Design of cinnamaldehyde amino acid Schiff base compounds based on the quantitative structure-activity relationship

Hui Wang; Mingyue Jiang; Shujun Li; Chung-Yun Hse; Chunde Jin; Fangli Sun; Zhuo Li

doi:10.1098/rsos.170516

Design of cinnamaldehyde amino acid Schiff base compounds based on the quantitative structure-activity relationship

R Soc Open Sci. 2017 Sep 6;4(9):170516. doi: 10.1098/rsos.170516. eCollection 2017 Sep.

Authors

Hui Wang^{1

2}, Mingyue Jiang¹, Shujun Li¹, Chung-Yun Hse², Chunde Jin³, Fangli Sun³, Zhuo Li¹

Affiliations

¹ Key Laboratory of Bio-Based Material Science and Technology of the Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China.
² Southern Research Station, USDA Forest Service, Pineville, LA 71360, USA.
³ Key Laboratory of Wood Science and Technology, Zhejiang Agriculture and Forestry University, Zhejiang 311300, People's Republic of China.

Abstract

Cinnamaldehyde amino acid Schiff base (CAAS) is a new class of safe, bioactive compounds which could be developed as potential antifungal agents for fungal infections. To design new cinnamaldehyde amino acid Schiff base compounds with high bioactivity, the quantitative structure-activity relationships (QSARs) for CAAS compounds against Aspergillus niger (A. niger) and Penicillium citrinum (P. citrinum) were analysed. The QSAR models (R² = 0.9346 for A. niger, R² = 0.9590 for P. citrinum,) were constructed and validated. The models indicated that the molecular polarity and the Max atomic orbital electronic population had a significant effect on antifungal activity. Based on the best QSAR models, two new compounds were designed and synthesized. Antifungal activity tests proved that both of them have great bioactivity against the selected fungi.

Keywords: Schiff base; antifungal activity; cinnamaldehyde; quantitative structure–activity relationship.

Associated data

figshare/10.6084/m9.figshare.c.3860692