivatives'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Journal, Baghdad Science. "Synthesis of New N-Substituted Phenoxazine Derivatives." Baghdad Science Journal 13, no. 2 (2016): 360–65. http://dx.doi.org/10.21123/bsj.13.2.360-365.

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This work comprises the synthesis of new phenoxazine derivatives containing N-substituted phenoxazine starting from phenoxazine (1). Synthesis of ethyl acetate phenoxazine (2) through the reaction of phenoxazine with ethylchloroacetate, which reacted with hydrazine hydrate to give 10-aceto hydrazide phenoxazine (3), then reacted with formic acid to give 10-[N-formyl acetohydrazide] phenoxazine (4). Reaction of compound (4) with phosphorous pentaoxide or phosphorus pentasulphide to gave 10-[N-methylene-1,3,4-oxadiazole] phenoxazine (5) and 10-[N-methylene-1,3,4-thiadiazole] phenoxazine (6).

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2

Hu, Bin, Haizeng Song, Xinlei Zhang, Yuan He, Jingshun Ren, and Jingbin Huang. "Effects of Phenoxazine Chromophore on Optical, Electrochemical and Electrochromic Behaviors of Carbazole–Thiophene Derivatives." Polymers 16, no. 24 (2024): 3546. https://doi.org/10.3390/polym16243546.

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Phenoxazine, as an organic-small-molecule chromophore, has attracted much attention for its potential electrochromic applications recently. To develop appealing materials, phenoxazine chromophores were introduced at the N-position of carbazole–thiophene pigment, yielding two novel monomers (DTCP and DDCP), whose chemical structures were characterized by NMR, HRMS and FTIR. The results of the optical property study indicate that little influence could be observed in the presence of the phenoxazine chromophore. Corresponding polymer films on the surface of an ITO/glass electrode were obtained th

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3

Iqbal, Nadeem, and Yoshio Ueno. "Synthesis of crowned phenoxazine derivatives." Monatshefte f�r Chemie Chemical Monthly 123, no. 6-7 (1992): 655–58. http://dx.doi.org/10.1007/bf00816860.

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4

Kulszewicz-Bajer, Irena, Malgorzata Zagorska, Marzena Banasiewicz, et al. "Effect of the substituent position on the electrochemical, optical and structural properties of donor–acceptor type acridone derivatives." Physical Chemistry Chemical Physics 22, no. 16 (2020): 8522–34. http://dx.doi.org/10.1039/d0cp00521e.

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5

Ferreira, João Carlos Canossa, Carla Lopes, Ana Preto, Maria Sameiro Torres Gonçalves, and Maria João Sousa. "Novel Nile Blue Analogue Stains Yeast Vacuolar Membrane, Endoplasmic Reticulum, and Lipid Droplets, Inducing Cell Death through Vacuole Membrane Permeabilization." Journal of Fungi 7, no. 11 (2021): 971. http://dx.doi.org/10.3390/jof7110971.

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Phenoxazine derivatives such as Nile Blue analogues are assumed to be increasingly relevant in cell biology due to their fluorescence staining capabilities and antifungal and anticancer activities. However, the mechanisms underlying their effects remain poorly elucidated. Using S. cerevisiae as a eukaryotic model, we found that BaP1, a novel 5- and 9-N-substituted benzo[a]phenoxazine synthesized in our laboratory, when used in low concentrations, accumulates and stains the vacuolar membrane and the endoplasmic reticulum. In contrast, at higher concentrations, BaP1 stains lipid droplets and ind

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6

Ezeokonkwo, Mercy Amarachukwu, Kingsley Chizoba Iloka, Uchechukwu Chris Okoro, et al. "Synthesis and Antimicrobial Activity of New Derivatives of Angular Polycyclic Phenoxazine Ring System." Oriental Journal Of Chemistry 35, no. 4 (2019): 1320–26. http://dx.doi.org/10.13005/ojc/350410.

