Synthesis, Characterization, and Antifungal Activity of Phenylpyrrole-Substituted Tetramic Acids Bearing Carbonates

Wen-Qin Xu; Min Chen; Kun-Yao Wang; Zheng-Jiao Ren; Ai-Min Lu; Chun-Long Yang

doi:10.3390/molecules21030355

Synthesis, Characterization, and Antifungal Activity of Phenylpyrrole-Substituted Tetramic Acids Bearing Carbonates

Molecules. 2016 Mar 21;21(3):355. doi: 10.3390/molecules21030355.

Authors

Wen-Qin Xu^{1

2}, Min Chen^{3

4

5}, Kun-Yao Wang^{6

7}, Zheng-Jiao Ren^{8

9}, Ai-Min Lu^{10

11}, Chun-Long Yang^{12

13

14}

Affiliations

¹ Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China. 2013111008@njau.edu.cn.
² Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. 2013111008@njau.edu.cn.
³ Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China. chenmin@njau.edu.cn.
⁴ Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. chenmin@njau.edu.cn.
⁵ Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Ministry of Agriculture, Nanjing Agricultural University, Nanjing 210095, China. chenmin@njau.edu.cn.
⁶ Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China. 2014111008@njau.edu.cn.
⁷ Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. 2014111008@njau.edu.cn.
⁸ Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China. 2013111010@njau.edu.cn.
⁹ Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. 2013111010@njau.edu.cn.
¹⁰ Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. luaimin@njau.edu.cn.
¹¹ Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Ministry of Agriculture, Nanjing Agricultural University, Nanjing 210095, China. luaimin@njau.edu.cn.
¹² Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China. ycl@njau.edu.cn.
¹³ Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. ycl@njau.edu.cn.
¹⁴ Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Ministry of Agriculture, Nanjing Agricultural University, Nanjing 210095, China. ycl@njau.edu.cn.

Abstract

For the aim of discovering new fungicide, a series of phenylpyrrole-substituted tetramic acid derivatives bearing carbonates 6a-q were designed and synthesized via 4-(2,4-dioxopyrrolidin-3-ylidene)-4-(phenylamino)butanoic acids 4a-k and the cyclized products 1',3,4,5'-tetrahydro-[2,3'-bipyrrolylidene]-2',4',5(1H)-triones 5a-k. The compounds were characterized using IR, ¹H- and (13)C-NMR spectroscopy, mass spectrometry (EI-MS), and elemental analysis. The structure of 6b was confirmed by X-ray diffraction crystallography. The title compounds 6a-q were bioassayed in vitro against the phytopathogenic fungi Fusarium graminearum, Botrytis cinerea and Rhizoctonia solani at a concentration of 100 μg/mL, respectively. Most compounds displayed good inhibitory activity.

Keywords: antifungal activity; carbonate; crystal structure; pyrrole; synthesis; tetramic acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antifungal Agents / chemical synthesis*
Antifungal Agents / chemistry
Antifungal Agents / pharmacology
Carbonates / chemical synthesis
Carbonates / chemistry
Crystallography, X-Ray
Fungicides, Industrial / chemical synthesis*
Fungicides, Industrial / chemistry
Fungicides, Industrial / pharmacology
Fusarium / drug effects
Molecular Structure
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Pyrroles / pharmacology
Pyrrolidinones / chemical synthesis
Pyrrolidinones / chemistry
Structure-Activity Relationship
X-Ray Diffraction

Substances

Antifungal Agents
Carbonates
Fungicides, Industrial
Pyrroles
Pyrrolidinones
tetramic acid