TY - JOUR
T1 - Application of the Stille coupling reaction to the synthesis of C2-substituted endo-exo unsaturated pyrrolo[2,1-c][1,4]benzodiazepines (PBDs)
AU - Tiberghien, Arnaud C.
AU - Hagan, David
AU - Howard, Philip W.
AU - Thurston, David E.
PY - 2004/10/18
Y1 - 2004/10/18
N2 - The Stille coupling reaction has been used to introduce novel vinyl, alkynyl and heterocyclic substituents to the C2-position of pyrrolo[2,1-c][1,4]benzodiazepine dilactams. Sodium borohydride reduction followed by N10-SEM deprotection has provided five analogues (6b, 8a–d) that contain C2-endo/exo-unsaturation and novel C2-substituents. These analogues have significant multilog cytotoxicity profiles in the NCI 60-Cell Line screen, and provide new SAR data for the PBD family.
AB - The Stille coupling reaction has been used to introduce novel vinyl, alkynyl and heterocyclic substituents to the C2-position of pyrrolo[2,1-c][1,4]benzodiazepine dilactams. Sodium borohydride reduction followed by N10-SEM deprotection has provided five analogues (6b, 8a–d) that contain C2-endo/exo-unsaturation and novel C2-substituents. These analogues have significant multilog cytotoxicity profiles in the NCI 60-Cell Line screen, and provide new SAR data for the PBD family.
U2 - 10.1016/j.bmcl.2004.08.002
DO - 10.1016/j.bmcl.2004.08.002
M3 - Article
SN - 0960-894X
VL - 14
SP - 5041
EP - 5044
JO - Bioorganic & medicinal chemistry letters
JF - Bioorganic & medicinal chemistry letters
IS - 20
ER -