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MARIA N PREOBRAZHENSKAYA - One of the best experts on this subject based on the ideXlab platform.
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macrolactones built from the bis 3 4 indol 1 yl Maleimide scaffold
Tetrahedron, 2014Co-Authors: Alexander Y Simonov, Sergey A Lakatosh, Yuri N Luzikov, E E Bykov, A M Korolev, M I Reznikova, MARIA N PREOBRAZHENSKAYAAbstract:Abstract 15, 16, and 17-Membered lactones based on the bis-3,4(indol-1-yl)Maleimide framework were obtained using intramolecular esterification reaction starting from 3-(1-ω-carboxyalkyl-2,3-dihydroindol-1-yl)-4-(1-ω-hydroxyalkyl-2,3-dihydroindol-1-yl)-Maleimides. 3,4-Dibromo-Maleimide, ω-(2,3-dihydroindol-3-yl)alkanoic acids, and ω-(2,3-dihydroindol-3-yl)alkanoles were used as starting compounds. Substitution of Br for the substituted indolines followed by the intramolecular cyclization of O-silylated hydroxyl acids derivatives led to macrolactones that incorporated 4-(dihydroindol-1-yl)-3-(indol-1-yl)Maleimide moieties. Indoline nuclei in these compounds were dehydrogenated by DDQ in refluxing toluene to give 15, 16 or 17-membered lactones 3-[(ω-3-carboxyalkylindol-1-yl)-4-(ω-hydroxyalkylindol-1-yl)Maleimides. Quantum chemical calculations showed that the formation of macrolactones of smaller size (13-membered) corresponds to the higher Gibbs energy ΔG# and correlates with the absence of the target reaction product.
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Synthesis of 4-substituted 3-(indol-3-yl)Maleimides and azepines with annelated indole and Maleimide nuclei
Tetrahedron, 2005Co-Authors: Sergey A Lakatosh, Yuri N Luzikov, MARIA N PREOBRAZHENSKAYAAbstract:Abstract A series of 4-substituted 3-(indole-3-yl)Maleimides has been synthesized. Upon the action of CH3SO3H in TFA, the 3-(indole-3-yl)-4-(arylalkylamino)-Maleimides undergo cyclization to give 12b,13-dihydro-4bH-indolo[3,2-d]pyrrolo[3,4-b][1]benzazepine-5,7(6H,8H)-dione derivatives.
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synthesis of 6h pyrrolo 3 4 2 3 1 4 diazepino 6 7 1 hi indole 8 10 7h 9h diones using 3 bromo 4 indol 1 yl Maleimide scaffold
Organic and Biomolecular Chemistry, 2003Co-Authors: Sergey A Lakatosh, Yuri N Luzikov, MARIA N PREOBRAZHENSKAYAAbstract:Series of 3-arylalkyl- or 3-alkylamino-4-(indol-1-yl)Maleimides and bis(indol-1-yl)Maleimides were synthesised. The cyclization of the 3-substituted 4-(indol-1-yl)Maleimides under the action of acids resulted in the formation of diazepine[1,4] derivatives with indoline and Maleimide nuclei annelated. These compounds readily produced the corresponding indolomaleimidodiazepines[1,4] after dehydrogenation.
Sergey A Lakatosh - One of the best experts on this subject based on the ideXlab platform.
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New 3,4-bis(indol-1-yl)Maleimides as protein kinase inhibitors
Chemistry of Heterocyclic Compounds, 2019Co-Authors: Alexey A. Panov, Sergey A Lakatosh, Michael H. G. Kubbutat, Lyubov G. Dezhenkova, Frank Totzke, Kristof SchechtelAbstract:Several previously unknown derivatives of 3,4-bis(indol-1-yl)Maleimide, as well as 3-(2,3-dihydroindol-1-yl)-4-(indol-1-yl)Maleimide were synthesized as potential analogs for a known series of protein kinase inhibitors BIS I, IV, IX containing the structural motif of 3,4-bis(indol-3-yl)Maleimide. The activity of these synthesized compounds was characterized with regard to several human protein kinases and their cytotoxicity was determined.
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3,4-Disubstituted Maleimides: synthesis and biological activity
Chemistry of Heterocyclic Compounds, 2018Co-Authors: Alexey A. Panov, Sergey A Lakatosh, Alexander Y Simonov, Sergey N. Lavrenov, Alexey S. TreninAbstract:This review is devoted to methods for the synthesis of 3,4-disubstituted Maleimides – compounds that often show pronounced biological activity. We offer classification of synthetic methods, present comparative analysis of various approaches while describing their advantages and drawbacks. The areas of practical applications are indicated for several 3,4-disubstituted Maleimide derivatives in the role of pharmaceutical agents or reactive dyes. The majority of the considered publications are from the last 10 years.
