84890-97-1Relevant academic research and scientific papers
Lipidated cyclopropenes via a stable 3-N spirocyclopropene scaffold
Kumar, Pratik,Jiang, Ting,Zainul, Omar,Preston, Alyssa N.,Li, Sining,Farr, Joshua D.,Suri, Pavit,Laughlin, Scott T.
supporting information, p. 3435 - 3438 (2018/08/21)
Lipidated cyclopropenes serve as useful bioorthogonal reagents for imaging cell membranes due to the cyclopropene's small size and ability to ligate with pro-fluorescent tetrazines. Previously, the lipidation of cyclopropenes required modification at the C3 position because methods to append lipids at C1/C2 were not available. Herein, we describe C1/C2 lipidation with the biologically active lipid ceramide and a common phospholipid using a cyclopropene scaffold whose reactivity with 1,2,4,5-tetrazines has been caged.
NOVEL AZAPEPTIDE OR AZAPEPTIDOMIMETIC COMPOUNDS INHIBITING BCRP AND/OR P-GP
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Page/Page column 15, (2012/01/15)
The present invention relates to compounds of azapeptide or azapeptidomimetic type of formula (I): in which R1, R2, R3, X1, X2, X3, X4 and Y are as defined in claim 1, to pharmaceutical compositions containing them and to such compounds as adjuvant for an anticancer or anti-infectious medicament.
Stereoselective synthesis of both enantiomers of trans-2- (diphenylmethylideneamino)cyclopropanecarboxylic acid using a chiral pool approach and their incorporation in dipeptides
Meiresonne, Tamara,Mangelinckx, Sven,De Kimpe, Norbert
, p. 9566 - 9571,6 (2020/08/20)
The stereoselective synthesis of (1R,2R)- and (1S,2S)-trans-2- (diphenylmethylideneamino)cyclopropanecarboxylic acid has been accomplished in six steps starting from (2S)- and (2R)-β-benzyl N-(tert-butoxycarbonyl) aspartate, respectively. The key-step in
Discovery, synthesis, and biological evaluation of a novel group of selective inhibitors of filoviral entry
Yermolina, Maria V.,Wang, Jizhen,Caffrey, Michael,Rong, Lijun L.,Wardrop, Duncan J.
experimental part, p. 765 - 781 (2011/04/15)
Herein, we report the development of an antifiloviral screening system, based on a pseudotyping strategy, and its application in the discovery of a novel group of small molecules that selectively inhibit the Ebola and Marburg glycoprotein (GP)-mediated infection of human cells. Using Ebola Zaire GP-pseudotyped HIV particles bearing a luciferase reporter gene and 293T cells, a library of 237 small molecules was screened for inhibition of GP-mediated viral entry. From this assay, lead compound 8a was identified as a selective inhibitor of filoviral entry with an IC50 of 30 μM. To analyze functional group requirements for efficacy, a structure-activity relationship analysis of this 3,5-disubstituted isoxazole was then conducted with 56 isoxazole and triazole derivatives prepared using "click" chemistry. This study revealed that while the isoxazole ring can be replaced by a triazole system, the 5-(diethylamino)acetamido substituent found in 8a is required for inhibition of viral-cell entry. Variation of the 3-aryl substituent provided a number of more potent antiviral agents with IC50 values ranging to 2.5 μM. Lead compound 8a and three of its derivatives were also found to block the Marburg glycoprotein (GP)-mediated infection of human cells.
Synthesis and biological activity of novel L-amino acid based analgesic compounds
Pan, Junzhu,Wang, Qianqian,He, Gu,Ouyang, Liang,Guo, Li
experimental part, p. 359 - 364 (2011/10/31)
Synthesis and analgesic activity studies of a series of L-amino acid based compounds were described. These compounds were designed as potential N-type Calcium Channel Blockers and their structures were confirmed by 1H NMR and ESI-MS spectra. Some of the compounds exhibited significant analgesic activity in Mouse Hot-Plate tests. According to the data of pharmacological experiments, we carried out preliminary structure-activity studies and the results indicated that this kind of compounds was useful for the development of new analgesic drugs.
The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K
Gauthier, Jacques Yves,Chauret, Nathalie,Cromlish, Wanda,Desmarais, Sylvie,Duong, Le T.,Falgueyret, Jean-Pierre,Kimmel, Donald B.,Lamontagne, Sonia,Leger, Serge,LeRiche, Tammy,Li, Chun Sing,Masse, Frederic,McKay, Daniel J.,Nicoll-Griffith, Deborah A.,Oballa, Renata M.,Palmer, James T.,Percival, M. David,Riendeau, Denis,Robichaud, Joel,Rodan, Gideon A.,Rodan, Sevgi B.,Seto, Carmai,Therien, Michel,Truong, Vouy-Linh,Venuti, Michael C.,Wesolowski, Gregg,Young, Robert N.,Zamboni, Robert,Black, W. Cameron
, p. 923 - 928 (2008/12/22)
Odanacatib is a potent, selective, and neutral cathepsin K inhibitor which was developed to address the metabolic liabilities of the Cat K inhibitor L-873724. Substituting P1 and modifying the P2 side chain led to a metabolically robust inhibitor with a long half-life in preclinical species. Odanacatib was more selective in whole cell assays than the published Cat K inhibitors balicatib and relacatib. Evaluation in dermal fibroblast culture showed minimal intracellular collagen accumulation relative to less selective Cat K inhibitors.
Further studies on lead compounds containing the opioid pharmacophore Dmt-Tic
Balboni, Gianfranco,Fiorini, Stella,Baldisserotto, Anna,Trapella, Claudio,Sasaki, Yusuke,Ambo, Akihiro,Marczak, Ewa D.,Lazarus, Lawrence H.,Salvadori, Severo
experimental part, p. 5109 - 5117 (2009/08/16)
Some reference opioids containing the Dmt-Tic pharmacophore, especially the δ agonists H-Dmt-Tic-GlyNH-Ph (1) and H-Dmt-TiC-NH-(S)CH(CH 2-COOH)-Bid (4) (UFP-512) were evaluated for the influence of the substitution of Gly with aspartic acid, it
New ion-exchange cum separation technique: A study for the synthesis of ω-guanidine containing peptides using ω-amino acid as surrogate
Gangopadhyay, Ashok K.,Lal, Bansi
, p. 1389 - 1419 (2008/02/01)
This article describes a systematic study for the introduction of ω-guanidine function at a late stage of synthesis using a protected amino group as a surrogate to improve overall yield. This concept was used to design and synthesize pseudo-peptides as GP IIb-IIIa receptor antagonist wherein glycine in endogenous ligand Arg-Gly-Asp (RGD) is replaced by 2-amino-thiazole-4-ylacetic acid (Tha) as a spacer. Further, we describe here a unique salt exchange cum purification technology based on reverse phase (RP-18) medium-pressure liquid chromatography. Copyright Taylor & Francis Group, LLC.
The effect of Glu→ Asp substitution on a 310type fold in BoC-(D)-GlU1-Ala2-Gly3-LyS4-NHMe
Bobade,Mhaske,Gaikwad
, p. 308 - 313 (2008/02/08)
The solution conformation of the peptide Boc-(D)-Asp1-Ala 2-Gly3-Lys4-NHMe based on NMR studies is compared with its (D)-Glu1 analog reported earlier. Results establish that (D)-Asp analog is devoid o
Cathepsin cysteine protease inhibitors
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Page/Page column 22, (2010/11/08)
This invention relates to a novel class of compounds which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is i
