129053-74-3Relevant academic research and scientific papers
Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: A mechanistic interpretation and conversion into 4- and 7-oxoindoles
Montalban, Antonio Garrido,Baum, Sven M.,Cowell, Justin,McKillop, Alexander
experimental part, p. 4276 - 4279 (2012/09/25)
An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4,5,6,7- tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4- and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4- and 7-oxo-4,5,6,7-tetrahydroindole derivatives are discussed. In addition, the reaction sequences appear to be stereospecific allowing for the direct introduction of a chiral center α to the nitrogen and preparation of enantiomerically enriched products.
PHOTOCHEMOTHERAPEUTIC HETEROCYCLIC AGENTS HAVING ANTIPROLIFERATIVE AND ANTINEOPLASTIC ACTIVITY
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Page/Page column 4, (2012/06/01)
The present invention concerns the synthesis of new analogs of angelicins, pyrrolo [3,2-h]quinoline, for the treatment of pathologies having hyperproliferative character included those having neoplastic nature. The treatment is based on the combined actio
Synthesis of pyrrolo[3,2-h]quinolinones with good photochemotherapeutic activity and no DNA damage
Barraja, Paola,Caracausi, Libero,Diana, Patrizia,Carbone, Anna,Montalbano, Alessandra,Cirrincione, Girolamo,Brun, Paola,Palu, Giorgio,Castagliuolo, Ignazio,Dall'Acqua, Francesco,Vedaldi, Daniela,Salvador, Alessia
experimental part, p. 4830 - 4843 (2010/08/06)
In the search for new photochemotherapeutic agents, a series of derivatives of the ring system pyrrolo[3,2-h]quinoline - bioisosters of the angular furocoumarin angelicin - were synthesized through a four-step synthetic approach, in reasonable overall yields. Eight of the synthesized derivatives showed a remarkable phototoxicity against a panel of four human tumor cell lines and a great dose UV-A dependence, reaching IC50 values at submicromolar level. The mode of cellular death photoinduced by pyrrolo[3,2-h]quinolines was evaluated through a series of flow cytometric analysis and other tests were performed to clarify their mechanism of action.
Dihydroindol-7(6H)-ones and 6,7-Dihydropyrroloazepine-4,8(1H,5H)-dione
Kasum, Bruno,Prager, Rolf H.,Tsopelas, Chris
, p. 355 - 365 (2007/10/02)
3-Methylcyclohexenones may be converted into dihydroindol-7(6H)-ones by conversion of the epoxide into the 2-benzylamino-3-methylcyclohexenone, which reacts with dimethylformamide dimethyl acetal to give N-benzyldihydroindol-7(6H)-ones.The limitations of the process are discussed, as is the failure to convert the dihydroindol-7(6H)-ones into dihydropyrroloazepinediones by Beckmann or Schmidt rearrangements.An example of the latter compounds was made by a simple procedure from pyrrolecarboxylic acid.
