Synthesis, molecular structure investigations and antimicrobial activity of 2-thioxothiazolidin-4-one derivatives

被引:19
作者
Barakat, Assem [1 ,3 ]
Al-Najjar, Hany J. [1 ]
Al-Majid, Abdullah Mohammed [1 ]
Soliman, Saied M. [2 ,3 ]
Mabkhot, Yahia Nasser [1 ]
Al-Agamy, Mohamed H. M. [4 ,5 ]
Ghabbour, Hazem A. [6 ]
Fun, Hoong-Kun [6 ,7 ]
机构
[1] King Saud Univ, Coll Sci, Dept Chem, Riyadh 11451, Saudi Arabia
[2] King Abdulaziz Univ, Coll Arts & Sci, Dept Chem, Rabigh 21911, Saudi Arabia
[3] Univ Alexandria, Fac Sci, Dept Chem, Alexandria 21321, Egypt
[4] Al Azhar Univ, Fac Pharm, Dept Microbiol & Immunol, Cairo, Egypt
[5] King Saud Univ, Coll Pharm, Dept Pharmaceut, Div Microbiol, Riyadh 11451, Saudi Arabia
[6] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia
[7] Univ Sains Malaysia, Sch Phys, Xray Crystallog Unit, George Town 11800, Malaysia
关键词
Rhodanine; 2-Thioxothiazolidin-4-one; Anti-microbial activity; X-Ray; OFT studies; S229A MUTANT; WILD-TYPE; CHEMISTRY; EFFICIENT; MURB;
D O I
10.1016/j.molstruc.2014.10.038
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070305 [高分子化学与物理];
摘要
A variety of 2-thioxothiazolidin-4-one derivatives were prepared and their in vitro antimicrobial activities were studied. Most of these compounds showed significant antibacterial activity specifically against Gram-positive bacteria, among which compounds 4a,e,g, 5b,e,g,h and 6f exhibit high levels of antimicrobial activity against Bacillus subtilis ATCC 10400 with Minimum Inhibitory Concentration (MIC) value of 16 mu g/mL. All compounds have antifungal activity against Candida albicans. Unfortunately, however, none of the compounds were active against Gram-negative bacteria. The chemical structure of 3 was confirmed by X-ray single crystal diffraction technique. DFT calculations of 3 have been performed on the free C10H7Cl2NO2S2, 3a and the H-bonded complex, C10H7Cl2NO2S2 center dot H2O, 3b to explore the effect of the H-bonding interactions on the geometric and electronic properties of the studied systems. A small increase in bond length was observed in the C12-O6 due to the H-bonding interactions between 3a and water molecule. MEP study has been used to recognize the most reactive sites towards electrophilic and nucleophilic attacks as well as the possible sites for the H-bonding interactions. The TD-DFT calculations have been used to predict theoretically the electronic spectra of the studied compound. The most intense transition band is predicted at 283.9 nm due to the HOMO-2/HOMO-1 to LUMO transitions. NBO analyses were carried out to investigate the stabilization energy of the various intramolecular charge transfer interactions within the studied molecules. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:519 / 529
页数:11
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