Synthesis, crystal structure and 3D-QSAR studies of antifungal (bis-)1,2,4-triazole Mannich bases containing furyl and substituted piperazine moieties

Zhang, Yan; Zhan, Yizhou; Ma, Yangmin; Hua, Xuewen; Wei, Wei; Zhang, Xiǎo; Song, Haibin; Li, Zhengming; Wang, Baolei

doi:10.1016/j.cclet.2017.08.035

Cited by 26 publications

(22 citation statements)

References 26 publications

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“…The inclusion of fluorine into organic molecules can affect the lipophilicity and thus enhance the rate of cell penetration and transport of a drug to an active site (Figure 2) [10][11][12][13]. Except addition of fluorine atom in the structure of some molecules for exerting antifungal activity, using piperazine moiety also led to emerging antifungal activities in some structures (Figure 3) [14][15][16][17][18][19]. With respect to above explanations and in continue of our efforts in design and synthesis of novel antimicrobial agents containing fluorine and piperazine substituents (Figure 4a), here in, we reported synthesis of a series of benzimidazole derivatives and their bioactivity as antifungal agents (Figure 4b).…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Bioactivity of Benzimidazole–2–Carbamates as Soil–Borne Anti–Fungal Agents †,‡

Al-Harthy

Al-Sadi

Zoghaib

et al. 2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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The design and synthesis of new, safe and potent molecules to apply against soil-borne pathogens is a critical goal for organic and bio-medicinal chemists. Herein, we designed and synthesized a series of benzimidazole-based carbamate derivatives (7a–f), as soil-borne anti-fungals. The derivatives 7a–f were all synthesized in multi-step reactions with acceptable yields. The structures of 7a–f were all identified and characterized using 1H-NMR, IR, HRMS, and melting point calculations. The final compounds were tested on five soil-borne pathogens. The results of various bio-assays showed that compounds 7a-3, 7a-2, 7b-2, 7a-1 and 7b-1 significantly affected the growth of Pythium aphanidermatum, a serious pathogen affecting vegetable crops worldwide. Compounds 7a-1 and 7b-1 were the most efficacious, which resulted in a 96% growth inhibition in Pythium at 100 mg L−1. In conclusion, we reported the potent carbamate derivatives as soil-borne anti-fungals, and believe that the synthesis of more derivatives related to the current scaffold would be beneficial.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Bioactivity of Benzimidazole–2–Carbamates as Soil–Borne Anti–Fungal Agents †,‡

Al-Harthy

Al-Sadi

Zoghaib

et al. 2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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“…1 The heterocyclic compounds possess extraordinary potential in organic chemistry, medicinal chemistry, pesticidal chemistry and other related areas. [2][3][4][5][6][7][8] It is reported that the structures of approximate 70% of the commercial pesticides produced in the last 20 years contain a heterocycle feature, 9 therefore studies of the synthesis and various biological properties of novel heterocyclic derivatives could result in further significant discoveries. As one kind of heterocyclic compound, N-pyridylpyrazole derivatives have received continuous attention in agrochemical research during the last decade.…”

Section: Introductionmentioning

confidence: 99%

“…Thousands of pesticides have been commercialized and exert their various important roles all over the world, but scientists still need to research and develop new agrochemicals owing to the environmental pollution and/or resistance issues of the pesticides available . The heterocyclic compounds possess extraordinary potential in organic chemistry, medicinal chemistry, pesticidal chemistry and other related areas . It is reported that the structures of approximate 70% of the commercial pesticides produced in the last 20 years contain a heterocycle feature, therefore studies of the synthesis and various biological properties of novel heterocyclic derivatives could result in further significant discoveries.…”

Section: Introductionmentioning

confidence: 99%

One‐pot synthesis, structure and structure–activity relationship of novel bioactive diphenyl/diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(arylamino)methylphosphonates

