C2-symmetric BINOL-squaramide as efficient organocatalyst for the enantioselective α-amination of 1,3-dicarbonyl compounds with dialkyl azodicarboxylates

Tang, Shi; Wang, Zhiyong; Liu, Bin; Dong, Chune

doi:10.1016/j.cclet.2015.03.033

Cited by 12 publications

(3 citation statements)

References 31 publications

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“…Relative binding affinities were determined by a competitive fluorometric binding assay, as described previously [ 29 ]. Briefly, 40 nM fluorescence tracer (coumestrol, Sigma-Aldrich) and 0.8 μM purified human ERα or ERβ ligand binding domain were diluted in 100 mM potassium phosphate buffer (pH 7.4), containing 100 μg/ml bovine γ-globulin (Sigma-Aldrich), and an equal volume of test compound was added.…”

Section: Methodsmentioning

confidence: 99%

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Selenophene and thiophene-core estrogen receptor ligands that inhibit motility and development of parasitic stages of Haemonchus contortus

et al. 2016

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BackgroundParasitic worms represent a substantial disease burden in animals and humans worldwide. The control of parasitic roundworms (nematodes) relies heavily on the use of anthelmintic drugs. However, widespread drug resistance in nematodes seriously compromises the effectiveness of many anthelmintics around the world. Thus, there is a need to discover new drugs, with unique modes of action, against parasites.MethodsHere, we synthesised and tested 74 selective estrogen receptor modulators (SERMs) for in vitro-activity on parasitic larvae of Haemonchus contortus (barber’s pole worm), one of the most important nematode pathogens of small ruminants (including sheep and goats) and a key representative of one of the largest groups of parasitic nematodes (the Strongylida) of animals. We also studied the morphology of treated and untreated larvae using scanning electron microscopy (SEM), and assessed the agonistic/antagonistic activity of SERMs in a human embryonic kidney cell line using a luciferase reporter assay system.ResultsWe identified three SERMs (one selenophene and two thiophene-core compounds) with potent inhibitory activities (at 3–25 μM) on the motility and development of parasitic stages of H. contortus. An SEM examination of treated H. contortus revealed considerable damage to the cuticle of fourth- but not exsheathed, third-stage larvae; this damage appeared to be consistent with that observed upon treatment with monepantel but not moxidectin (control compounds).ConclusionThe potency of the three SERMs compared favourably with commercially available anthelmintics, such that they warrant further assessment as nematocides. Future studies could focus on assessing the selectivity of these SERMs to parasites, characterising their target(s) and/or designing analogs that are parasite-specific.Electronic supplementary materialThe online version of this article (doi:10.1186/s13071-016-1612-4) contains supplementary material, which is available to authorized users.

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Section: Methodsmentioning

confidence: 99%

“…The values given are the average ± range of two independent determinations. IC 50 values were calculated using a published formula [ 29 ].…”

Section: Methodsmentioning

confidence: 99%

Selenophene and thiophene-core estrogen receptor ligands that inhibit motility and development of parasitic stages of Haemonchus contortus

et al. 2016

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“…[15][16][17][18] As a consequence of their smooth reactivity, the use of dialkyl malonates and related compounds in CÀ N bond forming reactions with dialkyl azodicarboxylates has long constituted a central playground for the organic chemist. [19][20][21] However, whereas several contributions describe the stereoselective addition of cyclic ketoesters to the N=N bond, [22][23][24][25][26][27][28][29][30][31][32] reactions employing acyclic β-dicarbonyl compounds bearing side chains at the α position are more unusual. [33][34][35] Therefore, at the beginning of the 2000s, Jørgensen and coworkers described the enantioselective amination of αsubstituted β-ketoesters employing a Cu(II) bis-oxazoline complex and furnishing the coupling products in high yields and enantiomeric excesses.…”

Section: Introductionmentioning

confidence: 99%

Decarboxylative Amination of SMAHOs by Dialkyl Azodicarboxylates

Pinaud,

Gall,

Presset

2024

Eur J Org Chem

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The decarboxylative addition of substituted malonic acid half oxyesters (SMAHOs) to dialkyl azodicarboxylates is described. The reaction was promoted by 1,4‐diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst in heated toluene. High yields of the coupling products were generally obtained, and the scope of the reaction proved rather important with the potential presence of functionalized pending chains at the α‐position, affording an original access to α‐aminoester derivatives.

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Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Li,

Ma,

Meng

et al. 2023

Adv Synth Catal

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Spirooxindoles are privileged scaffolds in diverse bioactive natural products and pharmaceuticals, significant achievements for the construction of these molecules have thus been made in the past years. Among them, organocatalysis, in particular, nucleophilic Lewis base catalysis, has recently emerged as an efficient and reliable method for the preparation of diverse and valuable functionalized spirooxindoles. According to different kinds of nucleophilic catalysts, we summarize and classify three catalytic strategies; these are tertiary amine‐catalyzed cycloadditions, NHC‐catalyzed cycloadditions, and tertiary phosphine‐catalyzed cycloadditions, respectively. Through these methods, potential bioactive spirooxindole skeletons owning various functional groups can be produced to enrich the small organic molecule library. In this review, we describe a comprehensive and updated advances of nucleophilic Lewis base catalytic cycloaddition reactions for the construction of spirooxindoles. Meanwhile, the related mechanism and the application of these annulation strategies in natural product total synthesis will be highlighted in detail.

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C2-symmetric BINOL-squaramide as efficient organocatalyst for the enantioselective α-amination of 1,3-dicarbonyl compounds with dialkyl azodicarboxylates

Cited by 12 publications

References 31 publications

Selenophene and thiophene-core estrogen receptor ligands that inhibit motility and development of parasitic stages of Haemonchus contortus

Selenophene and thiophene-core estrogen receptor ligands that inhibit motility and development of parasitic stages of Haemonchus contortus

Decarboxylative Amination of SMAHOs by Dialkyl Azodicarboxylates

Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

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