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Journal articles on the topic 'Benzotriazine'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Cui, Bingcun, Guosheng Huang, Jin Liu, et al. "Palladium-Catalyzed ortho-Monoacylation of Arenes with Aldehydes via 1,2,4-Benzotriazine-Directed C–H Bond Activation." Synthesis 52, no. 09 (2020): 1407–16. http://dx.doi.org/10.1055/s-0039-1691564.

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An efficient palladium-catalyzed C–H bond functionalization/ortho-monoacylation reaction of 3-aryl-1,2,4-benzotriazines with (hetero)aryl or alkyl aldehydes has been developed, which offers a facile and alternative strategy for direct modification and further diversification of 3-aryl-1,2,4-benzotriazines. Bioactive 1,2,4-benzotriazine has been employed as a novel directing group for the palladium-catalyzed regioselective monoacylation of sp2 C–H bond protocol with broad substrate scope and good functional group tolerance.

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2

Werstiuk, Nick Henry, Chandra Deo Roy, and Jiangong Ma. "A study of the vacuum pyrolysis of 1,2,3-benzotriazines. The Hel ultraviolet photoelectron spectra of benzazete and o-benzyne." Canadian Journal of Chemistry 73, no. 1 (1995): 146–49. http://dx.doi.org/10.1139/v95-022.

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A CW CO2 laser is used as a directed heat source to carry out the vacuum pyrolysis of 1,2,3-benzo-triazine (1a) and 4-methyl-1,2,3-benzotriazine (1b). We report the first HeI photoelectron (pe) spectrum of benzazete (2a), which correlates with ionization energies calculated with HAM/3 using an equilibrium geometry obtained at the ab initio HF/6-31G** level of the theory. The pe spectrum of o-benzyne (3) obtained in this study correlates with the spectrum published by Zhang and Chen, but not with the spectra reported in two earlier publications. Keywords: 1,2,3-benzotriazines, vacuum pyrolysis,

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3

Cortés, Edwar, Rodrigo Abonía, Justo Cobo, and Christopher Glidewell. "Four related esters: two 4-(aroylhydrazinyl)-3-nitrobenzoates and two 3-aryl-1,2,4-benzotriazine-6-carboxylates." Acta Crystallographica Section C Crystal Structure Communications 69, no. 7 (2013): 754–60. http://dx.doi.org/10.1107/s0108270113013590.

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The molecules of both methyl 4-[2-(4-chlorobenzoyl)hydrazinyl]-3-nitrobenzoate, C15H12ClN3O5, (I), and methyl 4-[2-(2-fluorobenzoyl)hydrazinyl]-3-nitrobenzoate, C15H12FN3O5, (II), contain an intramolecular N—H...O hydrogen bond, and both show electronic polarization in the nitrated aryl ring. In both compounds, molecules are linked by a combination of N—H...O and C—H...O hydrogen bonds to form sheets, which are built fromR43(18) rings in (I) and fromR44(28) rings in (II). In each of methyl 3-phenyl-1,2,4-benzotriazine-6-carboxylate, C15H11N3O2, (III), and methyl 3-(4-methylphenyl)-1,2,4-benzot

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4

Boulton, A. J., Mikl�s Kiss, and J. D. Kalenga Saka. "1,2,3-Benzotriazine 2-oxides." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1988): 1509. http://dx.doi.org/10.1039/p19880001509.

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5

Sparatore, Fabio, and Anna Sparatore. "3,3-Disubstituted 3,4-Dihydro-1,2,4-benzotriazines: Chemistry, Biological Activity, and Affinity to Sigma Receptors." Molecules 29, no. 1 (2023): 132. http://dx.doi.org/10.3390/molecules29010132.

