- Discovery of anti-cancer activity for benzo[1,2,4]triazin-7-ones: Very strong correlation to pleurotin and thioredoxin reductase inhibition
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The thioredoxin (Trx)–thioredoxin reductase (TrxR) system plays a key role in maintaining the cellular redox balance with Trx being over-expressed in a number of cancers. Inhibition of TrxR is an important strategy for anti-cancer drug discovery. The natu
- Sweeney, Martin,Coyle, Robert,Kavanagh, Paul,Berezin, Andrey A.,Lo Re, Daniele,Zissimou, Georgia A.,Koutentis, Panayiotis A.,Carty, Michael P.,Aldabbagh, Fawaz
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Read Online
- Redox Active Quinoidal 1,2,4-Benzotriazines
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Modifying the para-quinonimine 1,3-diphenyl-1,2,4-benzotriazin-7(1H)-one (2a) (E1/2-1/0 -1.20 V), by replacing the N1-phenyl by pentafluorophenyl, the C3-phenyl by trifluoromethyl, or the C7 carbonyl by ylidenemalononitrile, led to improved electron affinities as determined by cyclic voltammetry and computational studies. Combining structural changes further improved electron accepting abilities: the most electron deficient analogues (E1/2-1/0 ~ -0.65 V) involved combining the ylidenemalononitrile groups at C7 with the trifluoromethyl groups at C3. 1,2,5-Thiadiazolo fusion at C5-C6 did not affect the redox behavior but did enhance the UV-vis absorption profile. During the synthesis of the thiadiazolo analogues, 1,4-thiazino-fused analogues 6 were obtained in low yield, which thermally ring contract to the triazafluoranthenones 7. Compounds are fully characterized, and X-ray data are provided for selected analogues.
- Zissimou, Georgia A.,Kourtellaris, Andreas,Manoli, Maria,Koutentis, Panayiotis A.
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p. 9391 - 9402
(2018/07/05)
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- Preparation of Blatter Radicals via Aza-Wittig Chemistry: The Reaction of N-Aryliminophosphoranes with 1-(Het)aroyl-2-aryldiazenes
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Reacting N-aryliminophosphoranes with 1-(het)aroyl-2-aryldiazenes in preheated diphenyl ether at ca. 150-250 °C for 5-25 min affords in most cases the 1,3-diaryl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yls (aka Blatter radicals) in moderate to good yields. Al
- Savva, Anastasia C.,Mirallai, Styliana I.,Zissimou, Georgia A.,Berezin, Andrey A.,Demetriades, Marina,Kourtellaris, Andreas,Constantinides, Christos P.,Nicolaides, Constantinos,Trypiniotis, Theodossis,Koutentis, Panayiotis A.
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p. 7564 - 7575
(2017/07/26)
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- Ferromagnetic interactions in a 1d alternating linear chain of π-stacked 1,3-diphenyl-7-(thien-2-yl)-1,4-dihydro-1,2,4-benzotriazin-4-yl radicals
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X-ray studies show that 1,3-diphenyl-7-(thien-2-yl)-1,4-dihydro-1,2,4- benzotriazin-4-yl (6) adopts a distorted, slipped π-stacked structure of centrosymmetric dimers with alternate short and long interplanar distances (3.48 and 3.52A). Cyclic voltammograms of 7-(thien-2-yl)benzotriazin-4-yl 6 show two fully reversible waves that correspond to the -1/0 and 0/+1 processes. EPR and DFT studies on radical 6 indicate that the spin density is mainly delocalized over the triazinyl fragment. Magnetic susceptibility measurements show that radical 6 obeys Curie-Weiss behavior in the 5-300K region with C=0.378emuKmol-1 and I=+4.72K, which is consistent with ferromagnetic interactions between S=1/2 radicals. Fitting the magnetic susceptibility revealed the behavior is consistent with an alternating ferromagnetic chain (g=2.0071, J1=+7.12cm-1, J 2=+1.28cm-1).
