El-Sayed Hassan A, Moustafa Ahmed H, Haikal Abd El-Fattah Z, Abu-El-Halawa Rajab, El Ashry El Sayed H
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt.
Eur J Med Chem. 2011 Jul;46(7):2948-54. doi: 10.1016/j.ejmech.2011.04.019. Epub 2011 Apr 15.
4-(4-Chlorophenyl)-3-cyano-6-(thien-2-yl)-1H-pyridin-2-one (2) was obtained by reaction of 2-acetyl thiophene with 4-chlorobenzaldehyde and ethyl cyanoacetate in presence of ammonium acetate or by the reaction of α,β-unsaturated compound 1 with ethyl cyanoacetate in the presence of ammonium acetate. 4-(4-Chlorophenyl)-2-(2',3',4',6'-tetra-O-acetyl-β-d-gluco/galactopyranosyloxy)-6-(thien-2-yl)nicotinonitrile (5a and 5b), riboside 11, xyloside 12 and lactoside 16 were prepared by the reaction of 2 with glycosyl/galactosyl/xylosyl/lactosyl bromide and peracetylated xylose/ribose under the conventional and microwave irradiation methods. The reaction has regioselectively gave the O-glycosides and not the N-glycosides. The glycosides 5a,b, riboside 11, xyloside 12 and lactoside 16 were deacetylated in the presence of Et(3)N/MeOH and few drops of water to give 7a,b, 13, 14 and 17. The structure of the new synthesized compounds was confirmed by using IR, (1)H, (13)C NMR spectra and microanalysis. Selected members of these compounds were screened for antitumor and antibacterial activity.
4-(4-氯苯基)-3-氰基-6-(噻吩-2-基)-1H-吡啶-2-酮(2)是通过2-乙酰基噻吩与4-氯苯甲醛和氰基乙酸乙酯在乙酸铵存在下反应制得的，或者是通过α,β-不饱和化合物1与氰基乙酸乙酯在乙酸铵存在下反应制得的。4-(4-氯苯基)-2-(2',3',4',6'-四-O-乙酰基-β-D-葡萄糖/吡喃半乳糖氧基)-6-(噻吩-2-基)烟腈(5a和5b)、核糖苷11、木糖苷12和乳糖苷16是通过2与糖基/半乳糖基/木糖基/乳糖基溴以及全乙酰化木糖/核糖在常规方法和微波辐射方法下反应制备的。该反应区域选择性地生成了O-糖苷而非N-糖苷。糖苷5a、b、核糖苷11、木糖苷12和乳糖苷16在Et(3)N/MeOH和几滴水中脱乙酰化得到7a、b、13、14和17。通过红外光谱、(1)H、(13)C核磁共振光谱和微量分析确定了新合成化合物的结构。对这些化合物的选定成员进行了抗肿瘤和抗菌活性筛选。
