The Palladium-Mediated Cross Coupling of Bromotropolones With Organostannanes or Arylboronic Acids: Applications to the Synthesis of Natural Products and Natural Product Analogs

Banwell, Martin G.; Cameron, JM; Collis, Maree P.; Crisp, G. T.; Gable, R. W.; Hamel, Ernest; Lambert, John N.; Mackay, M. F.; Reum, Monica E.; Scoble, J. A.

doi:10.1071/ch9910705

Cited by 45 publications

(20 citation statements)

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“…(E)-2,3,4-Trimethoxy-6-(2-nitrovinyl)biphenyl (14 56.1, 60.0, 60.1, 105.6, 123.8, 129.3, 129.5, 130.7, 131.5, 136.9, 137.2 70 (s, 1 H), 6.84 (s, 1 H) …”

Section: H and 13mentioning

confidence: 99%

“…It was also shown that any alteration to the trioxygenated moiety of ring A, which serves as an anchor for tubulin binding, [13] leads to compounds with decreased anti-tubulin activity. [14] In contrast, the biological activity of ring C-substituted allocolchicinoids varies with the size, position, and nature of the substituents. [15] It was found that only natural (À)-(7S)-colchicine, which adopts an aR biaryl configuration, binds effectively to tubulin.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antitumor Evaluation of Nitrovinyl Biphenyls: Anticancer Agents Based on Allocolchicines

et al. 2011

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A new class of nitrovinyl biphenyl compounds based on the structures of colchicines and allocolchicines were designed, synthesized, and shown to inhibit tubulin polymerization and cause mitotic arrest. A majority of these compounds were found to possess potent anticancer properties, with IC(50) values in the range of 0.05-7 μM, and are equally potent with colchicine in HeLa and MCF-7 cells. Compounds 14 e and 14 f inhibited tubulin assembly by more than 60 %, and flow cytometry studies indicated growth arrest of cells in the G(2)/M phase of the cell cycle in a concentration-dependent manner. Treatment of cells with 14 f resulted in upregulation of cyclin B1 and aurora kinase B mRNA levels, corresponding to growth arrest in the G(2)/M phase of the cell cycle as the mode of action.

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“…(E)-2,3,4-Trimethoxy-6-(2-nitrovinyl)biphenyl (14 56.1, 60.0, 60.1, 105.6, 123.8, 129.3, 129.5, 130.7, 131.5, 136.9, 137.2 70 (s, 1 H), 6.84 (s, 1 H) …”

Section: H and 13mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Antitumor Evaluation of Nitrovinyl Biphenyls: Anticancer Agents Based on Allocolchicines

et al. 2011

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“…180–181 The synthesis of nezukone involved the formation of alkylidene cyclopropane from halocyclopropane followed by ring expansion. 31 …”

Section: Synthesis Of Naturally Occurring Tropones and Tropolonesmentioning

confidence: 99%

Synthesis of naturally occurring tropones and tropolones

et al. 2014

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Tropones and tropolones are an important class of seven-membered non-benzenoid aromatic compounds. They can be prepared directly by oxidation of seven-membered rings. They can also be derived from cyclization or cycloaddition of appropriate precursors followed by elimination or rearrangement. This review discusses the types of naturally occurring tropones and tropolones and outlines important methods developed for the synthesis of tropone and tropolone natural products.

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“…Compounds no. 261 to 264 were made from 1,4-cyclohexadiene using the Banwell ␣HT synthesis method (43,44), and specifics can be found in the supplemental material. Compounds were Ն95% pure by 1 H NMR analysis.…”

Section: Methodsmentioning

confidence: 99%

Troponoids Can Inhibit Growth of the Human Fungal Pathogen Cryptococcus neoformans

Donlin

Zunica

Lipnicky

et al. 2017

Antimicrob Agents Chemother

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Cryptococcus neoformans is a pathogen that is common in immunosuppressed patients. It can be treated with amphotericin B and fluconazole, but the mortality rate remains 15 to 30%. Thus, novel and more effective anticryptococcal therapies are needed. The troponoids are based on natural products isolated from western red cedar, and have a broad range of antimicrobial activities. Extracts of western red cedar inhibit the growth of several fungal species, but neither western red cedar extracts nor troponoid derivatives have been tested against C. neoformans. We screened 56 troponoids for their ability to inhibit C. neoformans growth and to assess whether they may be attractive candidates for development into anticryptococcal drugs. We determined MICs at which the compounds inhibited 80% of cryptococcal growth relative to vehicle-treated controls and identified 12 compounds with MICs ranging from 0.2 to 15 M. We screened compounds with MICs of Յ20 M for cytotoxicity in liver hepatoma cells. Fifty percent cytotoxicity values (CC 50 s) ranged from 4 to Ͼ100 M. The therapeutic indexes (TI, CC 50 /MIC) for most of the troponoids were fairly low, with most being Ͻ8. However, two compounds had TI values that were Ͼ8, including a tropone with a TI of Ͼ300. These tropones are fungicidal and are not antagonistic when used in combination with fluconazole or amphotericin B. Inhibition by these two tropones remains unchanged under conditions favoring cryptococcal capsule formation. These data support the hypothesis that troponoids may be a productive scaffold for the development of novel anticryptococcal therapies.

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The Palladium-Mediated Cross Coupling of Bromotropolones With Organostannanes or Arylboronic Acids: Applications to the Synthesis of Natural Products and Natural Product Analogs

Cited by 45 publications

References 0 publications

Synthesis and Antitumor Evaluation of Nitrovinyl Biphenyls: Anticancer Agents Based on Allocolchicines

Synthesis and Antitumor Evaluation of Nitrovinyl Biphenyls: Anticancer Agents Based on Allocolchicines

Synthesis of naturally occurring tropones and tropolones

Troponoids Can Inhibit Growth of the Human Fungal Pathogen Cryptococcus neoformans

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