Journal of Saudi Chemical Society
·
2017
·
IF 2.887
Lei Zhou,Pei-Yi Wang,Jian Zhou,Wu-Bin Shao,He-Shu Fang,Zhi-Bing Wu,Song Yang
Herein, a series of pyridinium-tailored 5-trifluoromethylpyrazoles containing 1,3,4-oxadiazole moieties were constructed through coupling key pharmaceutical fragments of pyridinium, pyrazole, and 1,3,4-oxadiazole scaffolds in single molecular architecture. Antimicrobial results suggested that this kind of compounds exhibited significant activities against three types of pathogenic bacteria and six fungal strains in vitro . The minimal EC 50 values of designed compounds against Xanthomonas oryzae pv . oryzae , Ralstonia solanacearum , and Xanthomonas axonopodis pv . citri could reach to 0.467, 1.04, and 0.600 μg/mL, respectively, through tuning and optimizing N -substituents, bridging atom, and alkyl length of the tailor. Antifungal assays revealed that all title molecules possessed considerable activity against Botrytis cinerea with the minimal EC 50 value up to 2.71 μg/mL; and compounds I-8 , I-10 , I-12 , II-12 , and IV-12 showed the strongest growth suppression toward Rhizoctonia solani with EC 50 values ranging from 10.2 to 24.0 μg/mL. Given the above results, this kind of compounds could serve as new lead compounds in the research of antimicrobial chemotherapy.
研究领域:
药理学
·
微生物学
·
有机化学
✓ 已验证
DOI
高影响因子
JOURNAL OF HETEROCYCLIC CHEMISTRY
·
2022
·Vol. 60
·期 1
·145-155
·
IF 2.035
Abdalla Khallaf,Ping Wang,Shuping Zhuo,Hongjun Zhu,Hui Liu
The insecticidal activity of 1,3,4-oxadiazole-ring containing pyridylpyrazole-4-carboxamides against diamondback ( Plutella xylostella ) and noctuid ( Spodoptera frugiperda ) moths were evaluated. Only substitutions on the 1,3,4-oxadiazole moiety dictated bioreactivity, with 8q2 m -CF 3 Ph being the most effective against Plutella xylostella, showing 80%–93% mortality at a concentration of 0.5–500 μg ml −1 while the others remained inactive or less active (highest mortality being 63%). The larvicidal activity against Spodoptera frugiperda was inferior compared with that of Plutella xylostella , with the highest mortality being 33%. A crystal of 8q5 was obtained and analyzed, revealing the effects of intramolecular H-bonds and intermolecular π π interactions.
研究领域:
昆虫学
·
有机化学
·
农药科学
✓ 已验证
DOI
高影响因子
MOLECULES
·
2016
·Vol. 22
·期 1
·64
·
IF 2.465
Shihu Su,Xia Zhou,Guoping Liao,Puying Qi,Linhong Jin
Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae,Ralstonia solanacearum,Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds5I-1–5I-7exerted remarkably higher activities with EC50values ranging from 0.45–1.86 μg/mL againstX. oryzaeand 1.97–20.15 μg/mL againstR. solanacearum. Exhilaratingly,5I-1,5I-2and5I-4displayed significant in vivo activity againstX. oryzaewith protective effect of 90.4%, 77.7%, and 81.1% at 200 μg/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases.Keywords:synthesis;1,3,4-oxadiazole/thiadiazole sulfone;aryloxymethyl;antibacterial activity;structure-activity relationship
研究领域:
药物化学
·
农业科学
·
植物病理学
✓ 已验证
DOI
PubMed
高影响因子
CHEMISTRY & BIODIVERSITY
·
2024
·Vol. 21
·期 3
·e202400043
·
IF 2.3
Yong Li,Zhongfu Luo,Wenjing Liu,Wenzhang Chen,Jianta Wang,Gaofeng Zhu,Bing Guo,Lei Tang,Lingling Fan
Four series of novel 1,3,4-oxadiazole/1,2,4-triazole hybrids of phthalide derivatives were designed and synthesized to search for novel potential antifungal agents. Preliminary antifungal activity assay results showed that compounds 4 a , 4 b , 4 m , 5 b , 5 f , 5 h , and 7 h exhibited moderate to excellent inhibitory activity against some phytopathogenic fungi. Among them, compound 5 b displayed the most outstanding antifungal effects against V. mali and S. sclerotiorum , with the EC 50 mean of 3.96 μg/mL and 5.60 μg/mL, respectively, which was superior to those of commercial fungicides hymexazol and chlorothalonil. Furthermore, compound 5 b could completely suppress the spore germination of V. mali at a concentration of 10 μg/mL. Finally, molecular docking revealed that the potential target for the antifungal activity of compound 5 b was succinate dehydrogenase (SDH). This research provides novel candidate compounds for the prevention of phytopathogenic fungi. Graphical
研究领域:
药物化学
·
植物病理学
✓ 已验证
DOI
PubMed
高影响因子
RESEARCH ON CHEMICAL INTERMEDIATES
·
2017
·Vol. 43
·期 11
·6115-6130
·
IF 1.369
Wang Pei-Yi,Shao Wu-Bin,Xue Hai-Tao,Fang He-Shu,Zhou Jian,Wu Zhi-Bing,Song Bao-An,Yang Song
In this paper, a variety of novel 1,3,4-oxadiazole derivatives possessing diamides were synthesized and tested for their antibacterial and antiviral activity. Preliminary antibacterial assays indicated that some intermediates and title compounds displayed excellent inhibition effects against plant pathogens Xanthomonas oryzae pv. oryzae ( Xoo ) and Xanthomonas axonopodis pv . citri ( Xac ). Further studies revealed that compound H15 exhibited the strongest activities against Xoo and Xac with minimal EC 50 values of 0.7 and 5.9 μg/mL, respectively. Antiviral bioassays suggested that some of these structures displayed appreciable curative activities and moderate protective effects against tobacco mosaic virus (TMV) in vivo. Among them, compound H8 exerted the best chemotherapeutic effect against TMV with the curative rate of 60.0% at 500 µg/mL, which was comparable with those of commercial agricultural antiviral agent ningnanmycin (54.2%). Given their significant biological activities, this kind of compound could serve as new leading compounds in the study of antibacterial and antiviral chemotherapy.
