A New and Facile Synthesis of Rutaecarpine Alkaloids

Lee, Chih-Shone; Liu, Cheng-Kuo; Cheng, Yen‐Yao; Teng, Che-Ming

doi:10.3987/com-08-11606

Cited by 18 publications

(6 citation statements)

References 47 publications

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“…Among a variety of synthetic methods for rutaecarpine, [16][17][18][19][20]24) the Fischer indole synthesis from the corresponding hydrazone of 6,7,8,9-tetrahydropyrido[2,1-b]quinazoline-6,11-dione (1) 24) and phenylhydrazine (2a) has been used as a simple and practical method and employed for preparing derivatives of rutaecarpines on ring E. 25) Benzo-annulation on ring E can, thus, be achieved by employing the ketone 1 and commercially available 1-and 2-hydrazinonaphthalenes.…”

Section: Resultsmentioning

confidence: 99%

“…15) Such a variety of intriguing biological properties have led not only to the development of synthetic methods [16][17][18][19][20] but also to the systematic examination of its metabolites. [21][22][23] Although the action mechanisms of antiinflammatory, 3) vasorelaxing, 6) antiplatelet, 8) and antiobesity 11) effect of rutaecarpine have been studied, those of cytotoxicity have not been pursued as yet.…”

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confidence: 99%

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Synthesis and Biological Properties of Benzo-Annulated Rutaecarpines

Hong

Lee

et al. 2010

Biological & Pharmaceutical Bulletin

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A series of benzo-annulated rutaecarpines were prepared from anthranilic acid and 3-aminonaphthalene-2-carboxylic acid by Fischer indole synthesis as key reaction. Cytotoxicity was somewhat increased by the introduction of benzo-annulation, which was not directly related to the inhibitory activity against topoisomerases (topo) I and II. Benzo-annulation on ring A led to significant increase of inhibitory activity against topo II while annulations on ring E increased inhibitory activity against topo I.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Synthesis and Biological Properties of Benzo-Annulated Rutaecarpines

Hong

Lee

et al. 2010

Biological & Pharmaceutical Bulletin

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“…Lee et al . [27,28] and Kamal et al [29] used a one-pot reductive-cyclization of nitro ( 9a ) and azide compounds ( 9b ), respectively, to construct the quinazolinone skeleton. Tryptamine was subjected to a Bischler-Napieralsky reaction to afford starting compound 7 , which was then condensed with 3e and 2-azidobenzoyl chloride ( 3f ) to afford 8a and 8b , respectively.…”

Section: Synthesis Of Rutaecarpinementioning

confidence: 99%

“…The reduction of the nitro group in 9a by tin chloride resulted in subsequent cyclization giving 1a in 94% yield [27,28]. On the other hand, the related 2-azobenzamide ( 9b ) undergoes an aza-Wittig reductive cyclization in the presence of Ph 3 P and NH 4 OH or Ni 2 B in HCl-MeOH under microwave irradiation [29].…”

Section: Synthesis Of Rutaecarpinementioning

confidence: 99%

Progress in Studies on Rutaecarpine. II.—Synthesis and Structure-Biological Activity Relationships

2015

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Rutaecarpine is a pentacyclic indolopyridoquinazolinone alkaloid found in Evodia rutaecarpa and other related herbs. It has a variety of intriguing biological properties, which continue to attract the academic and industrial interest. Studies on rutaecarpine have included isolation from new natural sources, development of new synthetic methods for its total synthesis, the discovery of new biological activities, metabolism, toxicology, and establishment of analytical methods for determining rutaecarpine content. The present review focuses on the synthesis, biological activities, and structure-activity relationships of rutaecarpine derivatives, with respect to their antiplatelet, vasodilatory, cytotoxic, and anticholinesterase activities.

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“…The alkaloid rutaecarpine (34) was synthesized by various methods [44,48,56,58,81,83,84,[91][92][93][94][95][96][97]. The principal starting compounds in these reactions were bi-or tricyclic quinazolinones and -diones (69-71) containing an indole moiety or various indoles condensed with a piperidine ring (73)(74)(75).…”

mentioning

confidence: 99%