Pyridoacridines in the 21st Century

Joule, J. A.; Álvarez, Mercedes

doi:10.1002/ejoc.201900401

Cited by 18 publications

(8 citation statements)

References 192 publications

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“…There are total 15 isomers according to the different ring systems distributed in a broad range of functional products, but only two isomers sharing two common bonds are well‐known owing to their existence in natural alkaloids (Figure 1). [ 1 ] Pyrido[2,3,4‐ kl ]acridine is a large family and more than 100 of these polycyclic heteroaromatics have been isolated from sessile marine invertebrates. [ 2 ] Correspondingly, pyrido[4,3,2‐ kl ]acridine is a quite small family and only discovered in nature as the necatorone and its dimer from fungi Lactarius necator .…”

Section: Background and Originality Contentmentioning

confidence: 99%

Divergent Syntheses of Pyridoacridine Alkaloids viaPalladium‐Catalyzed Reductive Cyclization with Nitro‐Biarenes

et al. 2021

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Main observation and conclusion A divergent and novel protocol for the preparation of both pyrido[2,3,4‐kl]acridine and pyrido[4,3,2‐kl]acridine alkaloids was developed. This method featured the remote palladium‐catalyzed reductive cyclization with Mo(CO)6 as reductant. A wide range of substrates including three types of nitro arenes were tolerated and afforded corresponding products in good to excellent yields. This method has been successfully applied to the total synthesis of norsegoline, styelsamine C and the skeleton of necatorone.

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Section: Background and Originality Contentmentioning

confidence: 99%

Divergent Syntheses of Pyridoacridine Alkaloids viaPalladium‐Catalyzed Reductive Cyclization with Nitro‐Biarenes

et al. 2021

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“…Pyridoacridines are a unique group of purely marine alkaloids that are often cytotoxic. They have been isolated from sponges, molluscs, tunicates, and cnidarians and it is suspected that 12 is trophically sequestered from the polyclad's prey [69,70]. It is unclear how 12 contributes to the defence of the polyclad considering several staurosporines were also isolated from this species [67,71].…”

Section: Pseudocerosinementioning

confidence: 99%

Natural Products in Polyclad Flatworms

et al. 2021

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Marine invertebrates are promising sources of novel bioactive secondary metabolites, and organisms like sponges, ascidians and nudibranchs are characterised by possessing potent defensive chemicals. Animals that possess chemical defences often advertise this fact with aposematic colouration that potential predators learn to avoid. One seemingly defenceless group that can present bright colouration patterns are flatworms of the order Polycladida. Although members of this group have typically been overlooked due to their solitary and benthic nature, recent studies have isolated the neurotoxin tetrodotoxin from these mesopredators. This review considers the potential of polyclads as potential sources of natural products and reviews what is known of the activity of the molecules found in these animals. Considering the ecology and diversity of polyclads, only a small number of species from both suborders of Polycladida, Acotylea and Cotylea have been investigated for natural products. As such, confirming assumptions as to which species are in any sense toxic or if the compounds they use are biosynthesised, accumulated from food or the product of symbiotic bacteria is difficult. However, further research into the group is suggested as these animals often display aposematic colouration and are known to prey on invertebrates rich in bioactive secondary metabolites.

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“…For example, substituted benzo[c]phenanthroline analogues of nitidine and fagaronine showed cytotoxic properties associated with DNA intercalation and induced G2/M phases arrests [12]. Synthetic pyrido [1,8] or [1,9] phenanthroline analogues of amphimedine exhibited cytotoxic activities in various cancer cell lines [13,14]. Recently, our group also reported several fused pyrrolo [1,7] or [4,7] phenanthrolines which showed moderate antiproliferative activity [15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Modelling and Anticancer Activities of New Fused Phenanthrolines

et al. 2020

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Three series of fused pyrrolophenanthroline derivatives were designed as analogues of phenstatin and synthesized in two steps starting with 1,7-phenanthroline, 4,7-phenanthroline and 1,10-phenanthroline, respectively. Two (Compounds 8a and 11c) of the four compounds tested against a panel of sixty human cancer cell lines of the National Cancer Institute (NCI) exhibited significant growth inhibition activity on several cell lines. Compound 11c showed a broad spectrum in terms of antiproliferative efficacy with GI50 values in the range of 0.296 to 250 μM. Molecular docking studies indicated that Compounds 8a and 11c are accommodated in the colchicine binding site of tubulin in two different ways.

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Pyridoacridines in the 21st Century

Cited by 18 publications

References 192 publications

Divergent Syntheses of Pyridoacridine Alkaloids viaPalladium‐Catalyzed Reductive Cyclization with Nitro‐Biarenes

Divergent Syntheses of Pyridoacridine Alkaloids viaPalladium‐Catalyzed Reductive Cyclization with Nitro‐Biarenes

Natural Products in Polyclad Flatworms

Design, Synthesis, Molecular Modelling and Anticancer Activities of New Fused Phenanthrolines

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