Final Thoughts on Chemistry for 3,4-Dichloro-1H-pyrrole-2,5-dione

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Acylation of Amines with Dichloromaleoyl Chloride

The reaction of dichloromaleoyl chloride (2) with ammonia in ether yields the ammonium salt of (Z)-2,3-dichloro-3-cyanoacrylic acid (6) and with aqueous ammonia the ammonium salt of (Z)-2-amino-3-chloro-3-cyanoacrylic acid (1).With primary aliphatic and aromatic amines dichloromaleamides 8 are obtained, the two chlorine atoms of which can be replaced with other amines to form after cis/trans isomerization diaminofumaramides 11.

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Rational design of substituted maleimide dyes with tunable fluorescence and solvafluorochromism

A series of maleimide derivatives were systematically designed and synthesized with tunable fluorescent properties. The facile modifications herein provide a simple methodology to expand the scope of maleimide-based dyes and also provide insight into the relationship between substitution pattern and optical properties.

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6H-Pyrrolo[3,2-b:4,5-b?]bis[1,4]benzothiazines: Facilely synthesized semiconductors for organic field-effect transistors

6H-Pyrrolo[3,2-b:4,5-b?]bis[1,4]benzothiazine (PBBTZ, 1) and its two 6-substituted derivatives (2 and 3) were conveniently synthesized. Their optical properties were studied by UV-vis and fluorescence spectroscopy, and electrochemical properties were investigated by cyclic voltammetry (CV). Good thermal stability was observed by thermogravimetric analysis. X-Ray analysis revealed a coplanar structure and a column stacking in the single crystal of compound 1. OFET measurements showed that 1-3 were p-type semiconductors. The performance of these devices displayed good reproducibility at ambient conditions. When devices containing 1 were fabricated on OTS-treated SiO 2/Si substrates at 60 C, the best performance was achieved with the average hole mobility as high as 0.34 cm2 V-1 s -1 and the on/off ratio about 106-107. This performance resulted from the well-ordered molecular packing as revealed by XRD and AFM analysis.

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TRIPHENYLBORANE-ROSIN AMINE ADDUCT AND USE OF THE SAME

The triphenylborane-rosin amine adduct shows superior prevention of adhesion, and thus, antifouling effects against coelenterates such as obelia and hydrozoas; shellfish such as barnacle, blue mussel and oyster, tubicolous polychaetes such as Hydroides norvegica, Serpula vermicularis, Pomatoleios kraussiiand Dexiospira spirillumand other aquatic organisms. The concurrent use of 1,3-dicyanotetrachlorobenzene, 2-(thiocyanomethylthio)benzothiazole, tetraalkylthiuramdisulfide, 2,3-dichloromaleimide, phenol, dialkylpolysulfide, polybutene, paraffin or petrolatum, and the above-mentioned compound results in the above-mentioned effects. Thus, the above-mentioned compound can be used to provide a preventive of fouling by the aquatic adhesion organisms, an antifouling agent for a fishnet and an antifouling coating, which have superior antifouling effects against fouling organisms such as coelenterates, shellfish, tubicolous polychaetes and the like.

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Development of a novel affinity labeling method for target identification of bioactive small molecules

Target identification (target-ID) is an important step in elucidating the mechanisms of action of bioactive small molecules. In the past few decades, a number of target-ID methods have been developed. Among these, affinity labeling has been reliably used for specific modifications, as well as for the identification of weakly interacting protein targets, membrane-associated protein targets, and target-interacting proteins under native cellular conditions, which are generally difficult to achieve by conventional pull-down methods. In general, affinity labeling utilizes chemical probes composed of a bioactive small molecule, a reactive group, and a detection unit. However, the design and synthesis of highly functionalized chemical probes is often time-consuming. To address this issue, we have recently developed some simple affinity labeling methods using small fluorogenic tags, such as 4-alkoxy-7-nitro-2,1,3-benzoxadiazole (O-NBD), 2,3-dichloromaleimide (diCMI), and 4-azidophthalimide (AzPI), and successfully achieved the specific fluorescent labeling of target proteins, even in living cells. These methods should be useful for target-ID in phenotypic drug discovery.

