128-53-0Relevant articles and documents
Photoreversible prodrugs and protags: Switching the release of maleimides by using light under physiological conditions
G?stl, Robert,Hecht, Stefan
, p. 4422 - 4427 (2015)
A water-soluble furyl-substituted diarylethene derivative has been prepared that can undergo reversible Diels-Alder reactions with maleimides to yield photoswitchable Diels-Alder adducts. Employing bioorthogonal visible light, the release of therapeutically effective concentrations of maleimide-based reactive inhibitors or labels from these "prodrugs" or "protags" could be photoreversibly triggered in buffered, aqueous solution at body temperature. It is shown how the release properties can be fine-tuned and a thorough investigation of the release dynamics is presented. Our system should allow for spatiotemporal control over the inhibition and labeling of specific protein targets and is ready to be surveyed in living organisms.
9,10-Dibromo-N-aryl-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-diones: Synthesis and Investigation of Their Effects on Carbonic Anhydrase Isozymes I, II, IX, and XII
G?ksu, Haydar,Topal, Meryem,Keskin, Ali,Gültekin, Mehmet S.,?elik, Murat,Gül?in, Ilhami,Tanc, Muhammet,Supuran, Claudiu T.
, p. 466 - 474 (2016)
N-substituted maleimides were synthesized from maleic anhydride and primary amines. 1,4-Dibromo-dibenzo[e,h]bicyclo-[2,2,2]octane-2,3-dicarboximide derivatives (4a-f) were prepared by the [4+2] cycloaddition reaction of dibromoanthracenes with the N-substituted maleimide derivatives. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the new derivatives were assayed against the human (h) isozymes hCA I, II, IX, and XII. All tested bicyclo dicarboximide derivatives exhibited excellent inhibitory effects in the nanomolar range, with Ki values in the range of 117.73-232.87 nM against hCA I and of 69.74-111.51 nM against hCA II, whereas they were low micromolar inhibitors against hCA IX and XII. A series of 9,10-dibromo-N-aryl-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-diones (4a-f) were synthesized from N-substituted maleimide derivatives and 9,10-dibromoanthracene. Compounds 4a-f were assayed against human carbonic anhydrases (hCA) IX and XII, which are the two tumor-associated isozymes, and hCA I and II, which represent the most common off-targets for the development of selective anticancer CA inhibitors.
Cp?Co(III)-Catalyzed C-H Alkylation with Maleimides Using Weakly Coordinating Carbonyl Directing Groups
Mandal, Rajib,Emayavaramban, Balakumar,Sundararaju, Basker
supporting information, p. 2835 - 2838 (2018/05/29)
A novel protocol for ortho-C-H alkylation of aromatic and heteroaromatic ketones and esters under Cp?Co(III) catalysis has been developed for the first time. The reaction proceeds through initial cyclometalation via weak chelation-assisted C-H bond activation, followed by coordination of activated alkene, insertion between Co-C, and protodemetalation.
Graphene Oxide as a Carbocatalyst for a Diels–Alder Reaction in an Aqueous Medium
Girish, Yarabhally R.,Pandit, Subrata,Pandit, Subhendu,De, Mrinmoy
supporting information, p. 2393 - 2398 (2017/09/11)
The Diels–Alder (DA) reaction, a [4+2] cycloaddition reaction, is highly important in synthetic organic chemistry and is frequently used in the synthesis of natural products containing six-membered rings. Herein, we report an efficient protocol for the DA reaction between 9-hydroxymethylanthracene and N-substituted maleimides using two-dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yields, a wide substrate scope, low temperature, excellent functional group tolerance, atom economy, and water as a green solvent are noteworthy features of this protocol. The heterogeneous GO catalyst can be easily recovered and used multiple times without any significant loss in catalytic activity.
