scholarly journals Total synthesis of the isoquinolinium metabolite ETM-204 of Trabectidin

Author(s):  
Christian Lembacher-Fadum ◽  
Simon Gissing ◽  
Georg Pour ◽  
Rolf Breinbauer

AbstractEcteinascidin-743 (Trabectidin, Trabectedin®, Yondelis®) is a synthetically obtained pharmaceutical drug originally isolated from a marine tunicate. Trabectedin is used for the chemotherapy of soft-tissue sarcoma and ovarian cancer. The isoquinolinium metabolite ETM-204 has been found in biotransformation and degradation studies of Trabectedin. We report the first total synthesis of ETM-204 and its full spectroscopic characterization confirming the postulated structure. Central elements of the 12-step synthesis starting from 2-methyl-6-nitrophenol are a Cu-mediated conversion of an iodoarene to a phenol, a Skattebøl-formylation, and a modified Pomeranz–Fritsch cyclization to assemble the isoquinoline ring. The pH-dependence of its visual absorbance could be clarified. Graphic abstract

2017 ◽  
Vol 28 ◽  
pp. vi66-vi67
Author(s):  
L. Porcelli ◽  
A. Azzariti ◽  
S. Strippoli ◽  
R. Di Fonte ◽  
M. Garofoli ◽  
...  

2008 ◽  
Vol 9 (9) ◽  
pp. 1609-1618 ◽  
Author(s):  
Patrick Schöffski ◽  
Herlinde Dumez ◽  
Pascal Wolter ◽  
Cristiana Stefan ◽  
Agnieszka Wozniak ◽  
...  

Author(s):  
Willy J.M. Jansen ◽  
Geertruida M. Kolfschoten ◽  
Caroline A.M. Erkelens ◽  
Jannette Van Ark-Otte ◽  
Herbert M. Pinedo ◽  
...  

Author(s):  
J. P. Brunschwig ◽  
R. M. McCombs ◽  
R. Mirkovic ◽  
M. Benyesh-Melnick

A new virus, established as a member of the herpesvirus group by electron microscopy, was isolated from spontaneously degenerating cell cultures derived from the kidneys and lungs of two normal tree shrews. The virus was found to replicate best in cells derived from the homologous species. The cells used were a tree shrew cell line, T-23, which was derived from a spontaneous soft tissue sarcoma. The virus did not multiply or did so poorly for a limited number of passages in human, monkey, rodent, rabbit or chick embryo cells. In the T-23 cells, the virus behaved as members of the subgroup B of herpesvirus, in that the virus remained primarily cell associated.


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