Tandem Stille/Suzuki—Miyaura Coupling of a Hetero‐Bis‐Metalated Diene. Rapid, One‐Pot Assembly of Polyene Systems.

Coleman, Robert S.; Walczak, Matthew C.

doi:10.1002/chin.200542108

Cited by 1 publication

(2 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Disconnection of the tetraene gave three fragments: pyrone 2 , the central butadiene connector 3 , and vinyl bromide 4 . It had been shown earlier that the hetero-bis-metallated butadiene 3 could be used for the synthesis of an extended polyene chain via sequential Stille and Suzuki coupling reactions . With this strategy in mind, we proceeded with the synthesis of 1 .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Biological Evaluation of Polyenylpyrrole Derivatives as Anticancer Agents Acting through Caspases-Dependent Apoptosis

et al. 2010

View full text Add to dashboard Cite

A class of polyenylpyrroles and their analogues were designed from a hit compound identified in a fungus. The compounds synthesized were evaluated for their cell cytotoxicity against human non-small-cell lung carcinoma cell lines A549. Two compounds were found to exhibit high cytotoxicity against A549 cells with IC(50) of 0.6 and 0.01 μM, respectively. The underlying mechanisms for the anticancer activity were demonstrated as caspases activation dependent apoptosis induction through loss of mitochondrial membrane potential, release of cytochrome c, increase in B-cell lymphoma-2-associated X protein (Bax) level, and decrease in B-cell lymphoma-2 (Bcl-2) level. The two compounds were nontoxic to normal human lung Beas-2b cells (IC(50) > 80 μM), indicating that they are highly selective in their cytotoxicity activities. Furthermore, one compound showed in vivo anticancer activity in human-lung-cancer-cell-bearing mice. These results open promising insights on how these conjugated polyenes mediate cytotoxicity and may provide a molecular rationale for future therapeutic interventions in carcinogenesis.

show abstract

Section: Resultsmentioning

confidence: 99%

“…It had been shown earlier that the hetero-bis-metallated butadiene 3 could be used for the synthesis of an extended polyene chain via sequential Stille and Suzuki coupling reactions. 12 With this strategy in mind, we proceeded with the synthesis of 1.…”

Section: Resultsmentioning

confidence: 99%