scholarly journals Design and synthesis of novel n-butyphthalide derivatives as promising botanical fungicides

2020 ◽  
Vol 0 (0) ◽  
Author(s):  
Zhongfu Luo ◽  
Yu Deng ◽  
Bilan Luo ◽  
Yong Li ◽  
Qing Lan ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Suzuki Reaction ◽  
Phytopathogenic Fungi ◽  
Inhibition Activity ◽  
Mycelium Growth ◽  
Design And Synthesis ◽  
Structure Activity ◽  
Mycelium Growth Rate ◽  
Rate Method

AbstractIn order to obtain novel botanical fungicides, three series of novel 6-substituted n-butyphthalide derivatives have been designed and synthesized via nucleophilic addition, reduction, nitrification, amination, sulfonation, Sandmeyer and Suzuki reaction. The mycelium growth rate method was used to evaluate the inhibition activity against eight phytopathogenic fungi in vitro. Preliminary bioassay tests showed that compounds 6f, 6n, 6p, 6r and 7a exhibited better activity for some fungi at 50 μg/mL than the positive drug hymexazol and lead compound n-butyphthalide (NBP). The preliminary structure–activity relationships indicated that the antifungal activity is significantly affected by the substituents on the benzene ring.

Synthesis and antifungal activities of 3-substituted phthalide derivatives

2019 ◽  
Vol 74 (11-12) ◽  
pp. 811-818 ◽  
Author(s):  
Lingling Fan ◽  
Bilan Luo ◽  
Zhongfu Luo ◽  
Li Zhang ◽  
Judi Fan ◽  
...  
Keyword(s):  
Growth Rate ◽  
Bioactive Compounds ◽  
Mycelial Growth ◽  
Phytopathogenic Fungi ◽  
Antifungal Activities ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Mycelial Growth Rate ◽  
Rate Method

AbstractIn order to obtain novel bioactive compounds with significant antifungal activities, two series of 3-substituted phthalide derivatives were designed and synthesized via reduction, bromine substitution, and etherification. In addition, the antifungal activities of all target compounds against nine phytopathogenic fungi in vitro were tested by using the mycelial growth rate method at the concentration of 50 μg mL−1. Preliminary bioassay tests showed that some compounds exhibited more potent antifungal activities as compared with hymexazol. The preliminary structure-activity relationships (SARs) of all target compounds were also investigated.

scholarly journals Design, Synthesis and Antibacterial Evaluation of 3-Substituted Ocotillol-Type Derivatives

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3320 ◽  
Author(s):  
Kai-Yi Wang ◽  
Zhi-Wen Zhou ◽  
Heng-Yuan Zhang ◽  
Yu-Cheng Cao ◽  
Jin-Yi Xu ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Triterpenoid Saponin ◽  
Bacterial Strains ◽  
Design Synthesis ◽  
Design And Synthesis ◽  
Good Antibacterial Activity ◽  
Structure Activity ◽  
In Vitro Antibacterial Activity ◽  
Free Hydroxyl

Antibiotic resistance has become a serious global problem that threatens public health. In our previous work, we found that ocotillol-type triterpenoid saponin showed good antibacterial activity. Based on preliminary structure-activity relationship, novel serious C-3 substituted ocotillol-type derivatives 7–26 were designed and synthesized. The in vitro antibacterial activity was tested on five bacterial strains (B. subtilis 168, S. aureus RN4220, E. coli DH5α, A. baum ATCC19606 and MRSA USA300) and compared with the tests on contrast. Among these derivatives, C-3 position free hydroxyl substituted compounds 7–14, showed good antibacterial activity against Gram-positive bacteria. Furthermore, compound 22 exhibited excellent antibacterial activity with minimum inhibitory concentrations (MIC) values of 2 μg/mL against MRSA USA300 and 4 μg/mL against B. subtilis. The structure-activity relationships of all current ocotillol-type derivatives our team synthesised were summarized. In addition, the prediction of absorption, distribution, metabolism, and excretion (ADME) properties and the study of pharmacophores were also conducted. These results can provide a guide to further design and synthesis works.

scholarly journals Novel Inulin Derivatives Modified with Schiff Bases: Synthesis, Characterization, and Antifungal Activity

