No Cover Image

Journal article 509 views 23 downloads

Synthesis and In Vitro Antimicrobial SAR of Benzyl and Phenyl Guanidine and Aminoguanidine Hydrazone Derivatives

Wolfgang Dohle, Xiangdong Su, Yamni Nigam, Ed Dudley, Barry V. L. Potter Orcid Logo

Molecules, Volume: 28, Issue: 1, Start page: 5

Swansea University Authors: Yamni Nigam, Ed Dudley

  • 62274_VoR.pdf

    PDF | Version of Record

    © 2022 by the authors. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license

    Download (5.28MB)

Check full text

DOI (Published version): 10.3390/molecules28010005

Abstract

A series of benzyl, phenyl guanidine, and aminoguandine hydrazone derivatives was designed and in vitro antibacterial activities against two different bacterial strains (Staphylococcus aureus and Escherichia coli) were determined. Several compounds showed potent inhibitory activity against the bacte...

Full description

Published in: Molecules
ISSN: 1420-3049
Published: MDPI AG 2022
Online Access: Check full text

URI: https://cronfa.swan.ac.uk/Record/cronfa62274
Tags: Add Tag
No Tags, Be the first to tag this record!
first_indexed 2023-02-01T15:30:56Z
last_indexed 2023-02-02T04:16:50Z
id cronfa62274
recordtype SURis
fullrecord <?xml version="1.0"?><rfc1807><datestamp>2023-02-01T15:33:25.2789356</datestamp><bib-version>v2</bib-version><id>62274</id><entry>2023-01-06</entry><title>Synthesis and In Vitro Antimicrobial SAR of Benzyl and Phenyl Guanidine and Aminoguanidine Hydrazone Derivatives</title><swanseaauthors><author><sid>16d566efd3e2b483b5f08651f5515efb</sid><firstname>Yamni</firstname><surname>Nigam</surname><name>Yamni Nigam</name><active>true</active><ethesisStudent>false</ethesisStudent></author><author><sid>c7d05f992a817cd3b9a5f946bd909b71</sid><firstname>Ed</firstname><surname>Dudley</surname><name>Ed Dudley</name><active>true</active><ethesisStudent>false</ethesisStudent></author></swanseaauthors><date>2023-01-06</date><deptcode>HEAL</deptcode><abstract>A series of benzyl, phenyl guanidine, and aminoguandine hydrazone derivatives was designed and in vitro antibacterial activities against two different bacterial strains (Staphylococcus aureus and Escherichia coli) were determined. Several compounds showed potent inhibitory activity against the bacterial strains evaluated, with minimal inhibitory concentration (MIC) values in the low &#xB5;g/mL range. Of all guanidine derivatives, 3-[2-chloro-3-(trifluoromethyl)]-benzyloxy derivative 9m showed the best potency with MICs of 0.5 &#xB5;g/mL (S. aureus) and 1 &#xB5;g/mL (E. coli), respectively. Several aminoguanidine hydrazone derivatives also showed good overall activity. Compounds 10a, 10j, and 10r&#x2013;s displayed MICs of 4 &#xB5;g/mL against both S. aureus and E. coli. In the aminoguanidine hydrazone series, 3-(4-trifluoromethyl)-benzyloxy derivative 10d showed the best potency against S. aureus (MIC 1 &#xB5;g/mL) but was far less active against E. coli (MIC 16 &#xB5;g/mL). Compound 9m and the para-substituted derivative 9v also showed promising results against two strains of methicillin-resistant Staphylococcus aureus (MRSA). These results provide new and potent structural leads for further antibiotic optimisation strategies.</abstract><type>Journal Article</type><journal>Molecules</journal><volume>28</volume><journalNumber>1</journalNumber><paginationStart>5</paginationStart><paginationEnd/><publisher>MDPI AG</publisher><placeOfPublication/><isbnPrint/><isbnElectronic/><issnPrint/><issnElectronic>1420-3049</issnElectronic><keywords>benzyl guanidine; benzyl aminoguanidine hydrazone; guanylation; antimicrobial activity; methicillin-resistant Staphylococcus aureus (MRSA)</keywords><publishedDay>20</publishedDay><publishedMonth>12</publishedMonth><publishedYear>2022</publishedYear><publishedDate>2022-12-20</publishedDate><doi>10.3390/molecules28010005</doi><url/><notes/><college>COLLEGE NANME</college><department>Healthcare Science</department><CollegeCode>COLLEGE CODE</CollegeCode><DepartmentCode>HEAL</DepartmentCode><institution>Swansea University</institution><apcterm/><funders>We acknowledge provision of financial support from Research &amp; Innovation, Swansea University, UK.