Synthesis, crystal structure, biological activity and theoretical calculations of novel isoxazole derivatives

Jin, Ruyi; Sun, Xiaohong; Liu, Y.F.; Long, Wei; Chen, B.; Shen, Sa-Sa; Ma, Huijun

doi:10.1016/j.saa.2015.07.057

Cited by 19 publications

(7 citation statements)

References 22 publications

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“…And, the results of spectral analysis were compared with computed molecular geometric parameters, vibrational frequencies, 1 H-NMR and 13 C-NMR chemical shifts. The theoretical geometric structure parameters such as bond lengths and angles, computed frequencies and chemical shifts values are in compliance with experimental values and similar papers or other isoxazole studies [8,23,26,30,31]. And also, electronic absorption spectrum analysis of the (3) compound was examined both experimental and with TD-DFT/B3LYP/6-311G(d,p)/CPCM methods in gas phase and different solvent media such as DMSO, THF and MeOH.…”

Section: Molecular Electrostatic Potential Analysissupporting

confidence: 66%

The Investigation of Spectroscopic and Theoretical Methods of Bisisoxaoline Derivative of Norbornadien

Eryılmaz¹,

Mesci²,

Gül³

et al. 2016

ANADOLU UNIVERSITY JOURNAL OF SCIENCE AND TECHNOLOGY a - Applied Sciences and Engineering

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In this study, the synthesis of bisisoxaoline derivative of norbornadien from heterocyclic compounds was performed via 1,3-dipolar cycloaddition reaction, the structural properties of derivative characterized by spectroscopic analysis such as FT-IR, 1 H-NMR, 13 C-NMR, UV-Vis and the single-crystal X-ray diffraction technique. The 3,4,4a,7a,8,diisoxazole compound was optimized using Density Functional Theory (DFT/B3LYP) method with 6-311G(d,p) basis set in the ground state and the geometric parameters compared with single-crystal X-ray diffraction technique. The compound crystallizes in the monoclinic space group C2/c with a = 20.634(4) Å, b = 11.179(2) Å, c = 11.0690(17) Å and Z = 4 unit cell parameters. Also, the spectral results were examined with calculated vibrational frequencies, 1 H-NMR, 13 C-NMR chemical shift values and absorption wavelengths, theoretically. The energetic behaviour of the compound in different solvent media was examined with TD-DFT/B3LYP method and 6-311G(d,p) basis set using the Conductor Polarizable Continuum Model (CPCM). The frontier molecular orbitals (FMOs), molecular electrostatic potential (MEP) and electronic structure parameters (dipole moment, electronegativity, chemical hardness-softness, ionization potential, electron affinity, etc.) were examined to get information about the chemical stability of the structure.

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Section: Molecular Electrostatic Potential Analysissupporting

confidence: 66%

The Investigation of Spectroscopic and Theoretical Methods of Bisisoxaoline Derivative of Norbornadien

Eryılmaz¹,

Mesci²,

Gül³

et al. 2016

ANADOLU UNIVERSITY JOURNAL OF SCIENCE AND TECHNOLOGY a - Applied Sciences and Engineering

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“…Some of them marketed as therapeutic agents such as valdecoxib, cloxacillin, andleflunomide (Figure ) . Many other isoxazole derivatives have been developed asmarket products such as isoxaflutole, hymexazol, sulfafurazole and leflunomide . Also, isoxazoles have applications in functional materials, such as liquid crystalline compounds and exhibit GABAA antagonist,and antinociceptive .…”

Section: Introductionmentioning

confidence: 99%

PhI(OAc)₂‐Mediated One‐Pot Synthesis and their Antibacterial Activity of Flavone and Coumarin Based Isoxazoles Under Mild Reaction Conditions

et al. 2019

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A facile synthetic method of flavone and coumarin based isoxazoles, and tri‐substituted isoxazoles is reported using aromatic aldehydes, hydroxylamine hydrochloride and O‐propargyl flavones/coumarin, and internal acetylene via one‐pot condensation and subsequent [3+2] cycloaddition in the presence of phenyliodinediacetate (PIDA) under mild reaction conditions. This methodology is also successfully applied for O‐propargyl flavone containing heterocyclic ring such as furan and thiophene. One‐pot, high yields (90‐75%), shorter reaction time, easy work‐up and purification by recrystallization are the key advantages of our protocol. All synthesized compounds were tested for antibacterial activity, showed MICconcentration ≥ 1024μg/mL, and compared with standard drugs concentration. MICs data revealed high values against all tested antibiotics which were found in the range of 4 ≥ 4,096 μg mL−1.

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“…In the area of medicinal chemistry, five-membered heterocyclic compounds, especially heterocycles having more than one hetero atom, have shown a diverse range of biological activities. Among them, thiazolidinone, which bears a sulfur atom at 1-position, a nitrogen atom at 3-position and a carbonyl group at 2-, 4-, or 5-positions, has received a great deal of attention over the years since it is a significant and versatile moiety that has occupied a prominent position in medicinal chemistry [15,16,17,18,19,20,21,22,23,24]. Derivatives containing a thiazolidinone moiety have demonstrated a wide range of pharmacological properties, including anti-HIV, anti-malarial, anti-inflammatory and hypoglycaemic activities [25,26,27].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking Analysis, and Carbonic Anhydrase Inhibitory Evaluations of Benzenesulfonamide Derivatives Containing Thiazolidinone

Zhang

Yin

et al. 2019

Molecules

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To find novel human carbonic anhydrase (hCA) inhibitors, we synthesized thirteen compounds by combining thiazolidinone with benzenesulfonamide. The result of the X-ray single-crystal diffraction experiment confirmed the configuration of this class of compounds. The enzyme inhibition assays against hCA II and IX showed desirable potency profiles, as effective as the positive controls. The docking studies revealed that compounds (2) and (7) efficiently bound in the active site cavity of hCA IX by forming sufficient interactions with active site residues. The fragment of thiazolidinone played an important role in the binding of the molecules to the active site.

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Synthesis, crystal structure, biological activity and theoretical calculations of novel isoxazole derivatives

Cited by 19 publications

References 22 publications

The Investigation of Spectroscopic and Theoretical Methods of Bisisoxaoline Derivative of Norbornadien

The Investigation of Spectroscopic and Theoretical Methods of Bisisoxaoline Derivative of Norbornadien

PhI(OAc)₂‐Mediated One‐Pot Synthesis and their Antibacterial Activity of Flavone and Coumarin Based Isoxazoles Under Mild Reaction Conditions

Synthesis, Molecular Docking Analysis, and Carbonic Anhydrase Inhibitory Evaluations of Benzenesulfonamide Derivatives Containing Thiazolidinone

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Synthesis, crystal structure, biological activity and theoretical calculations of novel isoxazole derivatives

Cited by 19 publications

References 22 publications

The Investigation of Spectroscopic and Theoretical Methods of Bisisoxaoline Derivative of Norbornadien

The Investigation of Spectroscopic and Theoretical Methods of Bisisoxaoline Derivative of Norbornadien

PhI(OAc)2‐Mediated One‐Pot Synthesis and their Antibacterial Activity of Flavone and Coumarin Based Isoxazoles Under Mild Reaction Conditions

Synthesis, Molecular Docking Analysis, and Carbonic Anhydrase Inhibitory Evaluations of Benzenesulfonamide Derivatives Containing Thiazolidinone

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PhI(OAc)₂‐Mediated One‐Pot Synthesis and their Antibacterial Activity of Flavone and Coumarin Based Isoxazoles Under Mild Reaction Conditions