1234-27-1Relevant academic research and scientific papers
Urea-based flexible dicarboxylate linkers for three-dimensional metal-organic frameworks
Glomb, Sebastian,Makhloufi, Gamall,Gruber, Irina,Janiak, Christoph
, p. 35 - 46 (2018)
The metal-organic frameworks (MOFs) 3D-[Mn2(L1)2(DMF)]·2DMF (1), 3D-[Cd2(L2)2(DMF)3] (3), [Zn2(L2)2(DMF)3] (4) and 3D-[Mn2(L2)2(DMF)3] (5) are the first examples of three-dimensional metal-organic networks constructed from a single ditopic dicarboxylate linker (i.e., without bridging co-ligands) with an urea group in the linker axis (L12? = 4,4′-(carbonylbis(azanediyl))dibenzoate; L22? = 4,4′-(carbonylbis(azanediyl))bis(3-methylbenzoate), DMF = dimethylformamide). From Cd2+and L12? a 1D coordination polymer 1D-[Cd(L1)(DMF)3] (2) is formed. The urea group is engaged in hydrogen bonding with the C(4)[R12(6)] motif to an oxygen atom of a DMF solvent (in 1) or a metal-coordinated carboxylate group (in 3–5). Network 1 has infinite channels with parallelepiped cross sections and 30% solvent-filled volume. The 3 D frameworks 3–5 are of diamond (6,6), dia topology with a single framework having large voids with 17.6 ? and 19.7 ? nodal separation. Thus, four symmetry-related nets interpenetrate, organized via H-bonds in the C(4)[R12(6)] motif, still leaving about 50% solvent-filled void volume in the fourfold interpenetrated structure.
Urea Metal-Organic Frameworks for Nitro-Substituted Compounds Sensing
Azhdari Tehrani, Alireza,Esrafili, Leili,Abedi, Sedigheh,Morsali, Ali,Carlucci, Lucia,Proserpio, Davide M.,Wang, Jun,Junk, Peter C.,Liu, Tianfu
, p. 1446 - 1454 (2017)
Urea groups are known to form strong hydrogen bonds with molecules containing atom(s) that can act as hydrogen bond acceptor(s). Thus, urea is a particularly interesting building block for designing receptors for neutral or charged guests. In the quest for new sensors with enhanced performance for the detection of nitro-substituted compounds, two pillared metal-organic frameworks containing urea functional groups were synthesized and structurally characterized. The sensing properties of these frameworks toward nitro-analytes were investigated and compared to each other. The study clearly reveals the importance of urea groups orientation inside the pore cavity of MOFs, as well as the supramolecular interactions between the interpenetrated networks. This work is interesting as it represents the first example of urea-functionalized MOFs for nitro-analytes recognition.
Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3
Song, Hai-Xia,Han, Zhou-Zhou,Zhang, Cheng-Pan
supporting information, p. 10907 - 10912 (2019/08/02)
Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.
Novel Symmetrical Benzazolyl Derivatives Endowed with Potent Anti-Heparanase Activity
Messore, Antonella,Madia, Valentina Noemi,Pescatori, Luca,Saccoliti, Francesco,Tudino, Valeria,De Leo, Alessandro,Bortolami, Martina,De Vita, Daniela,Scipione, Luigi,Pepi, Federico,Costi, Roberta,Rivara, Silvia,Scalvini, Laura,Mor, Marco,Ferrara, Fabiana Fosca,Pavoni, Emiliano,Roscilli, Giuseppe,Cassinelli, Giuliana,Milazzo, Ferdinando M.,Battistuzzi, Gianfranco,Di Santo, Roberto,Giannini, Giuseppe
, p. 10834 - 10859 (2019/01/03)
Heparanase is the only mammalian endo-β-d-glucuronidase involved in a variety of major diseases. The up-regulation of heparanase expression increases tumor size, angiogenesis, and metastasis, representing a validated target in the anti-cancer field. To date, only a few small-molecule inhibitors have been described, but none have gotten through pre-clinical development. Previously, we explored 2-(4-(4-(bromo-methoxybenzamido)benzylamino)phenyl) benzazole derivatives as anti-heparanase agents, proposing this scaffold for development of broadly effective heparanase inhibitors. Herein, we report an extended investigation of new symmetrical 2-aminophenyl-benzazolyl-5-acetate derivatives, proving that symmetrical compounds are more effective than asymmetrical analogues, with the most-potent compound, 7g, being active at nanomolar concentration against heparanase. Molecular docking studies were performed on the best-acting compounds 5c and 7g to rationalize their interaction with the enzyme. Moreover, invasion assay confirmed the anti-metastatic potential of compounds 5c, 7a, and 7g, proving the inhibition of the expression of proangiogenic factors in tumor cells.
Urea-containing metal-organic frameworks as heterogeneous organocatalysts
Tehrani, Alireza Azhdari,Abedi, Sedigheh,Morsali, Ali,Wang, Jun,Junk, Peter C.
, p. 20408 - 20415 (2015/10/19)
Two novel pillared metal-organic frameworks (MOFs) containing a urea-functional group are introduced. Herein, the urea functional group was incorporated into the MOF backbone by preparing a urea-ditopic ligand. These frameworks (TMU-18 and TMU-19) were fabricated using the synthesized urea-containing ligand, 4,4′-bipyridine (bipy) and 1,2-bis(4-pyridyl)ethane (bpe), and using zinc nitrate as the metal source. Subsequently, TMU-18 and TMU-19 were characterized by X-ray diffraction, IR spectroscopy, elemental analysis, scanning electron microscopy (SEM) and thermogravimetric analysis. Furthermore, their potential efficiency as organocatalysts was evaluated in the regioselective methanolysis of epoxides.
UREYLENE DERIVATIVES
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, (2008/12/04)
The invention concerns compounds of Formula (I) or a salt, solvate or pro-drug thereof. The compounds may be used in therapy, particularly anti-cancer therapy.
Rational design of substituted diarylureas: A scaffold for binding to G-quadruplex motifs
Drewe, William C.,Nanjunda, Rupesh,Gunaratnam, Mekala,Beltran, Monica,Parkinson, Gary N.,Reszka, Anthony P.,Wilson, W. David,Neidle, Stephen
experimental part, p. 7751 - 7767 (2009/12/07)
The design and synthesis of a series of urea-based nonpolycyclic aromatic ligands with alkylaminoanilino side chains as telomeric and genomic G-quadruplex DNA interacting agents are described. Their interactions with quadruplexes have been examined by means of fluorescent resonance energy transfer melting, circular dichroism, and surface plasmon resonance-based assays. These validate the design concept for such urea-based ligands and also show that they have significant selectivity over duplex DNA, as well as for particular G-quadruplexes. The ligand-quadruplex complexes were investigated by computational molecular modeling, providing further information on structure-activity relationships. Preliminary biological studies using short-term cell growth inhibition assays show that some of the ligands have cancer cell selectivity, although they appear to have low potency for intracellular telomeric G-quadruplex structures, suggesting that their cellular targets may be other, possibly oncogene-related quadruplexes.