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Synthesis of angular polycyclic phenoxazine derivatives incorporating different phenols is reported in 30-99% yields. O-arylation of 6-chlorodibenzo[a,j] phenoxazin-5-one with a variety of electron-deficient, electron-neutral and electron-rich phenols under the catalytic palladium (II) acetate/t-BuXphos system furnished the compounds of interest. The highest yields were obtained when the intermediate was coupled with electron-rich phenols. IR, 1H-NMR, 13C-NMR and Mass spectra data, confirmed the structures of all the synthesized compounds. Study on the in vitro biological evaluation of the com

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7

Zhang, Lu, Xin Huang, Shan Zhen, et al. "Pd-Catalyzed double N-arylation of primary amines to synthesize phenoxazines and phenothiazines." Organic & Biomolecular Chemistry 15, no. 30 (2017): 6306–9. http://dx.doi.org/10.1039/c7ob01540b.

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8

Sridhar, M. A., M. Ramegowda, N. K. Lokanath, J. Shashidhara Prasad, G. B. Ere Gowda, and K. N. Thimmaiah. "Structural Studies of Some Phenoxazine Derivatives." Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals 326, no. 1 (1999): 189–214. http://dx.doi.org/10.1080/10587259908025415.

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9

Pal, Sanjima, V. Badireenath Konkimalla, Laxmi Kathawate та ін. "Targeting a chemorefractory COLO205 (BRAF V600E) cell line using substituted benzo[α]phenoxazines". RSC Advances 5, № 100 (2015): 82549–63. http://dx.doi.org/10.1039/c5ra14949e.

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10

Ibraheem, Israa, and Suad Al.Araji. "Synthesis of New N-Substituted Phenoxazine Derivatives." Baghdad Science Journal 13, no. 2 (2016): 360–65. http://dx.doi.org/10.21123/bsj.2016.13.2.2ncc.0360.

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11

Kozlovskaya, Liubov I., Graciela Andrei, Alexey A. Orlov, et al. "Antiviral activity spectrum of phenoxazine nucleoside derivatives." Antiviral Research 163 (March 2019): 117–24. http://dx.doi.org/10.1016/j.antiviral.2019.01.010.

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12

Chen, Yiyang, Zhixing Peng, Yuhan Tao, Zaibin Wang, Ping Lu, and Yanguang Wang. "Polymorphism-dependent emissions of two phenoxazine derivatives." Dyes and Pigments 161 (February 2019): 44–50. http://dx.doi.org/10.1016/j.dyepig.2018.09.015.

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13

IQBAL, N., and Y. UENO. "ChemInform Abstract: Synthesis of Crowned Phenoxazine Derivatives." ChemInform 23, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199245211.

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14

Ekerendu, Effiong E., Uchechukwu C. Okoro, Cosmas C. Eze, et al. "Novel Cholinesterase Inhibitors: Synthesis, in silico and in vitro Studies." Asian Journal of Chemistry 35, no. 7 (2023): 1683–91. http://dx.doi.org/10.14233/ajchem.2023.27588.

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The synthesis of new functionalized linear diaza and triaza phenothiazine and phenoxazines and their in silico and in vitro anti-Alzheimer activity is reported. Fifteen new amide derivatives (8-11 & 13-24) were synthesized by the reactions of phenothiazines/phenoxazine (6 or 12) and various aliphatic and aromatic primary amides (7) in the presence of nickel catalyst and anhydrous potassium carbonate under nitrogen atmosphere. The FTIR, 1H NMR, 13C NMR and HR-MS spectra of the synthesized compounds were in agreement with the assigned structures. All the 15 new derivatives were screened for

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15

Pal, Sanjima, Sunita Salunke-Gawalib та V. Badireenath Konkimallaa. "Induction of Autophagic Cell Death in Apoptosis-resistant Pancreatic Cancer Cells using Benzo[α]phenoxazines Derivatives, 10-methyl-benzo[α]phenoxazine-5-one and benzo[α]phenoxazine-5-one". Anti-Cancer Agents in Medicinal Chemistry 17, № 1 (2017): 115–25. http://dx.doi.org/10.2174/1871520616666160624091519.

