Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: Preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core
Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: Preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core
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DOI：
10.1016/j.bmcl.2012.10.019
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发表时间：
2012-12-15
影响因子：
2.7
通讯作者：
Naik, Nagaraja
中科院分区：
文献类型：
--
作者：
Harini, Salakatte Thammaiah;Kumar, Honnaiah Vijay;Naik, Nagaraja
以香兰素、丙酮和乙酸铵为原料，经Mannich反应、N-甲基化和肟化四步反应，合成了香草醛衍生物2，6-bis(4-hydroxy-3-methoxyphenyl)-piperidin-4-one-2(5a-m)。进一步地，为了提高香兰素衍生的哌啶-4-酮肟的生物活性，4与取代的苯甲酰氯在强碱t-BuOK存在下进行酯化反应，合成了一系列香兰素衍生的哌啶-4-酮肟酯(5a-m)。对合成的类似物进行了抗氧化性和抗菌活性的筛选，证明了苯酯取代基对哌啶-4-酮肟核的生物活性有明显的影响。在所测试的化合物中，5I和5J的抗氧化性优于标准的丁基羟基苯甲醚(BHA)，而5b和5d的抗菌活性和抗真菌活性分别强于标准的链霉素和氟康唑。(C)2012爱思唯尔有限公司。保留所有权利。
The study has been achieved the efficient synthesis of vanillin derived piperidin-4-one oxime esters (5a-m) via four step reaction involved Mannich reaction of vanillin, acetone and ammonium acetate to obtain 2,6-bis(4-hydroxy-3-methoxyphenyl)-piperidin-4-one 2 followed by N-methylation and oximation. Further, to enhance the biological activity of vanillin derived piperidin-4-one oxime core, esterification of 4 with substituted benzoyl chlorides in the presence of strong organic base t-BuOK accomplished a series of vanillin derived piperidin-4-one oxime esters (5a-m). The synthesized analogues are screened for their antioxidant and antimicrobial studies and the preponderant effect of the phenyl ester substituents on the biological activity of piperidin-4-one oxime core was demonstrated. Among the tested compounds, 5i and 5j are emerged as outperformed antioxidants than standard Butylated hydroxy anisole (BHA) whereas, compounds 5b and 5d manifested potent antibacterial and antifungal activity than standard streptomycin and fluconazole respectively. (C) 2012 Elsevier Ltd. All rights reserved.