50468-37-6Relevant academic research and scientific papers
Carbonylative synthesis of phthalimides and benzoxazinones by using phenyl formate as a carbon monoxide source
Chavan, Sujit P.,Bhanage, Bhalchandra M.
, p. 2405 - 2410 (2015)
A simple and efficient palladium-catalyzed carbonylative cyclization of N-substituted 2-iodobenzamides and 2-iodoanilides was investigated for the synthesis of phthalimides and benzoxazinones, respectively, by using phenyl formate as a CO source. The present catalytic protocol circumvents the use of an expensive phosphine ligand as well as solvent in the case of the phthalimide synthesis. Moreover, mild reaction conditions and a tolerance of various functional groups enhance the general applicability of this method.
Novel phthalimide derivatives with TNF-α and IL-1β expression inhibitory and apoptotic inducing properties
Coêlho, Lucas Cunha Duarte,De Oliveira Cardoso, Marcos Veríssimo,Moreira, Diogo Rodrigo Magalh?es,De Moraes Gomes, Paulo André Teixeira,Cavalcanti, Suellen Melo Tibúrcio,Oliveira, Arsenio Rodrigues,De Oliveira Filho, Gevanio Bezerra,Pessoa De Siqueira, Lucianna Rabelo,De Oliveira Barbosa, Miria,De Oliveira Borba, Elizabeth Fernanda,Da Silva, Teresinha Gon?alves,Kaskow, Belinda,Karimi, Mahdad,Abraham, Lawrence J.,Leite, Ana Cristina Lima
, p. 758 - 765 (2014/06/10)
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.
A facile deprotection of secondary acetamides
Koenig, Stefan G.,Vandenbossche, Charles P.,Zhao, Hang,Mousaw, Patrick,Singh, Surendra P.,Bakale, Roger P.
supporting information; experimental part, p. 433 - 436 (2009/07/04)
(Chemical Equation Presented) Imidoyl chlorides, generated from secondary acetamides and oxalyl chloride, can be harnessed for a selective and practical deprotection sequence. Treatment of these intermediates with 2 equiv of propylene glycol and warming enables the rapid release of amine hydrochloride salts in good yields. Notably, the reaction conditions are mild enough to allow for a swift deprotection with no observed epimerization of the amino center.
Mild Conversion of Carboxamides and Carboxylic Acid Hydrazides to Acids and Esters
Greenlee, William J.,Thorsett, Eugene D.
, p. 5351 - 5353 (2007/10/02)
A mild and selective conversion of unsubstituted carboxamides and carboxylic acid hydrazides to the corresponding acids and esters is brought about by the use of acidic resins.Application of the procedure to several carboxamides and carboxylic acid hydrazides is described.
