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Synthetic Transformations of Higher Terpenoids. 40. Synthesis and Assessment of Analgesic Activity of N-Containing Derivatives of Lambertianic Acid
Chemistry of Natural Compounds ( IF 0.8 ) Pub Date : 2021-09-22 , DOI: 10.1007/s10600-021-03502-y
Yu. V. Kharitonov 1 , E. E. Shul’ts 1 , T. V. Rybalova 1 , A. V. Pavlova 1 , T. G. Tolstikova 1
Affiliation  

New labdanoid derivatives containing hydrophilic substituents (amino, methylamino) in the C-4 position were synthesized via selective transformations of lambertianic acid chloride. A one-pot method was proposed to prepare 16-formyllambertianic acid amide and included selective formylation of lambertianic acid by POCl3 in DMF followed by amidation by aqueous NH4OH. The molecular structure of the compound was studied by an X-ray crystal structure analysis. Analgesic activity in a chemical irritation model was found for newly synthesized 4-amino-18-nor-15,16-epoxylabda-8(17),13,14-triene and 4-(pyrrolidin-1-yl)-18-nor-15,16-epoxylabda-8(17),13,14-triene oxalates and 16-hydroxymethyl)lambertianic acid amide.



中文翻译:

高级萜类化合物的合成转化。40. 朗伯酸含氮衍生物镇痛活性的合成与评价

通过朗伯坦酰氯的选择性转化,合成了在 C-4 位含有亲水性取代基(氨基、甲氨基)的新型劳丹脂衍生物。提出了一种一锅法来制备 16-甲酰基琥珀酸酰胺,包括在 DMF中通过 POCl 3对朗伯酸进行选择性甲酰化,然后通过 NH 4 OH水溶液进行酰胺化。通过X射线晶体结构分析研究了该化合物的分子结构。在化学刺激模型中发现了新合成的 4-amino-18-nor-15,16-epoxylabda-8(17),13,14-triene 和 4-(pyrrolidin-1-yl)-18-nor 的镇痛活性-15,16-epoxylabda-8(17),13,14-triene 草酸盐和 16-羟甲基)lambertianic 酰胺。

更新日期:2021-09-23
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