555-59-9Relevant academic research and scientific papers
Dichloro Butenediamides as Irreversible Site-Selective Protein Conjugation Reagent
Abegg, Daniel,Adibekian, Alexander,Afonso, Cláudia F.,Bernardes, Gon?alo J. L.,Corzana, Francisco,Laserna, Victor,Martin, Esther M.,Ravn, Peter
supporting information, p. 23750 - 23755 (2021/10/01)
We describe maleic-acid derivatives as robust cysteine-selective reagents for protein labelling with comparable kinetics and superior stability relative to maleimides. Diamide and amido-ester derivatives proved to be efficient protein-labelling species with a common mechanism in which a spontaneous cyclization occurs upon addition to cysteine. Introduction of chlorine atoms in their structures triggers ring hydrolysis or further conjugation with adjacent residues, which results in conjugates that are completely resistant to retro-Michael reactions in the presence of biological thiols and human plasma. By controlling the microenvironment of the reactive site, we can control selectivity towards the hydrolytic pathway, forming homogeneous conjugates. The method is applicable to several scaffolds and enables conjugation of different payloads. The synthetic accessibility of these reagents and the mild conditions required for fast and complete conjugation together with the superior stability of the conjugates make this strategy an important alternative to maleimides in bioconjugation.
Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction
Xu, Wen-Lei,Tang, Lei,Ge, Chen-Yu,Chen, Jie,Zhou, Ling
supporting information, p. 2268 - 2273 (2019/04/10)
A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).
Synthesis and biological evaluation of novel benzylidene-succinimide derivatives as noncytotoxic antiangiogenic inhibitors with anticolorectal cancer activity in vivo
Luo, Kaixiu,Bao, Yafeng,Liu, Feifei,Xiao, Chuanfan,Li, Ke,Zhang, Conghai,Huang, Rong,Lin, Jun,Zhang, Jihong,Jin, Yi
, p. 805 - 827 (2019/07/10)
A novel series of benzylidene-succinimide derivatives were synthesized, characterized and evaluated for their cytotoxicities against HCT116, and SW480 cancer cells and NCM460 normal human cells. Their antiangiogenic capabilities were evaluated using a chick chorioallantoic membrane (CAM) assay. The compound, XCF-37b, was selected as the most potent antiangiogenic inhibitor with noncytotoxicity to evaluate the pharmacological effects on human umbilical vein endothelial cells (HUVECs) and cancer cells in vivo and in vitro. The results showed that XCF-37b inhibited HT29-cell colon tumor growth in vivo, without showing cytotoxicity against the five other cancer cell lines in vitro. Experiments confirmed that XCF-37b had obvious antiangiogenic activity by HUVEC migration and invasion and rat aortic ring angiogenesis ex vivo. Mechanism studies showed that XCF-37b inhibited the AKT/mTOR and VEGFR2 signaling pathways, as evidenced by decreased expressions of phosphor-AKT (p-AKT), p-mTOR, p-VEGFR2 (Tyr175), p-Src (Tyr416), p-FAK (Tyr925), and p-Erk1/2 (Thr202/Tyr204). Moreover, XCF-37b significantly decreased the protein expressions of matrix metalloproteinase-2 (MMP-2), MMP-9 and hypoxia-inducible factor-1α (HIF-1α). XCF-37b generally regulated angiogenic inhibition through several regulatory pathways, without significantly interfering with colorectal cancer cell growth.
METHOD FOR RECYCLING CATALYSTS FOR PREPARING N-SUBSTITUTED MALEIMIDE
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Paragraph 0126; 0130; 0139-0143; 0149; 0160-0162, (2019/10/29)
The present invention relates to a method for recycling a catalyst for manufacturing N-substituted maleimide. Specifically, by recycling a zirconium hydrogen phosphate solid acid catalyst through washing or calcining, the recycled catalyst can be reused for N-substituted maleimide synthesis.COPYRIGHT KIPO 2019
Acetylcholinesterase inhibition by products generated in situ from the transformation of N-arylisomaleimides
Guevara, Juan A.,Trujillo, José G.,Quintana, Delia,Jiménez, Hugo A.,Arellano, Mónica G.,Bahena, José R.,Tamay, Feliciano,Ciprés, Fabiola J.
, p. 989 - 1003 (2017/12/18)
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.
