Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted-pyrrolidine-2,4-dione derivatives

Han, Bao Feng; Shi, Qing; Wang, Xianfeng; Liu, Jian Bo; Qiang, Sheng; Yang, Chui‐Ping

doi:10.1016/j.cclet.2012.07.002

Cited by 11 publications

(1 citation statement)

References 16 publications

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“…Second, tetramic acid derivatives contain a unique pyrroline-2-one or pyrrolidine-2,4-dione substructure that is easy to synthesize to some extent [ 5 ]. Third, tetramic acid derivatives are reported to exhibit various agricultural bioactivities including fungicidal [ 6 ], herbicidal [ 7 ], insecticidal [ 8 ], antibacterial and antiviral [ 9 ] properties. Encouraged by the above findings, series of tetramic acid derivatives bearing amino [ 10 ], strobilurin [ 6 ], phenylhydrazine [ 11 ], oxime ether [ 12 ] and pyrrole [ 13 ] groups were synthesized and reported for their antifungal activity against plant fungi in our previous work.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of novel 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone moiety as potential fungicides

Wang

Ren

Wang

et al. 2018

Chemistry Central Journal

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BackgroundTetramic acid, thiophene and hydrazone derivatives were found to exhibit favorable antifungal activity. Aiming to discover novel template molecules with potent antifungal activity, a series of novel 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives containing a hydrazone group were designed, synthesized, and evaluated for their antifungal activity.ResultsThe structures of 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone group were confirmed by FT-IR, 1H NMR, 13C NMR, 1H-1H NOESY, EI-MS and elemental analysis. Antifungal assays indicated that some title compounds exhibited antifungal activity against Fusarium graminearum (Fg), Rhizoctorzia solani (Rs), Botrytis cinerea (Bc) and Colletotrichum capsici (Cc) in vitro. Strikingly, the EC50 value of 5e against Rs was 1.26 µg/mL, which is better than that of drazoxolon (1.77 µg/mL). Meanwhile, title compounds 5b, 5d, 5e–5g, 5n–5q and 5t exhibited remarkable anti-Cc activity, with corresponding EC50 values of 7.65, 9.97, 6.04, 6.66, 7.84, 7.59, 9.47, 5.52, 6.41 and 7.53 µg/mL, respectively, which are better than that of drazoxolon (19.46 µg/mL).ConclusionsA series of 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone group were designed, synthesized and evaluated for their antifungal activity against Fg, Rs, Bc and Cc. Bioassays indicated that some target compounds exhibited obvious antifungal activity against the above tested fungi. These results provide a significant basis for the further structural optimization of tetramic acid derivatives as potential fungicides.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0452-z) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Design and synthesis of novel 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone moiety as potential fungicides

Wang

Ren

Wang

et al. 2018

Chemistry Central Journal

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Studies on the Synthesis and Bioactivities of 4‐Amino Derivatives of Tetramic Acid

Liu

Zhao

Song

et al. 2014

Journal of Heterocyclic Chem

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Design, Synthesis, and Antifungal Activity of 3‐(Thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one Derivatives Bearing a Carbonic Ester Group

Wang

Ren

Mei

et al. 2018

Journal of Heterocyclic Chem

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A series of 3‐(thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one derivatives bearing a carbonic ester group were designed and synthesized by integrating a thiophene nucleus and a pyrroline‐2‐one scaffold in a single molecular architecture. Their structures were confirmed by IR, 1H‐NMR, EI‐MS, and elemental analyses, and their antifungal activities against Fusarium graminearum (Fg), Rhizoctorzia solani (Rs), and Botrytis cinerea (Bc) were evaluated. The antifungal bioassays indicated that some title compounds exhibited desirable antifungal effects against the tested fungi. Strikingly, the title compounds 4i, 4k, 4n, and 4o showed obvious antifungal activities against Rs, with corresponding EC50 values of 35.26, 33.56, 23.90, and 30.48 μg/mL, respectively, which are better than that of hymexazol (37.86 μg/mL). These results indicated that 3‐(thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one derivatives bearing a carbonic ester group can serve as potential structural templates in the search for novel high‐efficient fungicides.

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Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted-pyrrolidine-2,4-dione derivatives

Cited by 11 publications

References 16 publications

Design and synthesis of novel 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone moiety as potential fungicides

Design and synthesis of novel 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone moiety as potential fungicides

Studies on the Synthesis and Bioactivities of 4‐Amino Derivatives of Tetramic Acid

Design, Synthesis, and Antifungal Activity of 3‐(Thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one Derivatives Bearing a Carbonic Ester Group

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