50848-29-8Relevant academic research and scientific papers
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 and antibacterial evaluation of new sulfone derivatives containing 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole moiety
Su, Shihu,Zhou, Xia,Liao, Guoping,Qi, Puying,Jin, Linhong
, (2017/01/24)
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 compounds 5I-1-5I-7 exerted remarkably higher activities with EC50 values ranging from 0.45-1.86 μg/mL against X. oryzae and 1.97-20.15 μg/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with 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.
Reactions of α-Halo Ketones with 5-Benzyl-and 5-Phenoxymethyl-2H,3H-1,3,4-oxadiazole-2-thiones
Andrushko, A. P.,Demchenko, A. M.,Krasovskii, A. N.,Rusanov, E. B.,Chernega, A. N.,Lozinskii, M. O.
, p. 1754 - 1758 (2007/10/03)
Alkylation of 5-substituted 2H,3H-1,3,4-oxadiazole-3-thiones with α-bromo ketones in alkaline solutions yields 5-substituted 2-aroylmethylthio-1,3,4-oxadiazoles; in acidic solutions these compounds re-arrange into 4-aryl-3-arylacetamido-2H,3H-1,3-thiazol-2-ones.
Synthesis, Characterization, Spectral and Antifungal Properties of Some 5-Substituted-1,3,4-oxadiazole-2-thiones and Their Mannich Bases
Holla, B. Shivarama,Kalluraya, Balakrishna,Nath, S. C.
, p. 549 - 557 (2007/10/02)
A series of 5-substituted aryloxymethyl-1,3,4-oxadiazole-2-thione (3a-e) and their Mannich bases 4-8 are synthesized and subjected to fungitoxic screening.The structures of these compounds are established on the basis of elemental analysis 1H-n.m.r. and mass spectral data.The mass spectral fragmentation pathways of these compounds are discussed.
