38229-08-2

Usage

Type of compound

Organic

Contains

Phenyl group, 3-phenylpropanoic acid moiety

Category

Isoindolinone derivative

Potential

Biological activities

Possible applications

Pharmaceuticals, materials science

Specific properties and uses

To be fully elucidated

InChI:InChI=1/C17H13NO4/c19-15-12-8-4-5-9-13(12)16(20)18(15)14(17(21)22)10-11-6-2-1-3-7-11/h1-9,14H,10H2,(H,21,22)

Upstream product

• 1242459-38-6 C₂₃H₂₉NO₄Si₂ 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 673-06-3 D-(R)-phenylalanine 
• 85-44-9 phthalic anhydride 
• 673-06-3 D-β-Phenyl-α-alanine 
• 63-91-2 L-phenylalanine 
• 63-91-2 L-phenylalanine 

Downstream Products

• 114863-26-2 benzoic acid-(N,N-phthaloyl-D-phenylalanine)-anhydride 
• 111978-68-8 N,N-phthaloyl-D-phenylalanine-butyl ester 
• 1242459-38-6 C₂₃H₂₉NO₄Si₂ 
• 228422-44-4 (R)-1-benzyl-3-hydroxypropylamine 
• 87-41-2 2-benzofuran-1(3H)-one 
• 866395-33-7 (2S,9R,12S,19R)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-20-phenyl-11-oxoeicosanoic acid methyl ester 
• 866395-30-4 (2S,9R,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-11-oxononadecanoic acid methyl ester 
• 866395-27-9 (2S,9R)-2,6-cyclo-6-aza-9-(benzyloxycarbonylamino)-10-phenyldecanoic acid methyl ester 
• 866395-42-8 (S)-1-((R)-3-Benzyloxycarbonylamino-4-phenyl-butyl)-pyrrolidine-2-carboxylic acid 
• 866395-24-6 (S)-1-mesyloxy-N-(benzyloxycarbonyl)-3-amino-4-phenylbutane 
• 866395-52-0 N-(1-benzyl-3-hydroxy-propyl)-2-hydroxymethyl-benzamide 
• 866395-50-8 methyl (R)-3-phthalimido-4-phenylbutyrate 
• 866395-47-3 (R)-1-diazo-3-phthalimido-4-phenylbutan-2-one 
• 348184-48-5 (S)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutan-1-ol 

Relevant academic research and scientific papers

NOVEL TRF1 MODULATORS AND ANALOGUES THEREOF

Novel TRF1 modulators and analogues thereof. There is provided compounds of Formula I, wherein R, R1, R2 and X have meanings written in the description. Such compounds are useful as TRF1 inhibitors and, for that reason, as medicaments, in the treatment of cancer, particularly high cancer stem cell cancer like glioblastoma and lung cancer, and can be also useful for the development of additional TRF1 inhibitors and increasing knowledge about TRF1 activity.

AMINO ACID DERIVATIVES FOR THE TREATMENT OF INFLAMMATORY DISEASES

The present disclosure provides certain amino acid derivatives that inhibit NF-kB activation and are therefore useful for the treatment of inflammatory diseases. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

Flupirtine and retigabine as templates for ligand-based drug design of KV7.2/3 activators

Drug induced liver injury (DILI) and tissue discoloration led to the recent discontinuation of the therapeutic use of the closely related drugs flupirtine and retigabine, respectively. Experience gained with these drugs strongly suggests that heterotetramer, voltage-gated potassium channels 2 and 3 (KV7.2/3) are valid targets for effective treatment of pain and epilepsy. Because the adverse effects are not related to the mechanism of action, it appears promising to investigate chemical modifications of these clinically validated, drug-like leads. In the present retro-metabolic drug design study, a series of 43 compounds were synthesized and characterized with regard to KV7.2/3 opening activity and efficacy. The most active compound 22d displays excellent potency (EC50 = 4 nM) and efficacy (154%) as a KV7.2/3 opener. Limited aqueous solubility hampered toxicity testing at concentrations higher than 63 μM, but this concentration was nontoxic to two hepatocellular cell lines (HEP-G2 and TAMH) in culture. The slightly less active but more soluble compound 25b (EC50 = 11 nM, efficacy 111%) showed an improved toxicity/activity ratio compared to flupirtine by three orders of magnitude and represents an attractive lead structure for the development of safer analgesics and antiepileptics.

Oximino naphthoquinone compound and preparation and application methods thereof

The invention belongs to the technical field of medicinal compounds and medicines and relates to an oximino naphthoquinone compound and preparation and application methods thereof, particularly to a compound shown as formula (I). The oximino naphthoquinone compound can serve as a double-target selective inhibitor of STAT3 (signal transducer and activator of transcription-3) and IDO1 (indoleamine 2, 3-dioxygenase 1) for treating ovarian cancer, colon cancer, lung cancer and the like.

