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Synthesis and Characterization of the Biologically Active 2‐[1‐(4‐Chlorobenzyl)‐1 H ‐indol‐3‐yl]‐2‐oxo‐ N ‐pyridin‐4‐yl Acetamide
Author(s) -
Knaack Martin,
Emig Peter,
Bats Jan W.,
Kiesel Michael,
Müller Arndt,
Günther Eckhard
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200110)2001:20<3843::aid-ejoc3843>3.0.co;2-p
Subject(s) - acetamide , chemistry , indole test , stereochemistry , proton nmr , combinatorial chemistry , organic chemistry
The spectroscopic characterization of the new potent tubulin inhibitor 2‐[1‐(4‐chlorobenzyl)‐1 H ‐indol‐3‐yl]‐2‐oxo‐ N ‐pyridin‐4‐yl acetamide (D‐24851) ( 7 ), which is under preclinical development, is described. The synthesis was optimized and follows a straightforward route from the unsubstituted indole via the 1‐(4‐chlorobenzyl)‐indole ( 3 ) and the indol‐3‐yl‐2‐oxo‐acetyl chloride ( 5 ) to the indol‐3‐yl‐2‐oxo acetamide product. The structure was assigned by sophisticated NMR experiments, for example a 1,1‐ADEQUATE experiment, and X‐ray crystallography.