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

Rashmi Ranjan Khatua; Sarwat Asma Ziya Ahmad; Susmita Das; Roy Anindya; Faiz Ahmed Khan

doi:10.1055/a-2256-5509

Synlett, Table of Contents

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

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

Rashmi Ranjan Khatua

^aDepartment of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502284, India

,

Sarwat Asma Ziya Ahmad

^aDepartment of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502284, India

,

Susmita Das

^bDepartment of Biotechnology, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502284, India

,

Roy Anindya∗

^bDepartment of Biotechnology, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502284, India

,

Faiz Ahmed Khan ∗

^aDepartment of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502284, India

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Abstract

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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

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