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Synlett 2024; 35(16): 1872-1876
DOI: 10.1055/a-2256-5509
letter

Synthesis and Antibacterial Studies of Phenethylamine Alkaloid Natural Products Along with Their Analogues: Discolin A, B, E and Bacillimidazole B

Rashmi Ranjan Khatua
a   Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502284, India
,
Sarwat Asma Ziya Ahmad
a   Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502284, India
,
Susmita Das
b   Department of Biotechnology, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502284, India
,
Roy Anindya∗
b   Department of Biotechnology, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502284, India
,
Faiz Ahmed Khan  ∗
a   Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502284, India
› Author AffiliationsWe are grateful to the Science and Engineering Research Board (SERB), India for financial support (CRG/2022/004763).
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Abstract

The first total synthesis of phenethylamine alkaloid based natural products discolin A, B, E and bacillimidazole B is reported, which were isolated from marine sea bacteria Tenacibaculum discolor sv11 and marine sponge. Total syntheses of discolin A, B, E and bacillimidazole B are achieved in two linear steps including condensation reaction and N-alkylation reaction with an overall yield of 68%, 35%, 65%, and 32%, respectively. A total of 24 analogues are prepared with moderate to excellent yield. All the natural products and their analogues were screened for antibacterial activity. The most active compound showed an IC50 of 122.1 nM against P. aeruginosa.

Key words

discolin - marine bacteria - natural product - imidazole - antimicrobial - bacillimidazole

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2256-5509.
  • Supporting Information


Publication History

Received: 17 January 2024

Accepted: 29 January 2024

Accepted Manuscript online:
29 January 2024

Article published online:
23 February 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
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