Abstract:A new potential pharmaceutical compound, 2-(4-dimethylaminophenyl)-5-fluoro-6-(morpholin-4-yl)-1H-benzimidazole (4) was synthesized. The effect of the pH value of aqueous solution on the absorption spectrum of compound 4 and its interaction with β-cyclodextrin (β-CD) were investigated by UV-Vis spectrum, steady-state fluorescence and time-resolved spectroscopic measurements. The results indicate that compound 4 mainly exists in neutral molecular state when pH value of the aqueous phase is above 7.0. In the pH range from 7.0 to 3.8 the neutral molecular state and protonated univalent cationic form coexist. As the pH value decreases, the content of univalent cationic form increases. When 2.76<pH<3.8, the protonated univalent cationic form is the predominant species. With further decrease of the pH value, the univalent cation is protonated by another H+ to form a bivalent cation,and both univalent and bivalent cations coexist in the solution. The steady-state fluorescence and time-resolved spectroscopic measurements revealed that compound 4 is a sensitive molecular probe. The interaction of compound 4 and β-CD is very strong. The guest: host ratio of inclusion complex between compound 4 and β-CD formed in the aqueous solution (pH=9.50) is 1∶1,and the association constant was determined to be (1.02±0.04)×103 mol·L-1.
唐凌天,王祥云,刘新起,王 毅* . 2-对二甲氨基苯基-5-氟-6-吗啉苯并咪唑的合成及其光谱学性质研究 [J]. 光谱学与光谱分析, 2004, 24(05): 588-591.
TANG Ling-tian, WANG Xiang-yun, LIU Xin-qi, WANG Yi* . Synthesis of 2-(4-Dimethylaminophenyl)-5-Fluoro-6-(Morpholin-4-yl)-1H-Benzimidazole and Its Spectroscopic Research . SPECTROSCOPY AND SPECTRAL ANALYSIS, 2004, 24(05): 588-591.
[1] WANG Jin-yi, ZHOU Jing, CHENG Dong-liang et al(王进义, 周 晶, 程东亮等). Chemical Journal of Chinese Universities(高等学校化学学报), 2000, 21(12): 1861. [2] El-Abadelah M M, Sabri S S, Abu Zarga M H et al. Heterocycles, 1995, 41(12): 2713. [3] Singh M P, Sasmal S, Lu Wei et al. Synthesis, 2000, 10: 1380. [4] Preston P N. Chem. Rev., 1974, 74: 279. [5] Lee J C, Field D J, Lee L L Y. Biochemistry, 1980, 19: 6209. [6] CHENG Cun-gui, Lü Tian-xi, CHEN Jiang-wei et al(程存归, 吕天喜, 陈江伟等). Chinese Journal of Pharmaceuticals(中华医药工业杂志), 2000, 31(2): 71. [7] HU Tao, LIU Yun, DAI Gui-yuan et al(胡 涛, 刘 蕴, 戴桂元等). J. Xuzhou Normal Univ. (Natural Science)(徐州师范大学学报(自然科学版)), 2002, 20(1): 57. [8] YANG Ri-fang, YUN Liu-hong, DING Zhen-kai et al(杨日芳, 恽榴红, 丁振凯等). Chinese Journal of Medical Chemistry(中华医药化学杂志), 2003, 13(1): 1. [9] Loontiens F G, Regenfuss P, Zechel A et al. Biochemistry, 1990, 29: 9029. [10] FU Yun-feng, SHEN Xing-hai, XU Bao-cai(付云峰, 沈兴海, 徐宝财). Acta Scientiarum Naturalium Universitatis Pekinensis(Natural Science)(北京大学学报(自然科学版)), 2002, 38(2): 164. [11] Shen Xinghai, Belletete Michel, Durocher Gilles. J. Phys. Chem. B, 1997,101: 8212.