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Background: Intrinsic resistance to apoptotic cell death due to co-occurrence of mutated KRAS and p53 is frequently reported in pancreatic cancer that renders them aggressive, highly proliferative and metastatic. In addition, these cancer types are less sensitive to apoptosis inducing drugs where promotion of autophagic cell death could be a viable option for treatment under such circumstances. Objective: In this study we examined the potential of three intrinsically fluorescent benzo[α]phenoxazines or BPZs (R=Cl, CH3, H) to induce cytotoxic autophagy in chemo and apoptosis-resistant, KRAS and

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16

Antonio, Yulia, Patricia Barrera, Olga Contreras, et al. "Regiospecific lithiation of phenoxazine ortho to the oxygen atom. Synthesis of 4-mono- and 4,6-disubstituted phenoxazine derivatives." Journal of Organic Chemistry 54, no. 9 (1989): 2159–65. http://dx.doi.org/10.1021/jo00270a027.

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17

Ivakhnenko, E. P., P. A. Knyazev, N. I. Makarova, O. P. Demidov, A. G. Starikov та V. I. Minkin. "Electron Transfer in Reaction of 12H-Quinoxalino[2,3-b]phenoxazines with π-Acceptors". Журнал общей химии 94, № 2 (2024): 216–24. http://dx.doi.org/10.31857/s0044460x24020072.

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Using the reaction of 2,4-di-(tert-butyl)-12-(4-methoxyphenyl)-10-methoxy-12H-quinoxalino[2,3-b]phenoxazine with π-electron acceptors such as tetracyanoquinodimethane and 3,6-di-(tert-butyl)-o-quinone) as an example it was shown that derivatives of this N,O-pentaheterocyclic system are effective electron donors that, under mild conditions, carry out electron transfer reactions with the formation of stable cation and anion radical structures.

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18

Ferreira, João C. C., Sara Granja, Ana F. Almeida, et al. "Targeting Lysosomes in Colorectal Cancer: Exploring the Anticancer Activity of a New Benzo[a]phenoxazine Derivative." International Journal of Molecular Sciences 24, no. 1 (2022): 614. http://dx.doi.org/10.3390/ijms24010614.

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Colorectal cancer (CRC) has been ranked as one of the cancer types with a higher incidence and one of the most mortal. There are limited therapies available for CRC, which urges the finding of intracellular targets and the discovery of new drugs for innovative therapeutic approaches. In addition to the limited number of effective anticancer agents approved for use in humans, CRC resistance and secondary effects stemming from classical chemotherapy remain a major clinical problem, reinforcing the need for the development of novel drugs. In the recent years, the phenoxazines derivatives, Nile Bl

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19

Almtiri, Mohammed, Timothy J. Dowell, Iwei Chu, David O. Wipf, and Colleen N. Scott. "Phenoxazine-Containing Polyaniline Derivatives with Improved Electrochemical Stability and Processability." ACS Applied Polymer Materials 3, no. 6 (2021): 2988–97. http://dx.doi.org/10.1021/acsapm.1c00152.

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20

Malinska, M., J. Nowacki, A. Kapturkiewicz, and K. Wozniak. "On differences in electron densities of phenoxazine and phenothiazine derivatives." Acta Crystallographica Section A Foundations of Crystallography 67, a1 (2011): C685. http://dx.doi.org/10.1107/s010876731108264x.

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21

Osati, Samira, Saied Saeed Hosseiny Davarani, Nasser Safari та Mohammad Hossein Banitaba. "Electrochemical synthesis of novel π-extended phenoxazine derivatives of porphyrincatecholes". Electrochimica Acta 56, № 25 (2011): 9426–32. http://dx.doi.org/10.1016/j.electacta.2011.08.030.

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22

Pacheco, Maria Inês, Bárbara Guimarães, Patrícia Pereira-Silva, et al. "Combining Fluconazole with Benzo[a]phenoxazine Derivatives as a Promising Strategy Against Fluconazole-Resistant Candida Species." Molecules 29, no. 21 (2024): 5197. http://dx.doi.org/10.3390/molecules29215197.

