548-30-1Relevant academic research and scientific papers
Photooxidation of alkaloids: Considerable quantum yield enhancement by rose bengal-sensitized singlet molecular oxygen generation
Goerner, Helmut,Miskolczy, Zsombor,Megyesi, Monika,Biczok, Laszlo
, p. 1315 - 1320 (2011)
The photooxidation of sanguinarine, coralyne and berberine was studied in oxygenated alkaline methanol solutions. Rose bengal as photosensitizer significantly accelerates the process, indicating the importance of singlet molecular oxygen in the reaction mechanism. The quantum yield of sensitized oxidation was found to increase significantly with pH and reaches 0.4 for berberine at pH 13.8. The direct oxidation of alkaloids is less efficient, the quantum yield does not exceed 0.01 even in oxygen-saturated solutions. The photoinduced electron ejection does not play a role in the oxidation. The uncharged pseudobase forms, which are present in alkaline medium, are oxidized much more easily than the alkaloid cations. The quantum yield of rose bengal-sensitized photooxidation of berberine and coralyne alkaloids increases significantly with pH. Singlet molecular oxygen plays an important role in the reaction mechanism.
A facile synthesis of benzo[c]phenanthridine alkaloids: Oxynitidine and oxysanguinarine using lithiated toluamide-benzonitrile cycloaddition
Le, Thanh Nguyen,Gang, Seong Gyoung,Cho, Won-Jea
, p. 2763 - 2766 (2004)
Benzo[c]phenanthridine alkaloids oxynitidine and oxysanguinarine were synthesized from easily available starting benzonitrile 5 and toluamide 6 using toluamide-benzonitrile cycloaddition reaction in six steps. This method is so highly efficient that it could be a more useful way for preparing fully aromatized benzo[c]phenanthridine compounds.
Insecticidal and antibacterial 5-imino substituted derivative as well as preparation method and application thereof
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Paragraph 0062; 0068; 0073-0075; 0082; 0087-0089; 0096; 0101, (2021/03/11)
The invention discloses a 5-imino substituted derivative with insecticidal and antibacterial effects, and the 5-imino substituted derivative is a polysubstituted 1H-1,2,4-triazole amidine compound. The application reports the application of the 5-imino-su
The synthesis and biological evaluation of sanguinarine derivatives as anti-non-small cell lung cancer agents
Ding, Ke,Jiang, Liang,Lu, Xiaoyun,Wang, Xiaolu,Wang, Yuting,Xu, Fang,Zhang, Zhang
, p. 293 - 296 (2020/04/17)
A novel series of sanguinarine (SA) derivatives were synthesized and evaluated as anti-non-small cell lung cancer (NSCLC) agents. The compounds inhibited A549 and H1975 NSCLC cells with IC50 values of 0.96->30 ΜM and 0.79->30 ΜM, respectively. Compounds 8d-8j exhibited low micromolar inhibitory activity and indicated that the C6-position of SA was tolerated to be substituted by hydrophilic groups and CN. Further investigation of their mechanism of action showed that compound 8h induced apoptosis of A549 and H1975 cells by inhibiting the Akt signaling pathway and elevating the reactive oxygen species (ROS). This study provided a strategy for developing new anti-cancer agents.
New methods for the synthesis of naphthyl amines; Application to the synthesis of dihydrosanguinarine, sanguinarine, oxysanguinarine and (±)-maclekarpines B and C
Tatton, Matthew R.,Simpson, Iain,Donohoe, Timothy J.
supporting information, p. 11314 - 11316 (2014/11/07)
A new method for preparing naphthyl amines from 1,5 unsaturated dicarbonyl precursors is described; the utility of this new method was proven in the syntheses of several natural products, all containing the benzo[c]phenanthridine core and enabled by a radical promoted cyclisation of the naphthyl amine products formed in the key cyclisation. the Partner Organisations 2014.
Preparation of amino-substituted indenes and 1,4-dihydronaphthalenes using a one-pot multireaction approach: Total synthesis of oxybenzo[c]phenanthridine alkaloids
Calder, Ewen D. D.,McGonagle, Fiona I.,Harkiss, Alexander H.,McGonagle, Grant A.,Sutherland, Andrew
, p. 7633 - 7648 (2014/09/17)
Allylic trichloroacetimidates bearing a 2-vinyl or 2-allylaryl group have been designed as substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine. An intramolecular biaryl Heck coupling reaction, catalyzed using the Hermann-Beller palladacycle was used to effect the key step during the synthesis of the natural products.