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macrolactones built from the bis 3 4 indol 1 yl Maleimide scaffold
Tetrahedron, 2014Co-Authors: Alexander Y Simonov, Sergey A Lakatosh, Yuri N Luzikov, E E Bykov, A M Korolev, M I Reznikova, MARIA N PREOBRAZHENSKAYAAbstract:Abstract 15, 16, and 17-Membered lactones based on the bis-3,4(indol-1-yl)Maleimide framework were obtained using intramolecular esterification reaction starting from 3-(1-ω-carboxyalkyl-2,3-dihydroindol-1-yl)-4-(1-ω-hydroxyalkyl-2,3-dihydroindol-1-yl)-Maleimides. 3,4-Dibromo-Maleimide, ω-(2,3-dihydroindol-3-yl)alkanoic acids, and ω-(2,3-dihydroindol-3-yl)alkanoles were used as starting compounds. Substitution of Br for the substituted indolines followed by the intramolecular cyclization of O-silylated hydroxyl acids derivatives led to macrolactones that incorporated 4-(dihydroindol-1-yl)-3-(indol-1-yl)Maleimide moieties. Indoline nuclei in these compounds were dehydrogenated by DDQ in refluxing toluene to give 15, 16 or 17-membered lactones 3-[(ω-3-carboxyalkylindol-1-yl)-4-(ω-hydroxyalkylindol-1-yl)Maleimides. Quantum chemical calculations showed that the formation of macrolactones of smaller size (13-membered) corresponds to the higher Gibbs energy ΔG# and correlates with the absence of the target reaction product.
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Synthesis of 4-substituted 3-(indol-3-yl)Maleimides and azepines with annelated indole and Maleimide nuclei
Tetrahedron, 2005Co-Authors: Sergey A Lakatosh, Yuri N Luzikov, MARIA N PREOBRAZHENSKAYAAbstract:Abstract A series of 4-substituted 3-(indole-3-yl)Maleimides has been synthesized. Upon the action of CH3SO3H in TFA, the 3-(indole-3-yl)-4-(arylalkylamino)-Maleimides undergo cyclization to give 12b,13-dihydro-4bH-indolo[3,2-d]pyrrolo[3,4-b][1]benzazepine-5,7(6H,8H)-dione derivatives.
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synthesis of 6h pyrrolo 3 4 2 3 1 4 diazepino 6 7 1 hi indole 8 10 7h 9h diones using 3 bromo 4 indol 1 yl Maleimide scaffold
Organic and Biomolecular Chemistry, 2003Co-Authors: Sergey A Lakatosh, Yuri N Luzikov, MARIA N PREOBRAZHENSKAYAAbstract:Series of 3-arylalkyl- or 3-alkylamino-4-(indol-1-yl)Maleimides and bis(indol-1-yl)Maleimides were synthesised. The cyclization of the 3-substituted 4-(indol-1-yl)Maleimides under the action of acids resulted in the formation of diazepine[1,4] derivatives with indoline and Maleimide nuclei annelated. These compounds readily produced the corresponding indolomaleimidodiazepines[1,4] after dehydrogenation.
Yuri N Luzikov - One of the best experts on this subject based on the ideXlab platform.
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macrolactones built from the bis 3 4 indol 1 yl Maleimide scaffold
Tetrahedron, 2014Co-Authors: Alexander Y Simonov, Sergey A Lakatosh, Yuri N Luzikov, E E Bykov, A M Korolev, M I Reznikova, MARIA N PREOBRAZHENSKAYAAbstract:Abstract 15, 16, and 17-Membered lactones based on the bis-3,4(indol-1-yl)Maleimide framework were obtained using intramolecular esterification reaction starting from 3-(1-ω-carboxyalkyl-2,3-dihydroindol-1-yl)-4-(1-ω-hydroxyalkyl-2,3-dihydroindol-1-yl)-Maleimides. 3,4-Dibromo-Maleimide, ω-(2,3-dihydroindol-3-yl)alkanoic acids, and ω-(2,3-dihydroindol-3-yl)alkanoles were used as starting compounds. Substitution of Br for the substituted indolines followed by the intramolecular cyclization of O-silylated hydroxyl acids derivatives led to macrolactones that incorporated 4-(dihydroindol-1-yl)-3-(indol-1-yl)Maleimide moieties. Indoline nuclei in these compounds were dehydrogenated by DDQ in refluxing toluene to give 15, 16 or 17-membered lactones 3-[(ω-3-carboxyalkylindol-1-yl)-4-(ω-hydroxyalkylindol-1-yl)Maleimides. Quantum chemical calculations showed that the formation of macrolactones of smaller size (13-membered) corresponds to the higher Gibbs energy ΔG# and correlates with the absence of the target reaction product.
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Synthesis of 4-substituted 3-(indol-3-yl)Maleimides and azepines with annelated indole and Maleimide nuclei
Tetrahedron, 2005Co-Authors: Sergey A Lakatosh, Yuri N Luzikov, MARIA N PREOBRAZHENSKAYAAbstract:Abstract A series of 4-substituted 3-(indole-3-yl)Maleimides has been synthesized. Upon the action of CH3SO3H in TFA, the 3-(indole-3-yl)-4-(arylalkylamino)-Maleimides undergo cyclization to give 12b,13-dihydro-4bH-indolo[3,2-d]pyrrolo[3,4-b][1]benzazepine-5,7(6H,8H)-dione derivatives.
