19716-61-1Relevant articles and documents
The new shortcut synthesis of 8-oxocoptisine
Cui, Xiang Juan,Lu, Ying Ying,Zhao, Min,Qian, Shan,Wu, Yong
, p. 1281 - 1282 (2010)
8-Oxocoptisine 1, a natural protoberberine alkaloid, can be more easily achieved starting from readily available and inexpensive berberine hydrochlorate 2. The structure of the target compound 1 was confirmed by melting point, 1H NMR, IR, MS and elemental analysis.
Syntheses and Structure–Activity Relationships in Antibacterial Activity against Clostridium difficile and XBP1 Activation Property of 13-[(N-Alkylamino)methyl]-8-oxodihydrocoptisines
Li, Jing,Zhang, Hai-Jing,Deng, An-Jun,Li, Zhi-Hong,Xing, Ya-Ling,Wu, Lian-Qiu,Qin, Hai-Lin
, (2020)
13-[(N-Alkylamino)methyl]-8-oxodihydrocoptisines were synthesized to evaluate antibacterial activity against Clostridium difficile and activating x-box-binding protein 1 (XBP1) activity, biological properties both associated with ulcerative colitis. Improving structural stability and ameliorating biological activity were major concerns. Different substituents on the structural modification site were involved to explore the influence of diverse structures on the bioactivities. The target compounds exhibited the desired activities with definite structure–activity relationship. In the series of 13-[(N-n-alkylamino)methyl]-8-oxodihydrocoptisines, the length of n-alkyl groups has a definite effect on the bioactivity, elongation of the length increasing the antibacterial activity. The synthesized compounds were determined to display strong or weak XBP1-activating activity in vitro. The preliminary results of this study warrant further medicinal chemistry studies on these synthesized compounds.
Berberine and coptisine free bases
Dostál, Ji?í,Man, Stanislav,Se?ká?ová, Pavlína,Hulová, Dagmar,Ne?as, Marek,Potá?ek, Milan,Tou?ek, Jaromír,Dommisse, Roger,Van Dongen, Walter,Marek, Radek
, p. 135 - 142 (2004)
The free bases of protoberberine alkaloids berberine and coptisine and related compounds have been examined. The 1H and 13C NMR data of 8-hydroxy-7,8-dihydroberberine (2a), 8-hydroxy-7,8-dihydrocoptisine (2b), bis(7,8-dihydroberberin-8-yl) ether (3a), 8-oxoberberine (5a), and 8-oxocoptisine (5b) as well as X-ray data of compounds 2a, 5a, and 5b are reported and discussed.
Synthesis and Structure-Activity Relationships of N-Dihydrocoptisine-8-ylidene Aromatic Amines and N-Dihydrocoptisine-8-ylidene Aliphatic Amides as Antiulcerative Colitis Agents Targeting XBP1
Xie, Meng,Zhang, Hai-Jing,Deng, An-Jun,Wu, Lian-Qiu,Zhang, Zhi-Hui,Li, Zhi-Hong,Wang, Wen-Jie,Qin, Hai-Lin
, p. 775 - 783 (2016)
In this study, natural quaternary coptisine was used as a lead compound to design and synthesize structurally stable and actively potent coptisine analogues. Of the synthesized library, 13 N-dihydrocoptisine-8-ylidene amines/amides were found not only to
Gut Microbiota-Mediated Transformation of Coptisine Into a Novel Metabolite 8-Oxocoptisine: Insight Into Its Superior Anti-Colitis Effect
Ai, Gaoxiang,Huang, Ziwei,Cheng, Juanjuan,Xie, Jianhui,Zeng, Huifang,Liu, Yuhong,Li, Yucui,Huang, Xiaoqi,Chen, Jiannan,Su, Ziren
, (2021/04/19)
Coptisine (COP) is a bioactive isoquinoline alkaloid derived from Coptis Chinemsis Franch, which is traditionally applied for the management of colitis. However, the blood concentration of COP was extremely low, and its gut microbiota-mediated metabolites were thought to contribute to its prominent bioactivities. To comparatively elucidate the protective effect and underlying mechanism of COP and its novel gut microbiota metabolite (8-oxocoptisine, OCOP) against colitis, we used dextran sulfate sodium (DSS) to induce colitis in mice. Clinical symptoms, microscopic alternation, immune-inflammatory parameters for colitis were estimated. The results indicated that