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By reducing the 2-nitrophenylhydrazone of cyclohexanone with sodium dithionite, an unexpected yellow compound was obtained instead of the corresponding colorless amino derivative. Many years later, the structure of this compound, namely, cyclohexane-3-spiro-3,4-dihydro-1,2,4-benzotriazine, was demonstrated. From that time, the reduction of 2-nitrophenylhydrazones of different kinds of ketones, followed by air oxidation of the initially formed amino compounds, has represented a general way to synthesize a variety of 3,3-disubstituted 3,4-dihydro-1,2,4-benzotriazines. Many derivatives have been

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6

Elsaidi, Hassan, Fatemeh Ahmadi, Leonard Wiebe, and Piyush Kumar. "Development of [131I]I-EOE-TPZ and [131I]I-EOE-TPZMO: Novel Tirapazamine (TPZ)-Based Radioiodinated Pharmaceuticals for Application in Theranostic Management of Hypoxia." Pharmaceuticals 12, no. 1 (2019): 3. http://dx.doi.org/10.3390/ph12010003.

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Introduction: Benzotriazine-1,4-dioxides (BTDOs) such as tirapazamine (TPZ) and its derivatives act as radiosensitizers of hypoxic tissues. The benzotriazine-1-monoxide (BTMO) metabolite (SR 4317, TPZMO) of TPZ also has radiosensitizing properties, and via unknown mechanisms, is a potent enhancer of the radiosensitizing effects of TPZ. Unlike their 2-nitroimidazole radiosensitizer counterparts, radiolabeled benzotriazine oxides have not been used as radiopharmaceuticals for diagnostic imaging or molecular radiotherapy (MRT) of hypoxia. The radioiodination chemistry for preparing model radioiod

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7

Heravi, M. M., K. Aghapoor, M. A. Nooshabadi, and M. M. Mojtahedi. "Regioselective annelation of 3-(prop-2-ynylsulfanyl)-1,2,4-benzotriazine to thiazolo[2,3-c][1,2,4]benzotriazine." Monatshefte für Chemie - Chemical Monthly 128, no. 11 (1997): 1143–47. http://dx.doi.org/10.1007/bf00807564.

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8

Nicoló, F., M. Panzalorto, R. Scopelliti, G. Grassi, and F. Risitano. "5,7-Dimethyl-3-phenyl-1,2,4-benzotriazine." Acta Crystallographica Section C Crystal Structure Communications 54, no. 3 (1998): 405–7. http://dx.doi.org/10.1107/s0108270197014972.

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9

Shinde, Sujata S., Robert F. Anderson, Michael P. Hay, Swarna A. Gamage, and William A. Denny. "Oxidation of 2-Deoxyribose by Benzotriazinyl Radicals of Antitumor 3-Amino-1,2,4-benzotriazine 1,4-Dioxides." Journal of the American Chemical Society 126, no. 25 (2004): 7865–74. http://dx.doi.org/10.1021/ja048740l.

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10

HERAVI, M. M., K. AGHAPOOR, M. A. NOOSHABADI, and M. M. MOJTAHEDI. "ChemInform Abstract: Regioselective Annelation of 3-(Prop-2-ynylsulfanyl)-1,2,4-benzotriazine to Thiazolo[2,3-c][1,2,4]benzotriazine." ChemInform 29, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199811176.

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11

Posakony, Jeffrey J., Russell C. Pratt, Steven J. Rettig, Brian R. James, and Kirsten A. Skov. "Porphyrins incorporating heterocyclic N-oxides: (oxidopyridyl)porphyrins, porphyrin-N-oxides, and a tirapazamine-porphyrin conjugate." Canadian Journal of Chemistry 77, no. 2 (1999): 182–98. http://dx.doi.org/10.1139/v98-238.

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Porphyrins containing one to four 4-pyridyl groups as meso-substituents were synthesized via a mixed aldehyde condensation, and then "N-oxidized" with m-chloroperbenzoic acid to produce five novel (oxidopyridyl) porphyrins and seven porphyrin-N-oxides, which were characterized by analysis and spectroscopic methods, especially NMR; an X-ray crystal structure of 5-(1-oxido-4-pyridyl)-10,15,20-triphenylporphyrin was also obtained. Crystals of (oxidopyridyl)triphenylporphyrin are tetragonal, a = b = 15.174(1), c = 13.709(1) Å, Z = 4, space group I2d. The structure was solved by direct methods and

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12

Fauconnier, Theresa, Colin J. L. Lock, Russell A. Bell, James F. Britten, and K. D. Rainsford. "Studies of nonsteroidal anti-inflammatory drugs: azapropazone." Canadian Journal of Chemistry 72, no. 2 (1994): 382–89. http://dx.doi.org/10.1139/v94-059.