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synthesis of 6h pyrrolo 3 4 2 3 1 4 diazepino 6 7 1 hi indole 8 10 7h 9h diones using 3 bromo 4 indol 1 yl Maleimide scaffold
Organic and Biomolecular Chemistry, 2003Co-Authors: Sergey A Lakatosh, Yuri N Luzikov, MARIA N PREOBRAZHENSKAYAAbstract:Series of 3-arylalkyl- or 3-alkylamino-4-(indol-1-yl)Maleimides and bis(indol-1-yl)Maleimides were synthesised. The cyclization of the 3-substituted 4-(indol-1-yl)Maleimides under the action of acids resulted in the formation of diazepine[1,4] derivatives with indoline and Maleimide nuclei annelated. These compounds readily produced the corresponding indolomaleimidodiazepines[1,4] after dehydrogenation.
Frederic Dolle - One of the best experts on this subject based on the ideXlab platform.
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1 3 2 18f fluoropyridin 3 yloxy propyl pyrrole 2 5 dione design synthesis and radiosynthesis of a new 18f fluoropyridine based Maleimide reagent for the labeling of peptides and proteins
Bioconjugate Chemistry, 2005Co-Authors: Beatrice De Bruin, Bertrand Kuhnast, Francoise Hinnen, Loic Yaouancq, Mohamed Amessou, Raphael Boisgard, Bertrand Tavitian, Alain Samson, Ludger Johannes, Frederic DolleAbstract:FPyME (1-[3-(2-fluoropyridin-3-yloxy)propyl]pyrrole-2,5-dione) was designed as a [18F]fluoropyridine-based Maleimide reagent for the prosthetic labeling of peptides and proteins via selective conjugation with a thiol (sulfhydryl) function. Its pyridinyl moiety carries the radioactive halogen (fluorine-18) which can be efficiently incorporated via a nucleophilic heteroaromatic substitution, and its maleimido function ensures the efficient alkylation of a free thiol function as borne by cysteine residues. [18F]FPyME (HPLC-purified) was prepared in 17−20% non-decay-corrected yield, based on starting [18F]fluoride, in 110 min using a three-step radiochemical pathway. The developed procedure involves (1) a high-yield nucleophilic heteroaromatic ortho-radiofluorination on [3-(3-tert-butoxycarbonylaminopropoxy)pyridin-2-yl]trimethylammonium trifluoromethanesulfonate as the fluorine-18 incorporation step, followed by (2) rapid and quantitative TFA-induced removal of the N-Boc-protective group and (3) optimized ma...
Naoko Yoshie - One of the best experts on this subject based on the ideXlab platform.
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Self-healing bio-based furan polymers cross-linked with various bis-Maleimides
Polymer, 2013Co-Authors: Chao Zeng, Kenichi Hatanaka, Hidetake Seino, Naoko YoshieAbstract:Abstract A series of bio-based self-healing polymers was prepared by cross-linking a furan polymer, poly(2,5-furandimethylene succinate), with bis-Maleimide compounds by means of Diels–Alder reactions. In addition to the amount of the bis-Maleimide linker, the molecular structure of the bis-Maleimide played a key role in determining the extent of the Diels–Alder reaction and the mechanical and healing properties of the polymers. Bis-Maleimides with phenylene rings markedly enhanced the tensile strength of the network polymers but hindered healing. In contrast, bis-Maleimides with a flexible molecular structure tended to improve the polymer elongation, affording polymers with excellent healing ability. The efficiencies of self-healing (=healing without any external stimulus) and healing with an assistance of solvent (CHCl3) were over 70% and 80%, respectively, for the network polymer crosslinked by bis-Maleimide with flexible long-alkyl segment. Thus, our results indicate that the choice of bis-Maleimide linker is an important factor for designing furan-Maleimide–based self-healing polymers.
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Self-healing bio-based furan polymers cross-linked with various bis-Maleimides
Polymer (United Kingdom), 2013Co-Authors: Chao Zeng, Kenichi Hatanaka, Hidetake Seino, Jie Ren, Naoko YoshieAbstract:A series of bio-based self-healing polymers was prepared by cross-linking a furan polymer, poly(2,5-furandimethylene succinate), with bis-Maleimide compounds by means of Diels-Alder reactions. In addition to the amount of the bis-Maleimide linker, the molecular structure of the bis-Maleimide played a key role in determining the extent of the Diels-Alder reaction and the mechanical and healing properties of the polymers. Bis-Maleimides with phenylene rings markedly enhanced the tensile strength of the network polymers but hindered healing. In contrast, bis-Maleimides with a flexible molecular structure tended to improve the polymer elongation, affording polymers with excellent healing ability. The efficiencies of self-healing (=healing without any external stimulus) and healing with an assistance of solvent (CHCl3) were over 70% and 80%, respectively, for the network polymer crosslinked by bis-Maleimide with flexible long-alkyl segment. Thus, our results indicate that the choice of bis-Maleimide linker is an important factor for designing furan-Maleimide-based self-healing polymers. © 2013 Elsevier Ltd. All rights reserved.