Synthesis of the antifouling polyamine pseudoceratidine and its analogs: Factors influencing biocidal activity

Ponasik, James A.; Kassab, Darren J.; Ganem, Bruce

doi:10.1016/0040-4039(96)01310-x

Cited by 21 publications

(20 citation statements)

References 14 publications

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“…10,11 Commercially available 2,2,2-trichloro-1-(1 H -pyrrol-2-yl)ethenone ( 13 ) was brominated with Br 2 to give the known di-brominated pyrrole ( 14 ) 38 in 87% yield. Coupling of 14 with spermidine ( 15 ) in THF provided synthetic pseudoceratidine in 72% yield (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…8,9 The compound displayed more potent anti-fouling activity than its mono-substituted 4,5-dibromo-1 H -pyrrole-2-carboxylic acid spermidine analogs. 10 In these previous studies, it was found that both the substitution pattern of the terminal rings and the length of the triamine chain of pseudoceratidine derivatives affect the anti-fouling activity. Furthermore, pseudoceratidine also displayed the most potent antibacterial activity against Staphylococcus aureus , Listeria monocytogenes , Pseudomonas aeruginosa , Escherichia coli and Serratia liquefaciens .…”

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confidence: 98%

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Isolation, Derivative Synthesis, and Structure–Activity Relationships of Antiparasitic Bromopyrrole Alkaloids from the Marine Sponge Tedania brasiliensis

et al. 2018

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The isolation and identification of a series of new pseudoceratidine (1) derivatives from the sponge Tedania brasiliensis enabled the evaluation of their anti-parasitic activity against Plasmodium falciparum, Leishmania (Leishmania) amazonensis, Leishmania (Leishmania) infantum and Trypanosoma cruzi, the causative agents of malaria, cutaneous leishmaniasis, visceral leishmaniasis and Chagas disease, respectively. The new 3-debromopseudoceratidine (4), 20-debromopseudoceratidine (5), 4-bromopseudoceratidine (6), 19-bromopseudoceratidine (7) and 4,19-dibromopseudoceratidine (8) are reported. New tedamides A – D (9 – 12), with an unprecedented 4-bromo-4-methoxy-5-oxo-4,5-dihydro-1H-pyrrole-2-carboxamide moiety, are also described. Compounds 4 and 5, 6 and 7, 9 and 10, and 11 and 12 have been isolated as pairs of inseparable structural isomers differing in their sites of bromination or oxidation. Tedamides 9+10 and 11+12 were obtained as optically active pairs, indicating an enzymatic formation rather than an artefactual origin. N12-Acetyl pseudoceratidine (2) and N12-formyl pseudoceratidine (3) were obtained by derivatization of pseudoceratidine (1). The anti-parasitic activity of pseudoceratidine (1) led us to synthesize 23 derivatives (16, 17, 20, 21, 23, 25, 27 – 29, 31, 33, 35, 38, 39, 42, 43, 46, 47, 50 and 51) with variations in the polyamine chain and aromatic moiety in sufficient amounts for biological evaluation in anti-parasitic assays. The measured anti-malarial activity of pseudoceratidine (1) and derivatives 4, 5, 16, 23, 25, 31 and 50 provided an initial SAR evaluation of these compounds as potential leads for anti-parasitics against Leishmania amastigotes and against Plasmodium falciparum. The results obtained indicate that pseudoceratidine represents a promising scaffold for the development of new anti-malarial drugs.

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Section: Resultsmentioning

confidence: 99%

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confidence: 98%

Isolation, Derivative Synthesis, and Structure–Activity Relationships of Antiparasitic Bromopyrrole Alkaloids from the Marine Sponge Tedania brasiliensis

et al. 2018

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“…Many authors reported [76][77][78] In the same year, Williams et al 84 Analogous to the previously reports [87][88][89][90][91][92] [124][125][126] . For example, the pyrrolomycin A (150a) had distinguished antibiotic activity 127 , natural product dispacamide B (150b) and its d erivatives iso lated fr o m sp o n ge had e v id ent antibacterial activities 126,128,129 . Also, monodeoxypyoluteorin (150c) and 2-(2 ‫׳‬ -hydroxy benzoyl) pyrrole bromine (150d) 130,131 are pyrrole derivatives having antimicrobial activity against Staphylococcus aureus, Bacillus subtilis and Escherichia coli, added to antifun gal activit y a gainst Ca n d id a a lb ica n s.…”

Section: Synthesis Of Pyrrolopyrimidines From Pyrimidinesmentioning

confidence: 55%

Synthesis Strategies and Biological Value of Pyrrole and Pyrrolopyrimidine

Mohamed

El-Hameed

Sayed

2017

Journal of Advanced Pharmacy Research

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For several decades, interest in the synthesis pyrrole and pyrrolopyrimidine increases due to the importance of these heterocycles both from chemical and biological points of view. They possess several biological activities such as antimicrobial, analgesic, anti-inflammatory, anti-cancer, anti-viral, anti-convulsant, anti-hyperlipidemic, anti-depressant, antidiabetic, anti-allergic activities. These findings motivated us to present this review which highlights different methods of the synthesis of pyrrole and pyrrolopyrimidine derivatives as well as their biological importance from the past to recent years.

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“…Pseudoceratidine ( PAC-7 ), an antifouling agent that can prevent attachment of marine organisms ( e.g. , mollusks, barnacles) to hulls of ships and other submerged structures, was first isolated and synthesized in 1996 [ 63 , 82 ]. Its interesting spectrum of antimicrobial and marine biocidal effects are of potential industrial significance [ 83 ].…”

Section: Adomet Pathways and Marine-derived Adomet Metabolitesmentioning

confidence: 99%

Marine-Derived Metabolites of S-Adenosylmethionine as Templates for New Anti-Infectives

2009

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S-Adenosylmethionine (AdoMet) is a key biochemical co-factor whose proximate metabolites include methylated macromolecules (e.g., nucleic acids, proteins, phospholipids), methylated small molecules (e.g., sterols, biogenic amines), polyamines (e.g., spermidine, spermine), ethylene, and N-acyl-homoserine lactones. Marine organisms produce numerous AdoMet metabolites whose novel structures can be regarded as lead compounds for anti-infective drug design.

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Synthesis of the antifouling polyamine pseudoceratidine and its analogs: Factors influencing biocidal activity

Cited by 21 publications

References 14 publications

Isolation, Derivative Synthesis, and Structure–Activity Relationships of Antiparasitic Bromopyrrole Alkaloids from the Marine Sponge Tedania brasiliensis

Isolation, Derivative Synthesis, and Structure–Activity Relationships of Antiparasitic Bromopyrrole Alkaloids from the Marine Sponge Tedania brasiliensis

Synthesis Strategies and Biological Value of Pyrrole and Pyrrolopyrimidine

Marine-Derived Metabolites of S-Adenosylmethionine as Templates for New Anti-Infectives

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