Synthesis, biological activities and 3D-QSAR studies of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety

Liu, Jingbo; Li, Fengyun; Zhang, Haoxuan; Dong, Jingyue; Sun, Pengwei; Li, Yuxin; Li, Zhengming

doi:10.1016/j.cclet.2018.11.001

Cited by 5 publications

(5 citation statements)

References 20 publications

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“…All solvents and liquid reagents were dried by standard methods in advance and distilled before use. Intermediate compounds 3a-c and 6a-e were synthesized in Scheme 1 according to the literature [25,35].…”

Section: Methodsmentioning

confidence: 99%

“…After that, intermediates 3 were obtained by treating intermediates 2 with 4 mol/L hydrochloride in methanol in good yields. Intermediates 6 were synthesized by treating L-cysteine 5 with benzonitrile derivatives 4 in the presence of sodium bicarbonate and sodium hydroxide in the mixture of methanol and water, according to our previous report with some improvement [25]. Initial attempts to synthesize the title compounds I-III by coupling intermediates 3 and 6 with N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDCI) and 1-hydroxy-1H-benzotriazole (HOBT) as coupling reagents in the presence of triethylamine (Et 3 N) as acid binding reagent, however, yielded very low title compounds.…”

Section: Chemistrymentioning

confidence: 99%

“…Moreover, natural products have also frequently served as lead compounds in developing novel synthetic pesticides, which possess better efficacies than natural products [23]. Recently, our research group found that some (R)-2-aryl-4,5-dihydrothiazole-4-carboxylic acid derivatives containing amide and ester moieties displayed remarkable and broad-spectrum antifungal activities [24,25], indicating that (R)-2-aryl-4,5-dihydrothiazole-4-carboxylic acid derivatives could be used as new potential lead structures for the development of antifungal agents.…”

Section: Introductionmentioning

confidence: 99%

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(R)-2-Phenyl-4,5-Dihydrothiazole-4-Carboxamide Derivatives Containing a Diacylhydrazine Group: Synthesis, Biological Evaluation, and SARs

Liu

Gong

et al. 2019

Molecules

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A series of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a diacylhydrazine moiety were designed and synthesized. Their structures were confirmed by melting points, 1H NMR, 13C NMR, and elemental analysis (EA). Their antifungal and insecticidal activities were evaluated. The antifungal activity result indicated that most title compounds against Cercospora arachidicola, Alternaria solani, Phytophthora capsici, and Physalospora piricola exhibited apparent antifungal activities at 50 mg/L, and better than chlorothalonil or carbendazim. The EC50 values of (R)-N’-benzoyl-2-(4-chlorophenyl)-4,5-dihydrothiazole-4-carbohydrazide (I-5) against six tested phytopathogenic fungi were comparable to those of chlorothalonil. The CoMSIA model showed that a proper hydrophilic group in the R1 position, as well as a proper hydrophilic and electron-donating group in the R2 position, could improve the antifungal activity against Physalospora piricola, which contributed to the further optimization of the structures. Meanwhile, most title compounds displayed good insecticidal activities, especially compound (R)-N’-(4-nitrobenzoyl)-2-(4-nitrophenyl)-4,5-dihydrothiazole-4-carbohydrazide (III-3). The insecticidal mechanism results indicated that compound III-3 can serve as effective insect Ca2+ level modulators by disrupting the cellular calcium homeostasis in Mythimna separata.

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Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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(R)-2-Phenyl-4,5-Dihydrothiazole-4-Carboxamide Derivatives Containing a Diacylhydrazine Group: Synthesis, Biological Evaluation, and SARs

Liu

Gong

et al. 2019

Molecules

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“…Heterocyclic compounds are commonly used for the development of novel pesticides. 1,3,4-Oxadiazole, an important class of five-membered heterocycle, is found in many compounds and exhibits a wide range of biological activities. − Meanwhile, many studies have highlighted that the thioether/sulfoxide/sulfone groups are ideal substructures for developing agrochemicals and display various biological functions including herbicidal, antifungal, antiviral, and insecticidal activities. − Obviously, compounds containing 1,3,4-oxadiazole, thioether, sulfoxide, or sulfone moieties may show promising fungicidal activity, which is worth exploring.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Novel Psoralen-Based 1,3,4-Oxadiazoles as Potent Fungicide Candidates Targeting Pyruvate Kinase

