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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A method of synthesis of piperonolamine
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, (2022/01/07)
The present invention belongs to the field of organic chemical synthesis, specifically relates to a synthesis method of piperine, comprising: using catechol as a raw material to prepare piperonaldehyde; β - nitro-3,4-dioxenosylstyrene prepared with piperonaldehyde; β - nitro -3,4-dioxenesimethylenestyrene to obtain piperine ethylamine. Among them, the preparation of piperaldehyde from catechol as raw materials includes two ways: (1) catechol→3,4-dihydroxymandelic acid→3,4-dihydroxybenzaldehyde→ piperaldehyde; (2) catechol→ piperine ring → piperine. The raw materials used in the present invention are safe and readily available, low cost; the reaction conditions are mild, the operation is simple, the chemical yield is high, and the intermediate reagents are easy to recover; suitable for industrial production.
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.
Enantioselective synthesis and anti-parasitic properties of aporphine natural products
Amaral, Maiara,Anderson, Edward A.,McHugh, Eliza,Pieper, Pauline,Tempone, Andre G.
, (2019/12/09)
Chagas disease and visceral leishmaniasis are neglected protozoan diseases with significant impact in developing countries. Due to the limited number and toxicity of current therapies, new drug leads are urgently needed. In this work, four aporphine natural products were synthesized using an enantioselective, modular and convergent strategy, comprising eight steps in the longest linear sequence; key steps included Bischler-Napieralski cyclization/Noyori asymmetric reduction to construct the tetrahydroisoquinolines, and palladium-catalyzed arylation to close the C ring. Norglaucine, nordicentrine and dicentrine showed promising bioactivity against T. cruzi and L. infantum, suggesting potential for further development of these scaffolds as antiparasitic agents.