14426-43-8Relevant articles and documents
Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment
Wang, Xiaobin,Chai, Jianqi,Kong, Xiangyi,Jin, Fei,Chen, Min,Yang, Chunlong,Xue, Wei
, (2021/08/03)
Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.
Synthesis, Nematicidal Activity, and 3D-QSAR of Novel 1,3,4-Oxadiazole/ Thiadiazole Thioether Derivatives
Chen, Jixiang,Gan, Xiuhai,Yi, Chongfen,Wang, Shaobo,Yang, Yuyuan,He, Fangcheng,Hu, Deyu,Song, Baoan
, p. 939 - 944 (2018/09/22)
Forty one novel 1,3,4-oxadiazole/thiadiazole thioether derivatives containing phenoxy moiety were designed and synthesized. Bioassay demonstrated that some of them showed remarkable activities against Tylenchulus semipenetrans in vitro and in vivo. Compounds 20, 21, 35 and 39 showed excellent lethal activities after treatment for 48?h in vitro, with LC50 values of 13.4?±?1.8, 11.7?±?2.5, 13.7?±?2.4 and 13.3?±?1.1?mg·L–1, respectively, which were obviously superior to fosthiazate (49.1?±?2.8?mg·L–1) and avermectin (26.6?±?2.3?mg·L–1). Compound 21 can effectively control the citrus nematode disease caused by T. semipenetrans at 200?mg·L–1 in vivo with (68?±?3)% inhibitory effect, which was even better than that of avermectin ((63?±?2)%). The CoMFA and CoMSIA models of three-dimensional quantitative structure-activity relationships (3D-QSARs) were established. The compound 33 was designed based on the 3D-QSAR models with more vigorous nematicidal activities in vitro (LC50?=?9.8?±?1.4?mg·L–1) and in vivo ((70?±?5)%). These results demonstrated that compound 33 can be considered as a potential nematicide.
Synthesis, antibacterial and antifungal activities of 2,5-disubstituted-1, 3,4-oxadiazoles
Nadagouda,Khochage, Atul,Pradeepkumar,Korat, Haresh,Gadaginamath,Joshi
, p. 85 - 90 (2013/12/04)
A series of 2,5- distributed 1,3,4-oxadiazole derivatives were prepared and evaluated for their antibacterial and antifungal activities. 5-[(2, 4, 6-trichlorophenoxy) methyl]- 1,3,4-oxadiazol-2-thiol 5 was synthesized by the reaction of 2-(2,4,6,-trichlorophenoxy) acetic acid hydrazide 4 with CS 2 and KOH in ethanol. The compound 5 on reaction with ethyl chloroacetate gave ethyl-2-(5-(2,4,6-trichlorophenoxy)methyl)-1,3,4-oxadiazol- 2-ylthio) acetate 6 and this on further hydrolysis by sodium hydroxide, followed by acidification gave 2-(5-((2,4,6-trichlorophenoxy)methyl)-1l3,4-oxadiazol-2- ylthio) acetic acid. 7.The compound 5 on condensation with p-benzoquinone in dry acetone gave 2- (5-((2,4l6-trichlorophenoxy)methyl)-1,3l4-oxadiazol-2-ylthio) benzene-1,4-diol 8.1,3,4- Oxadiazole derivatives 9-15 were prepared by treating hydrazide 4 with aromatic acids, in presence of dehydrating agent. Structures of the newly synthesized compounds were confirmed on the basis of physico-chemical and spectral data. All the synthesized compounds were screened for their antibacterial and antifungal activities using broth micro dilution method. Compounds have shown moderate to good antibacterial and antifungal activities.
