5336-50-5

Usage

InChI:InChI=1/C14H15NO4/c1-2-19-14(18)11-9-15(13(17)12(11)16)8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3

Upstream product

• 23583-21-3 ethyl-3-benzylamino propionate 
• 95-92-1 oxalic acid diethyl ester 
• 140-88-5 ethyl acrylate 
• 100-46-9 benzylamine 
• 23574-01-8 3-benzylamino-propionic acid methyl ester 
• 6436-90-4 ethyl 2-(benzylamino)acetate 

Downstream Products

• 83794-09-6 1-benzyl-4-(4-methoxybenzylidene)-pyrrolidine-2,3-dione 
• 915296-85-4 (E)-1-benzyl-4-(2,4-dichlorobenzylidene)pyrrolidine-2,3-dione 
• 35921-27-8 1-benzyl-4-(2-chlorophenyl) pyrrolidine-2,3-dione 
• 4805-28-1 1-benzoyl-5-benzyl-2-(4-chlorophenyl)-5-azaspiro[2.4]heptane-6,7-dione 
• 21659-40-5 4-benzo[1,3]dioxol-5-ylmethylene-1-benzyl-pyrrolidine-2,3-dione 

Relevant academic research and scientific papers

Au(I)/(R)-BINOL-Ti(IV) concerted catalyzed asymmetric cascade cycloaddition reaction of arylalkynols

An efficient catalytic asymmetric cascade cycloaddition reaction of arylalkynols with dioxopyrrolidines was developed. This reaction was achieved using Au(I) and (R)-BINOL-Ti(IV) bimetallic catalysts and exclusively delivered a series of chiral oxo-bridged bicyclic benzooxacine compounds in up to 86% yield with 96% ee as well as >33:1 dr. Meanwhile, three new σ bonds and three new stereogenic centers were formed in a one-pot process.

Organocatalytic Enantioselective Synthesis of Tetrahydro-Furanyl Spirooxindoles via [3+2] Annulations of 3-Hydroxyoxindoles and Cyclic Ketolactams

Asymmetric construction of pharmacologically interesting tetrahydrofuranyl spirooxindole frameworks has been achieved through organocatalytic [3+2] annulations of the readily available 3-hydroxyoxindoles and pyrrolidone-derived cyclic ketolactams. A variety of chiral spiro tetrahydrofuranyl products, which contain four contiguous stereocenters including two tetrasubstituted carbon centers, have been rapidly synthesized with remarkable results (up to 99% yield, >95:5 dr, and 99:1 er). Synthetic derivatization of the hemiketal moiety enables the installation of various halogen atoms into the structurally complex molecules in a stereospecific manner. Preliminary screening of anticancer bioactivity was performed, and 4 w showed obvious inhibitory capacity to the proliferation on a panel of cancer cell lines. (Figure presented.).

KRAS G12C Mutant protein inhibitors

The invention discloses compounds which irreversibly inhibit KRAS G12C mutation. A pharmaceutically acceptable salt and of the compound contains the compound or a salt thereof, and the invention also discloses an application of the compound or a salt and of the compound in the treatment KRAS G12C of a proliferative disease such as a sudden tumor.

Enantioselective Organocatalyzed Michael Additions of Nitroalkanes to 4-Arylidenedihydrofuran-2,3-diones and 4-Arylidenepyrrolidine-2,3-diones

Tremendous efforts have been devoted to the development of organocatalytic enantioselective Michael additions of nitroalkanes to α,β-unsaturated carbonyl compounds. However, using highly substituted electrophiles remain challenging, since the additional substituents decrease the electrophilicity. β-Arylidene-α-ketolactones and α-ketolactams are used as highly electrophilic Michael acceptors that afford the corresponding products in moderate to good yields, with high enantioselectivities. This success relies on their rigid structure that prevents deconjugation and the efficient recognition of the α-dicarbonyl motif by the hydrogen-bond donor catalyst.

