Synthesis, structure, and catalytic activity of trinuclear zinc complexes with new chiral biaryl-based NO2 ligands

Zhao, Ning; Liang, Changhao; Ren, Wenshan; Song, Haibin; Zi, Guofu

doi:10.1016/j.jorganchem.2012.04.004

Cited by 21 publications

(5 citation statements)

References 36 publications

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“…As the potential model system, we chose the chiral C 1 -symmetric NOBIN-derived aminodiolate complexes IV (Figure ). , On the basis of previous experience, we decided to incorporate sterically demanding substituents in the ortho position of the aryloxide groups in order to prevent catalyst aggregation, ,, increase catalytic activity, and improve stereoselectivity . Thus, the ability to easily tune the ortho substituents R 1 and R 3 is important to adapt the catalyst design successfully.…”

Section: Resultsmentioning

confidence: 99%

C₁-Symmetric Rare-Earth-Metal Aminodiolate Complexes for Intra- and Intermolecular Asymmetric Hydroamination of Alkenes

Reznichenko

Hultzsch

2013

Organometallics

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A series of novel C 1 -symmetric aminodiolate rare-earth-metal complexes have been prepared via arene elimination from [Ln(o-C 6 H 4 CH 2 NMe 2 ) 3 ] (Ln = Y, Lu) and the corresponding aminodiol proligand. The NOBIN-derived aminodiolate ligands feature sterically demanding triphenylsilyl and methyldiphenylsilyl ortho substituents on the naphtholate moiety and substituents of varying steric demand ranging from tert-butyl to tris(3,5-xylyl)silyl on the phenolate moiety.Complexes with a triphenylsilyl substituent on the naphtholate moiety displayed good catalytic activity in the hydroamination/ cyclization of aminoalkenes, while complexes with a methyldiphenylsilyl substituent exhibited somewhat lower reactivity. The highest enantioselectivities for fiveand six-membered-ring formation were observed utilizing complex 9c-Lu (R 1 = Ph, R 2 = Me, R 3 = SiPh 3 ) in the cyclization of (2,2-diphenylpent-4-enyl)amine (92% ee, N t = 200 h −1 at 25 °C) and (2,2-diphenylhex-5enyl)amine (73% ee, N t = 20 h −1 at 25 °C). The complexes can be applied in asymmetric intermolecular hydroaminations of 1heptene and 4-phenyl-1-butene with benzylamine with enantioselectivities of up to 40% ee using complex 9b-Y (R 1 = Ph, R 2 = Me, R 3 = SiPh 2 Me). Here the higher catalytic activities are achieved with catalysts having a methyldiphenylsilyl substituent on the naphtholate moiety. Lanthanum aminodiolate catalysts generated in situ from [La{CH(C 6 H 5 )NMe 2 } 3 ] did not exhibit improved catalytic activity in the intermolecular hydroamination in comparison to the corresponding yttrium and lutetium catalysts. The overall catalytic activities of the aminodiolate complexes are somewhat diminished in comparison to previously studied binaphtholate complexes due to the presence of the additional amine donor site in the ligand framework.

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Section: Resultsmentioning

confidence: 99%

C₁-Symmetric Rare-Earth-Metal Aminodiolate Complexes for Intra- and Intermolecular Asymmetric Hydroamination of Alkenes

Reznichenko

Hultzsch

2013

Organometallics

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Section: Introductionmentioning

confidence: 99%

“…[2] Examples of the previously discovered zinc binding groups are secondary amines, amides, imines, imidazoles, carboxylates, aminocarboxylates, sulfydryls, hydroxamates, phosphonates, and phosphinates. [27][28][29] Organosilanes are important intermediates in the synthesis of many valuable compounds, particularly in pharmaceutical and medicinal chemistry. [30,31] These compounds are characterized by high resistance to hydrolysis and thermolysis.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and biological evaluation of new heterocycles bearing both silicon and phosphorus as potent MMP‐2 inhibitors