研究领域:
药理学
·
植物病理学
·
有机化学
✓ 已验证
DOI
高影响因子
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
·
2024
·Vol. 59
·期 12
·2214-2220
·
IF 0.8
Liu Shan-Ming,Zhang Wei,Yang Shun,Zou Jing-Pei,Qian Jing-Jing,Li Rui,Liu Wei-Wei,Dong Jing-Quan,Shi Da-Hua
A series of 1,3,4-oxadiazole derivatives were synthesized starting from substituted phenylacetic acids, and their structures were confirmed by IR, NMR, and HRMS data. The synthesized compounds showed potent in vitro cholinesterase inhibitory activities with IC 50 values of 8.59 μM against butyrylcholinesterase ( 6a ) and 7.12 μM against acetylcholinesterase ( 6f ). Molecular docking studies indicated that compound 6f could interact with the peripheral anion that binds to acetylcholinesterase. Moreover, compound 6c also exhibited strong anti-inflammatory effect. This compound could significantly reduce LPS-induced secretion of inflammatory cytokines IL-6, IL-1β, and TNF-α in RAW 264.7 cells. These results suggested that 1,3,4-oxadiazole derivatives may be promising lead compounds for the treatment of Alzheimer’s disease.
研究领域:
药物化学
·
神经科学
·
药理学
✓ 已验证
DOI
高影响因子
NEW JOURNAL OF CHEMISTRY
·
2021
·Vol. 45
·期 25
·11380-11389
·
IF 3.591
Rui Yang,Yifei Liu,Zhen Dong,Haiyan Li,Zhiwen Ye
As an environmentally friendly energetic group, the azide group can not only control the melting point but also increase the energy of the compound. Therefore, the design and synthesis of energetic compounds with azido groups have long been a focus of research in the field of energetic materials. 3-R-4-(5-methyleneazide-1,2,4-oxadiazol-3-yl)furazan energetic materials were synthesized and fully characterized. Using computational chemistry methods, the interactions of some compounds were studied, and the physical and chemical properties of all of compounds were examined. The results show that 3-amino-4-(5-methyleneazide-1,2,4-oxadiazol-3-yl)furazan (2) has a melting point similar to that of TNT and can be a potential carrier for molten-cast explosives. Hydroxylamine salt (4) has an excellent detonation velocity and detonation pressure of 9090 m s−1 and 35.76 GPa, respectively, and its energy is significantly higher than that of RDX, enabling replacement of RDX as a high-energy explosive. Although the detonation performance of compound 4 is slightly lower than that of HMX, its sensitivity is better than that of HMX, which shows that compound 4 still has a high application value. Non-covalent interactions (NCIs) and Hirshfeld surface models indicate that hydrogen bonding and π–π interactions are the key factors that reduce the sensitivity of compounds. Therefore, our results for 3-R-4-(5-methyleneazide-1,2,4-oxadiazol-3-yl)furazan energetic materials suggest that it may be competitive for application in both molten-cast explosives and high-energy explosives.
研究领域:
化学
·
材料科学
·
爆炸物研究
✓ 已验证
DOI
高影响因子
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
·
2020
·
IF 2.751
Jie Xiang,Dengyue Liu,Jixiang Chen,Deyu Hu,Baoan Song
In this study, thirty 1,3,4-oxadiazole sulfone derivatives containing 3,4-dichloroisothiazolamide moiety were designed and synthesized, and their antibacterial activities were evaluated. Bioassay results showed that some compounds exhibited excellent antibacterial activities against Xanthomonas oryzae pv. oryzae ( Xoo ) and Xanthomonas oryzae pv. oryzicola ( Xoc ) in vitro and in vivo . Notably, the EC 50 values of compounds 2 and 3 against Xoo were 0.79 and 0.85 μg/mL, respectively, which were superior to those of the control agents isotianil, bismerthiazol, and thiodiazole copper. In addition, in vivo antibacterial activities revealed that the compound 2 at 50 μg/mL possessed protective and curative activities of 43.99% and 41.06% against Xoo , respectively, which were better than positive controls. Furthermore, the preliminary mechanism study disclosed that compound 2 exhibited effective antibacterial activity against Xoo by inhibiting the formation of extracellular polysaccharides from Xoo , increasing cell permeability , and changing the shape of cells. This study suggested that 1,3,4-oxadiazole sulfone derivatives containing 3,4-dichloroisothiazolamide moiety displayed excellent antibacterial activity and could be further explored and developed as commercial pesticides.
研究领域:
植物病理学
·
农药化学
·
微生物学
✓ 已验证
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）