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The structure of azapropazone, 5-(dimethylamino)-9-methyl-2-propyl-1H-pyrazolo[1,2-a][1,2,4]benzotriazine-1,3(2H)-dione, was determined by single crystal X-ray diffraction. Crystals were orthorhombic (P212121), with a = 5.570(1) Å, b = 14.593(3) Å, c = 19.270(4) Å, and Z = 4. Intensities were measured on a Rigaku AFC6-R diffractometer with Cu-Kα radiation and 2316 reflections were used to determine the structure. Contrary to previous postulates, the tricyclic portion of the molecule is not planar. Azapropazone is a zwitterion with the negative charge delocalized over the β-keto-enol system and

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13

Mahran, Asma M., Thoraya A. Farghaly, and Afaf A. Nada. "Hydrazonoyl halides in heterocycles: synthesis and anti-microbial activity of new 1,2,4-benzotriazine and bis-1,2,4-benzotriazine derivatives." Research on Chemical Intermediates 41, no. 5 (2013): 2961–69. http://dx.doi.org/10.1007/s11164-013-1404-9.

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14

Ziarani, Ghodsi Mohammadi, Manizheh Mostofi, and Negar Lashgari. "Chemistry and Biological Activity of [1,2,3]-Benzotriazine Derivatives." Current Organic Chemistry 22, no. 28 (2019): 2717–51. http://dx.doi.org/10.2174/1385272822666181109123711.

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15

Riedl, Zsuzsanna, György Hajós, Walter J. Peláez, Ioulia T. Gafarova, Elizabeth L. Moyano, and Gloria I. Yranzo. "Flash vacuum pyrolysis (F.V.P.) of 1,2,4-benzotriazine derivatives." Tetrahedron 59, no. 6 (2003): 851–56. http://dx.doi.org/10.1016/s0040-4020(02)01598-3.

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16

Zeman, E. M., M. A. Baker, M. J. Lemmon, et al. "Structure-activity relationships for benzotriazine DI-N-oxides." International Journal of Radiation Oncology*Biology*Physics 16, no. 4 (1989): 977–81. http://dx.doi.org/10.1016/0360-3016(89)90899-7.

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17

Khaligh, Nader Ghaffari, Mohad Rafie Johan, and Juan Joon Ching. "Saccharin and tert-Butyl Nitrite: Cheap and Efficient Reagents for the Synthesis of 1,2,3-Benzotriazine-4-(3H)-ones from 2-Aminobenzamides under Metal-Free Conditions." Australian Journal of Chemistry 71, no. 3 (2018): 186. http://dx.doi.org/10.1071/ch17590.

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A mild and eco-friendly protocol for the synthesis of 1,2,3-benzotriazine-4-(3H)-ones is described using saccharin as a cheap and efficient catalyst and tert-butyl nitrite as a diazotization reagent for the first time. The current method has advantages such as cost effectiveness, energy efficiency, and simple experimental procedure, good yield of the desired product, and metal-free and environmentally benign conditions.

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18

Neugebauer, Franz A., and Gösta Rimmler. "ENDOR and triple resonance studies of 1,4-dihydro-1,2,4-benzotriazinyl radicals and 1,4-dihydro-1,2,4-benzotriazine radical cations." Magnetic Resonance in Chemistry 26, no. 7 (1988): 595–600. http://dx.doi.org/10.1002/mrc.1260260712.