Dong

Wei

et al. 2022

J. Agric. Food Chem.

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Pyruvate kinase (PK) has been considered as a promising fungicide target discovered in our previous studies. Natural compounds are important sources for discovery and development of new pesticides. To continue our ongoing studies on the discovery of novel PK-targeted fungicides, a series of novel psoralen derivatives including a 1,3,4-oxadiazole moiety were designed by a computer-aided pesticide molecular design method, synthesized, and evaluated for their fungicidal activity. The bioassay results indicated that compounds 11d, 11e, 11g, 11i, and 12a showed excellent in vitro fungicidal activity against Botrytis cinerea with EC 50 values of 4.8, 3.3, 6.3, 5.4, and 3.9 μg/mL, respectively. They were more active than the corresponding positive control YZK ,3,4]-thiadiazole] (with an EC 50 value of 13.4 μg/mL). Compounds 11g and 11i displayed promising in vivo fungicidal activity against B. cinerea with 80 and 70% inhibition at a concentration of 200 μg/mL, respectively. They possessed much higher fungicidal activity than the positive control psoralen and comparable activity with the positive control pyrisoxazole. Enzymatic assays indicated that 11i showed good BcPK inhibition with an IC 50 value of 39.6 μmol/L, comparable to the positive control YZK-C22 (32.4 μmol/L). Molecular docking provided a possible binding mode of 11i in the BcPK active site. Our studies suggested that the psoralen-based 1,3,4-oxadiazole 11i could be used as a new fungicidal lead targeting PK for further structural optimization.

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“…Plant diseases caused by fungi have caused severe losses to agriculture in the world every year, even emerged threat to human health and global food security [ 1 – 4 ]. It is well known that agrochemical application is one of a key measure for reducing crops loss caused by plant diseases in modern agriculture [ 5 , 6 ]. However, the frequent application of traditional fungicides has brought a series of risks, such as environment pollution, resistance and so on [ 7 , 8 ].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and fungicidal evaluation of novel psoralen derivatives containing sulfonohydrazide or acylthiourea moiety

Dong

Hong

et al. 2022

Mol Divers

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To search a novel lead structure for antiphytopathogenic fungus agent, a series of novel psoralen derivatives possessing sulfonohydrazide or acylthiourea structure were designed and synthesized, and their fungicidal activity against seven phytopathogens was evaluated. Their structures were confirmed by melting points, 1 H NMR, 13 C NMR and HRMS, and the typical crystal structure was determined by X-ray diffraction for validation. Preliminary fungicidal activity showed that some of the title compounds exhibited certain-to-high fungicidal activity. Compound I-13 exhibited good fungicidal activity against Botrytis cinerea , Cercospora arachidicola and Physalospora piricola with EC 50 values of 12.49, 13.22 and 12.12 μg/mL, respectively. Compounds II-9 and II-15 showed over 90% inhibition against B. cinerea at 50 μg/mL in vitro. In particular, II-9 exhibited significant higher fungicidal activity with a lower EC 50 value of 9.09 μg/mL than the positive control YZK-C22 (13.41 μg/mL). Our studies found that sulfonohydrazide or acylthiourea-containing psoralen derivatives were promising fungicide leads deserve for further study. Graphical abstract Supplementary Information The online version contains supplementary material available at 10.1007/s11030-022-10402-y.

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Synthesis, biological activities and 3D-QSAR studies of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety

Cited by 5 publications

References 20 publications

(R)-2-Phenyl-4,5-Dihydrothiazole-4-Carboxamide Derivatives Containing a Diacylhydrazine Group: Synthesis, Biological Evaluation, and SARs

(R)-2-Phenyl-4,5-Dihydrothiazole-4-Carboxamide Derivatives Containing a Diacylhydrazine Group: Synthesis, Biological Evaluation, and SARs

Design, Synthesis, and Biological Evaluation of Novel Psoralen-Based 1,3,4-Oxadiazoles as Potent Fungicide Candidates Targeting Pyruvate Kinase

Design, synthesis and fungicidal evaluation of novel psoralen derivatives containing sulfonohydrazide or acylthiourea moiety

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