362488-92-4Relevant academic research and scientific papers
Enantioselective synthesis of an advanced intermediate for the synthesis of brefeldin A and analogues
Legrand, Frédéric,Archambaud, Sylvie,Collet, Sylvain,Aphecetche-Julienne, Karine,Guingant, André,Evain, Michel
, p. 389 - 393 (2008)
A synthesis of methyl (1R,2R,4S)-2-[(E)-2-iodovinyl]-4-(methoxymethoxy) cyclopentanecarboxylate is described in nine steps from a prochiral anhydride. A desymmetrization reaction followed by an epimerization and a Takai reaction are the key steps of the t
Total synthesis of (+)-brefeldin C, (+)-nor-Me brefeldin A and (+)-4-epi-nor-Me brefeldin A
Archambaud, Sylvie,Legrand, Frederic,Aphecetche-Julienne, Karine,Collet, Sylvain,Guingant, Andre,Evain
experimental part, p. 1364 - 1380 (2010/05/03)
A total synthesis of (+)-brefeldin C (BFC) and two brefeldin A (BFA) analogues - (+)-nor-Me BFA and (+)-4-epi-nor-Me BFA - has been developed. Key features of the syntheses include desymmetrization of meso anhydrides, a Carreira reaction to control the ab
α,β-Cyclic-β-benzamido hydroxamic acids: Novel templates for the design, synthesis, and evaluation of selective inhibitors of TNF-α converting enzyme (TACE)
Ott, Gregory R.,Asakawa, Naoyuki,Lu, Zhonghui,Liu, Rui-Qin,Covington, Maryanne B.,Vaddi, Krishna,Qian, Mingxin,Newton, Robert C.,Christ, David D.,Traskos, James M.,Decicco, Carl P.,Duan, James J.-W.
, p. 694 - 699 (2008/09/17)
Selective inhibitors of TNF-α Converting Enzyme (TACE) based on (1R,2S)-cyclopentyl, (3S,4S)-pyrrolidinyl, and (3R,4S)-tetrahydrofuranyl β-benzamido hydroxamic acids have been synthesized and evaluated. This study has led to the discovery of novel inhibitors whose profiles include activity against TACE in an enzyme assay, potency in the suppression of LPS-stimulated TNF-α in human whole blood, selectivity against a panel of MMPs and oral bioavailability.
