21946-94-1Relevant articles and documents
Glycine-selective α-carbon-nitrogen bond cleavage of dipeptides by nickel peroxide
Easton, Christopher J.,Eichinger, Sharon K.,Pitt, Michael J.
, p. 5609 - 5616 (1997)
Nickel peroxide selectively cleaves the α-carbon-nitrogen bond of glycine residues in dipeptide derivatives to give the corresponding amides. The glycine selectivity is attributable to preferential complexation of the reactant residue to nickel peroxide and subsequent reaction via a stable α-centered glycyl radical. The oxidation process serves as a chemical model for peptidylglycine α-amidating monooxygenase (PAM) and, in addition, may have potential for the synthesis of α,β-didehydro amino acid residues within peptides.
Selective Removal of Aminoquinoline Auxiliary by IBX Oxidation
Zhang, Zhiguo,Li, Xiang,Song, Mengmeng,Wan, Yameng,Zheng, Dan,Zhang, Guisheng,Chen, Gong
, p. 12792 - 12799 (2019/07/03)
8-Aminoquinoline (AQ) is a widely used bidentate auxiliary in metal-catalyzed directed C-H functionalization reactions. Herein, we report an efficient and chemoselective method to convert various N-quinolyl carboxamides to primary amides with the treatment of a stoichiometric amount of 2-iodoxybenzoic acid oxidant or the combination of a catalytic amount of 2-iodobenzoic acid and Oxone co-oxidant in mixed solvents of H2O and HFIP. Its unique compatibility with the Phth-protected α-amino acid (αAA) substrates enhances the overall synthetic utility of the AQ-directed palladium-catalyzed C-H functionalization strategy for synthesis of complex αAAs.
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.
Rapid procedure for N-phthaloylation of α-amino carboxamides, α-amino alcohols, α-amino esters and dipeptide derivatives
Casimir,Guichard,Tourwe,Briand
, p. 1985 - 1988 (2007/10/03)
A rapid, one-pot synthesis and mild procedure for the N-phthaloylation of α-amino carboxamides is described. In acetonitrile, these derivatives react with mono-methylphthalate in the presence of BOP and i-Pr2NEt to afford the intermediate Nα-[(o-methoxycarbonyl)benzoyl]amino carboxamides, which undergo rapid cyclization in the presence of aqueous sodium carbonate to afford the corresponding Nα-phthaloylamino carboxamides in excellent yields. The reaction also works efficiently with α-amino esters, α-amino alcohols and dipeptide esters or amides.
Ultrasound and ZnCl2 promoted synthesis of phthaloyl derivatives of α-amino carboxamides
Casimir,Guichard,Briand
, p. 75 - 80 (2007/10/03)
A new, one-step and racemization-free synthesis of phthaloyl derivatives of α-amino carboxamides is described. Under ultrasound, α-amino carboxamides and dipeptide derivatives react with monomethyl phthalate in the presence of BOP, ZnCl2 and i-
Cyclic amides
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, (2008/06/13)
Cyclic amides are inhibitors of tumor necrosis factor and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 3-phenyl-3-(1-oxoisoindolin-2-yl)propionamide.
Ring closure of N-phthaloylglutamines
-
, (2008/06/13)
Cyclic imides are inhibitors of tumor necrosis factor α and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 2-(2,6-dioxo-3-piperidinyl)-4-azaisoindoline-1,3-dione.
