Design, synthesis, and evaluation of unsymmetrical difluoro‐boron complexes with imidazoline as potential fungicides

Wang, Kewei; Cui, Jingnan; Xie, Lei; Qian, Xuhong

doi:10.1002/hc.20567

Cited by 4 publications

(2 citation statements)

References 23 publications

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“…In medicinal chemistry, boron compounds have great potential in drug discovery. These compounds have been reported in the literature as having potential biological activities [1][2][3][4][5]. Some of these are: heterocyclic aminoboron compounds (antituberculosis agents) [6], boron-containing GSK2251052 (antimicrobial agent) [7], oxaboroles (antibacterial prototypes) [8], α-amino cyclic boronates (inhibitors of HCV NS3 protease) [9], benzoxaboroles (anti-inflammatory agents) [10], boronic acid esters (antibacterial agents) [11], boron-containing thiosemicarbazones (antifungal agents) [12], organoboron derivatives (antimicrobial and antifertility activities) [13] and aryl boronate esters (antimicrobial agents) [14].…”

Section: Introductionmentioning

confidence: 99%

Crystal structure, 1H and 13C NMR spectral studies of 1,2,4,5-oxadiazaborole derivatives

Pir¹,

Ağirbaş²,

Şahın³

2019

Journal of Boron

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Substituent effects on 1 H and 13 C NMR chemical shifts of 5-substituted phenyl-3-phenyl-4,5-dihydro-1,2,4,5-oxadiazaboroles (1a-r) were studied respectively. Single and duel substituent parameters were used for the correlation analysis of substituent-induced chemical shifts with σ, F and R constants. The calculations have shown the polar and resonance substituent effects on N-H proton and C=N carbon atoms. The ρ value was found positive for compounds (1a-r), which means that the substituent effect is normal. Additionally, crystal structure of compound (1i) was also studied. Density functional theory (DFT) calculations were carried out to calculate the theoretical chemical shifts, bond distances and bond angles.

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Section: Introductionmentioning

confidence: 99%

Crystal structure, 1H and 13C NMR spectral studies of 1,2,4,5-oxadiazaborole derivatives

Pir¹,

Ağirbaş²,

Şahın³

2019

Journal of Boron

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“…Some biological activities of boron‐containing compounds are reported in the literature . Among these are heterocyclic aminoboron compounds (antituberculosis agent), boron‐containing GSK2251052 (antimicrobial agent), oxaborole compounds (antibacterial prototypes), α‐amino cyclic boronates (inhibitors of HCV NS3 protease), benzoxaborole compounds (anti‐inflammatory agent), boronic acid picolinate esters (antibacterial agent with anti‐inflammatory activity), boron‐containing thiosemicarbazones (antifungal agent), oxazaborolidines (antibacterial agent), difluoro‐boron complexes (potential fungicides) …”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, antimicrobial activity, and QSAR studies of some new 6‐substituted phenyl 3‐(4‐chlorophenyl)‐3a,4,8,8a‐tetrahydro‐[1,3,2]dioxaborepino [5,6‐d]isoxazoles

Pir

Ağirbaş

Budak

et al. 2017

Heteroatom Chemistry

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3‐(4‐Chlorophenyl)‐3a,4,8,8a‐tetrahydro‐[1,3,2]dioxaborepino[5,6‐d] isoxazoles were synthesized from the reaction of (3‐(4‐chlorophenyl)‐4,5‐dihydroisoxazole‐4,5‐diyl)dimethanol with substituted phenylboronic acids. Crystal structure of 1‐(4‐(3‐(4‐chlorophenyl)‐3a,4,8,8a‐tetrahydro‐[1,3,2]dioxaborepino[5,6‐d]isoxazol‐6‐yl)phenyl) ethanone was studied and the values of selected bond distances (Å), bond angles (°), and dihedral angles (°) were found in agreement with the calculated (DFT, B3LYP/6‐311++G(d,p)) values. Antimicrobial activity of these new compounds was also studied against a panel of microorganisms including Staphylococcus aureus, Enterococcus faecalis, Pseudomonas aeruginosa, Escherichia coli, Streptococcus mutans, and Candida albicans. Most of the dioxaborepines exhibited fair activities against these microorganisms. The pMIC values of the compounds were first correlated with Hammett polar substituent constant (σ) together with lipophilic constant (π) and statistically significant 2D correlations were obtained. In addition, the pMIC values of the compounds were correlated with some theoretical descriptors and fair 2D‐QSAR models with clogP, SAA, and μ as independent variables were obtained.

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ChemInform Abstract: Design, Synthesis, and Evaluation of Unsymmetrical Difluoro‐Boron Complexes with Imidazoline as Potential Fungicides.

et al. 2010

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Design, synthesis, and evaluation of unsymmetrical difluoro‐boron complexes with imidazoline as potential fungicides

Abstract: A series of unsymmetrical difluoroboron(BF 2 ) complexes with pyridine and imidazoline were synthesized by reaction of new chelating ligands (arylmethyl-imidazolidinylidene)-pyridin-2-ylamine with boron trifluoride diethyl etherate. All the ligands

Cited by 4 publications

References 23 publications

Crystal structure, 1H and 13C NMR spectral studies of 1,2,4,5-oxadiazaborole derivatives

Crystal structure, 1H and 13C NMR spectral studies of 1,2,4,5-oxadiazaborole derivatives

Synthesis, characterization, antimicrobial activity, and QSAR studies of some new 6‐substituted phenyl 3‐(4‐chlorophenyl)‐3a,4,8,8a‐tetrahydro‐[1,3,2]dioxaborepino [5,6‐d]isoxazoles

ChemInform Abstract: Design, Synthesis, and Evaluation of Unsymmetrical Difluoro‐Boron Complexes with Imidazoline as Potential Fungicides.

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