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基于四氢哒嗪支架的扩展型氟化三肽的合成。

Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold.

作者信息

Milcent Thierry, Retailleau Pascal, Crousse Benoit, Ongeri Sandrine

机构信息

UMR 8076, BioCIS, CNRS, Université Paris-Saclay, avenue des sciences, 91400 Orsay, France.

Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, 91198 Gif-sur-Yvette, France.

出版信息

Beilstein J Org Chem. 2024 Dec 4;20:3174-3181. doi: 10.3762/bjoc.20.262. eCollection 2024.

DOI:10.3762/bjoc.20.262
PMID:39669444
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11635284/
Abstract

The synthesis of tripeptides incorporating new fluorinated heterocyclic hydrazino acids, based on the tetrahydropyridazine scaffold is described. Starting from simple fluorinated hydrazones, these non-proteinogenic cyclic β-amino acids were easily prepared by a zinc-catalyzed aza-Barbier reaction followed by an intramolecular Michael addition. Preliminary conformational studies on tripeptides including this scaffold in the central position show an extended conformation in solution (NMR) and in the solid state (X-ray).

摘要

本文描述了基于四氢哒嗪支架合成包含新型氟化杂环肼基酸的三肽。从简单的氟化腙开始，通过锌催化的氮杂 - 巴比耶反应，然后进行分子内迈克尔加成，可轻松制备这些非蛋白质ogenic环状β - 氨基酸。对在中心位置包含该支架的三肽进行的初步构象研究表明，其在溶液（核磁共振）和固态（X射线）中均呈伸展构象。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/86d7923734a0/Beilstein_J_Org_Chem-20-3174-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/6dd287f0ce66/Beilstein_J_Org_Chem-20-3174-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/65bb7d48c954/Beilstein_J_Org_Chem-20-3174-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/3012bd478dee/Beilstein_J_Org_Chem-20-3174-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/6301e7ad3bf9/Beilstein_J_Org_Chem-20-3174-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/03102f52f794/Beilstein_J_Org_Chem-20-3174-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/418f80b0ed20/Beilstein_J_Org_Chem-20-3174-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/0e2924c151b1/Beilstein_J_Org_Chem-20-3174-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/aaa1e702cefc/Beilstein_J_Org_Chem-20-3174-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/80b54a921179/Beilstein_J_Org_Chem-20-3174-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/7fad3cb37158/Beilstein_J_Org_Chem-20-3174-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/86d7923734a0/Beilstein_J_Org_Chem-20-3174-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/6dd287f0ce66/Beilstein_J_Org_Chem-20-3174-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/65bb7d48c954/Beilstein_J_Org_Chem-20-3174-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/3012bd478dee/Beilstein_J_Org_Chem-20-3174-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/6301e7ad3bf9/Beilstein_J_Org_Chem-20-3174-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/03102f52f794/Beilstein_J_Org_Chem-20-3174-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/418f80b0ed20/Beilstein_J_Org_Chem-20-3174-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/0e2924c151b1/Beilstein_J_Org_Chem-20-3174-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/aaa1e702cefc/Beilstein_J_Org_Chem-20-3174-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/80b54a921179/Beilstein_J_Org_Chem-20-3174-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/7fad3cb37158/Beilstein_J_Org_Chem-20-3174-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74f/11635284/86d7923734a0/Beilstein_J_Org_Chem-20-3174-g006.jpg

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