title: Synthesis and biological evaluations of a series of thaxtomin analogues.
abstract: Thaxtomins are a unique family of phytotoxins with unique 4-nitroindole and diketopiperazine fragments possessing potential herbicidal activities. This work presents the total synthesis of natural product thaxtomin C and its analogues. The extensive structure-activity relationship study screens four effective compounds, including thaxtomin A and thaxtomin C. It is indicated that 4-nitro indole fragment is essential for phytotoxicity, while benzyl and m-hydroxybenzyl substituents on the diketopiperazine ring are favorable for the efficacy. The N-methylations on indole and diketopiperazine show weak influence on the herbicidal activities. The four selected compounds show effective herbicidal activities against Brassica campestris, Amaranthus retroflexus, and Abutilon theophrasti, which are comparable or better than dichlobenil, even at a dosage of 187.5 g ha(-1). Moreover, these four compounds show good crop-selective properties to different crops and exhibit moderate protoporphyrinogen oxidase (PPO) enzyme inhibition. The antifungal results indicate that thaxtomin C displays inhibition to a wide range of fungi.
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Hongbo
authors: H
authors: Zhang
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Qingpeng
authors: Q
authors: Wang
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Xin
authors: X
authors: Ning
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Hang
authors: H
authors: Hang
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Jing
authors: J
authors: Ma
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Xiande
authors: X
authors: Yang
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Xiaolin
authors: X
authors: Lu
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Jiabao
authors: J
authors: Zhang
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Yonghong
authors: Y
authors: Li
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Congwei
authors: C
authors: Niu
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Haoran
authors: H
authors: Song
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Xin
authors: X
authors: Wang
authors: ‡College of Pharmacy, §State Key Laboratory of Elemento-organic Chemistry, and ∥Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
authors: Peng George
authors: PG
authors: Wang
mesh_terms: D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D057685:Plant Weeds / Q000187:drug effects*; D013329:Structure-Activity Relationship; D058728:Weed Control
chemical_list: D006540:Herbicides; D007211:Indoles; D010879:Piperazines; C587641:thaxtomin C; C406691:thaxtomine A
keywords: antifungal; herbicide; structure−activity relationship; thaxtomin; weed control