Synthesis and biological evaluation of 2-phenyl-4-aminoquinolines as potential antifungal agents
- PDF / 1,087,588 Bytes
- 11 Pages / 595.276 x 790.866 pts Page_size
- 0 Downloads / 157 Views
ORIGINAL ARTICLE
Synthesis and biological evaluation of 2‑phenyl‑4‑aminoquinolines as potential antifungal agents Rui Yang1 · Wenhao Du1 · Huan Yuan1 · Tianhong Qin1 · Renxiao He1 · Yanni Ma2 · Haiying Du3 Received: 13 August 2019 / Accepted: 2 November 2019 © Springer Nature Switzerland AG 2019
Abstract A series of 2-phenyl-4-aminoquinolines were designed, synthesized and evaluated for their antifungal activities against three phytopathogenic fungi in vitro. All of the target compounds were fully elucidated by 1H NMR, 13C NMR and HRMS spectra. The results indicated that most of the target compounds demonstrated significant activities against the tested fungi. Among them, compound 6e exhibited more promising inhibitory activities against C. lunata (EC50 = 13.3 μg/mL), P. grisea (EC50 = 14.4 μg/mL) and A. alternate (EC50 = 15.6 μg/mL), superior to azoxystrobin, a commercial agricultural fungicide. The structure–activity relationship (SAR) revealed that the aniline moiety at position 4 of the quinoline scaffold played a key role in the potency of a compound. And the substitution positions of the aniline moiety significantly influenced the activities. These encouraging results yielded a variety of 2-phenylquinolines bearing an aniline moiety acting as promising antifungal agents. Graphic abstract
Keywords 4-Aminoquinoline · Phytopathogenic fungi · Antifungal activity · Structure–activity relationship
Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11030-019-10012-1) contains supplementary material, which is available to authorized users. * Rui Yang [email protected] * Haiying Du [email protected] 1
College of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, People’s Republic of China
2
Key Laboratory of Natural Products, Henan Academy of Sciences, Zhengzhou 450002, People’s Republic of China
3
College of Environment, Chengdu University of Technology, Chengdu 610059, People’s Republic of China
Phytopathogenic fungi have long been known as a severe threat to plant species. They cause serious economic loss to global agricultural production and even lead to food safety problem due to the mycotoxins produced by some kinds of fungi [1, 2]. Although some agricultural antifungal agents are currently available on the market, there is still an extremely urgent demand for new fungicides on account of some inevitable defects of the traditional antifungal agents, including toxicity to non-target organisms, high residue, growing resistance and so on [3, 4]. Quinoline and its derivatives, a class of important bioactive natural products, usually serve as a core fragment in a variety of active molecules, which exhibit extensive
13
Vol.:(0123456789)
biological activities [5–12], including antifungal property [13–16]. Over the past decades, some agricultural chemicals containing a quinoline moiety have been put on the market, such as the fungicides quinoxyfen and tebufloquin, the insecticide
Data Loading...