</funders><projectreference/><lastEdited>2023-02-01T15:33:25.2789356</lastEdited><Created>2023-01-06T15:18:40.6896177</Created><path><level id="1">Faculty of Medicine, Health and Life Sciences</level><level id="2">School of Health and Social Care - Healthcare Science</level></path><authors><author><firstname>Wolfgang</firstname><surname>Dohle</surname><order>1</order></author><author><firstname>Xiangdong</firstname><surname>Su</surname><order>2</order></author><author><firstname>Yamni</firstname><surname>Nigam</surname><order>3</order></author><author><firstname>Ed</firstname><surname>Dudley</surname><order>4</order></author><author><firstname>Barry V. L.</firstname><surname>Potter</surname><orcid>0000-0003-3255-9135</orcid><order>5</order></author></authors><documents><document><filename>62274__26447__bf9207a0e21c46d282547a6f187b51fb.pdf</filename><originalFilename>62274_VoR.pdf</originalFilename><uploaded>2023-02-01T15:31:44.3113240</uploaded><type>Output</type><contentLength>5537961</contentLength><contentType>application/pdf</contentType><version>Version of Record</version><cronfaStatus>true</cronfaStatus><documentNotes>&#xA9; 2022 by the authors. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license</documentNotes><copyrightCorrect>true</copyrightCorrect><language>eng</language><licence>https://creativecommons.org/licenses/by/4.0/</licence></document></documents><OutputDurs/></rfc1807>
spelling 2023-02-01T15:33:25.2789356 v2 62274 2023-01-06 Synthesis and In Vitro Antimicrobial SAR of Benzyl and Phenyl Guanidine and Aminoguanidine Hydrazone Derivatives 16d566efd3e2b483b5f08651f5515efb Yamni Nigam Yamni Nigam true false c7d05f992a817cd3b9a5f946bd909b71 Ed Dudley Ed Dudley true false 2023-01-06 HEAL A series of benzyl, phenyl guanidine, and aminoguandine hydrazone derivatives was designed and in vitro antibacterial activities against two different bacterial strains (Staphylococcus aureus and Escherichia coli) were determined. Several compounds showed potent inhibitory activity against the bacterial strains evaluated, with minimal inhibitory concentration (MIC) values in the low µg/mL range. Of all guanidine derivatives, 3-[2-chloro-3-(trifluoromethyl)]-benzyloxy derivative 9m showed the best potency with MICs of 0.5 µg/mL (S. aureus) and 1 µg/mL (E. coli), respectively. Several aminoguanidine hydrazone derivatives also showed good overall activity. Compounds 10a, 10j, and 10r–s displayed MICs of 4 µg/mL against both S. aureus and E. coli. In the aminoguanidine hydrazone series, 3-(4-trifluoromethyl)-benzyloxy derivative 10d showed the best potency against S. aureus (MIC 1 µg/mL) but was far less active against E. coli (MIC 16 µg/mL). Compound 9m and the para-substituted derivative 9v also showed promising results against two strains of methicillin-resistant Staphylococcus aureus (MRSA). These results provide new and potent structural leads for further antibiotic optimisation strategies. Journal Article Molecules 28 1 5 MDPI AG 1420-3049 benzyl guanidine; benzyl aminoguanidine hydrazone; guanylation; antimicrobial activity; methicillin-resistant Staphylococcus aureus (MRSA) 20 12 2022 2022-12-20 10.3390/molecules28010005 COLLEGE NANME Healthcare Science COLLEGE CODE HEAL Swansea University We acknowledge provision of financial support from Research & Innovation, Swansea University, UK. 2023-02-01T15:33:25.2789356 2023-01-06T15:18:40.6896177 Faculty of Medicine, Health and Life Sciences School of Health and Social Care - Healthcare Science Wolfgang Dohle 1 Xiangdong Su 2 Yamni Nigam 3 Ed Dudley 4 Barry V. L. Potter 0000-0003-3255-9135 5 62274__26447__bf9207a0e21c46d282547a6f187b51fb.pdf 62274_VoR.pdf 2023-02-01T15:31:44.3113240 Output 5537961 application/pdf Version of Record true © 2022 by the authors. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license true eng https://creativecommons.org/licenses/by/4.0/
