1,5-Disubstituted 1,2,3-Triazoles as Amide Bond Isosteres Yield Novel Tumor-Targeting Minigastrin Analogs
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چکیده
منابع مشابه
1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics.
Since the discovery of Cu(I)-catalysed click chemistry, the field of peptidomimetics has expanded to include 1,4-connected 1,2,3-triazoles as useful peptide bond isosteres. Here, we report the synthesis of triazole-containing analogues of the naturally occurring tyrosinase inhibitor cyclo-[Pro-Val-Pro-Tyr] and show that the analogues retain enzyme inhibitory activity, demonstrating the effectiv...
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Proline is unique among the natural amino acids in the similar propensity of its peptide bond to be in the cis or trans conformation.1 This attribute affects many processes, including the rate at which proteins fold,2 their structures,3 and their activities.4 Other aliphatic amino acids can serve as mimics for proline residues with transpeptide bonds. In contrast, chemical synthesis is needed t...
متن کاملIn vitro and in vivo biological evaluation of new 4,5-disubstituted 1,2,3-triazoles as cis-constrained analogs of combretastatin A4.
To find new and better antivascular agents for cancer therapy, a series of combretastatin A4 (CA4) analogs were prepared from 1,3-diaryl-2-nitroprop-1-enes (6-12) obtained in a two-step synthesis from appropriate arylaldehydes and 2-aryl-1-nitroethanes (4 or 5). Treatment of these 1,3-diaryl-2-nitroprop-1-enes 6-12 by sodium azide in DMSO yielded the targeted compounds. The synthesized 1,2,3-tr...
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A facile and one-pot multicomponent synthesis of novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes at room temperature is reported. At the first step, in the presence of I2/NaN3 reagents, various alkenes were converted to the corresponding azido iodides and in the next step, the reaction of these compounds with phenylacetylene in the presence of catalytic amount of sodium ascorbate/ CuSO4...
متن کاملAn evaluation of peptide-bond isosteres.
Peptide-bond isosteres can enable a deep interrogation of the structure and function of a peptide or protein by amplifying or attenuating particular chemical properties. In this Minireview, the electronic, structural, and conformational attributes of four such isosteres-thioamides, esters, alkenes, and fluoroalkenes-are examined in detail. In particular, the ability of these isosteres to partak...
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ژورنال
عنوان ژورنال: ACS Medicinal Chemistry Letters
سال: 2021
ISSN: 1948-5875,1948-5875
DOI: 10.1021/acsmedchemlett.0c00636