Alkaloids from Crinum firmifolium var. hygrophilum

Razafimbelo, Judith; Andriantsiferana, Marta; Baudouin, Geneviève; Tillequin, François

doi:10.1016/0031-9422(95)00565-x

Cited by 28 publications

(13 citation statements)

References 24 publications

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“…from Madagascar and Argentina, respectively, have been indicated in the remediation of parasitic infections which could also include malaria. 19,20 Interestingly, the first antimicrobial screen recorded on the Amaryllidaceae was in relation to its antiplasmodial effects. 21 In this seminal work, 44 different plants from 18 genera were examined for activity against the avian malarial parasite Plasmodium gallinaceum.…”

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Antiplasmodial Studies Within the Plant Family Amaryllidaceae

Nair

Staden

2019

Natural Product Communications

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Plants have long served as a first line of defense response to malaria. They have also spawned several classes of antimalarial drugs such as quinine and artemisinin. However, most if not all of these drugs have succumbed to multidrug resistance, thus reigniting interest in the identification of novel chemotherapies against this parasitic disease. The starting point for many of such endeavors lies with the plants themselves whose extracts have served as herbal remedies, which originate from traditional medicine (TM). Several species of the Amaryllidaceae have been shown to have such functions in TM. This survey examines those plants of the family, which have hitherto been examined for antiplasmodial effects against the malarial parasite Plasmodium falciparum. Also considered are the alkaloid constituents of these plants, which have demonstrated activities against various strains of the pathogen. Particular emphasis is made on those plants which both demonstrate such activity as well as have a place in traditional therapies for malaria.

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“…from Madagascar and Argentina, respectively, have been indicated in the remediation of parasitic infections which could also include malaria. 19,20…”

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confidence: 99%

Antiplasmodial Studies Within the Plant Family Amaryllidaceae

Nair

Staden

2019

Natural Product Communications

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“…The spectral data of our synthetic compound 17 are identical with those reported in the literatiure. 22 Since 17 has been converted into 3-hydroxy-8,9-methylenedioxy-phenanthridine (5) by Pd/C-catalyzed hydrogenolysis of 17, our work constitutes a formal total synthesis of this natural product. 22 Scheme 4 Formal total synthesis of alkaloid 3-hydroxy-8,9-methylenedioxyphenanthridine (5)…”

Section: Template For Synthesis Thiemementioning

confidence: 99%

Tf2O-Promoted Morgan–Walls Reaction: From a Flexible Approach to Functionalized Phenanthridines and Quinazolines to the Short and Divergent Total Syntheses of Alkaloids

Huang

2022

Synthesis

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A new protocol for the direct transformation of secondary amides (N-acyl-o-xenylamines) into phenanthridines under mild conditions is reported. The method features trifluoromethanesulfonic anhydride (Tf2O)/2-fluoropyridine as the efficient amide activation system and MeCN or CH2Cl2 as the solvent. For some substrates, MeCN participated in the reaction, which affords a mild access to polysubstituted quinazolines. By employing the Tf2O/2,4,6-tri-tert-butylpyrimidine (TTBP) combination, the method was extended to an N-formyl-o-xenylamine, which represents a recalcitrant amide substrate type for the dehydracyclization reaction. More importantly, a one-pot method was established for the direct and divergent synthesis of four types of phenanthridinoids from o-xenylamines, which features both tert-N-formyl-o-xenylamines and phenanthridinium salt as key and versatile intermediates. The investigation resulted in one of the shortest and the most efficient total syntheses of three natural products: trisphaeridine, 5,6-dihydrobicolorine, N-methylcrinasiadine, and in the formal total syntheses of other three ones: 3-hydroxytrisphaeridine, bicolorine, and zephycandidine A.

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“…After reduction of the imine function with NaBH 4 , treatment with an excess of LDA permitted to ensure the cyclization of cycle C [13]. A spontaneous air oxidation step achieved the preparation of the two different phenanthroline cores [14]. Selective introduction of aminoalkyl side chains in a position to the nitrogen atom on cycle A was realized in three steps.…”

Section: Chemistrymentioning

confidence: 99%