title Synthesis and In Vitro Antimicrobial SAR of Benzyl and Phenyl Guanidine and Aminoguanidine Hydrazone Derivatives
spellingShingle Synthesis and In Vitro Antimicrobial SAR of Benzyl and Phenyl Guanidine and Aminoguanidine Hydrazone Derivatives
Yamni Nigam
Ed Dudley
title_short Synthesis and In Vitro Antimicrobial SAR of Benzyl and Phenyl Guanidine and Aminoguanidine Hydrazone Derivatives
title_full Synthesis and In Vitro Antimicrobial SAR of Benzyl and Phenyl Guanidine and Aminoguanidine Hydrazone Derivatives
title_fullStr Synthesis and In Vitro Antimicrobial SAR of Benzyl and Phenyl Guanidine and Aminoguanidine Hydrazone Derivatives
title_full_unstemmed Synthesis and In Vitro Antimicrobial SAR of Benzyl and Phenyl Guanidine and Aminoguanidine Hydrazone Derivatives
title_sort Synthesis and In Vitro Antimicrobial SAR of Benzyl and Phenyl Guanidine and Aminoguanidine Hydrazone Derivatives
author_id_str_mv 16d566efd3e2b483b5f08651f5515efb
c7d05f992a817cd3b9a5f946bd909b71
author_id_fullname_str_mv 16d566efd3e2b483b5f08651f5515efb_***_Yamni Nigam
c7d05f992a817cd3b9a5f946bd909b71_***_Ed Dudley
author Yamni Nigam
Ed Dudley
author2 Wolfgang Dohle
Xiangdong Su
Yamni Nigam
Ed Dudley
Barry V. L. Potter
format Journal article
container_title Molecules
container_volume 28
container_issue 1
container_start_page 5
publishDate 2022
institution Swansea University
issn 1420-3049
doi_str_mv 10.3390/molecules28010005
publisher MDPI AG
college_str Faculty of Medicine, Health and Life Sciences
hierarchytype
hierarchy_top_id facultyofmedicinehealthandlifesciences
hierarchy_top_title Faculty of Medicine, Health and Life Sciences
hierarchy_parent_id facultyofmedicinehealthandlifesciences
hierarchy_parent_title Faculty of Medicine, Health and Life Sciences
department_str School of Health and Social Care - Healthcare Science{{{_:::_}}}Faculty of Medicine, Health and Life Sciences{{{_:::_}}}School of Health and Social Care - Healthcare Science
document_store_str 1
active_str 0
description A series of benzyl, phenyl guanidine, and aminoguandine hydrazone derivatives was designed and in vitro antibacterial activities against two different bacterial strains (Staphylococcus aureus and Escherichia coli) were determined. Several compounds showed potent inhibitory activity against the bacterial strains evaluated, with minimal inhibitory concentration (MIC) values in the low µg/mL range. Of all guanidine derivatives, 3-[2-chloro-3-(trifluoromethyl)]-benzyloxy derivative 9m showed the best potency with MICs of 0.5 µg/mL (S. aureus) and 1 µg/mL (E. coli), respectively. Several aminoguanidine hydrazone derivatives also showed good overall activity. Compounds 10a, 10j, and 10r–s displayed MICs of 4 µg/mL against both S. aureus and E. coli. In the aminoguanidine hydrazone series, 3-(4-trifluoromethyl)-benzyloxy derivative 10d showed the best potency against S. aureus (MIC 1 µg/mL) but was far less active against E. coli (MIC 16 µg/mL). Compound 9m and the para-substituted derivative 9v also showed promising results against two strains of methicillin-resistant Staphylococcus aureus (MRSA). These results provide new and potent structural leads for further antibiotic optimisation strategies.
published_date 2022-12-20T04:21:45Z
_version_ 1763754435830349824
score 11.016235

Similar Items