Synthesis and biological activity of mycalolide analogs

Suenaga, Kiyotake; Kimura, Tomoyuki; Kuroda, Takeshi; Matsui, Keita; Miya, Saori; Kuribayashi, Satomi; Sakakura, Akira; Kigoshi, Hideo

doi:10.1016/j.tet.2006.06.046

Cited by 33 publications

(23 citation statements)

References 34 publications

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“…The commonly described literature procedure for this reaction requires heating a mixture of the aldehyde and N ‐methyl formamide (NMF) in the presence of catalytic amounts of Brønsted acids, such as PPTS or p ‐toluenesulfonic acid (PTSA). An important issue was the efficient removal of the water that was generated within this condensation process, either by using molecular sieves or by azeotropic distillation 103. However, on applying these procedures to our model systems, we obtained varying results.…”

Section: Resultsmentioning

confidence: 99%

“…An important issue was the efficient removal of the water that was generated within this condensation process, either by using molecular sieves or by azeotropic distillation. [103] However, on applying these procedures to our model systems, we obtained varying results. Even in the case of simple aldehyde 126, only low yields or even no conversion were observed.…”

Section: Aldol Condensation Strategy Towards Rhizopodinmentioning

confidence: 99%

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Modular Total Synthesis of Rhizopodin: A Highly Potent G‐Actin Dimerizing Macrolide

Kretschmer

Dieckmann

et al. 2013

Chemistry A European J

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A highly convergent total synthesis of the potent polyketide macrolide rhizopodin has been achieved in 29 steps by employing a concise strategy that exploits the molecule's C2 symmetry. Notable features of this convergent approach include a rapid assembly of the macrocycle through a site-directed sequential cross-coupling strategy and the bidirectional attachment of the side chains by means of Horner-Wadsworth-Emmons (HWE) coupling reactions. During the course of this endeavor, scalable routes for synthesis of three main building blocks of similar complexity were developed that allowed for their stereocontrolled construction. This modular route will be amenable to the development of syntheses of other analogues of rhizopodin.

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Section: Resultsmentioning

confidence: 99%

Section: Aldol Condensation Strategy Towards Rhizopodinmentioning

confidence: 99%

Modular Total Synthesis of Rhizopodin: A Highly Potent G‐Actin Dimerizing Macrolide

Kretschmer

Dieckmann

et al. 2013

Chemistry A European J

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“…Trisoxazole macrolides have displayed a range of biological activities, including cytotoxic, proteasome inhibiting, actin-depolymerising, antimalarial, and antifungal activities. Mycalolides A-C (91-93) have reported cytotoxic activity against B-16 melanoma cells (IC 50 values ranging from 0.5-1.0 ng/mL) [49], mycalolide B (92) has displayed activity against HeLa cells (IC 50 value of 0.0035 µg/mL) [64], and mycalolides C (93) and D (94) have shown moderate activity (average LC 50 values of 2.5 and 0.6 µM, respectively) against the National Cancer Instituteʼs 60-human tumour cell line panel [53]. The sulphated and hydroxylated mycalolides have also shown considerable cytotoxicity.…”

Section: Polyketides Macrolidesmentioning

confidence: 99%

“…Additionally, the activity of mycalolide B (92) has been further explored in an effort to characterise both the actin depolymerising activity [65] and actomyosin inhibitory activity [66]. Through the exploration of an analogue of mycalolide B (92), Suenaga et al [64] documented that the side chain portion of the compound is responsible for actin-depolymerisation activity and that the macrocyclic ring is essential to cytotoxicity. Six other unrelated macrolides with various biological activities have been isolated from the family Mycalidae (l " Figs.…”

Section: Polyketides Macrolidesmentioning

confidence: 99%

Chemical and Biological Aspects of Marine Sponges from the Family Mycalidae

2016

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Sponges are a useful source of bioactive natural products. Members of the family Mycalidae, in particular, have provided a variety of chemical structures including alkaloids, polyketides, terpene endoperoxides, peptides, and lipids. This review highlights the compounds isolated from Mycalid sponges and their associated biological activities. A diverse group of 190 compounds have been reported from over 40 specimens contained in 49 references. Over half of the studies have reported on the biological activities for the compounds isolated. The polyketides, in particular the macrolides, displayed potent cytotoxic activities (

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“…Various additional small agents have been discovered that target actin show cytotoxicity 2 at concentrations above 100 nM. For example, ulapualides, 4 mycalolides, 5 kabiramides, 6 sphinxolides/reidispongiolides, 7 swinholides, 7 and bistramides 8 are all actin-depolymerizing agents. Complexes between these macrolides and actin are similar to the aplyronine A-actin complex.…”

Section: Introductionmentioning

confidence: 99%