- Benzene Triimides: Facile Synthesis and Self-Assembly Study
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Herein, we report an efficient one-pot condensation of maleimide derivatives in the presence of acetic acid and water to afford a series of benzene triimides (BTIs). The structure, physicochemical properties and electrochemistry behavior of BTIs were studied by means of X-ray crystallography, UV-Vis spectra, cyclic voltammetry and differential pulse voltammetry. Owing to the planar structure and unique electron-deficient nature, BTIs can self-assemble into different motifs including nanorod, nanotube, nanobrick and cross-linked structure depending on different N-substituents. The origin for different self-assemblies was ascribed to the intermolecular lone pair-π interaction or a balance of lone pair-π and π-π stacking.
- Tuo, De-Hui,He, Qing,Wang, Qi-Qiang,Ao, Yu-Fei,Wang, De-Xian
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- The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation
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Adenylate cyclases (ACs), play a critical role in the conversion of adenosine triphosphate (ATP) into the second messenger cyclic adenosine monophosphate (cAMP). Studies have indicated that adenylyl cyclase type 2 (AC2) is potential drug target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells. The SAR (structure activity relationship) based on the derivatives of compound 8 was further explored on recombinant AC2 cells and compound 73 was found to be the most active agonist with the EC50 of 90 nM, which is 160-fold more potent than the reported agonist Forskolin and could selectively activate AC2 to inhibit the expression of Interleukin-6. The discovery of a new class of AC2-selective agonists would provide a novel chemical probe to study the physiological function of AC2.
- Li, Shanshan,Song, Gao,Wang, Liang-Liang,Weng, Zhiying,Xu, Guowei,Yang, Weimin,Yang, Yanming,Yang, Yaqing,Zhang, Jiajun,Zuo, Zhili
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supporting information
(2020/02/27)
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- Cheap and efficient preparation method of benzene triimide and derivative thereof
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The invention discloses a preparation method of benzene triimide (BTI) and a derivative thereof, wherein the structural general formula of the compound is represented by a formula I. The preparation method comprises the following steps: under the condition of refluxing in a mixed solution of acetic acid and water, carrying out an intermolecular aromatic ring construction reaction on a maleimide derivative represented by a formula II to obtain the benzene triimide (BTI) and the derivative I thereof. According to the invention, the cheap and easily available raw materials maleic anhydride and maleimide and the cheap and easily available primary amine compound are selected and subjected to simple addition, elimination and amination to rapidly prepare a large amount of maleimide derivatives, and further the maleimide derivatives are subjected to an intermolecular cyclization reaction to rapidly prepare the benzene triimide (BTI) and the derivative thereof in one step, so that the reactionconditions are mild, and the obtained product is stable in air and easy to separate and purify, and has good application prospect.
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Paragraph 0145; 0152; 0153
(2020/05/01)
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- Regioselective hydroarylation and arylation of maleimides with indazoles: Via a Rh(iii)-catalyzed C-H activation
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Switchable Rh(iii)-catalyzed highly regioselective hydroarylation and oxidative arylation of maleimides with 2-arylindazoles via C-H activation have been demonstrated. The reaction affords 3-(2-(2H-indazol-2-yl)phenyl)succinimide and 3-(2-(2H-indazol-2-yl)phenyl)maleimide derivatives in high yields with wide functional group tolerance. A mechanistic study was performed to depict C-H bond cleavage that might be involved in the turnover limiting step.
- Ghosh, Asim Kumar,Samanta, Sadhanendu,Ghosh, Payel,Neogi, Sukanya,Hajra, Alakananda
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supporting information
p. 3093 - 3097
(2020/05/08)
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- Graphene Oxide as a Carbocatalyst for a Diels–Alder Reaction in an Aqueous Medium
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The Diels–Alder (DA) reaction, a [4+2] cycloaddition reaction, is highly important in synthetic organic chemistry and is frequently used in the synthesis of natural products containing six-membered rings. Herein, we report an efficient protocol for the DA reaction between 9-hydroxymethylanthracene and N-substituted maleimides using two-dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yields, a wide substrate scope, low temperature, excellent functional group tolerance, atom economy, and water as a green solvent are noteworthy features of this protocol. The heterogeneous GO catalyst can be easily recovered and used multiple times without any significant loss in catalytic activity.
- Girish, Yarabhally R.,Pandit, Subrata,Pandit, Subhendu,De, Mrinmoy
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supporting information
p. 2393 - 2398
(2017/09/11)
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- Nanoporous hypercrosslinked polymers containing Tg enhancing comonomers
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Hypercrosslinked polymers containing functionalized alternating copolymer sequences of substituted stilbene or styrene and N-aryl substituted maleimides have been synthesized. Alternating copolymers containing these comonomers possess semi-rigid structures, and incorporation of these units into the precursor polymer particles for hypercrosslinking leads to a systematic increase in Tg and chain stiffness of these materials as the concentration of the comonomers is increased. Surface area and porosity of the subsequent hypercrosslinked polymers were investigated using nitrogen adsorption/desorption isotherms at 77 K. These hypercrosslinked polymers exhibit BET surface areas ranging from 1058 m2/g at 25 mol% alternating copolymer incorporation down to loss of measurable surface area at ca. 60% incorporation. The experimental surface area results correlate with predictions from simulations and serve as model systems for future studies on specifically functionalized hypercrosslinked polymer particles.
