37902-58-2Relevant articles and documents
Cyclodextrin effect on intramolecular catalysis
Granados,Andres,De Rossi, R. Hoyos
, p. 405 - 406 (2000)
HPCD inhibits the hydrolysis reaction of monoamides and monoesters of phthalic and maleic acid at pH 2. The magnitude of inhibition depends on the leaving group. For some of the substrates, the reaction in the cavity is more than 100 times slower than that in solution.
Hydrophobic acceleration in the Diels—Alder reaction of 9-hydroxymethylanthracene with N-phenylmaleimide
Kiselev,Kashaeva,Potapova,Kornilov,Latypova,Konovalov
, p. 2202 - 2205 (2016)
The Diels—Alder reaction rates of 9-hydroxymethylanthracene with N-phenylmaleimide and N-ethylmaleimide in water, butan-1-ol, ethylene glycol, acetonitrile, chloroform, and 1,4-dioxane have been compared.
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
, p. 257 - 261 (2017)
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.
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.
Photoinduced Decarboxylative Amino-Fluoroalkylation of Maleic Anhydride
Sun, Youwen,Zhang, Guozhu
, p. 419 - 422 (2019/12/24)
A photoinduced decarboxylative three-component coupling reaction involving amine, maleic anhydride, and fluorinated alkyl iodides has been developed, leading to synthetically valuable fluoroalkyl-containing acrylamides with a high E selectivity. A broad array of substrates including monoprotected amino acid are capable coupling partners. Preliminary mechanistic studies suggest a stepwise process. This reaction represents the first example of photoinduced decarboxylative difunctionalization of maleic anhydride.
Design, synthesis and biological evaluation of novel 3,4-dihydro-2(1H)-quinolinone derivatives as potential chitin synthase inhibitors and antifungal agents
Ji, Qinggang,Li, Baihui,Shen, Yangli,Wu, Hu,Wu, Xiaobo,Yuan, Lvjiang
, (2020/04/15)
A series of 3,4-dihydro-2(1H)-quinolinone derivatives contained butenediamide fragment were designed and synthesized. Their inhibition potency against chitin synthase and antimicrobial activities were screened in vitro. The enzymatic assays showed that all the synthesized compounds had inhibition potency against chitin synthase at concentration of 300 μg/mL. Compound 2d displayed excellent potency with inhibition percentage (IP) value of 82.3%, while IP value of the control polyoxin B was 87.5%. Compounds 2b, 2e and 2s whose IP values were above 70% showed good inhibition potency against chitin synthase. Moreover, the IC50 value of 2b was comparable with that of polyoxin B (0.09 mM). The Ki of compound 2b was 0.12 mM and the result from Lineweaver-Burk plot showed that 2b was non-competitive inhibitor to bind chitin synthase. The antifungal experiment showed that these compounds had excellent antifungal activity against fungal strains, especially for candida albicans. The antifungal activities against C .albicans of compounds 2b, 2d, 2e and 2l were comparable with that of fluconazole and were superior to that of polyoxin B. Meanwhile, the other compounds against C. albicans showed better antifungal activity (MIC 2 μg/mL) than polyoxin B except for compound 2n (MIC 4 μg/mL). The trial of drug combination use showed that these synthesized compounds had synergistic effects with fluconazole and polyoxin B. It indicated that these compounds were not competing with polyoxin B to bind with chitin synthase, which was also consistence with the result of enzymatic assays. The antibacterial experiment showed that these compounds had no activity against selected strains including three Gram-positive and three Gram-negative bacteria. These results showed that the designed compounds were chitin synthase inhibitors and had selective antifungal activity.
The base-catalysed Tamura cycloaddition reaction: Calculation, mechanism, isolation of intermediates and asymmetric catalysis
Lockett-Walters, Bruce,Trujillo, Cristina,Twamley, Brendan,Connon, Stephen
supporting information, p. 11283 - 11286 (2019/09/30)
A combined experimental and computational investigation has revealed that the base-catalysed Tamura cycloaddition between homophthalic anhydride and activated alkenes/alkynes-a reaction previously thought of as a Diels-Alder type process-proceeds via a stepwise mechanism involving conjugate addition and ring closure; which allowed the first catalytic asymmetric α-substitution reactions to be demonstrated with up to >99% ee.
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
-
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