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The rise in non-albicans Candida species, exhibiting unpredictable antifungal resistance, complicates treatment and contributes to the growing threat of invasive, life-threatening infections. This study evaluates the antifungal activity of four benzo[a]phenoxazine derivatives (C34, C35, A42, and A44) against 14 Candida strains following EUCAST standards. Fluconazole interactions are analysed through fractional inhibitory concentration index (FICI) calculation and response surface analysis based on the Bliss model. Macrophage-like J774A.1 cells are used to assess Candida killing in the presence

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23

Ferreira, João Carlos Canossa, M. Sameiro T. Gonçalves, Ana Preto, and Maria João Sousa. "Anticancer Activity of Benzo[a]phenoxazine Compounds Promoting Lysosomal Dysfunction." Cells 13, no. 16 (2024): 1385. http://dx.doi.org/10.3390/cells13161385.

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Specific cancer therapy remains a problem to be solved. Breast and colorectal cancer are among the cancers with the highest prevalence and mortality rates. Although there are some therapeutic options, there are still few effective agents for those cancers, which constitutes a clinical problem that requires further research efforts. Lysosomes play an important role in cancer cells’ survival, and targeting lysosomes has gained increased interest. In recent years, our team has been synthetizing and testing novel benzo[a]phenoxazine derivatives, as they have been shown to possess potent pharmacolo

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24

Sousa, Ana Catarina, Lígia O. Martins, and M. Paula Robalo. "Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores." Molecules 26, no. 12 (2021): 3719. http://dx.doi.org/10.3390/molecules26123719.

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Laccases are multicopper oxidases that have shown a great potential in various biotechnological and green chemistry processes mainly due to their high relative non-specific oxidation of phenols, arylamines and some inorganic metals, and their high redox potentials that can span from 500 to 800 mV vs. SHE. Other advantages of laccases include the use of readily available oxygen as a second substrate, the formation of water as a side-product and no requirement for cofactors. Importantly, addition of low-molecular-weight redox mediators that act as electron shuttles, promoting the oxidation of co

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25

Onoabedje, Efeturi A., Uchechukwu C. Okoro, Amitabha Sarkar, and David W. Knight. "Synthesis and structure of new alkynyl derivatives of phenothiazine and phenoxazine." Journal of Sulfur Chemistry 37, no. 3 (2016): 269–81. http://dx.doi.org/10.1080/17415993.2015.1131827.

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26

Goryunov, L. I., V. D. Shteingartz, and I. Grobe. "Synthesis of Dimethylphosphorothiol Derivatives of Dibenzo-p-dioxin, Phenoxazine, and Phenoxathiyne." Russian Journal of Organic Chemistry 40, no. 5 (2004): 757–58. http://dx.doi.org/10.1023/b:rujo.0000043729.02916.27.

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27

Zhao, Yuling, Yanyan Wang, Xinyu Li, Yanmei Li, Youjia Wang, and Tianzhi Yu. "Effects of phenothiazine and phenoxazine on photophysical properties of coumarin derivatives." Chemical Papers 74, no. 1 (2019): 305–10. http://dx.doi.org/10.1007/s11696-019-00882-y.

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28

Shruti, Jaya Dwivedi, Dharma Kishore, and Shalu Sain. "Recent advancement in the synthesis of phenoxazine derivatives and their analogues." Synthetic Communications 48, no. 12 (2018): 1377–402. http://dx.doi.org/10.1080/00397911.2018.1448090.

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29

ALEKSEEVA, V. I., L. E. MARININA, and L. P. SAVVINA. "ChemInform Abstract: Synthesis and Spectral Properties of Benzo(b)phenoxazine Derivatives." ChemInform 26, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199535198.

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30

Kozlovskaya, Liubov I., Viktor P. Volok, Anna A. Shtro, et al. "Phenoxazine nucleoside derivatives with a multiple activity against RNA and DNA viruses." European Journal of Medicinal Chemistry 220 (August 2021): 113467. http://dx.doi.org/10.1016/j.ejmech.2021.113467.

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31

Malińska, Maura, Jacek Nowacki, Andrzej Kapturkiewicz, and Krzysztof Woźniak. "Differences in electron densities of phenoxazine and phenothiazine derivatives—charge density studies." RSC Advances 2, no. 10 (2012): 4318. http://dx.doi.org/10.1039/c2ra01148d.