- Zhou, Xu,Huang, Jing,Barr, Kevin W.,Lin, Zhixing,Maya, Fernando,Abbott, Lauren J.,Colina, Coray M.,Svec, Frantisek,Turner, S. Richard
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- Discovery and structural optimization of pyrazole derivatives as novel inhibitors of Cdc25B
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Structural optimization and preliminary structure-activity relationship studies of a series of N-substituted maleimide fused-pyrazole analogues with Cdc25B inhibitory activity, starting from a high-throughput screening hit, are illustrated. A simplified 3,5-diacyl pyrazole analogue was obtained as the most potent compound (118, IC50 = 0.12 μM) with a 270-fold increase in potency.
- Chen, Hai-Jun,Liu, Yong,Wang, Li-Na,Shen, Qiang,Li, Jia,Nan, Fa-Jun
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scheme or table
p. 2876 - 2879
(2010/07/04)
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- Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors
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The endocannabinoid 2-arachidonoylglycerol (2-AG) plays a major role in many physiological processes, and its action is quickly terminated via enzymatic hydrolysis catalyzed by monoglyceride lipase (MGL). Regulating its endogenous level could offer therapeutic opportunities; however, few selective MGL inhibitors have been described so far. Here, we describe the synthesis of N-substituted maleimides and their pharmacological evaluation on the recombinant human fatty acid amide hydrolase (FAAH) and on the purified human MGL. A few N-arylmaleimides were previously described (Saario, S. M.; Salo, O. M.; Nevalainen, T.; Poso, A.; Laitinen, J. T.; Jarvinen, T.; Niemi, R. Characterization of the Sulfhydryl-Sensitive Site in the Enzyme Responsible for Hydrolysis of 2-Arachidonoylglycerol in Rat Cerebellar Membranes. Chem. Biol. 2005, 12, 649-656) as MGL inhibitors, and along these lines, we present a new set of maleimide derivatives that showed low micromolar IC50 and high selectivity toward MGL vs FAAH. Then, structure-activity relationships have been investigated and, for instance, 1-biphenyl-4-ylmethylmaleimide inhibits MGL with an IC50 value of 790 nM. Furthermore, rapid dilution experiments reveal that these compounds act as irreversible inhibitors. In conclusion, N-substituted maleimides constitute a promising class of potent and selective MGL inhibitors.
- Matuszak, Nicolas,Muccioli, Giulio G.,Labar, Geoffray,Lambert, Didier M.
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experimental part
p. 7410 - 7420
(2010/04/30)
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- Substituent chemical shifts of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides
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NMR spectra of a series of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides were examined to estimate the electronic effect of the amide and imide groups on the chemical shifts of the hydrogen and carbon nuclei of the benzene ring.
- Lee, Hye Sun,Yu, Ji Sook,Lee, Chang Kiu
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scheme or table
p. 711 - 715
(2010/07/05)
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- Non-hydroxylic clathrate hosts of [4 + 2]π cycloadducts of phencyclone and N-arylmaleimides: Recognition of aromatic guests
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A series of non-hydroxylic crystalline host compounds, [4 + 2]π cycloadducts of phencyclone and N-arylmaleimides having a bicyclo[2.2.1]heptene-7-one system, was synthesized and their inclusion behavior investigated. X-Ray crystal analyses of the inclusion compounds of the N-(1-naphthyl) derivative with butan-2-one, the N-(m-tolyl) derivative with p-xylene, together with the guest-free host and the N-(p-tolyl) derivative with m-xylene indicate that the "space" surrounded by the phenanthrene ring, two phenyl rings and bridge carbonyl of the 1,3-diphenyl-1,3-dihydrocyclopenta[l]phenanthren-2-one moiety plays an important role, not only in the formation of inclusion complexes with the aromatic guests but also in host-host interactions. In every case, the N-aryl succinimide assists complex formation with the guests, in which the weak lattice forces due to C-H ... π and C-H ... O interactions are operative. Methyl-substituted benzenes are effectively recognized by the C-H ... π interactions between the guest molecules and the phenanthrene ring of the hosts.
- Yoshitake, Yasuyuki,Misaka, Junichi,Setoguchi, Koji,Abe, Masaki,Kawaji, Tomohiro,Eto, Masashi,Harano, Kazunobu
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p. 1611 - 1619
(2007/10/03)
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