202214-53-7Relevant articles and documents
Design and synthesis of fused tetrahydroisoquinoline-iminoimidazolines
Moas-Héloire, Valeria,Renault, Nicolas,Batalha, Vania,Arias, Angela Rincon,Marchivie, Mathieu,Yous, Said,Deguine, Noémie,Buée, Luc,Chavatte, Philippe,Blum, David,Lopes, Luisa,Melnyk, Patricia,Agouridas, Laurence
, p. 15 - 25 (2015)
In the aim of identifying new privileged structures, we describe the 5-steps synthesis of cyclic guanidine compounds "tetrahydroisoquinoline-iminoimidazolinesg" derived from tetrahydroisoquinoline-hydantoin core. In order to evaluate this new minimal structure and the impact of replacing a carbonyle by a guanidine moiety, their affinity towards adenosine receptor A2A was evaluated and compared to those of tetrahydroisoquinoline-hydantoin compounds.
Backbone-Fluorinated 1,2,3-Triazole-Containing Dipeptide Surrogates
Engel-Andreasen, Jens,Wellh?fer, Isabelle,Wich, Kathrine,Olsen, Christian A.
, p. 11613 - 11619 (2017/11/10)
The 1,2,3-triazole moiety can be incorporated as a peptide bond bioisostere to provide protease resistance in peptidomimetics. Herein, we report the synthesis of peptidomimetic building blocks containing backbone-fluorinated 1,4-disubstituted 1,2,3-triazole moieties. Synthetic protocols for the preparation of various Xaa-Gly dipeptide surrogates in the form of Xaa-ψ[triazole]-F2Gly building blocks were established, and selected examples were introduced into the endogenous peptide opioid receptor ligand Leu-enkephalin as a model compound.
Asymmetric syntheses of α-methyl γ-amino acid derivatives
Zhu, Ye,Khumsubdee, Sakunchai,Schaefer, Amber,Burgess, Kevin
scheme or table, p. 7449 - 7457 (2011/11/29)
This project was undertaken to demonstrate the potential of asymmetric hydrogenations mediated by the chiral, carbene-oxazoline analogue of Crabtree's catalyst "cat" in asymmetric hydrogenations of allylic amine derivatives of amino acids. Peripheral feat
Potent and fully noncompetitive peptidomimetic inhibitor of multidrug resistance P-glycoprotein
Arnaud, Ophélie,Koubeissi, Ali,Ettouati, Laurent,Terreux, Rapha?l,Alamé, Ghina,Grenot, Catherine,Dumontet, Charles,Di Pietro, Attilio,Paris, Jo?lle,Falson, Pierre
supporting information; experimental part, p. 6720 - 6729 (2010/11/16)
Nα-Boc-l-Asp(OBn)-l-Lys(Z)-OtBu (reversin 121, 1), an inhibitor of the P-gp ABC transporter, was used to conceive compounds inhibiting the drug efflux occurring through the Hoechst 33342 and daunorubicin transport sites of P-gp, respectively H and R sites. Replacement of the aspartyl residue by trans-4-hydroxy-l-proline (4(R)Hyp) gave compounds 11 and 15 characterized by half-maximal inhibitory concentrations (IC50) of 0.6 and 0.2 μM, which are 2-and 7-fold lower than that of the parent molecule. The difference in IC50 between 11 and 15 rests on the carbonyl group of the peptidyl bond, reduced in 15. Those compounds are rather specific of P-gp, having no or limited activity on MRP1 and BCRP. 15 displayed no marked cytotoxicity up to 10-fold its IC50. Importantly, 15 equally inhibited the Hoechst 33342 and daunorubicin effluxes through a typical noncompetitive inhibition mechanism, suggesting its binding to a site different from the H and R drug-transport sites.
Synthesis of a constrained enkephalin analog to illustrate a novel route to the piperazinone ring structure
Shreder, Kevin,Zhang, Li,Goodman, Murray
, p. 221 - 224 (2007/10/03)
The synthesis of a constrained, piperazinone analog of Leu-enkephalin is presented. A key step in this synthesis was the use of the secondary amine, Boc-Tyr(OtBu)Ψ[CH2NH]Gly-OMe, to ring open the β-lactone of Z-protected L-serine (the Vederas lactone). The resulting free acid was then coupled to H-Phe-Leu-OtBu in a one-pot fashion using standard carbodiimide coupling conditions. This linear precursor cyclized upon hydrogenolysis of the Z group to form the N4-substituted, 6-carboxy-derived piperazinone (5). Deprotection of compound 5 using 1:1 TFA:CH2Cl2 yielded the target compound 1.