Oxindole spiro-tetrahydrofuran compound as well as preparation method and application thereof

The invention provides an indole tetrahydrofuran oxide compound or a crystal form thereof, wherein the indole tetrahydrofuran oxide compound is as shown in a formula (I). R1 is selected from benzene rings, naphthalene rings and thiophene rings or cinnamyl, R2 is selected from H, F, Cl, Br and I or C1-3 alkoxy, R3 is selected from H and benzyl or C1-C3 alkyl, and R4 is H, F, Cl, Br, I and C1-3 alkoxy or C1-C3 alkyl. The invention further provides a method for preparing the compound. The compound is simple and convenient in preparation method, moderate in reaction and high in yield and has anti-tumor activity and a wide market application prospect.

NHC-catalyzed asymmetric α-regioselective [4 + 2] annulation to construct α-alkylidene-δ-lactones

The unprecedented NHC-catalyzed [4 + 2] annulation of α-bromoenals with dioxopyrrolidines is described. This protocol features broad substrate scope and allows rapid assembly of α-alkylidene-δ-lactones in good to high yields with excellent enantioselectivities. Notably, this process includes α-regioselective activation of azolium dienolate intermediates, which has not yet been reported.

Structure-based optimization of 2,3-dioxopyrrolidines as potential inhibitors of flaviviral methyltransferases

Various studies have shown that NS5 RNA methyltransferase (MTase) is a key enzyme involved in mRNA capping, a step crucial for flaviviral replication. Therefore, it has been identified as a potential target for therapeutic intervention in infections arising due to flaviviruses. In this paper, we report computer-assisted design of 2,3-dioxopyrrolidines, which were synthesised as guided by molecular docking studies on DENV and ZIKA MTase. Their chemical structures and geometric configuration were characterized by FT-IR, NMR (13C and 1H), MS and small molecule X-ray crystallography. Subsequently, their inhibitory potential was evaluated using an enzyme-based assay in DENV MTase (N7 and 2'O-MTase) and Zika virus MTase (N7 and 2'O-MTase). Furthermore, these molecules were also screened against RNMT (human N7 MTase). The most potent lead (compound W07) is seen to inhibit MTase from DENV with IC50 = 24.6±3.8 M and ZIKA with IC50 = 9.0±1.7 M. However, it also inhibits human N7 MTase, indicating plausible toxicity in humans. There is scope to further optimize these molecules to achieve selectivity towards flaviviral MTases.

Synthesis of new pyrrolo[3,4-b]indol-3-ones as latent substrates for pyrrolo[3,4-b]indoles

We report the synthesis of new examples of the 1,4-dihydropyrrolo[3,4-b]indol-3(2H)-one ring system via Fischer indolization between the appropriate phenylhydrazines and pyrrolidine-2,3-diones. Lithiation at the C-1 position with lithium diisopropylamide following by quenching with iodomethane affords 1-methyl-1,4-dihydropyrrolo[3,4-b]indol-3(2H)-ones in excellent yield.

A practical synthesis of functionalized isoindolinones via [3?+?3] benzannulation of 1,3-bissulfonylpropenes and 4-arylmethylene-2,3-dioxopyrrolidines

A straightforward synthesis of isoindolinones has been developed via a [3 + 3] benzannulation of 4-arylmethylene-2,3-dioxopyrrolidines and 1,3-bissulfonylpropenes (or 4-sulfonylcrotonates). A series of functionalized isoindolinones were obtained in excellent yields. The reaction could be carried out under mild conditions without transition metal catalyst. The finding provides a practical approach for the preparation of isoindolinone derivatives with potential biological activities.

Halogenated dihydropyran pyrrolidone compound as well as crystal form and preparation method thereof

The invention provides a compound as shown in a formula (A) as well as a preparation method thereof. The invention also provides a crystal form I of the compound as shown in the formula (A). The crystal form is an orthorhombic system, the space group is P212121 and the unit cell parameters are as shown in the description. The invention also provides a preparation method of the crystal form I. Thehalogenated dihydropyran pyrrolidone compound and the crystal form thereof are prepared successfully. Furthermore, the compound or the crystal form thereof has anti-tumor activity, the hygroscopicityis not improved obviously, the stability is high and great convenience is provided for later-period product transportation, storage or preparation process.