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19

Heravi, Majid M., Naser Montazeri, Mohammad Rahimizadeh, Mehdi Bakavoli, and Mitra Ghassemzadeh. "REGIOSELECTIVE CYCLIZATION OF S-ACRYLIC ACID DERIVATIVE OF 1,2,4-BENZOTRIAZINE TO 10H-[1,3]THIAZIN0 [2,3-C][1,2,4] BENZOTRIAZIN-4-ONE." Phosphorus, Sulfur, and Silicon and the Related Elements 170, no. 1 (2001): 187–90. http://dx.doi.org/10.1080/10426500108040595.

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20

Junnotula, Venkatraman, Ujjal Sarkar, Sarmistha Sinha, and Kent S. Gates. "Initiation of DNA Strand Cleavage by 1,2,4-Benzotriazine 1,4-Dioxide Antitumor Agents: Mechanistic Insight from Studies of 3-Methyl-1,2,4-benzotriazine 1,4-Dioxide." Journal of the American Chemical Society 131, no. 3 (2009): 1015–24. http://dx.doi.org/10.1021/ja8049645.

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21

Lai, Kwong Khee, Carl H. Schwalbe, Keith Vaughan, Ronald J. Lafrance, and Clive D. Whiston. "Crystal and molecular structure of 3-ethyl-4-hydroxy-1,2,3(4H)-benzotriazine and 6-chloro-4-hydroxy-3-methyl-4-phenyl-1,2,3-benzotriazine." Canadian Journal of Chemistry 63, no. 3 (1985): 581–85. http://dx.doi.org/10.1139/v85-095.

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The crystal structures of the title compounds have been determined from X-ray data collected on a four-circle diffractometer and refined by the full-matrix least-squares method. The former compound crystallizes in the orthorhombic system, space group Pbcn, with a = 14.346(8), b = 7.239(1), c = 17.276(2) Å, and has been refined to a conventional R factor of 0.043 for 890 observed reflections. Corresponding results for the latter compound are monoclinic, P21/n, a = 12.222(4), b = 7.482(2), c = 14.170(8) Å, β = 94.06(4)°, R = 0.060 for 2128 observed data. The triazine rings of both compounds exhi

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22

Fauconnier, Theresa, Alex D. Bain, Paul Hazendonk, R. A. Bell, and Colin JL Lock. "Structure and dynamics of azapropazone derivatives studied by crystallography and nuclear magnetic resonance." Canadian Journal of Chemistry 76, no. 4 (1998): 426–30. http://dx.doi.org/10.1139/v98-031.

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The X-ray crystal structure of a derivative of the nonsteroidal anti-inflammatory drug, azapropazone, has been determined using a data set obtained from a charge-coupled device (CCD) area detector. Azapropazone itself, 5-(dimethylamino)-9-methyl-2-propyl-1H-pyrazolo[1,2-a][1,2,4]benzotriazine- 1,3(2H)-dione, has previously been shown to be nonplanar, probably due to steric interactions between the pyrazolidine ring and the exocyclic dimethylamino group. The derivative studied in this work, 3-dimethylamino-7-methyl-1,2,4-benzotriazine, does not have the pyrazolidine ring and is shown here to be

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23

Tocher, Joanne H., Narinder S. Virk, and David I. Edwards. "Electrochemical studies and dna damaging effects of the benzotriazine-N-oxides." Biochemical Pharmacology 39, no. 4 (1990): 781–86. http://dx.doi.org/10.1016/0006-2952(90)90159-i.

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24

Henrie, Robert N., Marjorie J. Plummer, Sandra E. Smith, Walter H. Yeager, and Debra A. Witkowski. "Discovery and Optimization of a PSI Electron-Accepting 1,2,4-Benzotriazine Herbicide." Quantitative Structure-Activity Relationships 12, no. 1 (1993): 27–37. http://dx.doi.org/10.1002/qsar.19930120105.

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25

Nakhai, Azadeh, Birgitta Stensland, Per H. Svensson, and Jan Bergman. "Synthesis of Benzotriazine and Aryltriazene Derivatives Starting from 2-Azidobenzonitrile Derivatives." European Journal of Organic Chemistry 2010, no. 34 (2010): 6588–99. http://dx.doi.org/10.1002/ejoc.201000328.

