Synthesis and antibacterial activities of marine natural product ianthelliformisamines and subereamine synthetic analogues

Khadake, Shivaji Narayan and Karamathulla, Shaik and Jena, Tapan Kumar and Monisha, Mohan and Tuti, Nikhil Kumar and Khan, Faiz Ahmed and Anindya, Roy (2021) Synthesis and antibacterial activities of marine natural product ianthelliformisamines and subereamine synthetic analogues. Bioorganic & Medicinal Chemistry Letters, 39. p. 127883. ISSN 0960894X

Full text not available from this repository. (Request a copy)


Marine sponges of the genus Suberea produce variety of brominated tyrosine alkaloids which display diverse range of biological activities including antiproliferative, antimicrobial and antimalarial activities. In continuation of our search for biologically active marine natural products for antibacterial compounds, we report here the synthesis and evaluation of biological activity of panel of ianthelliformisamines and subereamine analogues using the literature known acid-amine coupling reaction. Several derivatives of Ianthelliformisamine were achieved by the coupling of Boc-protected polyamine chain with brominated aromatic acrylic acid derivatives by varying the bromine substituents on aromatic acid derivatives, amine spacer as well as geometry of the double bond, and then Boc-deprotection using TFA. Similarly, subereamine analogues were also synthesized employing coupling reaction between various brominated phenyl acrylic acids with commercially available chiral amino ester derivatives followed by ester hydrolysis. We screened these synthetic analogues for antibacterial activity against both Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) strains. One of the compound 7c showed bactericidal activity against Staphylococcus aureus with an IC50 value of 3.8 μM (MIC = 25 μM).

[error in script]
IITH Creators:
IITH CreatorsORCiD
Khadake, Shivaji NarayanUNSPECIFIED
Karamathulla, ShaikUNSPECIFIED
Jena, Tapan KumarUNSPECIFIED
Tuti, Nikhil KumarUNSPECIFIED
Item Type: Article
Uncontrolled Keywords: Bromotyrosine; Ianthelliformisamines; Marine sponges; Suberea; Subereamines
Subjects: Social sciences
Divisions: Department of Biotechnology
Depositing User: . LibTrainee 2021
Date Deposited: 08 Jul 2021 05:50
Last Modified: 08 Jul 2021 05:50
Publisher URL:
OA policy:
Related URLs:

Actions (login required)

View Item View Item
Statistics for RAIITH ePrint 8172 Statistics for this ePrint Item