In vitro antifungal activity of sanguinarine and chelerythrine derivatives against phytopathogenic fungi
Yang, Xin-Juan,Miao, Fang,Yao, Yao,Cao, Fang-Jun,Yang, Rui,Ma, Yan-Ni,Qin, Bao-Fu,Zhou, Le
, p. 13026 - 13035 (2013/02/23)
In order to understand the antifungal activity of some derivatives of sanguinarine (S) and chelerythrine (C) and their structure-activity relationships, sixteen derivatives of S and C were prepared and evaluated for in vitro antifungal activity against seven phytopathogenic fungi by the mycelial growth rate method. The results showed that S, C and their 6-alkoxy dihydro derivatives S1-S4, C1-C4 and 6-cyanodihydro derivatives S5, C5 showed significant antifungal activity at 100 μg/mL against all the tested fungi. For most tested fungi, the median effective concentrations of S, S1, C and C1 were in a range of 14-50 μg/mL. The structure-activity relationship showed that the C=N+ moiety was the determinant for the antifungal activity of S and C. S1-S5 and C 1-C5 could be considered as the precursors of S and C, respectively. Thus, the present results strongly suggested that S and C or their derivatives S1-S5 and C1-C5 should be considered as good lead compounds or model molecules to develop new anti-phytopathogenic fungal agents.
Synthesis of benzo[c]phenanthridine alkaloids by Pd(OAc) 2-induced direct aromatic carbonylation
Kumazawa, Eri,Tokuhashi, Takashi,Horibata, Akiyoshi,Tokuda, Masao,Orito, Kazuhiko,Kurono, Nobuhito,Senboku, Hisanori,Ohkuma, Takashi
, p. 4622 - 4633,12 (2020/08/31)
The Pd(OAc)2-induced carbonylation of alkoxy-substituted 1-amino-2-phenyltetralins and 1-amino-2-phenylnaphthalenes was examined to provide the benzo[c]phenanthridine ring system. The carbonylation of substrates containing methylenedioxy groups
Enantioselective synthesis of chelidonine, a B/C-cis-11- hydroxyhexahydrobenzo[c]phenanthridine alkaloid
Ito, Miki,Konno, Fujiko,Kumamoto, Takuya,Suzuki, Noriyuki,Kawahata, Masatoshi,Yamaguchi, Kentaro,Ishikawa, Tsutomu
, p. 8041 - 8049 (2011/11/12)
Both enantiomers of chelidonine, a B/C-cis-11-hydroxyhexahydrobenzo[c] phenanthridine alkaloid, were synthesized by manipulation of the B/C-dehydro ring juncture of benzo[c]phenanthridine skeleton using Sharpless asymmetric dihydroxylation and stereospecific catalytic hydrogenation after introduction of oxygen functions on the C ring as key reaction steps for the construction of stereogenic centers.
Structural modification of sanguinarine and chelerythrine and their antibacterial activity
Miao, Fang,Yang, Xin-Juan,Zhou, Le,Hu, Hai-Jun,Zheng, Feng,Ding, Xu-Dong,Sun, Dong-Mei,Zhou, Chun-Dong,Sun, Wei
experimental part, p. 863 - 875 (2011/07/08)
In this study, five derivatives of sanguinarine (1) and chelerythrine (2) were prepared, with 1 and 2 as starting materials, by reduction, oxidation and nucleophilic addition to the iminium bond C=N+. The structures of all compounds were elucidated on account of their MS, 1H-NMR and 13C-NMR data. The antibacterial activities of all compounds were screened, using Staphylococcus aureus, Escherichia coli, Aeromonas hydrophila and Pasteurella multocida as test bacteria. The minimum bacteriostatic concentration and minimum bactericidal concentration of the active compounds were determined by the turbidity method. The structure-activity relationships of 1 and 2 were discussed. The results showed that 1, 2 and their pseudoalcoholates were found to be potent inhibitors to S. aureus, E. coli and A. hydrophila, while the other derivatives were found to be inactive. The pseudoalcoholates might be the prodrugs of 1 and 2. The iminium bond in the molecules of 1 or 2 was the determinant for antibacterial activity, and the substituents at the 7 and 8 positions influenced the antibacterial activities of 1 and 2 against different bacteria.
