Work

Concise Synthesis of Pseudane IX, Its N-Oxide, and Novel Carboxamide Analogs with Antibacterial Activity

Year: 2024

Type: article

Abstract: A four-step synthesis of the natural product pseudane IX, starting from 3-oxododecanoic acid phenylamide and including only one chromatographic purification, was accomplished with an overall yield of 52%. The same synthetic sequence, but with a controlled partial reduction of a nitro group in the penultimate intermediate, led to the N-oxide of pseudane IX (NQNO). A shortened three-step variation of the synthesis allowed for the preparation of novel carboxamide analogs of the natural product. An agar diffusion assay against six different bacterial strains revealed significant antibacterial activity of the novel analogs against S. aureus at a concentration of 100 µg/mL. One of the novel compounds showed a remarkably broad spectrum of antibacterial activity, comparable to that of the positive control NQNO.

Source: Molecules

DOI: 10.3390/molecules29153676

Authors: Plamen Angelov, Yordanka Mollova-Sapundzhieva, Francisco Alonso, Bogdan Goranov, Paraskev Nedialkov, Denitsa Bachvarova

Institutions: Plovdiv University, University of Alicante, University of Food Technologies, Medical University of Sofia

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,069

Funders: Bulgarian National Science Fund, Generalitat Valenciana