Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 23, 2014
Previous Article Next Article

Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation

Author affiliations

Abstract

Ianthelliformisamines A–C are a novel class of bromotyrosine-derived antibacterial agents isolated recently from the marine sponge Suberea ianthelliformis. We have synthesized ianthelliformisamines A–C straightforwardly by the condensation of (E)-3-(3,5-dibromo-4-methoxyphenyl)acrylic acid and the corresponding Boc-protected polyamine followed by Boc-deprotection with TFA. Further, using this reaction protocol, a library of their analogues (39 analogues) has been synthesized by employing 3-phenylacrylic acid derivatives and Boc-protected polyamine chains through various combinations of these two fragments differing in phenyl ring substitution, double bond geometry or chain length of the central spacer of the polyamine chain (shown in red color). All the synthesized compounds (ianthelliformisamines A–C and their analogues) were screened for antibacterial activity against both Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) strains. All synthetic analogues of ianthelliformisamine A showed bacterial growth inhibition against both strains (Escherichia coli and Staphylococcus aureus), having MIC values in the range of 117.8–0.10 μM, while none of the synthetic analogues of ianthelliformisamine C as well as the parent compound showed any detectable antibacterial activity. Interestingly, some of the synthetic analogues of ianthelliformisamines A and B exerted a bactericidal effect against both E. coli and S. aureus strains, decreasing viable bacterial count by 99% at concentrations as low as 2 × MIC.

Graphical abstract: Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 20 Dec 2013, accepted on 24 Feb 2014 and first published on 24 Feb 2014


Article type: Paper
DOI: 10.1039/C3OB42537A
Citation: Org. Biomol. Chem., 2014,12, 3847-3865
  •   Request permissions

    Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation

    F. A. Khan, S. Ahmad, N. Kodipelli, G. Shivange and R. Anindya, Org. Biomol. Chem., 2014, 12, 3847
    DOI: 10.1039/C3OB42537A

Search articles by author