Design, Synthesis, Antifungal Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moiety

Sun, Na-Bo; Shi, Yanhong; Liu, Xinghai; Ma, Yangmin; Tan, Cheng‐Xia; Weng, Jian‐Quan; Jin, Jiye; Li, Baoju

doi:10.3390/ijms141121741

Cited by 14 publications

(16 citation statements)

References 30 publications

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“…7 Several examples of CoMFA models for the discovery/design/development of antifungals against phytopathogens can be found in available publications with successful results comprising different scaffolds/moieties. 5,6,8−10…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-Assisted Synthesis, Antifungal Activity against Fusarium oxysporum, and Three-Dimensional Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from 2-Amino Acids

2019

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A high-yielding, green, and fast synthesis of alkyl 2-substituted {[(alkylsulfanyl)carbonothioyl]amino}acetate-type compounds is described. The one-pot, three-component condensation of alkyl 2-aminoesters, carbon disulfide, and electron-deficient olefins was the key reaction to be developed. The products were obtained easily and efficiently, with good overall yields after two steps (79–91%), employing short reaction times, without the use of a catalyst, and ultrasonic irradiation in water. This procedure was exploited to produce antifungals against the phytopathogenic fungus Fusarium oxysporum . Some synthesized compounds exhibited good performance as mycelial growth inhibitors (IC 50 < 80 μM). Structural and antifungal datasets were integrated to explore the comprehensive three-dimensional quantitative structure–activity relationship (3D-QSAR) using comparative molecular field analysis (CoMFA) and explain the observed activity. This integration resulted in an excellent CoMFA model ( r 2 = 0.812; q 2 = 0.771) after substructure-based alignment. According to this model, synthesized compounds possessing steric bulky electron-withdrawing groups in the dithiocarbamate moiety can be considered as promising F. oxysporum inhibitors.

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Section: Introductionmentioning

confidence: 99%

Ultrasound-Assisted Synthesis, Antifungal Activity against Fusarium oxysporum, and Three-Dimensional Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from 2-Amino Acids

2019

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“…Recently, the 2,4-dichloro phenoxy moiety was reported to have antifungal properties. 21 The 2,4-dichloro phenoxy side chain is considered to be a new moiety with promising antifungal activity and it was selected to be in the side chain of the proposed design.…”

Section: Resultsmentioning

confidence: 99%

Stepwise design, synthesis, and in vitro antifungal screening of (Z)-substituted-propenoic acid derivatives with potent broad-spectrum antifungal activity

Khedr¹

2015

DDDT

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Fungal infections are a main reason for the high mortality rate worldwide. It is a challenge to design selective antifungal agents with broad-spectrum activity. Lanosterol 14α-demethylase is an attractive target in the design of antifungal agents. Seven compounds were selected from a number of designed compounds using a rational docking study. These compounds were synthesized and evaluated for their antifungal activity. In silico study results showed the high binding affinity to lanosterol 14α-demethylase (−24.49 and −25.83 kcal/mol) for compounds V and VII, respectively; these values were greater than those for miconazole (−18.19 kcal/mol) and fluconazole (−16.08 kcal/mol). Compound V emerged as the most potent antifungal agent among all compounds with a half maximal inhibitory concentration of 7.01, 7.59, 7.25, 31.6, and 41.6 µg/mL against Candida albicans, Candida parapsilosis, Aspergillus niger, Trichophyton rubrum, and Trichophyton mentagrophytes, respectively. The antifungal activity for most of the synthesized compounds was more potent than that of miconazole and fluconazole.

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“…In our previous work [ 29 – 33 ], some 1,2,4-triazole compounds were designed and synthesized. They showed good antifungal activities.…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted Synthesis, Antifungal Activity, and DFT Study of Some Novel Triazolinone Derivatives

Sun

Jin

2015

BioMed Research International

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A series of some novel 1,2,4-triazol-5(4H)-one derivatives were designed and synthesized under microwave irradiation via multistep reaction. The structures of 1,2,4-triazoles were confirmed by 1H NMR, MS, FTIR, and elemental analysis. The antifungal activities of 1,2,4-triazoles were determined. The antifungal activity results indicated that the compounds 5c, 5f, and 5h exhibited good activity against Pythium ultimum, and the compounds 5b and 5c displayed good activity against Corynespora cassiicola. Theoretical calculation of the compound 5c was carried out with B3LYP/6-31G (d). The full geometry optimization was carried out using 6-31G(d) basis set, and the frontier orbital energy and electrostatic potential were discussed, and the structure-activity relationship was also studied.

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Design, Synthesis, Antifungal Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moiety

Cited by 14 publications

References 30 publications

Ultrasound-Assisted Synthesis, Antifungal Activity against Fusarium oxysporum, and Three-Dimensional Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from 2-Amino Acids

Ultrasound-Assisted Synthesis, Antifungal Activity against Fusarium oxysporum, and Three-Dimensional Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from 2-Amino Acids

Stepwise design, synthesis, and in vitro antifungal screening of (Z)-substituted-propenoic acid derivatives with potent broad-spectrum antifungal activity

Microwave Assisted Synthesis, Antifungal Activity, and DFT Study of Some Novel Triazolinone Derivatives

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