- Reductive ring closure methodology toward heteroacenes bearing a dihydropyrrolo[3,2- B ]pyrrole core: Scope and limitation
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A newly developed reductive ring closure methodology to heteroacenes bearing a dihydropyrrolo[3,2-b]pyrrole core was systematically studied for its scope and limitation. The methodology involves (i) the cyclization of an o-aminobenzoic acid ester derivative to give an eight-membered cyclic dilactam, and (ii) the conversion of the dilactams into the corresponding diimidoyl chloride, which undergoes (iii) reductive ring closure to install the dihydropyrrolo[3,2-b]pyrrole core. The first step of the methodology plays the key role due to its substrate limitation, which suffers from the competition of oligomerization and hydrolysis. All the dilactams could successfully convert to the corresponding diimidoyl chlorides, most of which succeeded to give the dihydropyrrolo[3,2-b]pyrrole core. The influence of the substituents and the elongation of conjugated length on the photophysical properties of the obtained heteroacenes were then investigated systematically using UV-vis spectroscopy and cyclic voltammetry. It was found that chlorination and fluorination had quite a different effect on the photophysical properties of the heteroacene, and the ring fusing pattern also had a drastic influence on the band gap of the heteroacene. The successful preparation of a series of heteroacenes bearing a dihydropyrrolo[3,2-b]pyrrole core would provide a wide variety of candidates for further fabrication of organic field-effect transistor devices.
- Qiu, Li,Wang, Xiao,Zhao, Na,Xu, Shiliang,An, Zengjian,Zhuang, Xuhui,Lan, Zhenggang,Wen, Lirong,Wan, Xiaobo
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p. 11339 - 11348
(2015/01/09)
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- Synthesis and structure-activity relationship studies of small molecule disruptors of EWS-FLI1 interactions in Ewing's sarcoma
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EWS-FLI1 is an oncogenic fusion protein implicated in the development of Ewing's sarcoma family tumors (ESFT). Using our previously reported lead compound 2 (YK-4-279), we designed and synthesized a focused library of analogues. The functional inhibition of the analogues was measured by an EWS-FLI1/NR0B1 reporter luciferase assay and a paired cell screening approach measuring effects on growth inhibition for human cells containing EWS-FLI1 (TC32 and TC71) and control PANC1 cell lines devoid of the oncoprotein. Our data revealed that substitution of electron donating groups at the para-position on the phenyl ring was the most favorable for inhibition of EWS-FLI1 by analogs of 2. Compound 9u (with a dimethylamino substitution) was the most active inhibitor with GI50 = 0.26 ± 0.1 μM. Further, a correlation of growth inhibition (EWS-FLI1 expressing TC32 cells) and the luciferase reporter activity was established (R2 = 0.84). Finally, we designed and synthesized a biotinylated analogue and determined the binding affinity for recombinant EWS-FLI1 (Kd = 4.8 ± 2.6 μM).
- Tosso, Perrer N.,Kong, Yali,Scher, Lauren,Cummins, Ryan,Schneider, Jeffrey,Rahim, Said,Holman, K. Travis,Toretsky, Jeffrey,Wang, Kan,üren, Aykut,Brown, Milton L.
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p. 10290 - 10303
(2015/02/19)
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- TETRAHYDRONAPHTHALENE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND THEIR USE AS ANTI-INFLAMMATORY AGENTS
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The invention relates to tetrahydronaphthalene derivatives of general formula (I), to a method for their production and to their use as anti-inflammatory agents.
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Page/Page column 33-36
(2010/11/24)
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- ALKYLIDENE TETRAHYDRONAPHTHALENE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND THEIR USE AS ANTI-INFLAMMATORY AGENTS
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The invention relates to alkylidene tetrahydronaphthalene derivatives of general formula (I), to methods for their production and to their use as anti-inflammatory agents.
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Page/Page column 43-45
(2010/10/20)
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- Multiply-substituted tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents
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The invention relates to multiply-substituted tetrahydronaphthalene derivatives of formula (I) process for their production and their use as anti-inflammatory agents.
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Page/Page column 18, 19
(2010/02/14)
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- Rearranged pentanols, a process for their production and their use as anti-inflammatory agents
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The invention relates to the compounds of formula I, a process for their production and their use as anti-inflammatory agents.
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Page/Page column 11
(2010/02/12)
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- HETEROCYCLICALLY SUBSTITUTED PENTANOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF AS ANTI-INFLAMMATORY AGENTS
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The invention relates to pentanol derivatives of general formula (I), which are substituted by quinazoline, quinoxaline, cinnoline, indazole, phthalazine, naphthyridine, benzothiazole, dihydroindolone, dihydroisoindolone, benzimidazole, or indole, a method for the production thereof, and the use thereof as anti-inflammatory agents.
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Page/Page column 35-37
(2010/02/10)
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