1484-85-1Relevant articles and documents
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Reeve,Eareckson
, p. 3299 (1950)
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Erne,Ramirez
, p. 912,915 (1950)
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Structure–activity relationship and biological evaluation of berberine derivatives as PCSK9 down-regulating agents
Fan, Tian-Yun,Yang, Yu-Xin,Zeng, Qing-Xuan,Wang, Xue-Lei,Wei, Wei,Guo, Xi-Xi,Zhao, Li-Ping,Song, Dan-Qing,Wang, Yan-Xiang,Wang, Li,Hong, Bin
, (2021/06/01)
Proprotein convertase subtilisin/kexin type 9 (PCSK9) is a secreted protein and its deficiency markedly enhanced the survival rate of patient with cardiovascular diseases (CVDs). Forty berberine (BBR) derivatives were synthesized and evaluated for their activities on down-regulating the transcription of PCSK9 in HepG2 cells, taking BBR as the lead. Structure–activity relationship (SAR) analysis revealed that 2,3-dimethoxy moiety might be beneficial for activity. Among them, 9k displayed the most potent activity with IC50 value of 9.5 ± 0.5 μM, better than that of BBR. Also, it significantly decreased PCSK9 protein level at cellular level, as well as in the liver and serum of mice in vivo. Furthermore, 9k markedly increased LDLR expression and LDL-C clearance via down-regulating PCSK9 protein. The mechanism of action of 9k is targeting HNF1α and/or Sp1 cluster modulation upstream of PCSK9, a different one from BBR. Therefore, 9k might have the potential to be a novel PCSK9 transcriptional inhibitor for the treatment of atherosclerosis, worthy for further investigation.
A synthetic preparation method for small carbags hydrochloric acid
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Paragraph 0200-0202, (2021/12/08)
The present invention belongs to the field of organic chemistry, relates to a method of synthesizing berberine hydrochloride, comprising: S1: with 5-halo-o-quinoastearaldehyde and piperine ethylamine to obtain N- [2-(3,4-dimethoxyphenyl-5-yl) ethyl] -1- (5-halo-2,3-dimethoxybenzyl) methylimide; S2: to obtain 2- (3,4-diimoxyphenyl) -N- (5-bromo-2,3-dimethoxybenzyl) ethylamine; S3: to obtain 2-(3,4-dimethoxyphenyl) -N- (5-bromo-2 S4: to obtain 12-halogenated berberine derivative; S5: to obtain berberine. The present invention is free from the application of the by-product o-vanillin synthesis of o-resveratal raw material constraints, synthesis of 5- substitute o-resveratal and piperine ethylamine, and the use of the two preparation of berberine hydrochloride, with raw materials readily available, mild reaction conditions, easy to operate, high chemical yield, low cost and other advantages.
Method for total synthesis of berberine with guaiacol as raw material
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Paragraph 0015; 0017, (2019/04/26)
The invention discloses a method for total synthesis of berberine with guaiacol as a raw material. According to a drug synthesis method, guaiacol serves as the raw material, 2-hydroxy-3-methoxybenzaldehyde is obtained through a selective formylation reaction, 2,3-dimethoxybenzaldehyde is obtained through a methylation reaction, pentamethyleneamine is obtained through a methylenenation reaction with catechol as a raw material, and homopiperony lamine is obtained through a one-step catalytic addition reaction; 2,3-dimethoxybenzaldehyde and homopiperony lamine are subjected to a one-pot condensation hydrogenation reaction under the condition of a nickel-based catalyst, hydrochloric acid is added to a reaction product, a crystal substance is cooled, after the reaction product is refined, hydrochloric acid is added, and cooling crystallization and filtration washing are conducted to obtain the product berberine. According to the method, the technology is simplified, and the use of toxic cyanide is avoided; 2,3-dimethoxybenzaldehyde and homopiperony lamine are subjected to a one-pot condensation hydrogenation and salifying technology, the time is saved, the energy is saved, and the costis lowered; in the technological process, solvents are recycled.