5578-73-4Relevant academic research and scientific papers
Inclusion complex formation of sanguinarine alkaloid with cucurbit[7]uril: Inhibition of nucleophilic attack and photooxidation
Miskolczy, Zsombor,Megyesi, Monika,Tarkanyi, Gabor,Mizsei, Reka,Biczok, Laszlo
, p. 1061 - 1070 (2011)
The inclusion of sanguinarine, a biologically active natural benzophenanthridine alkaloid, in cucurbit[7]uril (CB7) was studied by NMR and ground-state absorption spectroscopy, as well as steady-state and time-resolved fluorescence measurements in aqueous solution. The iminium form of sanguinarine (SA+) produces very stable 1:1 inclusion complex with CB7 (K = 1.0 × 106 M-1), whereas the equilibrium constant for the binding of the second CB7 is about 3 orders of magnitude smaller. Marked fluorescence quantum yield and fluorescence lifetime enhancements are found upon encapsulation of SA+ due to the deceleration of the radiationless deactivation from the single-excited state, but the fluorescent properties of 1:1 and 1:2 complexes barely differ. The equilibrium between the iminium and alkanolamine forms is shifted 3.69 pK unit upon addition of CB7 as a consequence of the preferential encapsulation of the iminium form and the protection of the 6 position of sanguinarine against the nucleophilic attack by hydroxide anion. On the basis of thermodynamic cycle, about 225 M-1 is estimated for the equilibrium constant of the complexation between the alkanolamine form of sanguinarine (SAOH) and CB7. The confinement in the CB7 macrocycle can be used to impede the nucleophilic addition of OH- to SA+ and to hinder the photooxidation of SAOH.
Re-engineering and synthesis of cytotoxic 2,3:7,8-di(alkylenedioxy)-extended analogs of quaternary sanguinarine chloride
Li, Qi-Lin,Deng, An-Jun,Ji, Ming,Li, Zhi-Hong,Chen, Xiao-Guang,Qin, Hai-Lin
, p. 1137 - 1153 (2018/11/30)
A method was developed to synthesize 2,3:7,8-di(alkylenedioxy)-extended analogs of quaternary sanguinarine chloride. 1-Bromo-2-bromomethyl-3,4-alkylenedioxy benzenes and 6,7-alkylenedioxynaphthalen-1-amines were synthesized first. Reactions to construct the target compounds with these two series of synthons involved alterations on a published method for synthesizing 2,3,7,8-tetraoxygenated derivatives of benzo[c]phenanthridinium, substituting benzyl bromides for benzoic aldehydes, prolonging the radical annulation time, and conducting N-methylation with formic acid and NaBH4. All the target compounds showed the same or better in vitro growth inhibitory activities against cancer cell lines compared with the positive compound. The structure activity relationship relevant to cytotoxicity and lipophilicity of the target compounds was produced.
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.
Structure and NMR properties of 6-substituted-5,6-dihydrobenzo[c] phenanthridine alkaloids
Kadam, Shivaji S.,Maier, Lukas,Solomek, Tomas,Necas, Marek,Smejkal, Karel,Dostal, Jiri,Sklenar, Vladimir,Marek, Radek
, p. 814 - 821 (2013/10/01)
We report a preparation of new 6-substituted-5,6-dihydrobenzo[c] phenanthridines by the reaction of azoles with quaternary benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine. The prepared compounds have been characterized by NMR spectroscopy, mass spectrometry, and single-crystal X-ray diffraction. Conformational behaviors of carbazole derivatives in solution have been investigated by low-temperature NMR experiments. Barriers to rotation around newly formed C6-N bonds were determined to be 12-13 kcal/mol. Quantum chemical calculations have been used to reproduce the experimental observations. Large structural effects on several 1H NMR resonances were observed experimentally, analyzed by Density Functional Theory (DFT) calculations at B3LYP/6-311+G(d,p)/PCM level, and interpreted by ring-current effects of the benzo[c]phenanthridine and carbazole units. Copyright 2013 John Wiley & Sons, Ltd. Barrier to rotation around C-N bond was determined experimentally by low-temperature 1H NMR spectroscopy and calculated by using density functional theory (B3LYP/6-311+G(d,p)). Structural effects on selected 1H NMR resonances are rationalized by ring currents of benzo[c]phenanthridine and carbazole moieties. Copyright
Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: Application to the total synthesis of benzo[c]phenanthridine alkaloids
Lv, Pei,Huang, Kanglun,Xie, Longguan,Xu, Xiaohua
supporting information; experimental part, p. 3133 - 3135 (2011/05/15)
A concise and efficient synthesis of benzo[c]phenanthridines was accomplished by the palladium-catalyzed ring-opening coupling of azabicyclic alkene with o-iodobenzoates, followed by tandem cyclization. The strategy was successfully applied in the total synthesis of benzo[c]phenanthridine alkaloids such as sanguinarine, chelerythrine, nitidine and avicine.
A NOVEL AND BIOMIMETIC SYNTHESIS OF (+/-)-CHELAMINE, (+/-)-CHELIDONINE, SANGUINARINE, AND DIHYDROSANGUINARINE FROM COPTISINE VIA A COMMON INTERMEDIATE
Hanaoka, Miyoji,Yoshida, Shuji,Annen, Masami,Mukai, Chisato
, p. 739 - 742 (2007/10/02)
(+/-)-Chelamine and (+/-)-chelidonine, B/C cis hexahydrobenzophenanthridine alkaloids were stereoselectively synthesized from coptisine via the key intermediate, which was also converted to fully aromatized benzophenanthridine alkaloids, sanguinarine and dihydrosanguinarine.
