69088-05-7

Upstream product

• 136918-14-4 phthalimide 
• 63696-99-1 (S)-ethyl 2-(methylsulfonyloxy)propanoate 
• 64-17-5 ethanol 
• 4192-28-3 Phth-L-Ala-OH 
• 7699-00-5 (R)-Ethyl lactate 
• 897045-43-1 (S)-phthaloylalanine 
• 85-44-9 phthalic anhydride 
• 1074-82-4 potassium phtalimide 
• 535-11-5 Ethyl 2-bromopropionate 
• 79410-47-2 ethyl L-azidopropanoate 

Relevant academic research and scientific papers

Novel phthalimide derivatives with TNF-α and IL-1β expression inhibitory and apoptotic inducing properties

Modulation of the immune system is an emerging concept in the control of tumor growth. Bearing in mind the pharmacological properties of thalidomide and its phthalimide derivatives, we describe here the structural design, synthesis and pharmacological evaluation of N-acylhydrazones derived from phthalimide. The ability of these N-acylhydrazones in inhibiting the secretion of TNF-α in stimulated cells as well as in inhibiting the transcription of the TNF-α gene was evaluated. We identified N-acylhydrazones 6b and 9c, which substantially impaired TNF-α secretion, expression and reduced IL-1β production similar to thalidomide or Revlimid. N-Acylhydrazone 9c was also able to induce apoptosis in Jurkat cells, however it does not have either antiproliferative properties or cytotoxicity for mouse splenocytes. Beyond that, we have assayed the ability of these compounds to induce cell death and a number of them are able to induce apoptosis.

Nonsymmetrical azocarbonamide carboxylates as effective Mitsunobu reagents

A family of nonsymmetrical Mitsunobu reagents possessing both dialkyl amide and ester substituents was developed. These new reagents were readily prepared in a single pot from inexpensive, commercially available materials by using a scalable and environmentally friendly procedure. They were shown to exhibit activity parallel to that of diethyl azodicarboxylate/diisopropyl azodicarboxylate in a wide variety of Mitsunobu reactions. Importantly, the acyl hydrazine reaction byproducts were readily separable from the crude mixture by standard aqueous workup. In addition, the discovery of effective nonsymmetrical Mitsunobu reagents offers new directions for the ongoing development of this important reaction.

Synthesis of new cyclic imides derivatives with potential hypolipidemic activity

Certain new nitrogen-substituted derivatives of cyclic imides phthalimide (a), 1,8-naphthalimide (b), and diphenimide (c), were synthesized aiming to obtain potent hypolipidemic agents. Thus, 2-(N-imido) propanoic acids, 2-(N-phthalimido)-2-methylpropionic acid, and their ethyl esters were synthesized (Target derivative A). Also their corresponding N-substituted-2-(N- imido) propionamides and 2-(N-phthalimido)-2-methylpropionamides were prepared (Target derivative B). In addition, N-phthalimidomethyleneoxy acetate was prepared. Some of the newly prepared compounds were subjected to 3D studies and were found to be superimposed on Clofibrate, which is the first generation of fibrate drugs. The preliminary evaluation of hypolipidemic activity of the newly prepared compounds against triton WR-1339-induced hyperlipidemia in rat showed that several derivatives have demonstrated significant lowering of serum total cholesterol and triglyceride levels at dose of 150 mg/kg/i.p. comparing with Fenofibrate which is one of the second generations of fibrate drugs. Springer Science+Business Media, LLC 2010.

CsF in organic synthesis. Inversion of secondary mesylates and tosylates

Clean inversion of secondary mesylates and tosylates is effected by CsF in DMF. A variety of oxygen-, sulfur-, nitrogen-, and carbon-nucleophiles are employable. The reaction conditions have been optimized. The use of CsF in DMF is crucial and the reaction proceeds on the surface of solid CsF. It is suggested that hydrogen bonding between CsF and an active hydrogen of nucleophiles is responsible for the smooth reaction. Cesium carbonate fails to give rise to high specificity of inversion indicative of superiority of CsF.

NEW SYNTHETIC "TRICKS". ONE-POT PREPARATION OF N-SUBSTITUTED PHTHALIMIDES FROM AZIDES AND PHTHALIC ANHYDRIDE

N-Substituted phthalimides can be obtained in very good yields, under essentially neutral conditions, by mixing or heating an alkyl (or aryl) azide, triphenylphosohine, and phthalic anhydride in benzene or toluene, in the presence of a catalytic amount of tetrabutylammonium cyanide.Application of the reaction into the domain of carbohydrates is promising.

Phase-transfer Catalysis Using Chiral Catalysts. Influence of the Structure of the Catalyst on Stereoselectivity. Part 3.

Some chiral catalysts have been tested in the reaction of ethyl 2-bromopropionate with potassium phthalimide and in the borohydride reduction of phenyl t-butyl ketone under phase-transfer conditions.The mechanism of the N-alkylation reaction and the influ