pKa Determination of Newly Synthesized N-(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide Derivatives
pKa Determination of Newly Synthesized N-(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide Derivatives
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DOI：
10.1021/ie400316r
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发表时间：
2013-06
影响因子：
4.2
通讯作者：
M. Duran;M. Canbaz
中科院分区：
文献类型：
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作者：
M. Duran;M. Canbaz
本工作以4，5-二甲基-1-（苯胺基）-1H-咪唑-2（3 H）-乙酰胺衍生物和2-氯-N-（噻唑-2-基）乙酰胺化合物为原料，合成了9个新的药物前体化合物2-（4，5-二甲基-1-（苯胺基）-1H-咪唑-2-基硫基）-N-（苯并噻唑-2-基）乙酰胺衍生物。所合成的化合物的结构通过1H NMR、FTIR（傅里叶变换红外）、MS（质谱）和元素分析进行了确认。这些乙酰胺衍生物的酸度常数，通过紫外光谱研究确定。发现这些化合物的第一个质子化反应发生在咪唑环上的氮原子上，而第二个质子化反应发生在苯并噻唑环上的氮原子上。发现第一个PKa值在5.91和8.34之间变化，而第二个PKa值在3.02和4.72之间变化。
In this work, nine drug precursors, 2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)-N-(benzothiazole-2-yl) acetamide derivative compounds, were newly synthesized by reacting 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione derivatives with 2-chloro-N-(thiazol-2-yl) acetamide compounds. Structures of the synthesized compounds were confirmed by 1H NMR, FTIR (Fourier transform infrared), MS (mass spectroscopy), and elemental analysis. The acidity constants of these acetamide derivatives were determined via UV spectroscopic studies. It was found that the first protonation of these compounds occurs on the nitrogen at imidazole ring, while the second protonation of these compounds occurs on the nitrogen at benzothiazole ring. The first pKa values were found to vary between 5.91 and 8.34 while the second pKa values were varying between 3.02 and 4.72.