- A novel route to fully substituted 1H-pyrazoles
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A novel one-step synthesis route to fully substituted pyrazol-4-ols is reported. This simple yet nonobvious method for the construction of pyrazol-4-ols by the condensation-fragmentation-cyclization-extrusion reactions of thietanones with 1,2,4,5-tetrazin
- Suen, Yat Fan,Hope, Hakon,Nantz, Michael H.,Haddadin, Makhluf J.,Kurth, Mark J.
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- Temperature dependent NIR emitting lanthanide-PMO/silica hybrid materials
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Two materials-A mesoporous silica (MS) and a periodic mesoporous organosilica (PMO) functionalized with dipyridyl-pyridazine (dppz) units were grafted with near-infrared (NIR) emitting lanthanide (Nd3+, Er3+, Yb3+) complexes in an attempt to obtain hybrid NIR emitting materials. The parent materials: dppz-vSilica and dppz-ePMO were prepared by a hetero Diels-Alder reaction between 3,6-di(2-pyridyl)-1,2,4,5-Tetrazine (dptz) and the double bonds of either ethenylene-bridged PMO (ePMO) or vinyl-silica (vSilica) and subsequent oxidation. The dppz-vSilica is reported here for the first time. The prepared lanthanide-PMO/silica hybrid materials were studied in depth for their luminescence properties at room temperature and chosen Nd3+ and Yb3+ samples also at low temperature (as low as 10 K). We show that both the dppz-vSilica and dppz-ePMO materials can be used as "platforms" for obtaining porous materials showing NIR luminescence. To obtain NIR emission these materials can be excited either in the UV or Vis region (into the π → π? transitions of the ligands or directly into the f-f transitions of the Ln3+ ions). More interestingly, when functionalized with Nd3+ or Yb3+ β-diketonate complexes these materials showed interesting luminescence properties over a wide temperature range (10-360 K). The Yb3+ materials were investigated for their potential use as ratiometric temperature sensors.
- Kaczmarek, Anna M.,Esquivel, Dolores,Ouwehand, Judith,Van Der Voort, Pascal,Romero-Salguero, Francisco J.,Van Deun, Rik
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- Functionalized 2,5-dipyridinylpyrroles by electrochemical reduction of 3,6-dipyridinylpyridazine precursors
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The ring contraction of pyridinylpyridazine derivatives into the corresponding pyrroles by electrochemical reduction was studied, and the influence of the substituents of the pyridazine precursors on the process is discussed. Cyclic voltammetry studies underlines the electron-withdrawing or -donating effect of the substituent on the pyridazine ring, which determines the reaction pathway of their preparative electrolysis. The ring-contraction process, with extrusion of nitrogen, proceeds by two subsequent two-electron, two-proton processes via a 1,2-dihydropyridazine intermediate. The latter can either rearrange into an isolable 1,4-dihydropyridazine or undergo formation of pyrroles by disproportionation or by a second electrochemical reduction involving two-electrons and two protons. X-ray structure, fluorescence spectra, and conformational analysis of pyridinylpyrrole sequences supported this study. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Bakkali, Hicham,Marie, Cecile,Ly, Akarim,Thobie-Gautier, Christine,Graton, Jerome,Pipelier, Muriel,Sengmany, Stephane,Leonel, Eric,Nedelec, Jean-Yves,Evain, Michel,Dubreuil, Didier
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- TETRAZINE AND AZOLES BASED IONIC MATERIALS FOR PROPELLANTS AND ITS MANUFACTURING METHOD THEREOF
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The present invention relates to an azole-based ionic material for tetrazine-based propellant and a manufacturing method thereof. An azole-based ionic material for a tetrazine-based propellant comprising tetrazine-based azole-based cations in which 1 or 2 azole-based cations are connected to each other based on tetrazine is provided.
