Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-Type alkaloids

Verotta, Luisellá; Orsini, Fulvia; Sbacchi, M.; Scheildler, M.A; Amador, Tânia Alves; Elisabetsky, Elaine

doi:10.1016/s0968-0896(02)00078-0

Cited by 68 publications

(30 citation statements)

References 25 publications

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“…The potent antinociceptive activity of dimeric or polymeric pyrrolidinoindoline alkaloids that interact with opioid receptors was recently reported by Elisabetsky-Verotta's group. 51,52) The syntheses of these alkaloids have been accomplished so far by using the direct coupling reaction of tryptamine derivatives under various conditions [53][54][55][56][57] as well as by employing a multistep procedure via an elegant strategy. [58][59][60] Initially, we treated N b -carbomethoxytryptamine (67) with PIDA under the conditions developed above; however, this resulted mainly in the recovery of the starting material.…”

Section: Preparation Of Mitragynine Derivativesmentioning

confidence: 99%

Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa

2004

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The leaves of a tropical plant, Mitragyna speciosa KORTH (Rubiaceae), have been traditionally used as a substitute for opium. Phytochemical studies of the constituents of the plant growing in Thailand and Malaysia have led to the isolation of several 9-methoxy-Corynanthe-type monoterpenoid indole alkaloids, including new natural products. The structures of the new compounds were elucidated by spectroscopic and/or synthetic methods. The potent opioid agonistic activities of mitragynine, the major constituent of this plant, and its analogues were found in in vitro and in vivo experiments and the mechanisms underlying the analgesic activity were clarified. The essential structural features of mitragynines, which differ from those of morphine and are responsible for the analgesic activity, were elucidated by pharmacological evaluation of the natural and synthetic derivatives. Among the mitragynine derivatives, 7-hydroxymitragynine, a minor constituent of M. speciosa, was found to exhibit potent antinociceptive activity in mice.

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Section: Preparation Of Mitragynine Derivativesmentioning

confidence: 99%

Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa

2004

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“…Chimonanthine, meso-chimonanthine and psycotridine have been isolated by Verrota et al in 1999 [7]. These compounds showed an analgesic activity [8][9].…”

Section: Chimonantinementioning

confidence: 99%

Characterization Of Alkaloids From The Leaves Of Psychotria Malayana Jack Of Lombok Island On The Basis Of Gas Chromatography-Mass Spectroscopy

Hadi

Rahmawati

Asnawati

et al. 2014

J. Pure App. Chem. Res.

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The genus Psychotria is well known as a source of alkaloids and has contributed several novel indole-type alkaloids with quite a broad spectrum of bioactivities. This study was focused on identifying the alkaloids from the leaves of P. malayana Jack from Lombok island on the basis of Gas Chromatography-Mass Spectroscopy (GC-MS) data and the sample preparation followed acid-base extraction. The study showed that the major alkaloid contained by the leaves was hodgkinsine and other minor compounds, namely calycanthine, chimonantine, 2-ethyl-6-methylpyrazine, and 3-methyl-1,2,3,4-tetrahydrogamma-carboline. Bioactivities of the compounds were also discussed.

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“…The products 2a [29] (yield 85%) and 2b [30] (yield 91%) were synthesized following the procedure reported in literature [30] .…”

Section: Synthesis Of Methyl (2-(indol-3-yl)ethyl)carbamatesmentioning

confidence: 99%

A new scaffold of topoisomerase I inhibitors: Design, synthesis and biological evaluation

Mazza

Beccalli

Contini

et al. 2016

European Journal of Medicinal Chemistry

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Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-Type alkaloids

Cited by 68 publications

References 25 publications

Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa

Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa

Characterization Of Alkaloids From The Leaves Of Psychotria Malayana Jack Of Lombok Island On The Basis Of Gas Chromatography-Mass Spectroscopy

A new scaffold of topoisomerase I inhibitors: Design, synthesis and biological evaluation

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