Ahmed Mahmood, Abdul Qadir Muhammad, Imtiaz Shafiq Muhammad, Muddassar Muhammad, Hameed Abdul, Nadeem Arshad Muhammad, Asiri Abdullah M
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Acta Pharm. 2017 Sep 1;67(3):385-395. doi: 10.1515/acph-2017-0023.
Curcumin is a natural product with enormous biological potential. In this study, curcumin synthesis was revisited using different reaction solvents, a catalyst (n-butylamine) and a water scavenger [(n-BuO)3B], to develop the optimal procedure for its rapid acquisition. During synthesis, solvent choice was found to be an important parameter for better curcumin yield and high purity. In a typical reaction, acetyl acetone was treated with boron trioxide, followed by condensation with vanillin in the presence of tri-n-butyl borate as water scavenger and n-butylamine as catalyst at 80 °C in ethyl acetate to afford curcumin. Moreover, curcumin was also extracted from turmeric powder and spectroscopic properties such as IR, MS, 1H NMR and 13C NMR with synthetic curcumin were established to identify any impurity. The purity of synthetic and extracted curcumin was also checked by TLC and HPLC-DAD. To computationally assess its therapeutic potential against cyclin dependent kinases (CDKs), curcumin was docked in different isoforms of CDKs. It was observed that it did not dock at the active sites of CDK2 and CDK6. However, it could enter into weak interactions with CDK4 protein.
姜黄素是一种具有巨大生物学潜力的天然产物。在本研究中，使用不同的反应溶剂、一种催化剂（正丁胺）和一种脱水剂[硼酸三丁酯]对姜黄素的合成进行了重新研究，以开发快速获得姜黄素的最佳方法。在合成过程中，发现溶剂的选择是获得更高姜黄素产率和高纯度的一个重要参数。在典型反应中，乙酰丙酮与三氧化硼反应，然后在硼酸三丁酯作为脱水剂和正丁胺作为催化剂存在下，于80℃在乙酸乙酯中与香草醛缩合得到姜黄素。此外，还从姜黄粉中提取了姜黄素，并确定了其红外光谱、质谱、1H核磁共振和13C核磁共振等光谱性质，以鉴定合成姜黄素中的任何杂质。合成姜黄素和提取姜黄素的纯度也通过薄层色谱法和高效液相色谱-二极管阵列检测法进行了检测。为了通过计算评估其对细胞周期蛋白依赖性激酶（CDK）的治疗潜力，将姜黄素与不同亚型的CDK进行了对接。结果发现，它不会与CDK2和CDK6的活性位点对接。然而，它可以与CDK4蛋白形成弱相互作用。