OCOP dramatically ameliorated disease activity index (DAI), the shortening of colon length and colonic histopathological deteriorations. OCOP treatment also suppressed the mRNA expression and release of inflammatory mediators (TGF-β, TNF-α, IL-6, IL-18, IL-1β and IFN-γ) and elevated the transcriptional and translational levels of anti-inflammatory cytokine (IL-10) as well as the mRNA expression levels of adhesion molecules (ICAM-1 and VCAM-1). Besides, the activation of NF-κB pathway and NLRP3 inflammasome was markedly inhibited by OCOP. Furthermore, OCOP displayed superior anti-colitis effect to COP, and was similar to MSZ with much smaller dosage. Taken together, the protective effect of OCOP against DSS-induced colitis might be intimately related to inhibition of NF-κB pathway and NLRP3 inflammasome. And the findings indicated that OCOP might have greater potential than COP to be further exploited as a promising candidate in the treatment of colitis.
Coptisine derivatives, as well as preparation method, medicinal composition and anti-tumor application thereof
-
Paragraph 0029; 0052; 0053, (2017/10/26)
The invention discloses coptisine derivatives, a synthesis method thereof, and application of the coptisine derivatives to preparation of products for preventing, relieving and/or treating tumor products. The coptisine derivatives are an 8-iminodihydrogen
A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps
Zhou, Shiqiang,Tong, Rongbiao
supporting information, p. 7084 - 7089 (2016/05/19)
A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A3 reaction, Pd-catalyzed reductive carbocyclization, and PtO2-catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.
Derivatives Of Protoberberine Biological Alkaloids And Use Of Same Inhibiting Ulcerative Colitis
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Paragraph 0071; 0072, (2015/02/19)
Disclosed are derivatives of protoberberine biological alkaloids or physiologically acceptable salts thereof produced by means of a derivative reaction of a source material of biological alkaline quaternary ammonium salts of protoberberine alkaloids, a preparation method for same and pharmaceutical uses thereof. The derivatives of protoberberine biological alkaloids or the physiologically acceptable salts thereof show activity inhibiting ulcerative colitis and can be used in the preparation of drugs for same.
New synthetic method of 8-oxocoptisine starting from natural quaternary coptisine as anti-ulcerative colitis agent
Zhang, Zhi-Hui,Deng, An-Jun,Yu, Jin-Qian,Li, Zhi-Hong,Qin, Hai-Lin,Wu, Lian-Qiu,Zhang, Hai-Jing,Wang, Wen-Jie
, p. 841 - 846,6 (2014/11/07)
Quaternary coptisine (1), a natural bioactive quaternary protoberberine alkaloid (QPA), was treated with potassium ferricyanide in aqueous solution of 5 N sodium hydroxide leading to the acquisition of 8-oxocoptisine (2) with much higher yield than reported in the literature. This is the first report of the oxidation of a natural QPA by applying potassium ferricyanide as an oxidant. 8-Oxocoptisine showed significant anti-ulcerative colitis efficacy in vitro with EC50 value being 8.12 × 10-8 M.
DERIVATIVES OF PROTOBERBERINE BIOLOGICAL ALKALOIDS AND USE OF SAME INHIBITING ULCERATIVE COLITIS
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Paragraph 0048, (2014/10/28)
Disclosed are derivatives of protoberberine biological alkaloids or physiologically acceptable salts thereof produced by means of a derivative reaction of a source material of biological alkaline quaternary ammonium salts of protoberberine alkaloids, a preparation method for same and pharmaceutical uses thereof. The derivatives of protoberberine biological alkaloids or the physiologically acceptable salts thereof show activity inhibiting ulcerative colitis and can be used in the preparation of drugs for same.
