86689-00-1Relevant academic research and scientific papers
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
scheme or table, 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.
Bu3SnH-mediated radical cyclisation onto azoles
Allin, Steven M.,Barton, William R.S.,Russell Bowman,Bridge (née Mann), Emma,Elsegood, Mark R.J.,McInally, Tom,McKee, Vickie
, p. 7745 - 7758 (2008/12/21)
Alkyl radicals have been cyclised onto pyrroles, imidazoles and pyrazoles, and acyl radicals cyclised onto pyrroles, using Bu3SnH-, (TMS)3SiH- and Bu3GeH-mediated aromatic homolytic substitution for the synthesis of bicyclic N-heterocycles. The reactions yield intermediate π-radicals that lose hydrogen in the?rearomatisation step of the aromatic homolytic substitution. Mechanistic studies of these rearomatisation steps indicate aromatic homolytic substitution in which the initiator or breakdown products from the inhibitor are responsible for the H-abstraction step.
Regioselective Synthesis of Acylpyrroles
Kakushima, Masatoshi,Hamel, Pierre,Frenette, Richard,Rokach, Joshua
, p. 3214 - 3219 (2007/10/02)
The regioselective synthesis of several pyrrole derivatives is described.AlCl3-catalyzed acylation reactions of 1-(phenylsulfonyl)pyrrole (1) give 3-acyl derivatives, whereas the corresponding BF3*OEt2-catalyzed reactions give 2-acyl derivatives predominantly.Mild alkaline hydrolysis gives the corresponding acyl-1H-pyrroles in excellent yields.AlCl3-catalyzed reactions of 1 with 1,1-dichloromethyl methyl ether and oxalyl chloride give 1-(phenylsulfonyl)-2-formylpyrrole (6) and 1-(phenylsulfonyl)-2-(chlorocarbonyl)pyrrole (7), respectively. 3-Pyrrolylacetic acid (10) was prepared by thallium(III) nitrate promoted rearrangement of 1-(phenylsulfonyl)-3-acetylpyrrole (2a).Trifluoroacetic anhydride catalyzed cyclization of 4-butyric acid (14) gives 1-(phenylsulfonyl)-7-oxo-4,5,6,7-tetrahydroindole (17).Attempts to cyclize 14 at the 4-position have been unsuccessful.
