Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideOn March 31, 2012, Mallik, Shyam Kumar; Li, Da Yu; Cui, Minghua; Song, Hyun-Ok; Park, Hyun; Kim, Hak Sung published an article in Archives of Pharmacal Research. The article was 《Synthesis and evaluation of peptidyl α,β-unsaturated carbonyl derivatives as anti-malarial calpain inhibitors》. The article mentions the following:
Malarial calpain is a cysteine protease believed to be a central mediator essential for parasitic activities. N-Acetyl-L-leucyl-L-leucyl-L-norleucinal (ALLN), a calpain inhibitor, showed an excellent inhibitory effect on the erythrocytic stages of Plasmodium falciparum. However the aldehyde group of ALLN makes it susceptible to metabolism Therefore, we designed α,β-unsaturated carbonyl peptides that could serve as electrophiles for cysteine residues in calpain. Among the synthetic analogs based on the structure of ALLN, peptidyl esters (I) (R1 = i-Bu, R2 = Boc, Cbz; R1 = Ph, R2 = Cbz; Boc = tert-butoxycarbonyl, Cbz = benzyloxycarbonyl) showed the most potent anti-malarial effects, with the same IC50 values of 5.0 μM. Also they showed the high selective toxicity for the malaria vs. Hela cell with 40.6, 69.2 and 24.3 fold for I (R1 = i-Bu, R2 = Boc, Cbz; R1 = Ph, R2 = Cbz) resp. Dipeptidyl α,β-unsaturated carbonyl derivatives consisting of two amino acids gave better anti-malarial effects than those consisting with one amino acid. The fluctuation in anti-malarial activity with small changes in chem. structure indicates the possibilities of improving synthetic analogs. In the experiment, the researchers used many compounds, for example, (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide)
(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole.Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics