Asymmetric hydrogenation of N-sulfonylated-α-dehydroamino acids: Toward the synthesis of an anthrax lethal factor inhibitor
(Chemical Equation Presented) A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-α-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.
Shultz, C. Scott,Dreher, Spencer D.,Ikemoto, Norihiro,Williams, J. Michael,Grabowski, Edward J. J.,Krska, Shane W.,Sun, Yongkui,Dormer, Peter G.,DiMichele, Lisa
p. 3405 - 3408
(2007/10/03)
PROCESS FOR MAKING N-SULFONATED-AMINO ACID DERIVATIVES
This invention relates to a process for preparing optically active α -amino acid substrates which are used to make potent lethal factor (LF) inhibitors for the treatment of anthrax. This invention further relates to a process for synthesis of potent LF-inhibitors for the treatment of anthrax. Specifically, the invention concerns a novel, high-yielding and highly enantioselective asymmetric hydrogenation reaction of a tetrasubstituted ene-sulfonamide acid or ester.
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Page/Page column 24-25
(2008/06/13)
Structure-activity relationship study and drug profile of N-(4-fluorophenylsulfonyl)-L-valyl-L-leucinal (SJA6017) as a potent calpain inhibitor
Novel N-arylsulfonyldipeptidyl aldehyde derivatives were prepared by DMSO oxidation from the corresponding dipeptide alcohol, and their potencies as calpain inhibitors were evaluated in vitro. Among them, N-(4-fluorophenylsulfonyl)-L-valyl-L-leucinal (8,
Inoue, Jun,Nakamura, Masayuki,Cui, Ying-She,Sakai, Yusuke,Sakai, Osamu,Hill, Jeanette R.,Wang, Kevin K. W.,Yuen, Po-Wai
p. 868 - 871
(2007/10/03)
Thioaryl sulfonamide hydroxamic acid compounds
PCT No. PCT/US98/04298 Sec. 371 Date Sep. 10, 1999 Sec. 102(e) Date Sep. 10, 1999 PCT Filed Mar. 4, 1998 PCT Pub. No. WO98/39313 PCT Pub. Date Sep. 11, 1998A thioaryl sulfonamide hydroxamic acid compound that inter alia inhibits matrix metalloprotease act
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(2008/06/13)
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