24697-74-3Relevant articles and documents
Leonurine, an improved synthesis
Cheng,Yip,Yeung,Kong
, p. 571 - 572 (1979)
The uterotonic principle of Leonurus artemisia, a plant leaf, is leonurine. This paper reports the development of a simple, high-yield synthetic procedure of reproducing leonurine that is adaptable to large-scale preparation. The synthetic process includes condensation of syringic acid and 4-guanidino-1-butanol hydrochloride in the presence of dicyclohexylcarbodiimide, using 1:1 hexamethylphosphoric triamide-ethyl ether as solvent. Synthetic leonourine showed uterotonic activity in vitro and in vivo, just like its naturally occurring counterpart.
Design and synthesis of novel SCM-198 analogs as cardioprotective agents: Structure-activity relationship studies and biological evaluations
Liu, Junkai,Luo, Shanshan,Ma, Fenfen,Xu, Shengtao,Zhu, Yi Zhun
, (2020/06/03)
SCM-198 (Leonurine) has attracted great attention due to its cardioprotective effects in myocardial infarction (MI). However, no systematic modifications and structure-activity relationship (SAR) studies could be traced so far. In this study, 35 analogs of SCM-198 were designed, synthesized and their cardioprotective effects were evaluated. The cell viability assay on cardiomyocyte cell line H9c2 challenged with H2O2 showed that several analogs exhibited more potent cytoprotective effects than SCM-198 at 1 μM and 10 μM concentrations. LDH release level in cells treated with 1 μM 14o was comparable with cells treated with 10 μM SCM-198. Results of Bcl-2 expression and caspase-3 activation accordingly indicated higher protective activity of 14o than SCM-198. Moreover, in a mouse model of MI, the mice pretreated with 14o had much lower infarct size compared with that of SCM-198. The mechanism study suggested that 14o improved cardiac morphology and reduced apoptosis of cardiomyocytes in the border zone of infarction, as proved by H&E and TUNEL staining.
Synthetic method for leonurine
-
, (2017/07/21)
The invention relates to the technical field of organic chemistry, in particular to a synthetic method for leonurine. Gamma-butyrolactone is used as a starting material to be subjected to ammonolysis to obtain gamma-hydroxybutyric acid amide; the gamma-hydroxybutyric acid amide and acetyl syringic acid are subjected to a condensation reaction; a dehydration reaction and a reduction reaction are carried out to obtain leonurus amine; and the leonurus amine and S-methyl isothiourea sulfate are subjected to a reaction to obtain the leonurine. The target product leonurine is synthetized from the cheap industrial raw materials of the gamma-butyrolactone and the syringic acid used as the starting materials through reactions of ammonolysis, esterification, dehydration, reduction and the like. The reaction conditions are mild and easy to control; the yield is up to 65%; the product purity is 98% or above; and the synthetic method for leonutine provides the production with an excellent synthetic route and is suitable for large-scale production.
Six-step synthesis of Leonurine and toxicity study on zebrafish
Zhao, Hui,Hu, Xiang-Guo,Xu, Min-Jie,Cai, Qun-Xing,Liu, Yu-Jun,Su, Duo-Meng,Chen, Shi-Jin,Wang, Kai,Gong, Zhu-Nan
, p. 1172 - 1175 (2017/06/19)
Leonurine (1), an important ingredient in leonurus sibiricus L., can be used for some gynecological disease. We have developed a concise and efficient synthetic route of Leonurine, which can be optimized for mass production. Commercially available compound 6 and 2,3-dihydrofuran (7) were used as starting materials. And the toxicity study on zebrafish shows that Leonurine would promote the hatching of zebrafish embryos at low concentration and result in acute death or chronic lethal toxicity at high concentration.
Herba Leonuri (motherwort) a method of synthesis of alkali (by machine translation)
-
, (2016/10/10)
The invention discloses a method of synthesis for alkali Herba Leonuri (motherwort), characterized in that the raw material is 2,3-dihydrofuran [...] of the synthesis reaction, a product of the obtained 4-hydroxy butyl-O-oxime and alkoxyl carbonylation Syzygium aromaticum (clove) acid through esterification reaction, is obtained by reacting [...]leonurus siribicus amine, then the leonurus siribicus amine and methyl isothiourea reaction, to obtain Herba Leonuri (motherwort) alkali. The reaction process of the present invention good atom economy, to avoid excess use of the reagent, the pollution to the environment is reduced, high yield, the operation is easy. (by machine translation)
Leonurine-cysteine analog conjugates as a new class of multifunctional anti-myocardial ischemia agent
Liu, Chunhua,Guo, Wei,Shi, Xueru,Kaium,Gu, Xianfeng,Zhu, Yi Zhun
scheme or table, p. 3996 - 4009 (2011/10/31)
The design, synthesis and biological evaluation of novel Leonurine-cysteine analog conjugates 3,5-dimethoxy-4-(2-amino-3-prop-2-ynylsulfanyl-propionyl)- benzoic acid 4-guanidino-butyl ester (1a), 3,5-dimethoxy-4-(2-animo-3- allysulfanyl-propionyl)-benzoic acid 4-guanidino-butyl ester (1b) and 3,5-dimethoxy-4-(3-(2-chlorocarbonyl-ethyldisulfanyl)-propionyl)-benzoic acid 4-guanidino-butyl ester (2) were reported in this paper. We tested their effects on hypoxia-induced neonatal rat ventricular myocytes. Our data showed that all of them had cardioprotective effects. Both of 1a and 1b were able to modulate hydrogen sulfide production, and 1a possessed higher biological activity than 1b and 2, which indicated that there was positive correlation between conjugates and their precursors. Furthermore we illuminated that the cardioprotective mechanism of 1a were related to increase SOD and CAT activity, decrease MDA and ROS level, protect some cell organs and regulate apoptosis-associated genes and proteins expression (bcl-2 and bax) via the caspase-3 pathway in molecular level. These results indicated that 1a had the potential to be a new class of multifunctional anti-myocardial ischemia agent. Most importantly, these results provided us important clues for the further design and modification of this type of Leonurine-cysteine analog conjugates in future.
