- Acetylcholinesterase inhibition by products generated in situ from the transformation of N-arylisomaleimides
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When N-arylisomaleimides were transformed under enzymatic reaction conditions, the transformation reaction proved to be influenced by electronic effects. This was demonstrated qualitatively by 1H NMR spectroscopy and quantitatively by monitoring the kinetic of isomerization of N-phenylisomaleimide to N-phenylmaleimide. Subsequently, the first pseudo-order and activation energy (Ea) of the process were determined. The compounds showed in situ influence on AChE inhibition. The derivatives with electron-withdrawing groups exhibited a better effect than those having electron-donating groups. The in silico experiments show that the ligands evaluated established interactions with the CAS site. This suggests that these compounds could be useful for generating better reversible and competitive inhibitors of AChE.
- Guevara, Juan A.,Trujillo, José G.,Quintana, Delia,Jiménez, Hugo A.,Arellano, Mónica G.,Bahena, José R.,Tamay, Feliciano,Ciprés, Fabiola J.
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p. 989 - 1003
(2017/12/18)
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- METHOD FOR PRODUCING ISOMALEIMIDE
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PROBLEM TO BE SOLVED: To provide a simple method for producing maleimide containing no residual chloride ion, the IMI (isomaleimide) obtained by the present method being usable suitably as an insulation material in a printed wiring board and semiconductor
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Paragraph 0025
(2019/01/11)
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- Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore
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Several series of compounds containing the 1,4-dioxo-2-butenyl moiety have been prepared as candidate cytotoxins, including the methyl N-arylmaleamates, methyl N-arylfumaramates, and N-arylmaleimides. In addition, the N-arylisomaleimides were synthesized which are the structural isomers of N-arylmaleimides. These compounds were evaluated against human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 cells. Methyl N-arylfumaramates showed the highest cytotoxic potencies and, in particular, methyl N-(3,4-dichlorophenyl)fumaramate is six times more potent than melphalan towards L1210 cells and is equipotent with this drug in the Molt 4/C8 assay. Electrophilicity of compounds under investigation was demonstrated by carrying out thiolation using model benzyl mercaptan on representative compounds. Methyl N-(3,4-dichlorophenyl)fumaramate and methyl N-(4-chlorophenyl)maleamate inhibited human N-myristoyltransferase, a possible molecular target, in high micromolar range. QSAR and molecular modeling revealed some correlations between different structural features of a number of the molecules and cytotoxic potencies. Methyl N-arylfumaramates were well tolerated in mice in comparison to the analogs in other series of compounds tested. The data obtained in this investigation affords guidelines for preparing new series of molecules with greater potencies.
- Jha, Amitabh,Mukherjee, Chandrani,Prasad, Ashok K.,Parmar, Virinder S.,Vadaparti, Manjula,Das, Umashankar,De Clercq, Erik,Balzarini, Jan,Stables, James P.,Shrivastav, Anuraag,Sharma, Rajendra K.,Dimmock, Jonathan R.
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supporting information; experimental part
p. 1510 - 1515
(2010/06/16)
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- Cyanuric chloride: Decent dehydrating agent for an exclusive and efficient synthesis of kinetically controlled isomaleimides
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Starting from maleanilic and maleamic acids, a facile general approach to kinetically controlled isomaleimides has been described for the first time using cyanuric chloride as a dehydrating agent with 85-98% yields. The effect of a variety of substituents
- Haval, Kishan P.,Mhaske, Santosh B.,Argade, Narshinha P.
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p. 937 - 942
(2007/10/03)
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- 2-Chloro-1,3-dimethylimidazolinium chloride. 2. Its application to the construction of heterocycles through dehydration reactions
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2-Chloro-1,3-dimethylimidazolinium chloride (DMC) (1) can act as a powerful dehydrating equivalent to DCC (2) under nearly neutral conditions. Its application to the construction of heterocycles through dehydration reactions is described.
- Isobe, Toshio,Ishikawa, Tsutomu
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p. 6989 - 6992
(2007/10/03)
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- SYNTHESIS AND SOME REACTIONS OF N-ARYLMALEISOIMIDIUM PERCHLORATES
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N-Arylmaleisoimidium perchlorates (1a and b) were prepared by the action of acetic anhydride and perchlorid acid on the N-arylmaleamic acids (2a and b).Compound 1b reacted with amines via ring-opening to give N,N-disubstituted maleamides (4a-c), while the reaction of 1a with secondary amines gave N-phenylmaleimide (6).The reaction of 1a and b with aromatic hydrocarbons in the presence of anhydrous aluminium chloride gave good yields of trans-β-aroyl-N-arylacrylamides (7a-h).The reactions of some of the latter compounds with amines and phenylhydrazine are also discussed.
- Ismail, Mohamed Fekry,Enayat, Ebtesam Ismail,Bassiouny, Fakhry Abdel Aziz El,Younis, Hamed Ahmed
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p. 365 - 373
(2007/10/02)
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