113896-95-0Relevant articles and documents
Synthesis of gallinamide A analogues as potent falcipain inhibitors and antimalarials
Conroy, Trent,Guo, Jin T.,Elias, Nabiha,Cergol, Katie M.,Gut, Jiri,Legac, Jennifer,Khatoon, Lubna,Liu, Yang,McGowan, Sheena,Rosenthal, Philip J.,Hunt, Nicholas H.,Payne, Richard J.
, p. 10557 - 10563 (2014)
Analogues of the natural product gallinamide A were prepared to elucidate novel inhibitors of the falcipain cysteine proteases. Analogues exhibited potent inhibition of falcipain-2 (FP-2) and falcipain-3 (FP-3) and of the development of Plasmodium falciparum in vitro. Several compounds were equipotent to chloroquine as inhibitors of the 3D7 strain of P. falciparum and maintained potent activity against the chloroquine-resistant Dd2 parasite. These compounds serve as promising leads for the development of novel antimalarial agents.
Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO
Loke, Inga,Park, Natja,Kempf, Karl,Jagusch, Carsten,Schobert, Rainer,Laschat, Sabine
experimental part, p. 697 - 704 (2012/01/05)
α-Aminoesters react with Ph3PCCO in a domino addition-Wittig cyclization sequence affording enantiomerically pure tetramates. In the case of β-oxo functionalized α-aminoesters, e.g., esters of serine, threonine or β-hydroxyornithine the yields of this reaction depend heavily on the bulkiness of the β-OR group and on the configuration of β-carbon atom C-3. Smaller residues and 2R/3R-configured aminoesters give better yields. The alkoxycarbonyl group of the ester moiety and the residue on the N-atom are less important. These findings can be accounted for by assuming an early puckered transition state for the intramolecular ring-closing Wittig reaction. The addition of sub-stoichiometric amounts of benzoic acid or N-hydroxysuccinimide (for acid-sensitive compounds) is advantageous in some cases as it accelerates the formation of the intermediate amide ylides.
Desulfonylation of Amides Using Samarium Iodide
Knowles, Haydn,Parsons, Andrew F.,Pettifer, Robert M.
, p. 271 - 272 (2007/10/03)
The desulfonylation of N-sulfonyl amides can be achieved in reasonable to excellent yield by reaction with samarium(II) iodide (SmI2) in THF at room temperature. Deprotection of acyclic and cyclic amides bearing aryl and alkylsulfonyl groups is possible.