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32

Sherman, Douglas B., J. Bruce Pitner, Arounaguiry Ambroise, and K. Joseph Thomas. "Synthesis of Thiol-Reactive, Long-Wavelength Fluorescent Phenoxazine Derivatives for Biosensor Applications." Bioconjugate Chemistry 17, no. 2 (2006): 387–92. http://dx.doi.org/10.1021/bc050309d.

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33

Borowicz, Paweł, Jerzy Herbich, Andrzej Kapturkiewicz, Marcin Opallo, and Jacek Nowacki. "Radiative and nonradiative electron transfer in donor–acceptor phenoxazine and phenothiazine derivatives." Chemical Physics 249, no. 1 (1999): 49–62. http://dx.doi.org/10.1016/s0301-0104(99)00265-7.

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34

Shi, Xue-Liang, Jian-Feng Ge, Bao-Qiang Liu, et al. "Synthesis and in vitro antiprotozoal activities of 5-phenyliminobenzo[a]phenoxazine derivatives." Bioorganic & Medicinal Chemistry Letters 21, no. 19 (2011): 5804–7. http://dx.doi.org/10.1016/j.bmcl.2011.07.112.

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35

Anfinogenov, V. A., I. N. Okhtemenko, A. I. Khlebnikov, and V. D. Ogorodnikov. "ChemInform Abstract: Alcoholysis of 2,2-Dichloropropyl Derivatives of Carbazole, Phenothiazine, and Phenoxazine." ChemInform 32, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.200139034.

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36

Yang, Yiyu, Ran Xiao, Xiaosong Cao, et al. "Phenoxazine-Dibenzothiophene Sulfoximine Emitters Featuring Both Thermally Activated Delayed Fluorescence and Aggregation Induced Emission." Molecules 26, no. 17 (2021): 5243. http://dx.doi.org/10.3390/molecules26175243.

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In this work, we demonstrate dibenzothiophene sulfoximine derivatives as building blocks for constructing emitters featuring both thermally activated delayed fluorescent (TADF) and aggregation-induced emission (AIE) properties, with multiple advantages including high chemical and thermal stability, facile functionalization, as well as tunable electron-accepting ability. A series of phenoxazine-dibenzothiophene sulfoximine structured TADF emitters were successfully synthesized and their photophysical and electroluminescent properties were evaluated. The electroluminescence devices based on thes

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37

Zilinskaite, Vita, Dalius Gudeika, Juozas V. Grazulevicius, and Jonas Sidaravicius. "Synthesis and Properties of 1,3-Indandione-Disubstituted Derivatives of Carbazole, Phenothiazine, and Phenoxazine." Molecular Crystals and Liquid Crystals 590, no. 1 (2014): 80–89. http://dx.doi.org/10.1080/15421406.2013.873851.

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38

Tanimori, Shinji, Yoshihiro Kato, and Mitsunori Kirihata. "Palladium-Catalyzed One-Step Preparation of Novel Tricyclic Phenoxazine, Phenazine, and Dioxine Derivatives." Synthesis 2004, no. 13 (2004): 2103–6. http://dx.doi.org/10.1055/s-2004-829200.

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39

Hosseiny Davarani, Saied Saeed, Majid Kalate Bojdi, and Ali Mehdinia. "A New Way for Synthesis of Phenoxazine and Diphenoxazine Derivatives via Electrochemical Method." CHEMICAL & PHARMACEUTICAL BULLETIN 59, no. 10 (2011): 1209–13. http://dx.doi.org/10.1248/cpb.59.1209.

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40

Kulys, J., K. Krikstopaitis, F. W. Scheller, and U. Wollenberger. "Electrochemical Parameters of Phenoxazine Derivatives in Solution and at Monolayer-Modified Gold Electrodes." Electroanalysis 16, no. 3 (2004): 183–89. http://dx.doi.org/10.1002/elan.200302795.

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41

Reddy, Seelam Venkata, Gangula Mohan Rao, Baru Vijaya Kumar, et al. "Construction of phenoxazine rings containing nitro and sulfonic acid groups leading to phenoxazine-3-sulfonamide derivatives: their evaluation as novel and potential insulin secretagogues." MedChemComm 5, no. 5 (2014): 587. http://dx.doi.org/10.1039/c3md00377a.