Polymers ◽  
2019 ◽  
Vol 11 (6) ◽  
pp. 998 ◽  
Author(s):  
Yuan Chen ◽  
Yingqi Mi ◽  
Xueqi Sun ◽  
Jingjing Zhang ◽  
Qing Li ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Fusarium Oxysporum ◽  
Schiff Bases ◽  
Plant Pathogens ◽  
Mycelium Growth ◽  
Plant Disease Control ◽  
Mycelium Growth Rate ◽  
Rate Method ◽  
Phomopsis Asparagi ◽  
High Antifungal Activity

In this paper, we report chemical modifications of inulin by seven kinds of aromatic Schiff bases, which are different from their substituent groups. The obtained inulin derivatives were confirmed by FTIR, 1H NMR, and 13C NMR. Then, we studied their antifungal activity against four kinds of plant pathogens involving Botrytis cinerea, Fusarium oxysporum f. sp. cucumerium Owen, Fusarium oxysporum f. sp. niveum, and Phomopsis asparagi by the mycelium growth rate method. The results revealed that all inulin derivatives were endowed with significant antifungal activity compared to inulin. Among them, 6-amino-(N-4-chlorobenzylidene)-6-deoxy-3,4-di-O-acetyl inulin (4CBSAIL) and 6-amino-(N-3,4-dichlorobenzylidene)-6-deoxy-3,4-di-O-acetyl inulin (3,4DCBSAIL), which were synthesized from p-chlorobenzaldehyde and 3,4-dichlorobenzaldehyde, could completely inhibit the growth of the test fungi at 1.0 mg/mL. The inhibitory indices of the inulin derivatives were related to the type, position, and number of substituent groups (halogens) on the Schiff bases. The results confirmed that it was feasible to chemically modify inulin with Schiff bases to confer high antifungal activity to inulin. The products described in this paper have great potential as alternatives to some harmful pesticides used for plant disease control.

Synthesis and Antifungal Activities of Drimane-Amide Derivatives from Sclareol

2018 ◽  
Vol 21 (7) ◽  
pp. 501-509 ◽  
Author(s):  
Miaofeng Ma ◽  
Jili Feng ◽  
Dezhi Wang ◽  
Shu-Wei Chen ◽  
Hui Xu
Keyword(s):  
Antifungal Activity ◽  
Fungal Pathogens ◽  
Antifungal Agents ◽  
Control Plant ◽  
Phytopathogenic Fungi ◽  
Plant Diseases ◽  
Economic Losses ◽  
Mycelium Growth ◽  
Amide Derivatives

Aim and Objective: Plant diseases are caused by fungal pathogens lead to severe economic losses in many agriculture crops. And the increasing resistance of many fungi to commonly used antifungal agents necessitates the discovery and development of new fungicides. So this study was focused on synthesizing novel skeleton compounds to effectively control plant diseases. Materials and Methods: A series of drimane-amide derivatives were designed, synthesized by aminolysis reaction of amine with intermediate sclareolide which was prepared from sclareol. The structures of all the synthesized compounds were confirmed using 1H NMR, 13C NMR, and HRMS (ESI) spectroscopic data. Their in vitro antifungal activity were preliminarily evaluated by using the mycelium growth rate method against five phytopathogenic fungi: Botrytis cinerea, Glomerella cingulata, Alternaria alternate, Alternaria brassicae, and Fusarium graminearum. Results: 23 target compounds were successfully obtained in yields of 52-95%. Compounds A2 and A3 displayed favorable inhibitory potency against B. cinerea, G. cingulata and A. brassicae with IC50 values ranging from 3.18 to 10.48 µg/mL. These two compounds displayed higher fungicidal activity than sclareol against all the tested phytopathogenic fungi, and were more effective than the positive control thiabendazole against A. alternate and A. brassicae. The structure-activity relationship studies of compounds A1-10 indicated that both the position and type of substituent on the phenyl ring had significant effects on antifungal activity. Conclusion: The drimane-amide derivatives A2 and A3 were the most promising derivatives and should be selected as new templates for the potential antifungal agents.