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26

Fuchs, Tarra, Goutam Chowdhury, Charles L. Barnes, and Kent S. Gates. "3-Amino-1,2,4-benzotriazine 4-Oxide: Characterization of a New Metabolite Arising from Bioreductive Processing of the Antitumor Agent 3-Amino-1,2,4-benzotriazine 1,4-Dioxide (Tirapazamine)." Journal of Organic Chemistry 66, no. 1 (2001): 107–14. http://dx.doi.org/10.1021/jo001232j.

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27

Lee, Chun-I., Chien-Ming Huang, Wen-Hsin Huang, and An-Rong Lee. "Synthesis, Preferentially Hypoxic Apoptosis and Anti-Angiogenic Activity of 3- Amino-1,2,4-Benzotriazine-1,4-Dioxide Bearing Alkyl Linkers with a 3-Amino-1,2,4- Benzotriazine-1-Oxide Moiety." Anti-Cancer Agents in Medicinal Chemistry 14, no. 10 (2014): 1428–46. http://dx.doi.org/10.2174/1871520614666141014130554.

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28

Junnotula, Venkatraman, Ujjal Sarkar, Charles L. Barnes, Praveen K. Thallapally, and Kent S. Gates. "Crystal structures of 3-methyl-1,2,4-benzotriazine 1-oxide and 2-oxide." Journal of Chemical Crystallography 36, no. 9 (2006): 557–61. http://dx.doi.org/10.1007/s10870-006-9099-z.

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29

Zhu, H. "Addressing BCR/Abl resistance: Evolving dasatinib to a novel inhibitor of the T315I BCR/Abl mutation." Journal of Clinical Oncology 25, no. 18_suppl (2007): 13004. http://dx.doi.org/10.1200/jco.2007.25.18_suppl.13004.

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13004 We have previously shown that inhibition of the BCR/Abl.T315I mutation can be achieved by using a benzotriazine small molecule in both enzymatic and cell proliferation assays. We have further evolved the benzotriazenes into a class of structurally simplified BCR/Abl inhibitors with enhanced pharmaceutical properties. A representative of this new class, TG101114, inhibits Abl and Abl.T315I enzyme as well as proliferation of cells expressing either BCR/Abl or BCR/Abl.T315I. It displays desirable pharmaceutical properties (e.g. oral bioavailability>20% and T1/2>5 h). Consistent with i

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30

Hay, Michael P., Hong Nam Shin, Way Wua Wong, et al. "Benzotriazine Di-Oxide Prodrugs for Exploiting Hypoxia and Low Extracellular pH in Tumors." Molecules 24, no. 14 (2019): 2524. http://dx.doi.org/10.3390/molecules24142524.

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Extracellular acidification is an important feature of tumor microenvironments but has yet to be successfully exploited in cancer therapy. The reversal of the pH gradient across the plasma membrane in cells that regulate intracellular pH (pHi) has potential to drive the selective uptake of weak acids at low extracellular pH (pHe). Here, we investigate the dual targeting of low pHe and hypoxia, another key feature of tumor microenvironments. We prepared eight bioreductive prodrugs based on the benzotriazine di-oxide (BTO) nucleus by appending alkanoic or aminoalkanoic acid sidechains. The BTO a

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31

Mohammadi Ziarani, Ghodsi, Negar Lashgari, Manizheh Mostofi, and Mohammad Mahdavi. "Synthesis, Reaction and Biological Activity of Pyrazolo[5,1-c][1,2,4]benzotriazine 5-Oxides." HETEROCYCLES 96, no. 11 (2018): 1869. http://dx.doi.org/10.3987/rev-18-893.

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32

NOMOTO, Yuji, Hiroyuki OBASE, Haruki TAKAI, Masayuki TERANISHI, Joji NAKAMURA, and Kazuhiro KUBO. "Studies on cardiotonic agents. II. Synthesis of novel phthalazine and 1,2,3-benzotriazine derivatives." CHEMICAL & PHARMACEUTICAL BULLETIN 38, no. 8 (1990): 2179–83. http://dx.doi.org/10.1248/cpb.38.2179.

