522-30-5Relevant academic research and scientific papers
A Short Total Synthesis of Benzophenanthridine Alkaloids via a Rhodium(III)-Catalyzed C-H Ring-Opening Reaction
Aravindan, Narasingan,Jeganmohan, Masilamani
, p. 14826 - 14843 (2021/10/20)
The biologically important naturally available benzophenanthridines were prepared efficiently in three steps with overall good yields. A new synthetic methodology involving a rhodium(III) catalyzed redox-neutral ring-opening of 7-azabenzonorbornadienes with aromatic aldoximes is developed to synthesize the target molecules. The developed C-H ring-opening reaction is highly diastereoselective and compatible with various sensitive functional group substituted aromatic aldoximes as well as substituted 7-azabenzonorbornadienes. The ring-opening products were transformed into highly sensitive 13,14-dehydrobenzo phenanthridine derivatives by HCl hydrolysis. Subsequently, 13,14-dehydrobenzophenanthridines were converted into biologically important benzophenanthridine alkaloids in the presence of DDQ. A possible reaction mechanism was proposed for the C-H ring-opening reaction and supported by the deuterium labeling studies.
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.
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.
SANGUINARINE ANALOG PP2C INHIBITORS FOR CANCER TREATMENT
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, (2014/10/03)
Sanguinarine analogs as PP2C inhibitors are disclosed for the treatment of various cancers, as well as methods of synthesizing such analogs.
Total synthesis of benzo[c]phenanthridine alkaloids based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system and structural revision of broussonpapyrine
Ishihara, Yuhsuke,Azuma, Shuhei,Choshi, Tominari,Kohno, Kakujirou,Ono, Kanako,Tsutsumi, Hiroyuki,Ishizu, Takashi,Hibino, Satoshi
, p. 1320 - 1333 (2011/04/16)
Total syntheses of the des-N-methyl (nor) type of benzo[c]phenanthridine alkaloids 1a-f and 19 and benzo[c]phenanthridine alkaloids, chelerythrine (2d), and broussonpapyrine (2f) were achieved. The key step was the construction of tetracyclic 10,11-dihydrobenzo[c]phenanthridines using a microwave-assisted electrocyclic reaction of the 2-cycloalkenylbenzaldoxime methyl ether 4 as an aza 6π-electron system, which was derived in two steps from a Suzuki-Miyaura cross-coupling reaction of 2-bromobenzaldehyde 6 with 2-(3,4-dihydro-6,7- methylenedioxynaphthyl)boronic acid pinacol ester 7. In addition, the exact structure of broussonpapyrine (2f) (2,3,9,10-tetraoxygenated type) was determined to be chelerythrine (2d).
Pyrolysis and Photolysis of the N-Oxides of Protopines and Hexahydrobenzophenanthridines. Syntheses of the Secoberbines and Benzophenanthridines
Iwasa, Kinuko,Sugiura, Makiko,Takao, Narao
, p. 998 - 1008 (2007/10/02)
Pyrolysis and photolysis of the N-oxides of the protopines 9 and 16 produces the ring-enlarged compounds 10 and 17, whose reduction with zinc in acetic acid leads to the secoberbines (+/-)-corydalisol (11) and (+/-)-hypecorine (12) from 9, and the corresponding analogs (18 and 19) from 16.Pyrolysis of (+)-chelidonine N-oxide (24) generates dihydrosanguinarine (22).Keywords - pyrolysis; photolysis; N-oxide; protopine; sanguinarine; corydalisol; hypecorine
SYNTHESIS OF SANGUINARINE, CHELERYTHRINE, AND OXYSANGUINARINE
Smidrkal, Jan
, p. 1412 - 1420 (2007/10/02)
Benzophenanthridines Va and Vb have been prepared by photocyclization of amines IVa and IVb and transformed into the alkaloids sanguinarine (VIa) and chelerythrine (VIb).Oxysanguinarine (XIV) has been prepared from diazoketone XVIII.
