244033-75-8Relevant academic research and scientific papers
Composition comprising an ALLN derivative as an active ingredient for preventing and treating malaria infection
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Paragraph 0078; 0105-0106, (2018/05/16)
The present invention relates to an anti-malarial composition containing an ALLN (N-acetyl-L-Leucyl-Lleucyl-L-norleucinal) derivative compound as an active ingredient, wherein a compound of the present invention can be used as a pharmaceutical composition for preventing and treating a malaria infection containing the ALLN derivative compound as an active ingredient.
Anti-malarial activity of new N-acetyl-l-leucyl-l-leucyl-l-norleucinal (ALLN) derivatives against Plasmodium falciparum
Choi, Hwa-Jung,Cui, Minghua,Li, Da-Yu,Song, Hyun-Ok,Kim, Hak Sung,Park, Hyun
supporting information, p. 1293 - 1296 (2013/03/14)
Malaria is the most common of the parasitic diseases in tropical and subtropical regions. Adverse side effects of anti-malarial drugs have precluded them as a potential clinical drug. In this study, novel derivatives of N-acetyl-l-leucyl-l-leucyl-l-norleucinal (ALLN) based on a variety of dipeptidyl α,β-unsaturated amides containing lysine as a part were synthesized and evaluated. Lower toxicity was achieved by reducing or eliminating the tendency of forming chemically reactive and toxic intermediates and metabolites. The synthesized compounds were evaluated for anti-malarial efficacy against Plasmodium falciparum and cytotoxicity in human epitheloid carcinoma cervix (HeLa cells) by estimating the therapeutic index (TI). N-Methyl amide with N′-Boc protection among them exhibited strong anti-malarial activity and N-methyl amide with N′-m-methylbenzyl amide showed excellent anti-malarial activity with much lower toxicity than the ALLN. Therefore, the two chemicals, as well as the underlying design rationale, could be useful in the discovery and development of new anti-malarial drugs.
Hybrid peptides: Direct transformation of α/α, β-unsaturated γ-hybrid peptides to α/γ-hybrid peptide 12-helices
Bandyopadhyay, Anupam,Gopi, Hosahudya N.
supporting information; experimental part, p. 2770 - 2773 (2012/07/28)
A smooth transformation of unusual planar structures of α/vinylogous hybrid peptides to ordered α/γ4-hybrid peptide 12-helices and the stereochemical preferences of vinylogous amino acid residues in single crystals are studied.
α/γ4-Hybrid peptide helices: Synthesis, crystal conformations and analogy with the α-helix
Bandyopadhyay, Anupam,Jadhav, Sandip V.,Gopi, Hosahudya N.
supporting information; experimental part, p. 7170 - 7172 (2012/08/08)
Synthesis, crystal conformations of α/γ4-hybrid peptide helices containing proteinogenic amino acid side-chains, and the analogy with the α-helix are reported. Results suggest that α/ γ4-hybrid peptides adopted helical conformations
Novel CADD-based peptidyl vinyl ester derivatives as potential proteasome inhibitors
Mou, Ke,Xu, Bo,Ma, Chao,Yang, Xiaoming,Zou, Xiaomin,Lue, Yang,Xu, Ping
, p. 2198 - 2202 (2008/12/22)
A series of peptidyl vinyl ester derivatives bearing three different P1 substitutions as potential proteasome inhibitors were studied. The target molecules were designed based on CADD (computer aided drug design) protocol and synthesized. Their activities
Enantiomerically pure α-amino aldehydes from silylated α-amino acids
Soto-Cairoli, Buddy,Justo De Pomar, Jorge,Soderquist, John A.
, p. 333 - 336 (2008/09/19)
(Chemical Equation Presented) The disilylation of α-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the γ-amino esters 7 reveals that ≤2% racemization occurs in the 1 → 8 conversions.
Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters
Shie, Jiun-Jie,Fang, Jim-Min,Kuo, Tun-Hsun,Kuo, Chih-Jung,Liang, Po-Huang,Huang, Hung-Jyun,Wu, Yin-Ta,Jan, Jia-Tsrong,Cheng, Yih-Shyun E.,Wong, Chi-Huey
, p. 5240 - 5252 (2007/10/03)
The proteolytic processing of polyproteins by the 3CL protease of severe acute respiratory syndrome coronavirus is essential for the viral propagation. A series of tripeptide α,β-unsaturated esters and ketomethylene isosteres, including AG7088, are synthesized and assayed to target the 3CL protease. Though AG7088 is inactive (IC50 > 100 μM), the ketomethylene isosteres and tripeptide α,β-unsaturated esters containing both P1 and P2 phenylalanine residues show modest inhibitory activity (IC50 = 11-39 μM). The Phe-Phe dipeptide inhibitors 18a-e are designed on the basis of computer modeling of the enzyme-inhibitor complex. The most potent inhibitor 18c with an inhibition constant of 0.52 μM is obtained by condensation of the Phe-Phe dipeptide α,β-unsaturated ester with 4-(dimethylamino)cinnamic acid. The cell-based assays also indicate that 18c is a nontoxic anti-SARS agent with an EC50 value of 0.18 μM.
An intramolecular oxo Diels-Alder approach to 1-oxo-1,2,3,3a,4,7a- hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl esters
Murray, William V.,Mishra, Pranab K.,Turchi, Ignatius J.,Sawicka, Dorota,Maden, Amy,Sun, Sengen
, p. 8955 - 8961 (2007/10/03)
The diastereoselective synthesis of a series of 1-oxo-1,2,3,3a,4,7a- hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl esters via an oxo Diels-Alder reaction is described. Ab initio calculations predicted the products of the exo cycloaddition to be the thermodynamic products while the products resulting from the endo cycloaddition were predicted to be the kinetic products. The calculations were born out by experimental data.
Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels-Alder reaction
Murray, William V.,Mishra, Pranab K.,Sun, Sengen,Maden, Amy
, p. 7389 - 7392 (2007/10/03)
Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized
