797808-89-0Relevant academic research and scientific papers
Synthesis, crystal structure and antibacterial activity of 2-(p-Tolyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
Liu, Xianping,He, Daohang
, p. 3216 - 3218 (2014)
The compound 2-(p-tolyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole (m.f. C18H18N2O4) was synthesized and characterized by 1H NMR, 13C NMR, MS and X-ray single crystal diffraction analysis. In the crystal structure, the two phenyl rings and the 1,3,4-oxadiazole ring are nearly coplanar with the dihedral angles 4.55, 1.13 and 3.97°. There is an offset face-to-face p-p stacking interaction between 1,3,4- oxadiazole ring planes. The compound molecules are connected through the offset face-to-face p-p stacking interactions to generate a three-dimensional network. The results of preliminary biological activity assay showed that the title compound exhibited good antibacterial activity against Staphylococcus aureus and Escherichia coli.
Synthesis, biological evaluation, and structure-activity relationship study of novel stilbene derivatives as potential fungicidal agents
He, Daohang,Jian, Weilin,Liu, Xianping,Shen, Huifang,Song, Shaoyun
, p. 1370 - 1377 (2015)
A total of 22 novel stilbene derivatives containing the 1,3,4-oxadiazole moiety and trimethoxybenzene were designed and synthesized. Their chemical structures were characterized by 1H and 13C nuclear magnetic resonance, infrared, and high-resolution mass spectrometry. Bioassay results revealed that some of the title compounds showed potent in vivo fungicidal activities against three phytopathogenic fungi (Pseudoperonospora cubensis, Colletotrichum lagenarium, and Septoria cucurbitacearum) from cucurbits at 600 ～g/mL. Notably, compounds 4b, 4d, 4i, 4k, and 4l exhibited a broad spectrum and remarkably high activities against those fungi, some of which even showed a comparable control efficacy to that of the commercial fungicides. Three-dimensional quantitative structure-activity relationship based on comparative molecular field analysis with good predictive ability (q2 = 0.516; r2 = 0.920) was reasonably discussed. For the first time, the present work suggested that the stilbene derivatives containing the 1,3,4-oxadiazole moiety could be developed as potential fungicides for crop protection.
IBX/KI promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles
Khan, P. Rasvan,Durgaprasad,Reddy, S. Gopal,Reddy, G. Raveendra,Hussein, Ibnelwaleed A.,Reddy, B.V. Subba
, p. 64 - 69 (2018/03/05)
Background: Oxadiazoles are privileged scaffolds in different areas of medicinal, pesticidal, polymer and material science. They act as anticancer, benzodiazepine receptor agonists, antimicrobial, analgesic, diuretic and tyrosinase inhibitors etc. A number of compounds containing an oxadiazole moiety are in late stage clinical trials including zibotentan and furamizole. Despite numerous methods are reported, the majority of them suffer from major drawbacks such as the use of strong alkaline or acidic conditions, highly toxic and corrosive reagents and also involve the use of costly reagents, elevated temperatures and longer reaction times. Inspired by the potential application of hypervalent iodonium reagents in organic synthesis, we would like to explore the readily available IBX and KI reagents for the facile synthesis of 1, 3, 4-oxadiazoles. Method: Oxidative cyclization has successfully been developed for the synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles. Results: An efficient process for the one-pot synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles has been developed using IBX/KI system at 25°C. The reaction was successful with a wide range of substrates such as aromatic and heterocyclic aldehyde and arylhydrazides to afford the corresponding unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles. The mild reaction conditions, cost-effective reagents and short reaction time are noteworthy advantages of this methodology. Conclusion: We have developed a one-pot strategy for the synthesis of 1, 3, 4-oxadiazioles using a combination of IBX/KI at ambient temperature. This one-pot procedure proved to be quite general and worked well with a wide variety of aryl and heterocyclic aldehydes and variety of acylhydrazides. The advantage of this method lies in the simplicity of experimental procedure and the ready accessibility of the reagents, which render this, an experimentally attractive method for the preparation of unsymmetrical 1, 3, 4-oxadiazoles.