- Constantinides, Christos P.,Koutentis, Panayiotis A.,Rawson, Jeremy M.
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supporting information; experimental part
p. 7109 - 7116
(2012/07/14)
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- 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: Selected chemistry at the C-6, C-7 and C-8 positions
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1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one (6) reacts with tetracyanoethylene (TCNE) or tetracyanoethylene oxide (TCNEO) to give the deep green 2-[1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-ylidene]propanedinitrile (11) in 17 and 15% yields, respectively. Nucleophiles such as amines, alkoxides, thiols and Grignard reagents all reacted with the 1,3-diphenylbenzotriazinone 6 regioselectively at C-6, while halogenating agents reacted exclusively at C-8. Furthermore, 8-iodo-1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one (32) undergoes palladium-catalysed Suzuki-Miyaura and Stille coupling reactions to give 8-aryl- or heteroaryl-substituted benzotriazinones. By combining both the C-6 and C-8 chemistries 1,3,6,8-tetraphenylbenzo[e][1,2,4]triazin-7(1H)-one (42) and 1,3-diphenyl-6,8-di(thien-2-yl)-benzo[e][1,2,4]triazin-7(1H)-one (43) can be prepared. All new compounds are fully characterized. The Royal Society of Chemistry 2011.
- Koutentis, Panayiotis A.,Krassos, Harry,Lo Re, Daniele
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scheme or table
p. 5228 - 5237
(2011/09/14)
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- Characterization and magnetic properties of a "super stable" radical 1,3-diphenyl-7-trifluoromethyl-1,4-dihydro-1,2,4-benzotriazin-4-yl
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1,3-Diphenyl-7-trifluoromethyl-1,4-dihydro-1,2,4-benzotriazin-4-yl (4), prepared in SSSShigh yield via the catalytic oxidation of the corresponding amidrazone 5 by using Pd/C (1.6 mol ss%) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.1 equiv) in air, is stab
- Constantinides, Christos P.,Koutentis, Panayiotis A.,Krassos, Harry,Rawson, Jeremy M.,Tasiopoulos, Anastasios J.
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experimental part
p. 2798 - 2806
(2011/06/19)
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- Synthesis of 7-aryl/heteraryl-1,3-diphenyl-1,2,4-benzotriazinyls via palladium catalyzed Stille and Suzuki-Miyaura reactions
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Stille and Suzuki-Miyaura reactions of 7-iodo-1,3-diphenyl-1,4-dihydro-1,2, 4-benzotriazin-4-yl are presented as rare examples of cross-coupling reactions with stable organic radicals. Both the Stille and Suzuki-Miyaura reactions are in most cases high yi
- Constantinides, Christos P.,Koutentis, Panayiotis A.,Loizou, Georgia
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supporting information; experimental part
p. 3122 - 3125
(2011/05/12)
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- Catalytic oxidation of N -phenylamidrazones to 1,3-Diphenyl-1,4-dihydro-1, 2,4-benzotriazin-4-yls: An improved synthesis of blatters radical
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Blatters radical, 1,3-diphenyl-1,4-dihydro-1,2,4-benzotriazin-4-yl (1a, R =H), and several of its C-7 substituted analogues (R =CF3, Cl, Br, I, Me, OMe) were prepared in good-to-excellent yields through catalytic oxidation of the corresponding
- Koutentis, Panayiotis A.,Lo Re, Daniele
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experimental part
p. 2075 - 2079
(2010/08/13)
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- A Study of 1,4-Dihydro-1,2,4-benzotriazinyl Radicals
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The thermal cyclization of the azo compounds 2 to yield the 1,4-dihydro-1,2,4-benzotriazines 5 facilitates the synthesis of 1,4-dihydro-1,2,4-benzotriazinyl radicals (4).A series of these radicals were prepared and studied in detail (chemical properties,
- Neugebauer, Franz Alfred,Umminger, Irmgard
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p. 1205 - 1225
(2007/10/02)
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