A Simple Synthesis of Rutaecarpine

Jahng, Yurngdong; Lee, Seung Ho; Kim, Seung Ill; Park, Jae Gyu; Lee, Eung Seok

doi:10.3987/com-01-9244

Cited by 37 publications

(2 citation statements)

References 6 publications

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“…In fact, mackinazolinone was chemically prepared [81] some 30 years before its first isolation as an alkaloid from Mackinlaya species [82]. The Fischer indole synthesis was applied to the key intermediate 9-phenylhyrazono-9,10,11,12-tetrahydro-4 H -pyrido[2,1- b ]quinazolin-4-one ( 36 ), which could be prepared by three different routes: a condensation of the corresponding 9,9-dibromo compound 35 with phenylhydrazine [83a], a direct condensation of 34 with phenyldiazonium chloride [83b,c], and three-step conversion via 37 [84]. The intermediate diketone 37 could also be prepared 5 steps from isatoic anhydride in 32-49% overall yields [85].…”

Section: Synthesismentioning

confidence: 99%

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Progress in the Studies on Rutaecarpine

et al. 2008

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Rutaecarpine is an indolopyridoquinazolinone alkaloid isolated from Evodia rutaecarpa and related herbs, which has shown a variety of intriguing biological properties such as anti-thrombotic, anticancer, anti-inflammatory and analgesic, anti-obesity and thermoregulatory, vasorelaxing activity, as well as effects on the cardiovascular and endocrine systems. Recent progress in the studies on the isolation, synthesis, structure-activity relationship studies, biological activities and metabolism of rutaecarpine are reviewed.

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Section: Synthesismentioning

confidence: 99%

“…A series of synthetic procedures for 34 have been reported in the literature [86] since the first chemical synthesis [81] and isolation from natural sources [82], some of which are directly extended to the synthesis of rutaecarpine [72,84,85]. …”

Section: Synthesismentioning

confidence: 99%