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5-酰基-5-苯基-1,5-二氢-4-吡唑-4-酮对多胺和氨基糖苷的高选择性酰化作用

Highly selective acylation of polyamines and aminoglycosides by 5-acyl-5-phenyl-1,5-dihydro-4-pyrazol-4-ones.

作者信息

Marichev Kostiantyn O, Garcia Estevan C, Bhowmick Kartick C, Wherritt Daniel J, Arman Hadi, Doyle Michael P

机构信息

Department of Chemistry , The University of Texas at San Antonio , San Antonio , Texas 78249 , USA . Email:

出版信息

Chem Sci. 2017 Oct 1;8(10):7152-7159. doi: 10.1039/c7sc03184j. Epub 2017 Aug 30.

DOI:10.1039/c7sc03184j
PMID:29081946
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5635523/
Abstract

5-Acyl-5-phenyl-1,5-dihydro-4-pyrazol-4-ones, accessible from arylpropargyl phenyldiazoacetates, are highly selective acyl transfer reagents for di- and polyamines, as well as aminoalcohols and aminothiols. As reagents with a carbon-based leaving group, they have been applied for benzoyl transfer with a broad selection of substrates containing aliphatic amino in combination with other competing nucleophilic functional groups. The substrate scope and levels of selectivity for direct benzoyl transfer exceed those of known benzoylating reagents. With exceptional selectivity for acylation between primary amines bound to primary and secondary carbons, these new reagents have been used in direct site-selective monobenzoylation of aminoglycoside antibiotics.

摘要

5-酰基-5-苯基-1,5-二氢-4-吡唑-4-酮可由芳基炔丙基苯基重氮乙酸酯制得，是用于二胺和多胺以及氨基醇和氨基硫醇的高选择性酰基转移试剂。作为具有碳基离去基团的试剂，它们已被用于与多种含有脂肪族氨基并带有其他竞争性亲核官能团的底物进行苯甲酰基转移反应。直接苯甲酰基转移的底物范围和选择性水平超过了已知的苯甲酰化试剂。这些新试剂对连接在伯碳和仲碳上的伯胺之间的酰化具有出色的选择性，已用于氨基糖苷类抗生素的直接位点选择性单苯甲酰化反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/e9b763ce1d6e/c7sc03184j-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/db480a185a62/c7sc03184j-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/b0303ec0fb74/c7sc03184j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/27ab6a395c7c/c7sc03184j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/d4d10b628a82/c7sc03184j-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/8e1f665f847a/c7sc03184j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/e9b763ce1d6e/c7sc03184j-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/db480a185a62/c7sc03184j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/cb9acfa33037/c7sc03184j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/b0303ec0fb74/c7sc03184j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/27ab6a395c7c/c7sc03184j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/d4d10b628a82/c7sc03184j-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/8e1f665f847a/c7sc03184j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb89/5635523/e9b763ce1d6e/c7sc03184j-f4.jpg

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