- Dialkyl-14H-benzo[4,5]isoquino[2,3-a]perimidin-14-one-3,4,10, 11-tetracarboxylic diimides: A new family of n-type organic semiconductors
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Starting a family: A novel family of asymmetric arylenediimides, dialkyl-14H-benzo[4,5]isoquino[2,3-a]perimidin-14-one-3,4,10,11-tetracarboxylic diimides (BIPO-DI), was successfully designed and synthesized. The effects of different alkyl substitution on the structures were characterized by UV/Vis absorption spectrocopy and cyclic voltammetry. Field-effect transistors based on di-n-octyl BIPO-DI thin films show an electron mobility of 0.05 cm2 V-1 s-1 with a high current on/off ratio of 10 8. Copyright
- Zhu, Minliang,Zhang, Ji,Yu, Gui,Chen, Huajie,Huang, Jianyao,Liu, Yunqi
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- A ratiometric fluorescent probe with high sensitivity and selectivity for phosgene sensing in solution and gas
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Phosgene has attracted wide attention because of its important applications and value in modern industry, agriculture, and other fields, though it easily leaks and is difficult to detect. In this work, we designed and synthesized a naphthalimide-based fluorescent probe, which is easy to prepare, stable, and able to discriminate between phosgene, acetyl chloride, oxalyl chloride, thionyl chloride, phosphorus oxychloride, and tosyl chloride. Our results indicate that the probe can react with phosgene selectively and sensitively, showing remarkable ratiometric fluorescence changes. Furthermore, the probe can be made into test strips, which can determine phosgene in air effectively. The present work provides a novel class of naphthalimide-based derivatives with potential application in phosgene sensing in real time simply and safely with further optimization.
- Zhou, Wu,Chen, Qian,Wu, Aibin,Zhang, Ying,Yu, Weichu
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- Anticancer activity and topoisomerase II inhibition of naphthalimides with Ω-hydroxylalkylamine side-chains of different lengths
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Background: The substituted 1,8-Naphthalimides (1H-benzo[de]isoquinoline-1,3(2H)- diones) are known as DNA intercalators stabilizing DNA-Topoisomerase II complexes. This interaction disrupts the cleavage-relegation equilibrium of Topo II, resulting in formation of broken strands of DNA. Objective: To investigate the influence of type of substituents and substitution positions in 1,8- naphthalimde skeleton on the inhibition of Topoisomerase II activity. Method: The starting 1,8-naphthalimide were prepared from acenaphthene by introduction of appropriate substituents followed by condensation with ω-hydroxylakylamines of different chain length. The substituents were introduced to 1,8-naphthalimide molecule by nucleophilic substitution of leaving groups like nitro or bromo present in 4 or 4,5- positions using the ω- hydroxylalkylamines. The bioactivity of obtained compounds was examined in model cell lines. Results: Antiproliferative activity of selected compounds against HCT 116 human colon cancer cells, human non-small cell lung cells A549 and non-tumorigenic BEAS-2B human bronchial epithelium cells was examined. Several of investigated compounds exhibit a significant activity (IC50 μM to 7 μM) against model cancer cell lines. It was demonstrated that upon treatment with concentration of 200 μM, all derivatives display Topo II inhibitory activity, which may be compared with activity of Amonafide. Conclusion: The replacement of the nitro groups in the chromophore slightly reduces its anticancer activities, whereas the presence of both nitro group and ω-hydroxylalkylamine chain resulted in seriously increased anticancer activity. Obtained compounds showed Topo II inhibitory activity, moreover, influence of the substitution pattern on the ability to inhibit Topo II activity and cancer cells proliferation was observed.
