大麻素代谢物的合成：阿居列米酸和HU - 210。
Syntheses of Cannabinoid Metabolites: Ajulemic Acid and HU-210.
作者信息
Shao Wenbin, Liao Pingyong, Zhang Xiaoyan, Fan Binbin, Chen Ruijia, Chen Xilong, Zhao Xuejun, Liu Wenbin
机构信息
Shanghai Key Laboratory of Crime Scene Evidence, Shanghai Research Institute of Criminal Science and Technology, Shanghai 200072, China.
Shanghai Yuansi Standard Science and Technology Co., Ltd., Shanghai 200072, China.
出版信息
Molecules. 2024 Jan 21;29(2):526. doi: 10.3390/molecules29020526.
Cannabinoid metabolites have been reported to be more potent than their parent compounds. Among them, ajulemic acid (AJA) is a side-chain analog of Δ-THC-11-oic acid, which would be a good template structure for the discovery of more potent analogues. Herein, we optimized the key allylic oxidation step to introduce the C-11 hydroxy group with a high yield. A series of compounds was prepared with this condition applied including HU-210, 11-nor-Δ-tetrahydrocannabinol (THC)-carboxylic acid and Δ-THC-carboxylic acid.
据报道，大麻素代谢物比其母体化合物更具活性。其中，阿朱勒米酸（AJA）是Δ-四氢大麻酚-11-酸的侧链类似物，它将是发现更具活性类似物的良好模板结构。在此，我们优化了关键的烯丙基氧化步骤，以高产率引入C-11羟基。在应用该条件下制备了一系列化合物，包括HU-210、11-去甲-Δ-四氢大麻酚（THC）-羧酸和Δ-四氢大麻酚-羧酸。
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