18073-33-1Relevant academic research and scientific papers
Inhibitory properties of aldehydes and related compounds against phytophthora infestans—identification of a new lead
Mackrill, John J.,Kehoe, Roberta A.,Zheng, Limian,McKee, Mary L.,O’sullivan, Elaine C.,Prestwich, Barbara M. Doyle,McCarthy, Florence O.
, p. 1 - 24 (2020)
The pathogen Phytophthora infestans is responsible for catastrophic crop damage on a global scale which totals billions of euros annually. The discovery of new inhibitors of this organism is of paramount agricultural importance and of critical relevance t
Synthesis and cytotoxicity of novel bisellipticines and bisisoellipticines
Obaza-Nutaitis, Judy A.,Gribble, Gordon W.
, p. 171 - 187 (2019/07/31)
A series of bis-ellipticines 7-9 and bis-isoellipticines 10-12 tethered through the indole nitrogen was synthesized and screened for antitumor cytotoxicity in the L-1210 murine leukemia assay. Activity was only displayed by 1,10-bis(6-ellipticinyl)-?-decane (8).
A transition metal-free approach to a regioselective total synthesis of the natural product derivative 6-methylellipticine, a potent anticancer agent
Lin, Song-Bo,Wang, Wan-Wan,Meng, Jin-Peng,Li, Xi-Wang,Wu, Jun,Sun, Xiao-Ling
, (2019/11/26)
A transition metal-free and regioselective total synthesis of 6-methylellipticine, a potent anticancer agent, was developed. This synthetic approach mainly involved two key reactions: a direct amination of multi-functional phenol via an alkylation-Smiles
Synthesis method of natural product derivative 6-methylellipticine
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, (2018/04/01)
The invention relates to a synthesis technology of a natural product derivative, and aims at providing a synthesis method of a natural product derivative 6-methylellipticine. The target molecule 6-methylellipticine is synthesized from a cheap and easily available raw material 2,5-dimethylphenol through formylation, iodination, propylene glycol protection, amidation, methylation, transition metal catalysis-free carbazole preparation, propylene glycol protection removal, reductive amination and acid-catalyzed cyclization. The above whole synthesis route is novel, unique and reasonable, and the 6-methylellipticine is synthesized from the 2,5-dimethylphenol without a transition metal catalyst, wherein the method for transition metal catalysis-free synthesis of key intermediates comprising a compound 5 and a compound 7 have not been reported in literatures. The synthesis method has the advantages of cheap and easily available raw materials, simplicity in operation, greenness, and great reduction of the production cost.
Synthesis and in vitro antitumor activity of novel 2-alkyl-5- methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives
Mori, Ryota,Kato, Asako,Komenoi, Kousuke,Kurasaki, Haruaki,Iijima, Touru,Kawagoshi, Masashi,Kiran,Takeda, Sho,Sakai, Norio,Konakahara, Takeo
, p. 16 - 35 (2014/06/09)
Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine.
Synthesis and evaluation of novel ellipticines as potential anti-cancer agents
Deane, Fiona M.,O'Sullivan, Elaine C.,Maguire, Anita R.,Gilbert, Jayne,Sakoff, Jennette A.,McCluskey, Adam,McCarthy, Florence O.
, p. 1334 - 1344 (2013/05/21)
Drugs that inhibit DNA topoisomerase I and DNA topoisomerase II have been widely used in cancer chemotherapy. We report herein the results of a focused medicinal chemistry effort around novel ellipticinium salts which target topoisomerase I and II enzymes with improved solubility. The salts were prepared by reaction of ellipticine with the required alkyl halide and evaluated for DNA intercalation, topoisomerase inhibition and growth inhibition against 12 cancer cell lines. Results from the topoisomerase I relaxation assay indicated that all novel ellipticine derivatives behaved as intercalating agents. At a concentration of 100 μM, specific topoisomerase I inhibition was not observed. Two of the derivatives under investigation were found to fully inhibit the DNA decatenation reaction at a concentration of 100 μM, indicative of topoisomerase II inhibition. N-Alkylation of ellipticine was found to enhance the observed growth inhibition across all cell lines and induce growth inhibition comparable to that of Irinotecan (CPT-11; GI50 1-18 μM) and in some cell lines better than Etoposide (VP-16; GI50 = 0.04-5.2 μM). 6-Methylellipticine was the most potent growth inhibitory compound assessed (GI50 = 0.47-0.9 μM). N-Alkylation of 6-methylellipticine was found to reduce this response with GI50 values in the range of 1.3-28 μM.
Ellipticines and 9-acridinylamines as inhibitors of d-alanine:d-alanine ligase
Vehar, Bla?,Hrast, Martina,Kova?, Andreja,Konc, Janez,Mariner, Katherine,Chopra, Ian,O'Neill, Alex,Jane?i?, Du?anka,Gobec, Stanislav
experimental part, p. 5137 - 5146 (2011/10/04)
d-Alanine:d-alanine ligase (Ddl), an intracellular bacterial enzyme essential for cell wall biosynthesis, is an attractive target for development of novel antimicrobial drugs. This study focused on an extensive evaluation of two families of Ddl inhibitors encountered in our previous research. New members of both families were obtained through similarity search and synthesis. Ellipticines and 9-acridinylamines were both found to possess inhibitory activity against Ddl from Escherichia coli and antimicrobial activity against E. coli and Staphylococcus aureus. Ellipticines with a quaternary methylpyridinium moiety were the most potent among all studied compounds, with MIC values as low as 2 mg/L in strains with intact efflux mechanisms. Antimicrobial activity of the studied compounds was connected to membrane damage, making their development as antibacterial drug candidates unlikely unless analogues devoid of this nonspecific effect can be discovered.
Modifications to the Vilsmeier-Haack formylation of 1,4-dimethylcarbazole and its application to the synthesis of ellipticines
Deane, Fiona M.,Miller, Charlotte M.,Maguire, Anita R.,McCarthy, Florence O.
, p. 814 - 823 (2011/10/04)
Figure represented. An improved method for the preparation of 3-formyl-1,4-dimethylcarbazole, a key intermediate in the synthesis of ellipticine, is presented. Conditions of the Vilsmeier-Haack reaction have been modified to facilitate the production of 3-formyl-1,4-dimethylcarbazole as a major product leading to an overall improvement in yield of ellipticine from 3% to 14%. This approach was also applied to the synthesis of 6-methylellipticine and 9-methoxyellipticine.
A novel entry to pyrido[4,3-b]carbazoles: An efficient synthesis of ellipticine
Ishikura, Minoru,Hino, Ayako,Yaginuma, Toshikatsu,Agata, Isao,Katagiri, Nobuya
, p. 193 - 207 (2007/10/03)
The palladium catalyzed tandem cyclization-cross-coupling reaction of indolylborate (2) with vinyl bromide (9) was developed for the preparation of pyrido[4,3-b]carbazole as a key reaction. The cross-coupling reaction of 2a provided hexatriene (10), and then cyclization of 10 to pyrido[4,3- b]carbazole (12) was effected with irradiation or Lewis acid. Using indolylborate (2c) for the cross-coupling reaction, a novel construction of ellipticine was attained through similar reaction sequences.
An efficient total synthesis of ellipticine
Ishikura, Minoru,Hino, Ayako,Katagiri, Nobuya
, p. 11 - 14 (2007/10/03)
A total synthesis of ellipticine could be attained through the palladium catalyzed tandem cyclization-cross-coupling reaction of indolylborate (2b) with vinyl bromide (3) as a key reaction.