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42

Hernandez-Olmos, Victor, Aliaa Abdelrahman, Ali El-Tayeb, Diana Freudendahl, Stephanie Weinhausen, and Christa E. Müller. "N-Substituted Phenoxazine and Acridone Derivatives: Structure–Activity Relationships of Potent P2X4 Receptor Antagonists." Journal of Medicinal Chemistry 55, no. 22 (2012): 9576–88. http://dx.doi.org/10.1021/jm300845v.

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43

Shlenev, R. M., P. V. Vorontsov, S. I. Filimonov, A. V. Tarasov, A. S. Danilova, and P. A. Agat’ev. "Synthesis of dibenzo[1,4]dioxine, phenoxazine, and phenothiazine derivatives containing carboxamide and sulfonamide groups." Russian Journal of Organic Chemistry 52, no. 3 (2016): 448–52. http://dx.doi.org/10.1134/s1070428016030271.

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44

Ivakhnenko, Eugeny P., Pavel A. Knyazev, Galina V. Romanenko, et al. "The carboxyl derivatives of 6,8-di-(tert.-butyl)phenoxazine: Synthesis, oxidation reactions and fluorescence." Tetrahedron 75, no. 4 (2019): 538–44. http://dx.doi.org/10.1016/j.tet.2018.12.047.

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45

Yuanfu, Pei, Masahisa Otake, Martin Vacha, and Hisaya Sato. "Synthesis and characterization of a novel electroluminescent polymer based on phenoxazine and fluorene derivatives." Reactive and Functional Polymers 67, no. 11 (2007): 1211–17. http://dx.doi.org/10.1016/j.reactfunctpolym.2007.07.011.

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46

Schlereth, Daniela D., and Hanns-Ludwig Schmidt. "Spectroelectrochemical detection of phenothiazine and phenoxazine derivatives covalently bound to self-assembled cystamine monolayers." Journal of Electroanalytical Chemistry 380, no. 1-2 (1995): 117–25. http://dx.doi.org/10.1016/0022-0728(94)03618-d.

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47

Kolchina, E. F., and T. N. Gerasimova. "Cyclization of polyfluoro substituted 2-amino- and 2-acetylaminodiaryl ethers into derivatives of phenoxazine." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 39, no. 4 (1990): 755–58. http://dx.doi.org/10.1007/bf00960340.

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48

Shi, Xue-Liang, Jian-Feng Ge, Bao-Qiang Liu, et al. "ChemInform Abstract: Synthesis and in vitro Antiprotozoal Activities of 5-Phenyliminobenzo[a]phenoxazine Derivatives." ChemInform 43, no. 9 (2012): no. http://dx.doi.org/10.1002/chin.201209181.

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49

Souder, Kendall, Emma J. Beatty, Siena C. McGovern, et al. "Role of dipA and pilD in Francisella tularensis Susceptibility to Resazurin." Antibiotics 10, no. 8 (2021): 992. http://dx.doi.org/10.3390/antibiotics10080992.

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The phenoxazine dye resazurin exhibits bactericidal activity against the Gram-negative pathogens Francisella tularensis and Neisseria gonorrhoeae. One resazurin derivative, resorufin pentyl ether, significantly reduces vaginal colonization by Neisseria gonorrhoeae in a mouse model of infection. The narrow spectrum of bacteria susceptible to resazurin and its derivatives suggests these compounds have a novel mode of action. To identify potential targets of resazurin and mechanisms of resistance, we isolated mutants of F. tularensis subsp. holarctica live vaccine strain (LVS) exhibiting reduced

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50

Marinina, L. E., V. I. Alekseeva, L. P. Sawina, and E. A. Luk'yanets. "Synthesis and spectral luminescence properties of dibenzo[b,i]phenoxazine and several of its derivatives." Chemistry of Heterocyclic Compounds 24, no. 2 (1988): 220–25. http://dx.doi.org/10.1007/bf00473337.

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