Biomaterial Database

Synthesis and biological evaluations of a series of thaxtomin analogues. 2015

Hongbo Zhang, and Qingpeng Wang, and Xin Ning, and Hang Hang, and Jing Ma, and Xiande Yang, and Xiaolin Lu, and Jiabao Zhang, and Yonghong Li, and Congwei Niu, and Haoran Song, and Xin Wang, and Peng George Wang

‡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.

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.

UI	MeSH Term	Description	Entries
D007211	Indoles	Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D010879	Piperazines	Compounds that are derived from PIPERAZINE.
D006540	Herbicides	Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.	Algaecide,Algicide,Herbicide,Algaecides,Algicides
D013329	Structure-Activity Relationship	The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.	Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular
D057685	Plant Weeds	A plant growing in a location where it is not wanted, often competing with cultivated plants.	Annual Weeds,Invasive Weeds,Noxious Weeds,Parasitic Weeds,Perennial Weeds,Annual Weed,Invasive Weed,Noxious Weed,Parasitic Weed,Perennial Weed,Plant Weed,Weed, Annual,Weed, Invasive,Weed, Noxious,Weed, Parasitic,Weed, Perennial,Weed, Plant,Weeds, Annual,Weeds, Invasive,Weeds, Noxious,Weeds, Parasitic,Weeds, Perennial,Weeds, Plant
D058728	Weed Control	The prevention of growth and or spread of unwanted plants.	Control, Weed