29588-83-8

Upstream product

• 85-44-9 phthalic anhydride 
• 56-41-7 L-alanine 
• 73365-03-4 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanal 
• 1242459-33-1 C₁₇H₂₅NO₄Si₂ 
• 338-69-2 D-Alanine 

Downstream Products

• 82353-61-5 (R)-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2-methyl-pentanethioic acid S-phenyl ester 
• 82353-61-5 (2R,3S,4S)-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2-methyl-pentanethioic acid S-phenyl ester 
• 70386-38-8 L-1-bromo-3-phthalimido-2-butanone 
• 141725-08-8 (R)-2-Phthalimido-N-(2,6-dimethylphenyl)-N-[3-(3-pyridyl)propyl]propanamide hydrochloride 
• 111320-48-0 2,5-Diethoxyphenyl-(1-phthalimidoethyl)-keton 
• 2743-80-8 (R)-(3,4-Dimethoxyphenyl)-(1-phthalimidoethyl)-keton 
• 111114-02-4 (R)-Mesityl-(1-phthalimidoethyl)-keton 
• 87-41-2 2-benzofuran-1(3H)-one 
• 866395-51-9 2-hydroxymethyl-N-(3-hydroxy-1-methyl-propyl)-benzamide 
• 634585-85-6 ethyl 2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]-4-methyl-5-oxo-2,5-dihydroisoxazole-3-carboxylate 
• 73365-03-4 (R)-(+)-2-N-phthalimidopropanal 
• 338-69-2 D-Alanine 

Relevant academic research and scientific papers

Solid phase-solid state synthesis of N-alkyl imides from anhydrides

Preparation of N-alkyl imides from anhydrides is developed on polymer support in solid state assisted by microwave for the first time.

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.

KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation

A method for aerobic oxidation of aldehydes to carboxylic acids has been developed using organic nitroxyl and NOx cocatalysts. KetoABNO (9-azabicyclo[3.3.1]nonan-3-one N-oxyl) and NaNO2 were identified as the optimal nitroxyl and NOx sources, respectively. The mildness of the reaction conditions enables sequential asymmetric hydroformylation of alkenes/aerobic aldehyde oxidation to access α-chiral carboxylic acids without racemization. The scope, utility, and limitations of the oxidation method are further evaluated with a series of achiral aldehydes bearing diverse functional groups.

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.

Design, synthesis and mechanism of novel shikonin derivatives as potent anticancer agents

In this study, a series of novel shikonin derivatives (30-49) were designed and synthesized and their anti-proliferative activities were evaluated against five different cancer cell lines, including HeLa, HepG2, MCF-7, BGC and A549. Some of the compounds show strong anti-proliferative effects against HeLa, HepG2 and MCF-7 with IC50 values ranging from 1.26 to 18.50 μM and show lower side effects towards normal cell lines as compared to shikonin. Compared to other compounds and shikonin itself, compound 40 displayed much stronger anti-proliferative effects against various cancer cell lines. Furthermore, the flow cytometry results demonstrated that compound 40 could obviously induce apoptosis in a dose- and time-dependent manner and also cause cell cycle arrest at the G2/M phase. For further investigation of the aforementioned mechanisms, we performed Western blot experiments and found that the cleavage of PARP and upstream caspase-3 increased; moreover, caspase-9 was activated by cleavage but not caspase-8. These aforementioned results also indicate that compound 40 could induce caspase-9 involved apoptosis and G2/M phase cell cycle arrest via the P21, p-CDC2 (Tyr15) pathway independent of P53.

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.

Structure-driven design and synthesis of chiral dioxocyclam derivatives

Based on an analysis of previously reported structures and a potential geometry fit with substrates, a new family of chiral dioxocyclam derivatives have been designed. The synthesis of those ligands was accomplished starting from l-proline and α-d-amino acids (converted to β-amino acids) with a key step of macrocyclization reaction of amino esters. All ligands were converted into neutral copper(II) complexes (amide groups underwent deprotonation of upon treatment of ligands with copper(II) acetate). The complexes exhibit the desired shape of their active surfaces, as proved by X-ray analysis.

Design, development and synthesis of mixed bioconjugates of piperic acid-glycine, curcumin-glycine/alanine and curcumin-glycine-piperic acid and their antibacterial and antifungal properties

In the present communication different curcumin bioconjugates viz. 4,4′-di-O-glycinoyl-curcumin, 4,4′-di-O-d-alaninoyl-curcumin, 4,4′-di-O-(glycinoyl-di-N-piperoyl)-curcumin, 4,4′-di-O-piperoyl curcumin, curcumin-4,4′-di-O-β-D-glucopyranoside, 4,4′-di-O-acetyl-curcumin along with piperoyl glycine, have been synthesised and characterised by spectra UV, 1H NMR and elemental analysis. All the covalent bonds used are biodegradable. This makes these derivatives as potent prodrugs, which can get hydrolysed at the target sites. These bioconjugates were tested in vitro against different bacteria and fungi. The 4,4′-di-O-(glycinoyl-di-N-piperoyl)-curcumin and 4,4′-di-O- acetyl-curcumin are more effective than Cefepime, an antibacterial drug available in market, at the same concentration. The 4,4′-di-O-(glycinoyl- di-N-piperoyl)-curcumin and 4,4′-di-O-piperoyl curcumin had antifungal activity in vitro almost comparable with fluconazole, the most popular antifungal drug. The enhanced activity of these bioconjugates vis-a-vis the parent molecule that is curcumin may be due to improved cellular uptake or reduced metabolism of these bioconjugates resulting in building up of enough concentration inside the infected cells. It opens a new era for exploring suitably designed curcumin bioconjugates as potential antibacterial/antifungal drugs.

Microwave-assisted rapid synthesis of phthalimide derivatives

A simple, extremely fast, and high yielding method for the reaction of phthalic anhydride with a number of amino acids using microwave irradiation under solventless 'dry' conditions has been developed. The phthalimide derivatives are prepared in excellent yields and without racemization.