Wang

Zhu

et al. 2019

Pest Management Science

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BACKGROUND N‐Pyridylpyrazole derivatives have received continuous attention in agrochemical research during the last decade owing to their remarkable insecticidal or fungicidal potentials. To look for novel heterocyclic agrochemicals for increasing production of agriculture, a series of novel α‐aminophosphonate derivatives containing N‐pyridylpyrazole moiety were synthesized. RESULTS The structures of the title compounds were confirmed via melting point, IR, 1H NMR, 13C NMR, 31P NMR, HRMS and elemental analysis. The single crystal structure of diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(2,6‐dimethylphenylamino)methylphosphonate (compound 12b) was first reported. Moreover, the bioassays displayed that the title compounds exhibited modest or weak insecticidal activities against oriental armyworm at 200 μg mL−1. The first investigation on the fungicidal potential of chlorantraniliprole showed no significant activities towards the six tested fungi found in this study, however, most of the title compounds displayed apparent in vitro fungicidal activity against some plant fungi, in particular excellent activities towards Physalospora piricola. Compounds 11a and 11b had EC50 values of 18.8 and 17.4 μg mL−1, respectively, which were comparable with that of fungicide control triadimefon (EC50 = 24.7 μg mL−1) against Physalospora piricola. In addition, some compounds exhibited modest in vivo control efficacy at 0.5 mg mL−1 towards Sclerotinia sclerotiorum (11b: 30.1(±1.8)%), Rhizoctonia cerealis (11a: 20.4(±2.1)%; 11b: 30.2(±2.2)%), and Erysiphe graminis (11a: 30.3(±1.8)%; 12d: 40.2(±0.9)%). CONCLUSION Compounds 11a, 11b and 12d could be promising new lead structures for the development and discovery of novel fungicides towards Physalospora piricola and Erysiphe graminis. The structure‐activity relationship (SAR) analysis provided useful guidance and new understanding for the design of novel pyridylpyrazole‐containing agrochemicals. © 2019 Society of Chemical Industry

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“…The chemistry of 1,2,4-triazoles and their fused heterocyclic compounds has been attracting widespread attention due to their synthetic utility as agricultural [2] and industrial applications [3]. Also, many pharmaceutical drugs consist from a number of 1,2,4-triazole rings, including anticancer [4], anti-inflammatory [5], antimicrobial [6], analgesic [7], antiviral [8], antifungal [9], antibacterial [10] and anticonvulsant agent [11] such as Alprazolam, Anastrazole, Voriconazole, Estazolam (tranquilizer hypnotic, sedative) , Fluconazole, Itraconazole, Trazodone, Propiconazole, Myclobutanil, Triazolam, Tebuconazole, Trazodone (antidepressant, anxiolytic), Terconazole, Ribavirin, and Rizatriptan [12]. Furthermore, biheterocyclic compounds such as 1,2,4-triazole ring fused to other heterocyclic rings are as antimicrobial agents [13,14].…”

Section: Introductionmentioning

confidence: 99%

“…for C 18 H 13 BrN 4 S: C: 54.40, H: 3.27, N: 14.10, Br: 19.89, S: 8.06 %. Found: C: 54.38, H: 3.25, N: 14.11, Br: 19.88, S: 8.04 %.2.2.7General procedure for synthesis of 1,2,4-triazole-1,2,3-triazole(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)…”

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confidence: 99%

A Facile Synthesis and Biological Evaluation of New Bis-Triazole Compounds

2019

IJBPAS

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New 1,2,4-triazole and 1,2,3-triazole as bis heterocyclic were synthesized using click chemistry approach. The chemical structures of the new triazolo compounds were confirmed by spectroscopic (IR), 1 H-NMR, 13 C-NMR, mass spectrometry (MS) and elemental analysis techniques. The antibacterial and antifungal activities of the new compounds have been evaluated. Some gram positive and gram negative bacterial strains were sensitive against some tested compounds. The compounds 7, 10 and 20 were active against most of the tested bacterial strains. Compound 10 showed highest activity among the series of tested compounds than the standard drug amoxicillin against S.a: Staphylococcus aureus, S.e: Staphylococcus Epidermidis and P.m: Proteus Merabilis. Also, compound 11, 12 and 18 were active against all the tested gram positive bacterial strains whereas inactive towards the tested gram negative bacterial strains. The five compounds 7, 10, 12, 18 and 20 were active against the candida albicans.

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Synthesis, crystal structure and 3D-QSAR studies of antifungal (bis-)1,2,4-triazole Mannich bases containing furyl and substituted piperazine moieties

Cited by 26 publications

References 26 publications

Design, Synthesis and Bioactivity of Benzimidazole–2–Carbamates as Soil–Borne Anti–Fungal Agents †,‡

Design, Synthesis and Bioactivity of Benzimidazole–2–Carbamates as Soil–Borne Anti–Fungal Agents †,‡

One‐pot synthesis, structure and structure–activity relationship of novel bioactive diphenyl/diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(arylamino)methylphosphonates

A Facile Synthesis and Biological Evaluation of New Bis-Triazole Compounds

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