- Kasprzycki, Przemys?aw,Strama, Klaudia,Tomczyk, Mateusz D.,Walczak, Krzysztof Z.,Wawszków, Martyna,Wyrostek, Anna Byczek
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p. 550 - 560
(2019/07/12)
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- N, N '-dialkyl -14H-benzo [4,5] isoquinoline and [2,1-a] the naphthalene inlayspyrimidine -14-one -3, 4, 10, 11-bis-imide compound and its preparation method and application
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The invention discloses a N,N'-dialkyl-14H-benzo[4,5]isoquinolino[2,1-a]perimidine-14-one-3,4,10,11-diimide (BIPOI) compound, and a preparation method and an application thereof. The compound has a structure as shown in formula I, wherein R and R' are alkyls or aryls. The invention also provides a preparation method of the compound in formula I. The synthetic route provided in the invention is simple and effective; raw materials are commercialized cheap products, which realizes low synthesis cost; the synthetic method has universality, and can be popularized and applied to synthesis of other BIPOI compounds. An OFET prepared by using the BIPOI of the invention as an organic semiconductor layer has higher electron mobility and on/off ratio ( the maximum of mu is 0.05 cm2/V.s, and the on/off ratio is larger than 108), and the BIPOI of the invention has good application prospects in OFET.
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Paragraph 0054; 0062; 0063
(2017/01/31)
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- Isoquinolones
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Benzo[de]isoquinoline-1,3-dione of Formula or a pharmaceutically acceptable salt thereof wherein R is hydrogen or a protecting group typically used in the art for protecting alcohols and R1-R5are each independently chosen from H, Cl, Br, F, straight or branched alkyl C1-C8alkyl, C3-C8cycloalkyl, heterocycle or bridged heterocycle of 4-9 atoms containing 1-3 heteroatoms, —(CR′2)nOR6, —(CR′2)nN(R6)2, —(CR′2)nNR6COR7, —(CR′2)nNR6SO2OR7, —(CR′2)nNR6SO2N(R6)2, —(CR′2)nOSO2N(R6)2, —(CR′2)nCN, —(CR′2)n(NOR6)R7, NO2, CF3, —(CR′2)nSOmR7, —(CR′2)nSOmR7, —(CR′2)nCO2R6, —(CR′2)nCON(R6)2, Ph, and any two of R1-R5may form a substituted or unsubstituted ring of 5-7 total atoms having 0-2 heteroatoms are claimed which are selective inhibitors of bacterial DNA gyrase and DNA topoisomerase useful in antibacterial agents. Methods for their preparation and formulation as well as novel intermediates useful in the preparation of the final products are also claimed.
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- Reactions of isomeric dinitronaphthalic-1,8-anhydrides with alkylamines
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In the reaction products of 4,5-dinitronaphthalic-1,8-anhydride and of the 3,6-dinitro analogue with 1-butylamine only nitro groups in the former compound undergo reaction. 2,5-Dinitronaphthalic anhydride reacted partially. 4,5-Dibutylaminonaphthalic-N-butyl-1,8-imide was moderately fluorescent by comparison with 4-butylamino-N-butyl-1,8-imide, (FBYR). The ease of nucleophilic replacement of the nitro group in mononitro substituted rings increases with ring size and appears to be related to the stability of a Meisenheimer intermediate.
- Alexiou,Tyman
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- DIRECT SYNTHESIS OF BROMINE-SUBSTITUTED ACENAPHTHENES. V. BROMINATION OF 5,6-DINITROACENAPHTHENE
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The photochemical bromination of 5,6-dinitroacenaphthene leads to the formation of 1-bromo-5,6-dinitroacenaphthene, which is dehydrobrominated by pyridine to 5,6-dinitroacenaphthylene.Methods are described for the production of 1-bromo- and 1,2-dibromo-5,6-dinitroacenaphthylenes.The first representative of the 1,1,2-tribromo derivatives, i.e., 1,1,2-tribromo-5,6-dinitroacenaphthene, was isolated as a result of the addition of bromine to 1-bromo-5,6-dinitroacenaphthylene.
- Usachenko, V. G.,Petrenko, G. P.,Anikin, V. F.,Lyutikova, A. A.
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p. 1186 - 1189
(2007/10/02)
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