Synthesis, antimicrobial activity and 3D-QSAR study of novel 5-substituted-1,3,4-thiadiazole Schiff base derivatives

Lou, Jiayu; Wang, Huashan; Wang, Sanyan; Han, Jian; Wang, Meiyi

doi:10.1016/j.molstruc.2022.133629

Cited by 12 publications

(13 citation statements)

References 25 publications

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“…We synthesized novel benzimidazole−1,3,4-thiadiazole hybrid compounds, and their chemical structures were elucidated by 1 H and 13 C NMR, HRMS, and elemental analysis. The antimicrobial activities of the new compounds were tested against E. coli, S. marcescens, K. pneumoniae, P. aeruginosa, E. faecalis, B. subtilis, S. aureus, and four Candida species in vitro.…”

Section: Discussionmentioning

confidence: 99%

“…The biological activities of molecules containing triazole or thiadiazole are very diverse. Because of the variety of biological activities, 1,3,4 thiadiazole is one of the most beneficial isomeric forms. − The 1,3,4-thiadiazole structure is one of the most significant and well-known heterocycles, which is a common and complementary advantage of a range of pharmaceutical and natural substances. The thiadiazole ring is present as a key component in an assemblage of pharmacological categories because 1,3,4-thiadiazole derivatives have a wide range of biological activities, including antimicrobial, antiviral, anti-inflammatory, and analgesic, and anticancer activity …”

Section: Introductionmentioning

confidence: 99%

“…Benzimidazole−thiadiazole derivatives were prepared in five steps. The synthesized thiadiazoles were characterized by 1 H and 13 C NMR spectroscopy, high-resolution mass spectrometry (HRMS), and elemental analysis and studied as antimicrobial agents against bacterial and fungal species. In addition, molecular docking studies were performed with 14-α demethylase (CYP51) of Candida.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Molecular Docking, Dynamics, Quantum-Chemical Computation, and Antimicrobial Activity Studies of Some New Benzimidazole–Thiadiazole Hybrids

et al. 2022

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In this study, some new compounds, which are 2aminothiadiazole derivatives linked by a phenyl bridge to the 2position of the benzimidazole ring, were designed and synthesized as antimicrobial agents. The structures of the compounds were elucidated by 1 H and 13 C NMR spectroscopy, high-resolution mass spectrometry, and elemental analysis. The antifungal activities of the synthesized compounds were tested on Candida albicans, Candida krusei, Candida glabrata, and Candida parapsilosis. Compound 5f is more active against C. albicans and C. glabrata than standard fluconazole and varicanazole. Compounds were also evaluated for their counteracting activity against Gram-positive Escherichia coli, Serratia marcescens, Klebsiella pneumoniae, and Pseudomonas aeruginosa and Gram-negative Enterococcus faecalis, Bacillus subtilis, and Staphylococcus aureus. Compounds 5c and 5h had minimum inhibitory concentrations against E. faecalis close to that of the standard azithromycin. Molecular docking studies were performed against Candida species' 14-α demethylase enzyme. 5f was the most active compound against Candida species, which gave the highest docking interaction energy. The stabilities of compounds 5c and 5f with CYP51 were tested using 100 ns molecular dynamics simulations. According to the theoretical ADME calculations, the profiles of the compounds are suitable in terms of limiting rules. HOMO−LUMO analysis showed that 5h is chemically more reactive (represented with the lower ΔE = 3.432 eV) than the other molecules, which is compatible with the highest antibacterial activity result.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Molecular Docking, Dynamics, Quantum-Chemical Computation, and Antimicrobial Activity Studies of Some New Benzimidazole–Thiadiazole Hybrids

et al. 2022

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“…Schiff base, a class of compounds with imine groups (-CH=N-), is a common pharmacological group in many compounds, which has a wide range of biological activities [ 59 , 60 ]. The introduction of Schiff bases into 1,3,4-thiadiazoleis is interesting to study, and the 1,3,4-thiadiazole Schiff base derivatives also have biological activities [ 61 , 62 ]. For example, compound V in Figure 2 were found to exhibit obvious fungicidal activity [ 63 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

et al. 2022

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A series of novel indole Schiff base derivatives (2a–2t) containing a 1,3,4-thiadiazole scaffold modified with a thioether group were synthesized, and their structures were confirmed using FT-IR, 1H NMR, 13C NMR, and HR-MS. In addition, the antifungal activity of synthesized indole derivatives was investigated against Fusarium graminearum (F. graminearum), Fusarium oxysporum (F. oxysporum), Fusariummoniliforme (F.moniliforme), Curvularia lunata (C. lunata), and Phytophthora parasitica var. nicotiana (P. p. var. nicotianae) using the mycelium growth rate method. Among the synthesized indole derivatives, compound 2j showed the highest inhibition rates of 100%, 95.7%, 89%, and 76.5% at a concentration of 500 μg/mL against F. graminearum, F. oxysporum, F.moniliforme, and P. p. var. nicotianae, respectively. Similarly, compounds 2j and 2q exhibited higher inhibition rates of 81.9% and 83.7% at a concentration of 500 μg/mL against C. lunata. In addition, compound 2j has been recognized as a potential compound for further investigation in the field of fungicides.

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“…Schiff base, a class of compounds with imine groups (-CH=N-), is a common pharmacological group in many compounds, which has a wide range of antifungal [59][60], antibacterial [61][62] and other biological activities [63]. The introduction of Schiff bases into 1,3,4-thiadiazoleis an interesting study and the 1,3,4-thiadiazole Schiff base derivatives also have biological activities [64][65]. For example, Compounds Ⅴand Ⅵ in Figure 2 were found exhibiting obvious fungicidal activity [66][67].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

Wang¹,

Fan²,

Pan³

et al. 2022

Preprint

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A series of novel indole Schiff base derivatives (2a–2t) containing a 1,3,4-thiadiazole scaffold modified with a thioether group were synthesized, and their structures were confirmed using Fourier transformed-infrared spectroscopy (FT-IR), proton nuclear magnetic resonance spectroscopy (1H NMR), carbon nuclear magnetic resonance spectroscopy (13C NMR), and high resolution-mass spectroscopy (HR-MS). In addition, the antifungal activity of synthesized indole derivatives was investigated against Fusarium graminearum (F. graminearum), Fusarium oxysporum (F. oxysporum), Fusarium moniliforme (F. moniliforme), Curvularia lunata (C. lunata), and Phytophthora parasitica var. nicotiana (P. p. var. nicotianae) using the mycelium growth rate method. Among the synthesized indole derivatives, compound 2j showed the highest inhibition rates of 100%, 95.7%, 89%, and 76.5% at a concentration of 500 μg/mL against F. graminearum, F. oxysporum, F. moniliforme, and P. p. var. nicotianae, respectively. Similarly, compounds 2j and 2q exhibited higher inhibition rates of 81.9% and 83.7% at a concentration of 500 μg/mL against C. lunata. In addition, compound 2j has been recognized as a potential compound for further investigation in the field of fungicides.

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Synthesis, antimicrobial activity and 3D-QSAR study of novel 5-substituted-1,3,4-thiadiazole Schiff base derivatives

Cited by 12 publications

References 25 publications

Synthesis, Molecular Docking, Dynamics, Quantum-Chemical Computation, and Antimicrobial Activity Studies of Some New Benzimidazole–Thiadiazole Hybrids

Synthesis, Molecular Docking, Dynamics, Quantum-Chemical Computation, and Antimicrobial Activity Studies of Some New Benzimidazole–Thiadiazole Hybrids

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

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