29244-55-1Relevant academic research and scientific papers
Sequential reaction of p-toluidine with 2,3-dichloromaleic anhydride: Synthesis and molecular structure of 2-chloro-3-p-toluidino-N-p-tolylmaleimide
Watson, William H.,Wu, Guanmin,Richmond, Michael G.
, p. 983 - 988 (2003)
The reaction of equimolar amounts of p-toluidine with 2,3-dichloromaleic anhydride in refluxing toluene affords 2,3-dichloro-N-p-tolylmaleimide (1) and 2-chloro-3-p-toluidino-N-p-tolylmaleimide (2), as the major and minor products, respectively. While increasing the amount of p-toluidine relative to 2,3-dichloromaleic anhydride yields the latter compound as the major product, the replacement of the chloro group in 2-chloro-3-p-toluidino-N-p-tolylmaleimide by added p-toluidine was not observed in refluxing toluene. Both 1 and 2 were isolated by column chromatography and characterized in solution by IR and NMR spectroscopies. The solid-state structure of 2-chloro-3-p-toluidino-N-p- tolylmaleimide was solved by X-ray crystallography. Further, 2-Chloro-3-p-toluidino-N-p-tolylmaleimide crystallizes in the monoclinic space group C2/c, a = 33.191(8) A, b = 4.037(1) A, c = 24.876(6) A, β = 107.050(4)°, V = 3187(1) A3, Z = 8, and d Calc = 1.362 mg/m3; R = 0.0561, Rw = 0.1246 for 2087 reflections with I > 2σ(I).
Application of maleimide compound as chitin synthase inhibitor
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Paragraph 0120-0123; 0228-0231, (2020/07/12)
The invention discloses an application of a maleimide compound as shown in a formula I. In the formula I, R0 is phenyl, benzyl, phenethyl, phenylpropyl, p-fluorophenyl, p-chlorophenyl, p-bromophenyl,p-methoxyphenyl, p-methylphenyl or p-hydroxyphenyl, R1 is hydrogen, methyl, phenyl or chlorine; and R2 is hydrogen, methyl, phenyl or chlorine. The provided maleimide compound has a good inhibition effect on chitin synthase.
Anti-leishmanial and cytotoxic activities of a series of maleimides: Synthesis, biological evaluation and structure-activity relationship
Fan, Yongxian,Lu, Yuele,Chen, Xiaolong,Tekwani, Babu,Li, Xing-Cong,Shen, Yinchu
, (2018/11/24)
In the present study, 45 maleimides have been synthesized and evaluated for anti-leishmanial activities against L. donovani in vitro and cytotoxicity toward THP1 cells. All compounds exhibited obvious anti-leishmanial activities. Among the tested compounds, there were 10 maleimides with superior anti-leishmanial activities to standard drug amphotericin B, and 32 maleimides with superior anti-leishmanial activities to standard drug pentamidine, especially compounds 16 (IC50 50 50 > 10 μg/mL). The anti-leishmanial activities of 16 and 42 were 10 times better than that of amphotericin B. The structure and activity relationship (SAR) studies revealed that 3,4-non-substituted maleimides displayed the strongest anti-leishmanial activities compared to those for 3-methyl-maleimides and 3,4-dichloro-maleimides. 3,4-dichloro-maleimides were the least cytotoxic compared to 3-methyl-maleimides and 3,4-non-substituted maleimides. The results show that several of the reported compounds are promising leads for potential anti-leishmanial drug development.
3,4-Diaminomaleimide Dyes – Simple Luminophores with Efficient Orange-Red Emission in the Solid State
Imoto, Hiroaki,Fujii, Ryosuke,Naka, Kensuke
, p. 837 - 843 (2018/02/21)
Maleimides have been utilized from materials science to biochemistry. In particular, maleimide-based luminescent dyes have attracted much attention. Recently, we reported arylaminomaleimide dyes that exhibit effective blue-green emission in the solid stat
Color Tuning of the Aggregation-Induced Emission of Maleimide Dyes by Molecular Design and Morphology Control
Imoto, Hiroaki,Kizaki, Kohei,Watase, Seiji,Matsukawa, Kimihiro,Naka, Kensuke
, p. 12105 - 12111 (2015/08/18)
Aggregation-induced emission (AIE)-active maleimide dyes, namely, 2-p-toluidino-N-p-tolylmaleimide, 3-phenyl-2-toluidino-N-p-tolylmaleimide, 2-p-thiocresyl-3-p-toluidino-N-p-tolylmaleimide, and 2,3-dithiocresyl-N-arylmaleimides, were synthesized by facile
Inhibition of Bfl-1 with N-aryl maleimides
Cashman, John R.,MacDonald, Mary,Ghirmai, Senait,Okolotowicz, Karl J.,Sergienko, Eduard,Brown, Brock,Garcia, Xochella,Zhai, Dayong,Dahl, Russell,Reed, John C.
supporting information; experimental part, p. 6560 - 6564 (2010/12/24)
High-throughput screening of 66,000 compounds using competitive binding of peptides comprising the BH3 domain to anti-apoptotic Bfl-1 led to the identification of 14 validated 'hits' as inhibitors of Bfl-1. N-Aryl maleimide 1 was among the validated 'hits'. A chemical library encompassing over 280 analogs of 1 was prepared following a two-step synthesis. Structure-activity studies for inhibition of Bfl-1 by analogs of N-aryl maleimide 1 revealed a preference for electron-withdrawing substituents in the N-aryl ring and hydrophilic amines appended to the maleimide core. Inhibitors of Bfl-1 are potential development candidates for anti-cancer therapeutics.
Synthesis of novel 1,4-benzoxazine-2,3-dicarboximides from maleic anhydride and substituted aromatic amines
Wu, Peng,Hu, Yongzhou
experimental part, p. 70 - 84 (2009/04/06)
A series of novel 1,4-benzoxazine-2,3-dicarboximides starting from maleic anhydride and substituted aromatic amines were synthesized. Copyright Taylor & Francis Group, LLC.
Synthesis and characterization of new compounds containing 1,4-dithiintetracarboxydiimide units
Gǎinǎ, Constantin
, p. 601 - 607 (2007/10/03)
New compounds containing 1,4-dithiintetracarboxydiimide units were synthesized by the disubstitution reaction of N-substituted 2,3- dichloromaleimide with sodium sulflde nonahydrate or thiourea. IR, UV-vis and 1H-NMR spectroscopy, as well as elemental analysis, confirmed their structures. Thermal conversion of 1,4-dithiine ring to thiophene was monitored by differential calorimetry (DSC) and thermogravimetric (TGA) measurements.