Chiral sensors for determining the absolute configurations of α-amino acid derivatives

A simple strategy for configurational assignments of alpha-amino acids has been developed by comparison of the proton NMR chemical shift values of the alpha hydrogens of N-phthaloyl protected alpha-amino acids in the presence of (R)-CSA 1 and (S)-CSA 1, respectively. Highly resolved NMR spectra can be obtained directly on the mixed solution of the chiral solvating agents with N-phthaloyl protected alpha-amino acids in NMR tubes, giving well distinguishable proton signals without interference which dramatically improve the accuracy of assignment and hasten the assigning procedure. The strategy is widely applicable for varied natural and non-natural amino acids.

Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation

A series of dehydroabietic acid (DHAA) dipeptide derivatives containing the sulfonamide moiety were designed, synthesized and evaluated for inhibition of MMPs as well as the effects of in vitro cell migration. These compounds exhibited relatively good inhibition activity against MMPs with IC50 values in low micromolar range. A docking study of the most active compound 8k revealed key interactions between 8k and MMP-3 in which the sulfonamide moiety and the dipeptide group were important for improving activity. It is noteworthy that further antitumor activity screening revealed that some compounds exhibited better inhibitory activity than the commercial anticancer drug 5-FU. In particular, compound 8k appeared to be the most potent compound against the HepG2 cell line, at least partly, by inhibition of the activity of MMP-3 and apoptosis induction. The treatment of HepG2 cells with compound 8k resulted in inhibition of in vitro cell migration through wound healing assay and G1 phase of cell cycle arrested. In addition, 8k-induced apoptosis was significantly facilitated in HepG2 cells. Thus, we conclude that DHAA dipeptide derivatives containing the sulfonamide moiety may be the potential MMPs inhibitors with the ability to suppress cells migration.

Cooperative Effects between Chiral Cpx–Iridium(III) Catalysts and Chiral Carboxylic Acids in Enantioselective C?H Amidations of Phosphine Oxides

An enantioselective C?H amidation of phosphine oxides by using an iridium(III) catalyst bearing an atropchiral cyclopentadienyl (Cpx) ligand is reported. A very strong cooperative effect between the chiral Cpx ligand and a phthaloyl tert-leucine enabled the transformation. Matched–mismatched cases of the different acid enantiomers are shown. The amidated P-chiral arylphosphine oxides are formed in yields of up to 95 % and with excellent enantioselectivities of up to 99:1 er. Enantiospecific reduction provides access to valuable P-chiral phosphorus(III) compounds.

Design, synthesis and anti-cancer activity evaluation of podophyllotoxin-norcantharidin hybrid drugs

In this study, we designed and synthesized eighteen podophyllotoxin-norcantharidin hybrid drugs which could exhibit more potent anti-cancer activity than the parent drugs. Through the anti-proliferation assay, the most potent anti-cancer agent was screened out, namely Q9 (IC50?=?0.88?±?0.18?μM against MCF-7 cell line), and it showed lower cytotoxicity against non-cancer cells, human embryonic kidney cells (293T) (IC50?=?54.38?±?3.78?μM). Additionally, based on the flow cytometry analysis result, it can cause a remarkable cell cycle arrest at G2/M phase and induce apoptosis in MCF-7 cells more significantly than podophyllotoxin or norcantharidin per se. Moreover, the expression of cell cycle relative protein CDK1 was up regulated while a protein required for mitotic initiation, Cyclin B1 was down regulated. Furthermore, according to the confocal microscopy observation results, it was shown that Q9 was a potent tubulin polymerization inhibitor and the effect is comparable to that of colchicine. For further investigation on the aforementioned mechanisms, we performed western blot experiments, thus finding the increase of the cleavage of PARP. Consistent with these new findings, molecular docking observations suggested that compound Q9 could be developed as a potential anticancer agent.

Catalytic asymmetric protonation of α-amino acid-derived ketene disilyl acetals using P -Spiro diaminodioxaphosphonium barfates as chiral proton

Chiral diaminodioxaphosphonium salts have been developed and their unique abilities as a chiral proton have been revealed through the establishment of a highly enantioselective protonation of α-amino acid-derived ketene disilyl acetals.

Cyclomaltooligosaccharide-assisted spectroscopic discrimination of phthalimido-derived amino acids through the formation of molecular aggregates

Spectroscopic evidence was used to demonstrate the formation of molecular associates in an aqueous solution of phthalimido tryptophan. These molecular associates are loosely formed through π-π aromatic stacking, properties that are not sufficient to cause NMR spectroscopic enantiomeric discrimination. A cyclomaltooligosaccharide with a larger cavity, such as cyclomaltooctaose (γ-cyclodextrin), is capable of forming a ternary complex with these molecular associates and enhances π-π aromatic stacking interactions, resulting in NMR enantiomeric discrimination. Electrospray-ionization mass spectroscopy (ESIMS) and NOESY two-dimensional NMR spectroscopic methods were used to study these complexes. Association constants and thermodynamic data for these cyclomaltooligosaccharide complexes were also estimated.