1755-15-3Relevant articles and documents
On-Resin Preparation of Allenamidyl Peptides: A Versatile Chemoselective Conjugation and Intramolecular Cyclisation Tool
Brimble, Margaret A.,Cameron, Alan J.,Harris, Paul W. R.
supporting information, p. 18054 - 18061 (2020/09/07)
The ability to modify peptides and proteins chemoselectively is of continued interest in medicinal chemistry, with peptide conjugation, lipidation, stapling, and disulfide engineering at the forefront of modern peptide chemistry. Herein we report a robust method for the on-resin preparation of allenamide-modified peptides, an unexplored functionality for peptides that provides a versatile chemical tool for chemoselective inter- or intramolecular bridging reactions with thiols. The bridging reaction is biocompatible, occurring spontaneously at pH 7.4 in catalyst-free aqueous media. By this “click” approach, a model peptide was successfully modified with a diverse range of alkyl and aryl thiols. Furthermore, this technique was demonstrated as a valuable tool to induce spontaneous intramolecular cyclisation by preparation of an oxytocin analogue, in which the native disulfide bridge was replaced with a vinyl sulfide moiety formed by thia-Michael addition of a cysteine thiol to the allenamide handle.
ONE-BEAD-TWO-COMPOUND MACROCYCLIC LIBRARY AND METHODS OF PREPARATION AND USE
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Paragraph 0158; 0159, (2018/11/02)
A one-bead-two-compound combinatorial synthesis technique provides libraries of macrocyclic peptidomimetic compounds and compositions with use as ligands for the Ephrin type-A receptor 2 (EphA2). The one-bead-two-compound technique and libraries of macrocyclic compounds are useful as research tools in drug discovery and/or to treat or prevent a range of diseases or disorders.
A 2 - (grantane - 3 - amino) - 4 - tetrahydroindazole substituted benzamide compound and use thereof
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Paragraph 0061; 0062; 0063, (2017/08/25)
The invention belongs to the field of medicines, and particularly relates to a 2-(granatane3-amino)-4-tetrahydronaphthalene indazole-substituted benzamide compound and an application thereof. The 2-(granatane3-amino)-4-tetrahydronaphthalene indazole-substituted benzamide compound has a structure shown in a formula I in the specification, wherein R1 is a hydrogen group or an alkyl group and the like; R2 is a hydrogen group, an alkyl group or a hetero-atom-substituted alkyl group and the like. The compound is obtained by substituting the second site of 4-tetrahydronaphthalene indazole-substituted benzamide with granatane-3-amino. Growth of a plurality of tumor cells can be inhibited; the tumor cells can be induced to move towards an apoptosis channel; and the 2-(granatane3-amino)-4-tetrahydronaphthalene indazole-substituted benzamide compound has potential application value in the fields such as tumor treatment and auxiliary treatment.