57750-51-3Relevant academic research and scientific papers
Identification of novel TACE inhibitors compatible with topical application
Ouvry, Gilles,Berton, Ya?l,Bhurruth-Alcor, Yushma,Bonnary, Laetitia,Bouix-Peter, Claire,Bouquet, Karine,Bourotte, Marilyne,Chambon, Sandrine,Comino, Catherine,Deprez, Beno?t,Duvert, Denis,Duvert, Gwena?lle,Hacini-Rachinel, Feriel,Harris, Craig S.,Luzy, Anne-Pascale,Mathieu, Arnaud,Millois, Corinne,Pascau, Jonathan,Pinto, Artur,Polge, Ga?lle,Reitz, Arnaud,Reversé, Kevin,Rosignoli, Carine,Taquet, Nathalie,Hennequin, Laurent F.
, p. 1848 - 1853 (2017)
Targeting the Tumor Necrosis Factor α signalling with antibodies has led to a revolution in the treatment of psoriasis. Locally inhibiting Tumor Necrosis Factor α Converting Enzyme (TACE or ADAM17) could potentially mimic those effects and help treat mild to moderate psoriasis, without the reported side effect of systemic TACE inhibitors. Efforts to identify new TACE inhibitors are presented here. Enzymatic SAR as well as ADME and physico-chemistry data are presented. This study culminated in the identification of potent enzymatic inhibitors. Suboptimal cellular activity of this series is discussed in the context of previously published results.
Design, synthesis and preliminary evaluation of novel pyrrolidine derivatives as matrix metalloproteinase inhibitors
Cheng, Xian-Chao,Wang, Qiang,Fang, Hao,Tang, Wei,Xu, Wen-Fang
, p. 2130 - 2139 (2008/12/22)
A series of novel pyrrolidine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. The hydroxamates 8a-c were equally or more potent MMP-2 inhibitors than the positive control LY52. The binding mode of the most potent compound 8a with MMP-2 was proposed. Structure-activity relationships were also briefly discussed.
Two prolines with a difference: contrasting stereoelectronic effects of 4R/S-aminoproline on triplex stability in collagen peptides [pro(X)-pro(Y)-Gly]n.
Umashankara,Babu, I Ramesh,Ganesh, Krishna N
, p. 2606 - 2607 (2007/10/03)
4R/S-Aminoprolines when present in the X-position of collagen peptide [pro(X)-pro(Y)-Gly]n exhibit pH- and stereochemistry-dependent effects on triplex stability.
Studies of N-Terminal Templates for α-Helix Formation. Synthesis and Conformational Analysis of (2S,5S,8S,11S)-1-Acetyl-1,4-diaza-3-keto-5-carboxy-10-thiatricyclo4,8>tridecane (Ac-Hel1-OH)
Kemp, D. S.,Curran, Timothy P.,Davis, William M.,Boyd, James G.,Muendel, Christopher
, p. 6672 - 6682 (2007/10/02)
A convergent synthesis of the title compound, a conformationally restricted analogue of acetyl-L-prolyl-L-proline, from 1-acetyl-2(S)-carboxy-4(S)-mercaptopyrrolidine and trans-1-(tert-butoxycarbonyl)-2(S)-(methoxycarbonyl)-5(S)-pyrrolidine (Ac-Hel1-OH) is reported, along with a synthesis of (2S,8S,11S)-1-acetyl-1,4-diaza-3-keto-10-thiatricyclo4,8>tridecane.In the crystal and in CDCl3 solution the conformation of Ac-Hel1-OH is shown to approximate a staggered orientation at the 8,9-CC bond and an s-cis orientation at the acetyl amide bond.In DMF, DMSO, MeCN, and D2O significant amounts of the s-trans conformer are also present.
(2S,5S,8S,11S)-1-ACETYL-1,4-DIAZA-3-KETO-5-CARBOXY-10-THIA-TRICYCLO-(2.8.04,8)-TRIDECANE, 1 SYNTHESIS OF PROLYL-PROLINE-DERIVED, PEPTIDE-FUNCTIONALIZED TEMPLATES FOR α-HELIX FORMATION
Kemp, D. S.,Curran, Timothy P.
, p. 4931 - 4934 (2007/10/02)
A convergent synthesis is reported for the title compound 1 (X = OH) from L-4-hydroxyproline and (2S,5S)-trans-1-benzyl-2,5-dicarbomethoxypyrrolidine.The peptides αTemp-(L-Ala)n-OMe (n = 1,2,3,4) and αTemp-L-Ala-L-Phe-L-Lys(ε-Boc)-L-Lys(ε-Boc)-NHMe (αTemp
