Synthesis, Characterization, Biological Activity and Interaction with Bovine Serum Albumin of 8- or 6-(3-Chlorobenzoyl)coumarin Derivatives

doi:10.7503/cjcu20120666

Chem. J. Chinese Universities ›› 2013, Vol. 34 ›› Issue (2): 364.doi: 10.7503/cjcu20120666

• Organic Chemistry • Previous Articles Next Articles

Synthesis, Characterization, Biological Activity and Interaction with Bovine Serum Albumin of 8- or 6-(3-Chlorobenzoyl)coumarin Derivatives

YANG Shu-Ping¹, HAN Li-Jun², PAN Yan³, WANG Da-Qi⁴, WANG Nan-Nan¹, WANG Ting¹

1. School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, China;
2. School of Mathematics and Science, Huaihai Institute of Technology, Lianyungang 222005, China;
3. Department of Pharmacology, School of Basic Medical Sciences, Peking University and State Key Laboratory of Natural and Biomimetic Drugs, Beijing 100191, China;
4. School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, China

Received:2012-08-07 Online:2013-02-10 Published:2013-01-21

Abstract

Abstract:

Two new compounds, 4-methyl-7-hydroxy-8-(3-chlorobenzoyl)coumarin(1) and 4-methyl-7-hydroxy-6-(3-chlorobenzoyl)coumarin(2), were synthesized and characterized by elemental analysis, infrared spectra, ¹H NMR and single crystal X-ray diffraction methods. The crystals of compounds 1 and 2 belong to monoclinic system with space group P2₁/c, compound 1: a=1.21527(14) nm, b=1.01550(12) nm, c=1.5045(2) nm, β=112.377(2)°, V=1.7169(4) nm³, D_c=1.396 g/cm³, Z=4, F(000)=752, R₁=0.0415, wR₂=0.0981[I>2σ(I)], S=1.063; compound 2: a=2.0168(2) nm, b=0 .76229(12) nm, c=2.25497(17) nm, β=123.987(6)° , V=0.8745(6) nm³, D_c=1.454 g/cm³, Z=8, F(000)=1296, R₁=0.0604, wR₂=0.1384[I>2σ(I)], S=0.948. The results of antibacterial experiment showed that the title compounds had the activity for inhibiting growth of E. coli, B. subtilis and S. aureus. The antioxidation acti-vity of the title compounds were investigated by the O₂^-·, DPPH· and ·OH methods. The results showed that the title compounds had strong antioxidation activity. The interactions of title compounds and bovine serum albumin(BSA) were investigated by fluorescence spectroscopy at different temperatures. The results indicated that the title compounds caused the fluorescence quenching of BSA through a static quenching procedure. The corresponding thermodynamic parameters enthalpy change(ΔH), entropy change(ΔS), Gibbs free energy change(ΔG), between the title compounds and BSA were calculated. The interaction between the compound 1(ΔH>0, ΔS>0, ΔG<0) and BSA was driven mainly by hydrophobic force, whereas the interaction between compound 2(ΔH<0, ΔS<0, ΔG<0) and BSA was driven mainly by hydrogen bond force or van der Waals force. The binding average distance r between the donor(BSA) and acceptors(compounds 1 and 2) were obtained to be 2.59 and 2.38 nm, respectively, based on the Föster's theory, which indicate the energy transfer can occur from BSA to title compounds with high probability.

Key words: 4-Methyl-7-hydroxy-8- or 6-(3-chlorobenzoyl)coumarin, Crystal structure, Antibacterial activity, Antioxidation activity, Bovine serum albumin

CLC Number:

O626.3

TrendMD:

YANG Shu-Ping, HAN Li-Jun, PAN Yan, WANG Da-Qi, WANG Nan-Nan, WANG Ting. Synthesis, Characterization, Biological Activity and Interaction with Bovine Serum Albumin of 8- or 6-(3-Chlorobenzoyl)coumarin Derivatives[J]. Chem. J. Chinese Universities, 2013, 34(2): 364.

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Synthesis, Characterization, Biological Activity and Interaction with Bovine Serum Albumin of 8- or 6-(3-Chlorobenzoyl)coumarin Derivatives

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