156801-29-5Relevant articles and documents
Phosphine-Catalyzed Synthesis of Chiral N-Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling
Lorton, Charlotte,Saleh, Nidal,Voituriez, Arnaud
supporting information, p. 3340 - 3344 (2021/06/26)
Phosphine-catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2,5-dihydro-1H-pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.
PRODRUG MODULATORS OF THE INTEGRATED STRESS PATHWAY
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Paragraph 00304, (2020/05/19)
Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases, disorders and conditions.
Synthesis method of double different protected amino acids
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Paragraph 0019, (2019/07/04)
The invention relates to a synthesis method of double different protected amino acids.The technical problems of harsh reaction conditions, inapplicability of production enlarging and the like in an existing synthesis method are mainly solved. According to the technical scheme, the synthesis method of double different protected amino acids comprises the following steps: one of Boc20, Alloc-Cl or Cbz-Osuis added to amino alcohol under the action of an alkaline reagent to obtain a compound 1; the compound 1 reacts with methanesulfonyl chloride or paratoluensulfonyl chloride to obtain an intermediate, then a halide is added into acetone, heating and refluxing are executed to obtain a compound 2; the compound 2 is condensed with diethyl acetamidomalonate under the action of an alkaline agent togenerate a compound 3; the compound 3 is dissolved in alcohol and water, an inorganic base is added, heating, hydrolyzing and decarboxylating are executed to obtain a compound 4; acetylase is added into deionized water to obtain a compound 5 through enzymolysis; amino acid protection is executed, wherein one of Fmoc-Osu, Cbz-OSu, Alloc-Cl or Boc20 is added into thecompound 5 under the action of an alkaline agent to generatea target compound A.
A Peptoid with Extended Shape in Water
Morimoto, Jumpei,Fukuda, Yasuhiro,Kuroda, Daisuke,Watanabe, Takumu,Yoshida, Fumihiko,Asada, Mizue,Nakamura, Toshikazu,Senoo, Akinobu,Nagatoishi, Satoru,Tsumoto, Kouhei,Sando, Shinsuke
supporting information, p. 14612 - 14623 (2019/10/02)
The term "peptoids" was introduced decades ago to describe peptide analogues that exhibit better physicochemical and pharmacokinetic properties than peptides. Oligo(N-substituted glycine) (oligo-NSG) was previously proposed as a peptoid due to its high proteolytic resistance and membrane permeability. However, oligo-NSG is conformationally flexible, and ensuring a defined shape in water is difficult. This conformational flexibility severely limits the biological application of oligo-NSG. Here, we propose oligo(N-substituted alanine) (oligo-NSA) as a peptoid that forms a defined shape in water. The synthetic method established in this study enabled the first isolation and conformational study of optically pure oligo-NSA. Computational simulations, crystallographic studies, and spectroscopic analysis demonstrated the well-defined extended shape of oligo-NSA realized by backbone steric effects. This new class of peptoid achieves the constrained conformation without any assistance of N-substituents and serves as a scaffold for displaying functional groups in well-defined three-dimensional space in water, which leads to effective biomolecular recognition.
Synthesis, Antiviral Potency, in Vitro ADMET, and X-ray Structure of Potent CD4 Mimics as Entry Inhibitors That Target the Phe43 Cavity of HIV-1 gp120
Curreli, Francesca,Kwon, Young Do,Belov, Dmitry S.,Ramesh, Ranjith R.,Kurkin, Alexander V.,Altieri, Andrea,Kwong, Peter D.,Debnath, Asim K.
, p. 3124 - 3153 (2017/04/21)
In our attempt to optimize the lead HIV-1 entry antagonist, NBD-11021, we present in this study the rational design and synthesis of 60 new analogues and determination of their antiviral activity in a single-cycle and a multicycle infection assay to derive a comprehensive structure-activity relationship (SAR). Two of these compounds, NBD-14088 and NBD-14107, showed significant improvement in antiviral activity compared to the lead entry antagonist in a single-cycle assay against a large panel of Env-pseudotyped viruses. The X-ray structure of a similar compound, NBD-14010, confirmed the binding mode of the newly designed compounds. The in vitro ADMET profiles of these compounds are comparable to that of the most potent attachment inhibitor BMS-626529, a prodrug of which is currently undergoing phase III clinical trials. The systematic study presented here is expected to pave the way for improving the potency, toxicity, and ADMET profile of this series of compounds with the potential to be moved to the early preclinical development.
Functionalizing αvβ3- or α5β1-selective integrin antagonists for surface coating: A method to discriminate integrin subtypes in vitro
Rechenmacher, Florian,Neubauer, Stefanie,Polleux, Julien,Mas-Moruno, Carlos,De Simone, Mariarosaria,Cavalcanti-Adam, Elisabetta Ada,Spatz, Joachim P.,F?ssler, Reinhard,Kessler, Horst
supporting information, p. 1572 - 1575 (2013/04/10)
Stuck with the right choice: αvβ3- or α5β1-selective integrin ligands were functionalized for surface coating without losing activity and selectivity. The coating of nanostructured gold surfaces with these compounds stimulated subtype-selective cell adhesion of genetically modified αvβ3- or α5β1-expressing fibroblasts in vitro. Copyright
Phenols-useful templates for the synthesis of bi-functional orthogonally protected dendron building blocks via solid phase Mitsunobu reaction
Gellerman, Gary,Shitrit, Sagit,Shalit, Tzachi,Ganot, Orit,Albeck, Amnon
experimental part, p. 878 - 886 (2010/03/25)
Bi-functional dendritic building blocks for convergent dendrimer growth were successfully synthesized from phenolic templates in the solid phase via a Mitsunobu reaction. Each arm of the dendron building block carries an orthogonally protected secondary amine along the arm, and a peripheral primary amine or phenol group (building block type 1) or a tertiary amine junction with orthogonally protected peripheral primary amine or carboxyl groups (building block type 2). The synthetic routes reported in this work are general and applicable for the preparation of diverse building blocks, controlling protection, arm length, and peripheral moieties. These novel dendron units can form unusual dendritic architectures by solid-phase chemistry, which may be incorporated into specific complex structures expanding the scope of dendrimer science.