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33

Lipilin, D. L., A. Yu Tyurin, O. Yu Smirnov, A. M. Churakov, Yu A. Strelenko, and V. A. Tartakovsky. "Synthesis and tautomeric transformations of 2-(tert-butyl)-1,2,4-benzotriazine-3(2H)-thiones." Russian Chemical Bulletin 55, no. 7 (2006): 1239–42. http://dx.doi.org/10.1007/s11172-006-0405-x.

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34

Tocher, Joanne H., Narinder S. Virk, and David I. Edwards. "Electrochemical Properties As A Function of Ph for the Benzotriazine DI-N-Oxides." Free Radical Research Communications 10, no. 4-5 (1990): 295–302. http://dx.doi.org/10.3109/10715769009149898.

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35

HERAVI, M. M., Z. TAVALAIE, and O. SABZEVARI. "ChemInform Abstract: Synthesis of a Novel Heterocyclic System: Oxazolo[2,3-c][1,2,4]benzotriazine." ChemInform 29, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199847180.

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36

Xia, Qing, Ling Zhang, Jun Zhang, et al. "Synthesis, hypoxia-selective cytotoxicity of new 3-amino-1,2,4-benzotriazine-1,4-dioxide derivatives." European Journal of Medicinal Chemistry 46, no. 3 (2011): 919–26. http://dx.doi.org/10.1016/j.ejmech.2011.01.007.

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37

Jiang, Faqin, Qinjie Weng, Rong Sheng, et al. "Synthesis, Structure and Hypoxic Cytotoxicity of 3-Amino-1,2,4-benzotriazine-1,4-dioxide Derivatives." Archiv der Pharmazie 340, no. 5 (2007): 258–63. http://dx.doi.org/10.1002/ardp.200600201.

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38

Nakhai, Azadeh, Birgitta Stensland, Per H. Svensson, and Jan Bergman. "ChemInform Abstract: Synthesis of Benzotriazine and Aryltriazene Derivatives Starting from 2-Azidobenzonitrile Derivatives." ChemInform 42, no. 15 (2011): no. http://dx.doi.org/10.1002/chin.201115172.

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39

Lloyd, R. V., D. R. Duling, G. V. Rumyantseva, R. P. Mason, and P. K. Bridson. "Microsomal reduction of 3-amino-1,2,4-benzotriazine 1,4-dioxide to a free radical." Molecular Pharmacology 40, no. 3 (1991): 440–45. https://doi.org/10.1016/s0026-895x(25)12937-4.

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40

M., K. A. IBRAHIM, S. EL-GHARIB M., M. FARAG A., and R. H. ELMOGHAYER M. "Reaction of Ethyl Chloroglyoxalate Arylhydrazone with Heterocyclic Amidine and Difunction Amino Derivatives." Journal of Indian Chemical Society Vol. 65, Mar 1988 (1988): 194–96. https://doi.org/10.5281/zenodo.6035359.

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Chemistry Department, Faculty of Science, Cairo University, Giza, A. B. Egypt <em>Manuscript received 10 November 1986, revised 9 November 1987, accepted 13 January 1988</em> The ethyl chloroglyoxalate <em>p</em>-tolylhydrazones (1) react with 5-amino-3-phenyl- pyrazole, 3-aminotriazole and 2-aminobenzimidazole in triethylamine solution to give the corresponding pyrazolo[4,5-<em>c</em>]pyrazole (9), triazolo[4,5-<em>c</em>]triazole (12) and  benzimidazolylamidrazone derivatives (14), respectively. The reaction mechanism has been suggested as 1,3-dipolar cycloaddition of nitrileimine

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41

Qi, Wen, Pooja Yadav, Cho R. Hong, Ralph J. Stevenson, Michael P. Hay, and Robert F. Anderson. "Spin Trapping Hydroxyl and Aryl Radicals of One-Electron Reduced Anticancer Benzotriazine 1,4-Dioxides." Molecules 27, no. 3 (2022): 812. http://dx.doi.org/10.3390/molecules27030812.

