Structural analogues of quinoline alkaloids: Straightforward route to [1, 3]dioxolo[4, 5‐c]quinolines with antibacterial properties. (21st January 2020)

• Record Type: Journal Article
• Authors: Horák, Radim; Kořistek, Kamil; Šamšulová, Veronika; Slaninová, Ludmila; Grepl, Martin; Kvapil, Lubomír; Funk, Petr; Hradil, Pavel; Soural, Miroslav
• Is Part Of: Journal of heterocyclic chemistry. Volume 57:Number 4(2020)
• Page Start: 1605
• Page End: 1615
• Publication Date: 2020-01-21
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.3886
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract: Compounds bearing [1, 3]dioxolo‐quinoline scaffolds have been found in quinoline‐based natural products; the only exception is the [1, 3]dioxolo[4, 5‐ c ]quinoline moiety with a rare occurrence in both natural and synthetic derivatives. In this article, we report the preparation of diversely substituted and functionalized [1, 3]dioxolo[4, 5‐ c ]quinolines using [1, 3]dioxolo[4, 5‐c]quinoline‐4‐carbaldehyde (DQC) as the common intermediate. DQC was synthesized on a large scale from anthranilic acid and chloroacetone as the starting materials, with the rearrangement of acetonyl‐anthranilate as the key step. The developed method allows for the simple preparation of [1, 3]dioxolo[4, 5‐ c ]quinolines with various C2 substituents on the quinoline scaffold. Additionally, the synthetic route was successfully applied to the preparation of 3‐hydroxyquinoline‐4(1 H )‐ones. The target compounds were tested against representative Gram‐positive/negative bacteria, and two derivatives exhibited submicromolar minimum inhibitory concentrations against Micrococcus luteus . Abstract :