Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(6): 903-906
DOI: 10.1055/s-2005-861802
DOI: 10.1055/s-2005-861802
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Convenient Synthesis of Benzo[g]pyrrolo[3,2-c]quinoline-6,11-diones
Further Information
Received
25 October 2004
Publication Date:
21 February 2005 (online)
Publication History
Publication Date:
21 February 2005 (online)
Abstract
The synthesis of a new class of angular tetracyclic quinones is described. Our strategy involves Diels-Alder reaction of pyrroloquinolinequinone 9, generated in situ from pyrroloquinoline 8, and dienes. The required pyrroloquinoline 8 was prepared in four steps from commercially available compounds. All compounds were tested for trypanocidal activity in vitro against Trypanosoma cruzi epimastigotes.
Key words
benzo[g]pyrrolo[3,2-c]quinoline - heterocyclic quinones - pyrroloquinoline - Diels-Alder reaction - heterocycles
- 1
Fendrich G,Zimmermann W,Gruner J, andAuden JAL. inventors; Eur. Pat. Appl. EP 304400. ; Chem. Abstr. 1990, 112, 75295 -
2a
Gore MP.Gould SJ.Weller DD. J. Org. Chem. 1991, 56: 2289 -
2b
Gore MP.Gould SJ.Weller DD. J. Org. Chem. 1992, 57: 2774 -
2c
Mohri S.Stefinovic M.Snieckus V. J. Org. Chem. 1997, 62: 7072 -
3a
Tapia RA.Salas C.Morello A.Maya JD.Toro-Labbé A. Bioorg. Med. Chem. 2004, 12: 2451 -
3b
Tapia RA.Prieto Y.Pautet F.Walchshofer N.Fillion H.Fenet B.Sarciron M.-E. Bioorg. Med. Chem. 2003, 11: 3407 -
3c
Tapia RA.Alegria L.Pessoa CD.Salas C.Cortés MJ.Valderrama JA.Sarciron M.-E.Pautet FN.Walchshofer N.Fillion H. Bioorg. Med. Chem. 2003, 11: 2175 -
3d
Cuellar MA.Alegría LK.Prieto Y.Cortés MJ.Tapia RA.Preite MD. Tetrahedron Lett. 2002, 43: 2127 -
4a
Witherup K.Ranson RW.Graham AC.Bernard AM.Salvatore MJ.Limma WC.Anderson PS.Pitzenberger SM.Varga SL. J. Am. Chem. Soc. 1995, 117: 6682 -
4b
Leach CA.Brown TH.Ife RJ.Keeling DJ.Laing SM.Parsons ME.Price CA.Wiggall KJ. J. Med. Chem. 1992, 35: 1845 -
5a
Powell DA.Batey RA. Org. Lett. 2002, 4: 2913 -
5b
Snider BB.Ahn Y.Ohare SM. Org. Lett. 2001, 3: 4217 -
5c
Ma D.Xia C.Jiang J.Zhang J. Org. Lett. 2001, 3: 2189 ; and references cited therein -
6a
Ozawa T.Nagaoka S. J. Pharm. Soc. Jpn. 1955, 75: 1405 ; Chem. Abstr. 1956, 50, 10002a -
6b
Ozawa T.Nagaoka S. Yakugaku Zasshi 1959, 79: 226 ; Chem. Abstr. 1959, 53, 13146h -
7a
Badawey E.-S.Kappe T. Eur. J. Med. Chem. 1997, 32: 815 -
7b
Brown TH.Ife RJ.Keeling DJ.Laing SM.Leach CA.Parsons ME.Price CA.Reavill DR.Wiggall KJ. J. Med. Chem. 1990, 33: 52 - 8
Jacob P.Callery PS.Shulgin AT.Castagnoli N. J. Org. Chem. 1976, 41: 3627 -
9a
Luly JR.Rapoport H. J. Org. Chem. 1981, 46: 2745 -
9b
Snyder CD.Rapoport H. J. Am. Chem. Soc. 1972, 94: 227 - 10
Ohgaki E.Motoyoshiya J.Narita S.Nakurai T.Hayashi S.Hirakawa K. J. Chem. Soc., Perkin Trans. 1 1990, 3109 -
11a
Zani CL.Fairlamb AH. Mem. Inst. Oswaldo Cruz. 2003, 98: 565 -
11b
Zani CL.Chiari E.Krettli AU.Murta SMF.Cunningham ML.Fairlamb AH.Romanha AJ. Bioorg. Med. Chem. 1997, 5: 2185 -
11c
Ribeiro-Rodrigues R.Dos Santos WG.Zani CL.Oliveira AB.Romanha AJ. Bioorg. Med. Chem. Lett. 1995, 5: 1509 - 12
Maya JD.Bollo S.Nuñez-Vergara LJ.Squella JA.Repetto Y.Morello A.Périé J.Chauvière G. Biochem. Pharm. 2003, 65: 999