Lee San-Ha, Fei Xiang, Lee Chaelin, Do Hien Thi Thu, Rhee Inmoo, Seo Seung-Yong
College of Pharmacy, Gachon University.
Department of Bioscience and Biotechnology, Sejong University.
Chem Pharm Bull (Tokyo). 2019 Sep 1;67(9):966-976. doi: 10.1248/cpb.c19-00207. Epub 2019 Jun 28.
Honokiol, a biphenolic neolignan isolated from Magnolia officinalis, was reported to have a promising anti-inflammatory activity for the treatment of various diseases. There are many efforts on the synthesis and structure-activity relationship of honokiol derivatives. However, regioselective O-alkylation of honokiol remains a challenge and serves as a tool to provide not only some derivatives but also chemical probes for target identification and mode of action. In this study, we examined the reaction condition for regioselective O-alkylation, in which C2 and C4'-alkylated analogs of honokiol were synthesized and evaluated for inhibitory activity on nitric oxide production and cyclooxygenase-2 expression. Furthermore, we successfully synthesized a potential photoaffinity probe consisting of biotin and benzophenone based on a C4'-alkylated derivative.
厚朴酚是从厚朴中分离出的一种双酚型新木脂素，据报道它在治疗各种疾病方面具有良好的抗炎活性。人们对厚朴酚衍生物的合成及其构效关系进行了大量研究。然而，厚朴酚的区域选择性O-烷基化仍然是一个挑战，它不仅是提供一些衍生物的工具，也是用于靶点鉴定和作用模式研究的化学探针。在本研究中，我们考察了区域选择性O-烷基化的反应条件，合成了厚朴酚的C2和C4'-烷基化类似物，并评估了它们对一氧化氮生成和环氧合酶-2表达的抑制活性。此外，我们基于C4'-烷基化衍生物成功合成了一种由生物素和二苯甲酮组成的潜在光亲和探针。