Continuous efficient production method for high-purity N-substituted maleamic acid
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Paragraph 0034-0046, (2018/09/08)
The invention belongs to the technical field of fine chemicals and particularly relates to a continuous efficient production method for high-purity N-substituted maleamic acid. The method comprises the following steps: solutions are prepared from primary amine and maleic anhydride respectively by inert solvents in nitrogen protective atmosphere; the two solutions are added to an efficient mixer inproportion for mixing; the mole ratio of primary amine and maleic anhydride is 1:1.0-1.5, a reaction product is treated by a solid-liquid separation unit, and the product amido carboxylic acid is separated; a liquid solution separated out by the solid-liquid separation unit and a liquid solution obtained after separation of the product amido carboxylic acid are used for preparing the primary amine and maleic anhydride solutions circularly. With adoption of the method for continuously and efficiently synthesizing high-purity N-substituted maleamic acid with high yield and high selectivity witha reaction-separation coupling control reaction technology, the adding way of primary amine and maleic anhydride and standing time of a chemical reaction are controlled, and isomerization and Michaeladdition side reactions are avoided effectively through rapid reaction and rapid separation.
Four-Component Reaction for the Synthesis of Indolizines by Copper-Catalyzed Aerobic Oxidative Dehydrogenative Aromatization
Xu, Juanfang,Hu, Huayou,Liu, Yun,Wang, Xiang,Kan, Yuhe,Wang, Chao
supporting information, p. 257 - 261 (2017/01/24)
A one-pot, four-component reaction was developed for the synthesis of indolizines from pyridines, α-halide carbonyl compounds, primary amines, and maleic anhydride. The key step in this reaction involved the copper-catalyzed aerobic oxidative aromatization of a tetrahydrogen–indolizine intermediate. Oxygen gas was employed as a clean oxidant to facilitate the catalytic process. Notably, this transformation used readily available starting materials, exhibited broad substrate scope, was easy to handle, and required mild reaction conditions.
Synthesis and Evaluation of Novel Spiro[oxindole-isoxazolidine] Derivatives as Potent Antioxidants
Kaur, Manpreet,Singh, Baldev,Singh, Baljit,Arjuna, Anania
, p. 1348 - 1354 (2017/03/27)
The antioxidant activity of isatin derivatives can be described with the presence of enolic hydroxyl group at the second position of the ring because of the keto-enol tautomerism between NH and C O groups of indolone moiety. The reducing ability of the tested compounds was evaluated by their interaction with the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH) at various concentrations. Novel spiro[oxindole-isoxazolidine] derivatives (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i) have been synthesized by 1,3-dipolar cycloaddition reactions of variously substituted maleimides (1) with isatin ketonitrone (3) and tested for their in vitro antioxidant potency in the DPPH assay. All the synthesized compounds have been identified as potent in vitro antioxidants.
N-substituted benzal pyrrolidinedione and preparation method and application thereof
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Paragraph 0037, (2017/08/28)
The invention discloses an N-substituted benzal pyrrolidinedione compound and a preparation method and application thereof. The N-substituted benzal pyrrolidinedione compound has very high tumor cell growth inhibition activity and particularly has a remarkable inhibition effect on growth of vascular endothelial growth factor receptor subtype 2 (VEGFR-2) high-expression human colon cancer cells (HCT116), the IC50 value of the N-substituted benzal pyrrolidinedione compound can reach 5.93 micromoles, and the N-substituted benzal pyrrolidinedione compound has an obvious inhibition effect on new vessel generation of chick embryos.
Improvement of thermal properties of poly(vinyl chloride) using chemical blending assisted ultrasonic technique
Al-Ghamdi, Azza
, p. 2285 - 2288 (2017/10/05)
The thermal stabilization of poly(vinyl chloride) through blending techniques has been studied. Poly(vinyl chloride) was blended with modified polymer (cellulose acetate-diallyl amine) in different compositions to improve the thermal stability of poly(vinyl chloride). The thermal stability and morphology of the blend films were characterized by scanning electron microscope (SEM) and thermogravimetry. The results revealed that the presence of modified cellulose acetate improved the thermal stability of poly(vinyl chloride). This was attributed to the thermal stable diallylamine moieties among the cellulose acetate chains. The addition of traces of maleimide derivatives to poly(vinyl chloride) prior to the blend process led to an extra thermal stability of the blend film as shown from the values of the initial decomposition temperature (To) measured by thermogravimetry.
