Kinetic studies of conjugate addition of amines to allenic and acrylic esters and their correlation with antibacterial activities against Staphylococcus aureus

Kinetic studies of conjugate addition of amines to allenic and acrylic esters and their... Kinetic reactivities of various allenic and acrylic esters in conjugate addition reactions with various amines were inves- tigated. Competition experiments showed that amines reacted selectively with allenic esters, which was also confirmed by quantitative determination of the rate constants. The antibacterial activity against Staphylococcus aureus of allenic and acrylic ester derivatives were also determined. Allenic esters were found to exhibit a higher antibacterial activity than its acrylic counterparts. A correlation between the kinetic property and the antibacterial activity suggested that a conjugate addition may involve in the antibacterial mechanism of these unsaturated esters. Graphical abstract OR OR R= Ethyl, Ph, p-ClPh, p-OHPh, p-NO Ph - faster conjugate addition with amines - higher antibacterial activity Keywords Allenes  Alkenes  Kinetics  Antibiotics Introduction probes for biological studies [5–8] as well as the design of potent therapeutics [9–13]. Therefore, it is crucial to A conjugate addition is among the most important reac- investigate factors that play roles in efficiency of the tions in chemistry. The reaction has been used not only in reaction. One important factor is the nature of the elec- organic synthesis [1–4], but also in the design of chemical trophile in the reaction. Unsaturated esters such as http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Monatshefte für Chemie - Chemical Monthly Springer Journals

Kinetic studies of conjugate addition of amines to allenic and acrylic esters and their correlation with antibacterial activities against Staphylococcus aureus

Loading next page...
 
/lp/springer_journal/kinetic-studies-of-conjugate-addition-of-amines-to-allenic-and-acrylic-lwa0lz6NvG
Publisher
Springer Journals
Copyright
Copyright © 2018 by Springer-Verlag GmbH Austria, part of Springer Nature
Subject
Chemistry; Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry; Analytical Chemistry; Physical Chemistry; Theoretical and Computational Chemistry
ISSN
0026-9247
eISSN
1434-4475
D.O.I.
10.1007/s00706-018-2175-1
Publisher site
See Article on Publisher Site

Abstract

Kinetic reactivities of various allenic and acrylic esters in conjugate addition reactions with various amines were inves- tigated. Competition experiments showed that amines reacted selectively with allenic esters, which was also confirmed by quantitative determination of the rate constants. The antibacterial activity against Staphylococcus aureus of allenic and acrylic ester derivatives were also determined. Allenic esters were found to exhibit a higher antibacterial activity than its acrylic counterparts. A correlation between the kinetic property and the antibacterial activity suggested that a conjugate addition may involve in the antibacterial mechanism of these unsaturated esters. Graphical abstract OR OR R= Ethyl, Ph, p-ClPh, p-OHPh, p-NO Ph - faster conjugate addition with amines - higher antibacterial activity Keywords Allenes  Alkenes  Kinetics  Antibiotics Introduction probes for biological studies [5–8] as well as the design of potent therapeutics [9–13]. Therefore, it is crucial to A conjugate addition is among the most important reac- investigate factors that play roles in efficiency of the tions in chemistry. The reaction has been used not only in reaction. One important factor is the nature of the elec- organic synthesis [1–4], but also in the design of chemical trophile in the reaction. Unsaturated esters such as

Journal

Monatshefte für Chemie - Chemical MonthlySpringer Journals

Published: Feb 20, 2018

References

You’re reading a free preview. Subscribe to read the entire article.


DeepDyve is your
personal research library

It’s your single place to instantly
discover and read the research
that matters to you.

Enjoy affordable access to
over 18 million articles from more than
15,000 peer-reviewed journals.

All for just $49/month

Explore the DeepDyve Library

Search

Query the DeepDyve database, plus search all of PubMed and Google Scholar seamlessly

Organize

Save any article or search result from DeepDyve, PubMed, and Google Scholar... all in one place.

Access

Get unlimited, online access to over 18 million full-text articles from more than 15,000 scientific journals.

Your journals are on DeepDyve

Read from thousands of the leading scholarly journals from SpringerNature, Elsevier, Wiley-Blackwell, Oxford University Press and more.

All the latest content is available, no embargo periods.

See the journals in your area

DeepDyve

Freelancer

DeepDyve

Pro

Price

FREE

$49/month
$360/year

Save searches from
Google Scholar,
PubMed

Create lists to
organize your research

Export lists, citations

Read DeepDyve articles

Abstract access only

Unlimited access to over
18 million full-text articles

Print

20 pages / month

PDF Discount

20% off