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In this work, nineteen analogues of Agomelatine were readily synthesized through structural modification of the acetamide side-chain starting from the key common intermediate 2-(7-methoxynaphthalen-1-yl) ethanamine (3), which was prepared from commercially available compound 2-(7-methoxynaphthalen-1-yl) acetonitrile (2) in two steps. Corticosterone-induced PC12 pheochromocytoma cells phenotypic in vitro model was utilized to evaluate their potential antidepression activities. Imide compound 4a and acylamino carboxylic acid analogue 5b showed good protective effects on traumatic PC12 cells with protection rates of 34.2% and 23.2%, respectively. Further in vivo assessments in C57 mice FST (forced swim test) model demonstrated that compound 4a significantly reduced the immobility time of the tested subjects, indicating antidepressant-like activity. Preliminary toxicity assays conducted on human normal liver L02 cells and embryonic kidney 293 cells suggested a relatively low safety risk for compound 4a compared with the marketed drugs Agomelatine and Fluoxetine. The promising antidepressant-like efficacy of compound 4a, together with the relatively low toxicity to the normal tested cells and high liability of diffusion through the blood-brain barrier (BBB), presents us insights of exploration of me-better drug candidates of Agomelatine.

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Pyrazine-2,3-dicarbonitriles substituted with maleimide derivatives

Syntheses and spectroscopic characteristics are reported for eight pyrazine-2,3-dicarbonitriles substituted with maleimide residue in addition to phenyl, 2-thienyl, or 2-furyl substituent.

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Synthesis of Five-Membered Heterocycles from Maleimides

New heterocycles containing maleimide building blocks were prepared via 2-chloro-3-cyanomaleimide or 2,3-dichloromaleimides as key intermediates.Of the heterocyclic amines thus prepared, the following systems are useful as diazo components for preparing disperse dyes: 5-aminopyrazole-3,4-dicarboximides 5, 4-amino-5-alkoxycarbonylthiophene-2,3-dicarboximides 7, 5-aminoisothiazole-3,4-dicarboximides 9, 5-aminoisothiazole-3,4-dicarboxamide (10), 5-amino-3,4-dicyanoisothiazole (12), 5-amino-4-cyanothiophene-2,3-dicarboximides 15, and 2-aminothiazole-4,5-dicarboximides 17.

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Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions

Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions was investigated. Pyrrole derivatives with two aryl groups on adjacent positions include important classes of marine natural products, some of which display remarkable biological and pharmacological properties. These classes of heterocyclic derivatives have stimulated great interest from synthetic and medicinal chemists. Interest have been shown in terms of synthetic and atom efficiency, in the development and application of selective methods to form C-C bonds through C-H activation of hetero arenes, in which only one component of the transition metal-catalyzed reaction needed to posses a reactive functional group. It was found that the vicinal diaryl-substituted pyrrole, pyrroline and pyrrolidine derivatives include natural and unnatural compounds with notable biological and pharmacological properties.

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A solution of 6.64 g [0.04 mol] of dichloromaleimide (VI-2) in 40 ml of methanol is introduced at 65 C. and, over the course of about 10 minutes, a solution, likewise heated at 65 C., of 13.89 g [0.056 mol] of sodium thiosulfate pentahydrate in 40 ml of water is added dropwise. After the end of the addition, the mixture is stirred for hour more at 65 C. Thereafter the reaction mixture is cooled to 15 C., 10 and of water are added, and it is stirred for 15 minutes. Thereafter the solid is isolated by filtration with suction, washed with 30 ml of water and then 15 ml of MODEL and dried. This gives 3.6 g of dark-green solid, which according to HPLC analysis is composed to an extent of 99.6 area-% of the compound (I-2), corresponding to a yield of 71% of theory., 1193-54-0

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Reference£º
Patent; Bayer CropScience AG; US2011/257411; (2011); A1;,
Pyrroline – Wikipedia
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