The Research of Inhibition Mechanism and the Application on Botrytis cinerea of 5% Potash Alum Water Solution

2013 ◽  
Vol 647 ◽  
pp. 548-553 ◽  
Author(s):  
Yong Gang Li ◽  
Qi Xin Xi ◽  
Sheng Yan Wen ◽  
Ying Mei Li
Keyword(s):  
Botrytis Cinerea ◽  
Water Solution ◽  
Pathogenic Fungi ◽  
Gray Mold ◽  
Inhibition Mechanism ◽  
Control Effect ◽  
Mycelium Growth ◽  
Field Efficacy ◽  
Mycelium Growth Rate ◽  
Rate Method

Botrytis cinerea is a necrotrophic fungus that affects many plant species requiring new methods of control. In the present investigation, efficacy of potash alum, a traditionally known double salt in Indian and Chinese medicine system, was tested against fourteen plant pathogenic fungi, inhibition mechanism and field efficacy of 5% potash alum water solution (M1) against tomato gray mold caused by B. cinerea. The inhibition spectrum tests showed that M1 had some inhibition effect against fourteen pathologic fungi by adopting mycelium growth rate method. M1 had an inhibition rate of 81.5%, 100%, 100% and 93.58% against B. clnerea, P. aphanidermatum, F. equiset and S. sclerotiorum respectively. M1 could effectively inhibit mycelial growth, spores production and germination of B. cinerea. The results preliminary showed that M1 had no effect on tomato growth. Tomato gray mold caused by B. cinerea had effectively been prevented by using M1 with field efficacy, which control effect was 78.66%. So the study lay the groundwork for further research and application.

Synthesis and Fungicidal Activity of Novel N-Nitro-2-Pyrimidinamine Derivatives

2013 ◽  
Vol 634-638 ◽  
pp. 1184-1191
Author(s):  
Wen Yan Qu ◽  
Jian Zhao ◽  
Bei Bei Gao ◽  
Shuo Chen ◽  
Zhi Fu Jiang ◽  
...  
Keyword(s):  
Ethyl Acetoacetate ◽  
Fungicidal Activity ◽  
High Efficiency ◽  
Fungal Species ◽  
Dimethyl Malonate ◽  
Mycelium Growth ◽  
Structure Activity ◽  
Relationship Of

Two series of novel N-nitro-2-pyrimidinamine derivatives were synthesized from ethyl acetoacetate, dimethyl malonate and nitroguanidine with good yields and high efficiency. The fungicidal activities of the synthesized compounds against nine fungal species were studied both in vitro and in vivo. Some of these compounds like 4,6-dihydr oxy -N-nitro-2-pyrimidinamine and 4,6-dihydroxy-5-isopentyl-N-nitro-2-pyrimidinamine showed obvious inhibitory of the mycelium growth at 50 mg/L. The structure-activity relationship of these compounds was also discussed.

scholarly journals Design, Synthesis, and Activity Evaluation of Novel N-benzyl Deoxynojirimycin Derivatives for Use as α-Glucosidase Inhibitors

Molecules ◽  
2019 ◽  
Vol 24 (18) ◽  
pp. 3309 ◽  
Author(s):  
Zeng ◽  
Yin ◽  
Chen ◽  
Nie ◽  
Lin ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Hydroxyl Group ◽  
Inhibition Activity ◽  
Promising Candidate ◽  
Design Synthesis ◽  
Structure Activity ◽  
Glucosidase Inhibitors ◽  
Ic50 Value ◽  
Ic50 Values

To obtain α-glucosidase inhibitors with high activity, 19 NB-DNJDs (N-benzyl-deoxynojirimycin derivatives) were designed and synthesized. The results indicated that the 19 NB-DNJDs displayed different inhibitory activities towards α-glucosidase in vitro. Compound 18a (1-(4-hydroxy-3-methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol) showed the highest activity, with an IC50 value of 0.207 ± 0.11 mM, followed by 18b (1-(3-bromo-4-hydroxy-5-methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol, IC50: 0.276 ± 0.13 mM). Both IC50 values of 18a and 18b were significantly lower than that of acarbose (IC50: 0.353 ± 0.09 mM). According to the structure-activity analysis, substitution of the benzyl and bromine groups on the benzene ring decreased the inhibition activity, while methoxy and hydroxyl group substitution increased the activity, especially with the hydroxyl group substitution. Molecular docking results showed that three hydrogen bonds were formed between compound 18a and amino acids in the active site of α-glucosidase. Additionally, an arene‒arene interaction was also modelled between the phenyl ring of compound 18a and Arg 315. The three hydrogen bonds and the arene‒arene interaction resulted in a low binding energy (–5.8 kcal/mol) and gave 18a a higher inhibition activity. Consequently, compound 18a is a promising candidate as a new α-glucosidase inhibitor for the treatment of type Ⅱ diabetes.

Sign in / Sign up

Export Citation Format

Share Document