El‐Hussieny

Mansour

Hashem

et al. 2022

J Chinese Chemical Soc

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Matrix metalloproteinases (MMPs) attracted medicinal chemists as they are biological targets that are involved in various pathophysiological processes such as extracellular matrix protein degradation, cell-surface receptor release and cleavage, tumor growth, homeostatic control, and innate immunity. New heterocycles, bearing both silicon and phosphorus in their molecular structures, were successfully produced via reacting silylated isocyanates and/or isothiocyanates with appropriate phosphorus ylides. Reacting nucleophilic phosphacumulenes (2,6) with isocyanate 1 and isothiocyanate 9 yielded fourmembered ring heterocycles containing phosphorus and silicon (4 and 11) and six-membered rings heterocycles (5, 8 and 12). Moreover, novel heterocycles containing two phosphorus atoms and one silicon atom were produced by the reaction of diphosphorane 13 with 1 or 9. On the other side, four-membered (23, 26 and 29a) and six-membered heterocyclic derivatives (20b and 29b) containing two phosphorus atoms in their structures were also obtained from the reaction of phosphallene ylide 13 and substrates (18, 21, 24 and 27). All the final compounds were tested for their MMP-2 inhibitor activity showing IC 50 values in the range of 0.0408-0.4985 μM. The thiolactam derivative 11 and the azaphosphetidin-4-one derivative 15, both bearing silicon and phosphorous, showed the highest activity with IC 50 values of 0.0408 and 0.0693 μM, respectively, both are significantly higher than that of quercetin (IC 50 = 0.1631 μM). Docking simulations were carried out for the most two active compounds 11 and 15 in the vicinity of the active site of MMP-2 enzyme and both formed coordinate bonds with the zinc cation key interaction for MMP-2 enzyme. In conclusion, compounds 11 and 15 can be considered as potential MMP-2 inhibitors and can be subjected to further studies as antimetastatic agents.

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“…2 Several zinc binding groups (ZBG) have been discovered, which include secondary amines, amides, imines, imidazoles, carboxylates, aminocarboxylates, sulydryls, hydroxamates, phosphonates and phosphinates. [28][29][30][31][32] In recent years, interest in benzosulfonamides has been increased due to their high biological activity, however the broad-benzosulfonamides as MMP inhibitors, 33 hitherto have not been recognized.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, evaluation and 3D-QSAR analysis of benzosulfonamide benzenesulfonates as potent and selective inhibitors of MMP-2

Qiu

Wang

et al. 2014

RSC Adv.

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Synthesis, structure, and catalytic activity of trinuclear zinc complexes with new chiral biaryl-based NO2 ligands

Cited by 21 publications

References 36 publications

C₁-Symmetric Rare-Earth-Metal Aminodiolate Complexes for Intra- and Intermolecular Asymmetric Hydroamination of Alkenes

C₁-Symmetric Rare-Earth-Metal Aminodiolate Complexes for Intra- and Intermolecular Asymmetric Hydroamination of Alkenes

Design, synthesis, and biological evaluation of new heterocycles bearing both silicon and phosphorus as potent MMP‐2 inhibitors

Design, synthesis, evaluation and 3D-QSAR analysis of benzosulfonamide benzenesulfonates as potent and selective inhibitors of MMP-2

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Synthesis, structure, and catalytic activity of trinuclear zinc complexes with new chiral biaryl-based NO2 ligands

Cited by 21 publications

References 36 publications

C1-Symmetric Rare-Earth-Metal Aminodiolate Complexes for Intra- and Intermolecular Asymmetric Hydroamination of Alkenes

C1-Symmetric Rare-Earth-Metal Aminodiolate Complexes for Intra- and Intermolecular Asymmetric Hydroamination of Alkenes

Design, synthesis, and biological evaluation of new heterocycles bearing both silicon and phosphorus as potent MMP‐2 inhibitors

Design, synthesis, evaluation and 3D-QSAR analysis of benzosulfonamide benzenesulfonates as potent and selective inhibitors of MMP-2

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Product

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C₁-Symmetric Rare-Earth-Metal Aminodiolate Complexes for Intra- and Intermolecular Asymmetric Hydroamination of Alkenes

C₁-Symmetric Rare-Earth-Metal Aminodiolate Complexes for Intra- and Intermolecular Asymmetric Hydroamination of Alkenes