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Hypoxia in tumors results in resistance to both chemotherapy and radiotherapy treatments but affords an environment in which hypoxia-activated prodrugs (HAP) are activated upon bioreduction to release targeted cytotoxins. The benzotriazine 1,4-di-N-oxide (BTO) HAP, tirapazamine (TPZ, 1), has undergone extensive clinical evaluation in combination with radiotherapy to assist in the killing of hypoxic tumor cells. Although compound 1 did not gain approval for clinical use, it has spurred on the development of other BTOs, such as the 3-alkyl analogue, SN30000, 2. There is general agreement that th

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42

Hay, Michael P., Swarna A. Gamage, Mary S. Kovacs, et al. "Structure−Activity Relationships of 1,2,4-Benzotriazine 1,4-Dioxides as Hypoxia-Selective Analogues of Tirapazamine." Journal of Medicinal Chemistry 46, no. 1 (2003): 169–82. http://dx.doi.org/10.1021/jm020367+.

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43

Hay, Michael P., Frederik B. Pruijn, Swarna A. Gamage, et al. "DNA-Targeted 1,2,4-Benzotriazine 1,4-Dioxides: Potent Analogues of the Hypoxia-Selective Cytotoxin Tirapazamine." Journal of Medicinal Chemistry 47, no. 2 (2004): 475–88. http://dx.doi.org/10.1021/jm030399c.

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44

Jiang, Faqin, Bo Yang, Lingling Fan, Qiaojun He, and Yongzhou Hu. "Synthesis and hypoxic–cytotoxic activity of some 3-amino-1,2,4-benzotriazine-1,4-dioxide derivatives." Bioorganic & Medicinal Chemistry Letters 16, no. 16 (2006): 4209–13. http://dx.doi.org/10.1016/j.bmcl.2006.05.095.

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APPA RAO, B. V., MD YAKUB IQBAL, M. NARSIHMA REDDY, and K. CHAITANYA KUMAR. "Self-assembled nanofilm of 1,2-dihydro-3-(octadecylthio)benzotriazine on copper for corrosion protection." Bulletin of Materials Science 37, no. 2 (2014): 185–97. http://dx.doi.org/10.1007/s12034-014-0645-6.

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Birincioglu, Mustafa, Pawel Jaruga, Goutam Chowdhury, Henry Rodriguez, Miral Dizdaroglu, and Kent S. Gates. "DNA Base Damage by the Antitumor Agent 3-Amino-1,2,4-benzotriazine 1,4-Dioxide (Tirapazamine)." Journal of the American Chemical Society 125, no. 38 (2003): 11607–15. http://dx.doi.org/10.1021/ja0352146.

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Chopra, Sidharth, Gary A. Koolpe, Arlyn A. Tambo-ong, et al. "Discovery and Optimization of Benzotriazine Di-N-Oxides Targeting Replicating and Nonreplicating Mycobacterium tuberculosis." Journal of Medicinal Chemistry 55, no. 13 (2012): 6047–60. http://dx.doi.org/10.1021/jm300123s.

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Kotandeniya, Delshanee, Brian Ganley, and Kent S. Gates. "Oxidative DNA base damage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-Dioxide (Tirapazamine)." Bioorganic & Medicinal Chemistry Letters 12, no. 17 (2002): 2325–29. http://dx.doi.org/10.1016/s0960-894x(02)00468-7.

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Noronha, Glenn, Kathy Barrett, Jianguo Cao, et al. "Discovery and preliminary structure–activity relationship studies of novel benzotriazine based compounds as Src inhibitors." Bioorganic & Medicinal Chemistry Letters 16, no. 21 (2006): 5546–50. http://dx.doi.org/10.1016/j.bmcl.2006.08.035.

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Anderson, Robert F., Sujata S. Shinde, Michael P. Hay, Swarna A. Gamage, and William A. Denny. "Radical properties governing the hypoxia-selective cytotoxicity of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides." Organic & Biomolecular Chemistry 3, no. 11 (2005): 2167. http://dx.doi.org/10.1039/b502586a.

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