Synthesis and biological activity of analogues of batzelladine F

Bennett, Elliot L.; Black, Gregory P.; Browne, Patrick; Hizi, Amnon; Jaffar, Mohammed; Leyland, John P.; Martin, Claire; Oz-Gleenberg, Iris; Murphy, P. J.; Roberts, Terence D.; Thornhill, Andrew J.; Vale, Steven A.

doi:10.1016/j.tet.2013.01.083

Cited by 10 publications

(12 citation statements)

References 30 publications

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“…Four anti-parasitic batzelladines ( 74 – 77 ) against Trypanosoma cruzi and Leishmania infantum were recently recorded from Monanchora arbuscula [ 43 , 68 ]. Numerous synthetic batzelladines and their derivatives showed potent activities against HIV-1 and AIDS opportunistic infectious pathogens, inhibition of HIV-1 envelope-mediated fusion [ 69 ], inhibitors of HIV-1 Nef interactions with p53, actin and p56 lck [ 70 ], antimalarial, antileishmanial, antimicrobial and antiviral (HIV-1) activities [ 71 ], inhibitors against HIV-1 reverse transcriptase (RT) [ 72 ] and antileishmanial [ 73 ] ( Figure 5 and Figure 6 ).…”

Section: Chemistry and Biology Of Natural Products Isolated From mentioning

confidence: 99%

Batzella, Crambe and Monanchora: Highly Prolific Marine Sponge Genera Yielding Compounds with Potential Applications for Cancer and Other Therapeutic Areas

et al. 2018

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Pyrroloquinoline and guanidine-derived alkaloids present distinct groups of marine secondary metabolites with structural diversity that displayed potentialities in biological research. A considerable number of these molecular architectures had been recorded from marine sponges belonging to different marine genera, including Batzella, Crambe, Monanchora, Clathria, Ptilocaulis and New Caledonian starfishes Fromia monilis and Celerina heffernani. In this review, we aim to comprehensively cover the chemodiversity and the bioactivities landmarks centered around the chemical constituents exclusively isolated from these three marine genera including Batzella, Crambe and Monanchora over the period 1981–2017, paying a special attention to the polycyclic guanidinic compounds and their proposed biomimetic landmarks. It is concluded that these marine sponge genera represent a rich source of novel compounds with potential applications for cancer and other therapeutic areas.

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Section: Chemistry and Biology Of Natural Products Isolated From mentioning

confidence: 99%

Batzella, Crambe and Monanchora: Highly Prolific Marine Sponge Genera Yielding Compounds with Potential Applications for Cancer and Other Therapeutic Areas

et al. 2018

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“…41 and tetracyclic guanidine 17 were prepared as previously described. [46][47][48][49][50][51][52] The naturally occurring guanidine alkaloid nitensidine D (18) 52 was prepared as its hydrochloride salt in 53% yield by the reaction of geranylamine with 1H-pyrazole-1-carboxamidine hydrochloride. Miltefosine was used as a standard drug.…”

Section: Immunomodulatory Potential Of Compounds Quantification Of Nmentioning

confidence: 99%

Analogues of Marine Guanidine Alkaloids Are in Vitro Effective against Trypanosoma cruzi and Selectively Eliminate Leishmania (L.) infantum Intracellular Amastigotes

et al. 2016

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Synthetic analogues of marine sponge guanidine alkaloids showed in vitro antiparasitic activity against Leishmania (L.) infantum and Trypanosoma cruzi. Guanidines 10 and 11 presented the highest selectivity index when tested against Leishmania. The antiparasitic activity of 10 and 11 was investigated in host cells and in parasites. Both compounds induced depolarization of mitochondrial membrane potential, upregulation of reactive oxygen species levels, and increased plasma membrane permeability in Leishmania parasites. Immunomodulatory assays suggested an NO-independent effect of guanidines 10 and 11 on macrophages. The same compounds also promoted anti-inflammatory activity in L. (L.) infantum-infected macrophages cocultived with splenocytes, reducing the production of cytokines MCP-1 and IFN-γ. Guanidines 10 and 11 affect the bioenergetic metabolism of Leishmania, with selective elimination of parasites via a host-independent mechanism.

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“…The Murphy group also independently found that the originally proposed relative stereochemistry of the tricyclic core of batzelladine F ( 301f ) was incorrect. 400-403 They completed the biomimetic synthesis of crambescidin 359 ( 4b ) in 2003. 404,405 The synthesis of 4b started with the Wittig reaction of 326 and 333 (Fig.…”

Section: The Crambescidin/batzelladine Alkaloidsmentioning

confidence: 99%

Syntheses of cyclic guanidine-containing natural products

Chen

2015

Tetrahedron

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Naturally occurring guanidine derivatives frequently display medicinally useful properties. Among them, the higher order pyrrole-imidazole alkaloids, the dragmacidins, the crambescidins/batzelladines, and the saxitoxins/tetradotoxins have stimulated the development of many new synthetic methods over the past decades. We provide here an overview of the syntheses of these cyclic guanidine-containing natural products.

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Synthesis and biological activity of analogues of batzelladine F

Cited by 10 publications

References 30 publications

Batzella, Crambe and Monanchora: Highly Prolific Marine Sponge Genera Yielding Compounds with Potential Applications for Cancer and Other Therapeutic Areas

Batzella, Crambe and Monanchora: Highly Prolific Marine Sponge Genera Yielding Compounds with Potential Applications for Cancer and Other Therapeutic Areas

Analogues of Marine Guanidine Alkaloids Are in Vitro Effective against Trypanosoma cruzi and Selectively Eliminate Leishmania (L.) infantum Intracellular Amastigotes

Syntheses of cyclic guanidine-containing natural products

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