88425-45-0Relevant academic research and scientific papers
New carboxamides bearing benzenesulphonamides: Synthesis, molecular docking and pharmacological properties
Eze, Florence Uchenna,Okoro, Uchechukwu Chris,Ugwu, David Izuchukwu,Okafor, Sunday N.
, (2019/09/18)
Ten new derivatives of benzenesulphonamide bearing carboxamide functionality were synthesized and investigated for their in vitro antimicrobial, antioxidant and in vivo anti-inflammatory activities. Compound 9d inhibited carrageenan induced rat-paw oedema
Serine and threonine β-lactones: A new class of hepatitis A virus 3C cysteine proteinase inhibitors
Lall, Manjinder S.,Ramtohul, Yeeman K.,James, Michael N.G.,Vederas, John C.
, p. 1536 - 1547 (2007/10/03)
Hepatitis A virus (HAV) 3C enzyme is a cysteine proteinase essential for viral replication and infectivity and represents a target for the development of antiviral drugs. A number of serine and threonine β-lactones were synthesized and tested against HAV 3C proteinase. The D-N-Cbz-serine β-lactone 5a displays competitive reversible inhibition with a Ki value of 1.50 × 10-6 M. Its enantiomer, L-N-Cbz-serine β-lactone 5b is an irreversible inactivator with kinact = 0.70 min-1, KI = 1.84 × 10-4 M and kinact/KI = 3800 M-1 min-1. Mass spectrometry and HMQC NMR studies using 13C-labeled 5b show that inactivation of the enzyme occurs by nucleophilic attack of the cysteine thiol (Cys-172) at the β-position of the oxetanone ring. Although the N-Cbz-serine β-lactones 5a and 5b display potent inhibition, other related analogues with an N-Cbz side chain, such as the five-membered ring homoserine γ-lactones 14a and 14b, the four-membered ring β-lactam 33, 2-methylene oxetane 34, cyclobutanone 36, and 3-azetidinone 39, fail to give significant inhibition of HAV 3C proteinase, thus demonstrating the importance of the β-lactone ring for binding.
Synthesis and Reactivity of β-Lactones Derived from L-Threonine and Related Amino Acids
Pansare, Sunil V.,Vederas, John C.
, p. 2311 - 2316 (2007/10/02)
The synthesis and nucleophilic ring opening of optically pure N-protected α-amino-β-alkyl β-lactones was investigated.Treatment of N-BOC-L-threonine (8) and N-BOC-L-allo-threonine (9) under modified Mitsunobu conditions (Ph3P, dimethyl azodicarboxylate, -
alpha -AMINO ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS. A GENERAL SYNTHESIS OF D- alpha -AMINO ACIDS FROM L-SERINE.
Maurer,Takahata,Rapoport
, p. 1095 - 1098 (2007/10/02)
A short and chirally efficient synthesis of four D- alpha -amino acids is described with L-serine as the chiral educt. The key C-C bond-forming reactions are the aminoacylations of organometallics with the lithium salt of N-(phenylsulfonyl)-L-serine (2) to give optically pure N-blocked alpha -amino ketones. Reduction of the carbonyl group to carbinol or methylene followed by oxidation of the hydroxymethyl to carboxyl gives the N-blocked D-amino acids. The examples investigated (norleucine, alpha -aminopimelic acid, DOPA, and allothreonine) demonstrate the broad applicability of the method.
