Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model.

Journal of Enzyme Inhibition and Medicinal Chemistry
Xiu-Jiang DuXing-Hai Liu

Abstract

Thirty-six novel threoninamide carbamate derivatives were designed and synthesised using active fragment-based pharmacophore model. Antifungal activities of these compounds were tested against Oomycete fungi Phytophthora capsici in vitro and in vivo. Interestingly, compound I-1, I-2, I-3, I-6 and I-7 exhibited moderate control effect (>50%) against Pseudoperonospora cubensis in greenhouse at 6.25 μg/mL, which is better than that of control. Meanwhile most of these compounds exhibited significant inhibitory against P. capsici. The other nine fungi were also tested. More importantly, some compounds exhibited remarkably high activities against Sclerotinia sclerotiorum, P. piricola and R. solan in vitro with EC50 values of 3.74-9.76 μg/mL. It is possible that the model is reliabile and this method can be used to discover lead compounds for the development of fungicides.

References

Oct 27, 2007·Bioorganic & Medicinal Chemistry·Clemens LamberthRonald Zeun
Dec 17, 2009·Journal of Agricultural and Food Chemistry·Xiaojing YanHuizhu Yuan
Feb 22, 2017·Pest Management Science·Xing-Hai LiuHong-Ying Huang
Mar 21, 2019·Pest Management Science·Changcai WuDongmei She

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Citations

Sep 20, 2020·Pharmaceutics·Lucreţia UdrescuMihai Udrescu
Aug 8, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lingling XiaoXiaodan Wang

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Methods Mentioned

BETA
NMR
surface plasmon resonance
column chromatography

Software Mentioned

SYBYL
MMFF94x Forcefield
MOE

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