Masila Veronica M, Ndakala Albert J, Byamukama Robert, Midiwo Jacob O, Kamau Rahab W, Wang Mei, Kumarihamy Mallika, Zhao Jianping, Heydreich Matthias, Muhammad Ilias
Department of Chemistry, College of Natural and Applied Sciences, Makerere University, Kampala, Uganda.
Department of Chemistry, School of Physical Sciences, University of Nairobi, Nairobi, Kenya.
Nat Prod Res. 2021 Nov;35(21):3599-3607. doi: 10.1080/14786419.2020.1716346. Epub 2020 Jan 30.
In an attempt to synthesize carvotacetone analogues, new 3--benzyl-carvotacetone ( and previously reported 3-hydroxy-2-isopropyl-5-methyl--benzoquinone () were synthesized from piperitone (). In this work, we describe the synthesis of and other analogues from . Luche reduction of to -piperitol (, followed by benzylation yielded 3--benzyl-piperitol (). Riley oxidation of afforded corresponding ketone , and 3-benzyloxy-4-isopropylcyclohex-1-enecarbaldehyde (. Structures of these compounds were determined based on NMR, IR and LC-MS spectral data. Compound , exhibited antiplasmodial activities against chloroquine-sensitive (D6) and resistant (W2) strains of with IC value of 0.697 and 0.653µg/mL, respectively. In addition, compound was active against with an IC value of 3.11µg/mL, compared to reference standard fluconazole (IC value of 1.87µg/mL), while and were inactive against both organisms. This is the first report of the antiplasmodial and anticryptococcal activity of compound .
为了合成香芹酮类似物，从胡椒酮合成了新的3-苄基香芹酮（以及先前报道的3-羟基-2-异丙基-5-甲基苯醌（）。在这项工作中，我们描述了从合成和其他类似物的过程。将胡椒酮经卢奇还原为胡椒醇（，然后进行苄基化反应得到3-苄基胡椒醇（）。对进行赖利氧化反应得到相应的酮、以及3-苄氧基-4-异丙基环己-1-烯甲醛（）。这些化合物的结构通过核磁共振、红外光谱和液相色谱-质谱光谱数据确定。化合物对氯喹敏感（D6）和耐药（W2）的疟原虫菌株均表现出抗疟活性，其IC值分别为0.697和0.653μg/mL。此外，化合物对白色念珠菌有活性，IC值为3.11μg/mL，与参考标准氟康唑（IC值为1.87μg/mL）相比，而和对这两种微生物均无活性。这是关于化合物抗疟和抗隐球菌活性的首次报道。