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Paragraph 0059-0061
(2021/08/10)
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- Tetrazine Assists Reduction of Water by Phosphines: Application in the Mitsunobu Reaction
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Reaction of 3,6-disubstituted-1,2,4,5-tetrazines with water and PEt3forms the corresponding 1,4-dihydrotetrazine and OPEt3. Thus PEt3, as a stoichiometric reductant, reduces water, and the resulting two reducing equivalent
- Polezhaev, Alexander V.,Maciulis, Nicholas A.,Chen, Chun-Hsing,Pink, Maren,Lord, Richard L.,Caulton, Kenneth G.
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p. 13985 - 13998
(2016/09/21)
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- BIO-ORTHOGONAL DRUG ACTIVATION
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The invention relates to a Prodrug activation method, for therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention also relates to a Prodrug kit comprising at least one Prodrug and at least one Activator, wherein the Prodrug comprises a Drug and a first Bio-orthogonal Reactive Group (the Trigger), and wherein the Activator comprises a second Bio-orthogonal Reactive Group. The invention also relates to targeted therapeutics used in the above-mentioned method and kit. The invention particularly pertains to antibody-drug conjugates and to bi- and trispecific antibody derivatives.
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Paragraph 0192; 0193
(2016/05/19)
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- 3,6-Substituted-1,2,4,5-tetrazines: Tuning reaction rates for staged labeling applications
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Cycloaddition reactions involving tetrazines have proven to be powerful bioorthogonal tools for various applications. Conceivably, sequential and selective labeling using tetrazine-based reactions can be achieved by tuning the reaction rate. By varying th
- Wang, Danzhu,Chen, Weixuan,Zheng, Yueqin,Dai, Chaofeng,Wang, Ke,Ke, Bowen,Wang, Binghe
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p. 3950 - 3955
(2014/06/09)
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- Click to release: Instantaneous doxorubicin elimination upon tetrazine ligation
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Eliminated without a trace: The fastest click reaction, the highly selective inverse-electron-demand Diels-Alder reaction, has been modified to enable selective bioorthogonal release. Thus, the click reaction of a tetrazine with a drug-bound trans-cyclooctene caused the instantaneous release of the drug and CO2 (see scheme). One possible application is the chemically triggered release, and thereby activation, of a drug from a tumor-bound antibody-drug conjugate. Copyright
- Versteegen, Ron M.,Rossin, Raffaella,Ten Hoeve, Wolter,Janssen, Henk M.,Robillard, Marc S.
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supporting information
p. 14112 - 14116
(2014/01/06)
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- Clicking 1,2,4,5-tetrazine and cyclooctynes with tunable reaction rates
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Substituted tetrazines have been found to undergo facile inverse electron demand Diels-Alder reactions with "tunable" reaction rates.
- Chen, Weixuan,Wang, Danzhu,Dai, Chaofeng,Hamelberg, Donald,Wang, Binghe
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supporting information; scheme or table
p. 1736 - 1738
(2012/03/09)
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- PHARMACEUTICAL COMPOSITION FOR TREATING OF CANCER COMPRISING PYRIDYLPYRIDAZINE COMPOUNDS OR THEIR TRANSITION METAL COMPLEXES
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The present invention relates to a pharmaceutical composition for the treatment of cancer, which contains, as an active ingredient, a pyridylpyridazine compound or a transition metal complex thereof. As described above, the pyridylpyridazine compounds according to the present invention and the transition metal complexes thereof have anticancer activity and can be easily prepared at low cost. Thus, these compounds are useful as anticancer agents against various cancers, including lung cancer, adenocarcinoma, skin cancer, colon cancer, uterine cancer and brain cancer, which are expressed due to immune system abnormality.
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Page/Page column 8
(2008/06/13)
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- DIELS-ALDER REACTIONS WITH INVERSE ELECTRON DEMAND. II. THE REACTION OF BENZAMIDINE WITH ?-DEFICIENT HETEROAROMATIC COMPOUNDS
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Benzamidine (I) reacts with several s-tetrazines to give as-triazines in moderate to good yield, together with some s-triazines; separate experiments have shown that these are due to the fact that (I) also undergoes Diels-Alder-reactions with as- and even with s-triazines.
- Figeys, H. P.,Mathy, A.
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p. 1393 - 1396
(2007/10/02)
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