73326-98-4Relevant academic research and scientific papers
Efficient Syntheses of 'Ellipticine Quinone' and the Other Three Isomeric 5H-Pyridocarbazole-5,11(6H)-diones
Ashcroft, William R.,Beal, Michael G.,Joule, John A.
, p. 994 - 995 (1981)
6H-Pyridooxepinoindol-5(12H)-ones (3) are efficiently converted by hot alcoholic base in air into the corresponding 5H-pyridocarbazole-5,11(6H)-diones (5).
Regioselection Switch in Nucleophilic Addition to Isoquinolinequinones: Mechanism and Origin of the Regioselectivity in the Total Synthesis of Ellipticine
Castro, Joaquim A. M.,Ligiéro, Carolina B. P.,Maior, Christian R. S.,Miranda, Paulo C. M. L.,Morgon, Nelson H.,Naciuk, Fabrício F.,Rocco, Silvana A.,Serikava, Bruno K.
, (2022/03/02)
Ellipticine was synthesized in six steps and 20% global yield starting from the readily available 2,5-dimethoxy isoquinoline. Unprecedented regioselective control of the nucleophilic attack on the isoquinoline-5,8-dione is first described. Investigation of the possible pathways of this transformation through density functional theory calculations reveals unexpected N-oxide assistance in cascade tautomerizations, which was crucial for directing the nucleophilic attack and hastening the overall process. Using this strategy, we prepared the aniline-isoquinolinedione adduct and submitted it to an intramolecular double C-H cross-coupling activation to furnish ellipticinequinone, which gave ellipticine after a MeLi addition/BH3reduction sequence.
Identification of novel dynamin-related protein 1 (Drp1) GTPase inhibitors: Therapeutic potential of Drpitor1 and Drpitor1a in cancer and cardiac ischemia-reperfusion injury
Alizadeh, Elahe,Archer, Stephen L.,Chen, Kuang-Hueih,Dasgupta, Asish,Hurst, Timothy E.,Lima, Patricia D. A.,Martin, Ashley,Mewburn, Jeffrey D.,Neuber-Hess, Monica,Patel, Jignesh,Snieckus, Victor,Wells, Michael,Wu, Danchen
, p. 1447 - 1464 (2020/04/21)
Mitochondrial fission is important in physiological processes, including coordination of mitochondrial and nuclear division during mitosis, and pathologic processes, such as the production of reactive oxygen species (ROS) during cardiac ischemia-reperfusion injury (IR). Mitochondrial fission is mainly mediated by dynamin-related protein 1 (Drp1), a large GTPase. The GTPase activity of Drp1 is essential for its fissogenic activity. Therefore, we aimed to identify Drp1 inhibitors and evaluate their anti-neoplastic and cardioprotective properties in five cancer cell lines (A549, SK-MES-1, SK-LU-1, SW 900, and MCF7) and an experimental cardiac IR injury model. Virtual screening of a chemical library revealed 17 compounds with high predicted affinity to the GTPase domain of Drp1. In silico screening identified an ellipticine compound, Drpitor1, as a putative, potent Drp1 inhibitor. We also synthesized a congener of Drpitor1 to remove the methoxymethyl group and reduce hydrolytic lability (Drpitor1a). Drpitor1 and Drpitor1a inhibited the GTPase activity of Drp1 without inhibiting the GTPase of dynamin 1. Drpitor1 and Drpitor1a have greater potency than the current standard Drp1 GTPase inhibitor, mdivi-1, (IC50 for mitochondrial fragmentation are 0.09, 0.06, and 10 μM, respectively). Both Drpitors reduced proliferation and induced apoptosis in cancer cells. Drpitor1a suppressed lung cancer tumor growth in a mouse xenograft model. Drpitor1a also inhibited mitochondrial ROS production, prevented mitochondrial fission, and improved right ventricular diastolic dysfunction during IR injury. In conclusion, Drpitors are useful tools for understanding mitochondrial dynamics and have therapeutic potential in treating cancer and cardiac IR injury.
Concise synthesis and antiproliferative activity evaluation of ellipticine quinone and its analogs
Nishiyama, Takashi,Hatae, Noriyuki,Mizutani, Masataka,Yoshimura, Teruki,Kitamura, Tsuyoshi,Miyano, Mana,Fujii, Mami,Satsuki, Nanase,Ishikura, Minoru,Hibino, Satoshi,Choshi, Tominari
, p. 1 - 13 (2017/05/05)
We developed a concise protocol for the synthesis of ellipticine quinone from the appropriate 3-iodoindole-2-carbaldehydes in four steps. The key step is the construction of carbazole-1,4-quinone through tandem Ring-Closing Metathesis (RCM) and dehydrogen
Total synthesis of ellipticine quinones, olivacine, and calothrixin b
Ramkumar, Nagarajan,Nagarajan, Rajagopal
, p. 736 - 741 (2014/04/03)
A direct route to the synthesis of biologically active ellipticine quinones, olivacine, and calothrixin B is described. The prominent key steps involved are Friedel-Crafts hydroxyalkylation followed by oxidation and directed ortho-lithiation reactions of readily available indole-2-carboxylate esters with appropriately substituted pyridine and quinoline carboxaldehydes.
A new route to the synthesis of ellipticine quinone from isatin
Ramkumar, Nagarajan,Nagarajan, Rajagopal
, p. 1104 - 1106 (2014/02/14)
1-(2-Oxo-2-(pyridin-4-yl)ethyl)indoline-2,3-dione can be prepared and converted by treatment with sodium hydroxide into 2-isonicotinoyl-1H-indole-3- carboxylic acid as a key intermediate which can be transformed into ellipticine quinone in a two step sequ
A new route to the synthesis of ellipticine quinone from isatin
Ramkumar, Nagarajan,Nagarajan, Rajagopal
, p. 1104 - 1106 (2015/02/19)
1-(2-Oxo-2-(pyridin-4-yl)ethyl)indoline-2,3-dione can be prepared and converted by treatment with sodium hydroxide into 2-isonicotinoyl-1H-indole-3-carboxylic acid as a key intermediate which can be transformed into ellipticine quinone in a two step seque
Anionic [4+2] cycloaddition strategy in the regiospecific synthesis of carbazoles: formal synthesis of ellipticine and murrayaquinone A
Mal, Dipakranjan,Senapati, Bidyut Kumar,Pahari, Pallab
, p. 3768 - 3781 (2008/02/01)
Anionic [4+2] cycloaddition of furoindolones (e.g., 7 and 10) has been developed as an effective means to the synthesis of carbazoles. This reaction has been shown to be feasible with a wide variety of Michael acceptors to give carbazoles and fused carbaz
A new synthetic route to indoloquinones: Formal synthesis of ellipticine
Mal, Dipakranjan,Senapati, Bidyut K.,Pahari, Pallab
, p. 994 - 996 (2007/10/03)
The anionic [4+2] cycloaddition of furoindolones with arynes and quinol ethers is introduced as an efficient strategy for the synthesis of indoloquinones. The utility of the strategy is exemplified by a very short synthesis of elipticine.
Synthesis, electrochemistry, and bioactivity of the cyanobacterial calothrixins and related quinones
Bernardo, Paul H.,Chai, Christina L. L.,Heath, Graham A.,Mahon, Peter J.,Smith, Geoffrey D.,Waring, Paul,Wilkes, Bronwyn A.
, p. 4958 - 4963 (2007/10/03)
The calothrixins are quinone-based natural products isolated from Calothrix cyanobacteria which show potent antiproliferative properties against several cancer cell lines. Preliminary mechanistic studies suggest that the biological mode of action of the c
