RT info:eu-repo/semantics/article
T1 Post-Ugi transformations for the access to pyrrolobenzodiazepine scaffolds with different degrees of unsaturation
A1 Pertejo Fernández, Pablo
A1 Carreira Barral, Israel
A1 Peña Calleja, Pablo
A1 Quesada Pato, Roberto
A1 García Valverde, María
K1 Mixtures
K1 Inorganic carbon compounds
K1 Adducts
K1 Cyclization
K1 Chemical synthesis
K1 Química orgánica
K1 Chemistry, Organic
AB The synthesis of three novel families of pyrrolo[2,1-c][1,4]benzodiazepine-5-ones is described. The compounds were prepared according to a three-step sequence, involving an Ugi reaction, building of the pyrrolo nucleus, and reduction–cyclization to the corresponding diazepine. Depending on the amine employed in the synthesis of the Ugi adducts, different unsaturation degrees could be obtained in the pyrrolo ring (saturated or with endo or exo unsaturations), a key feature determining their biological activity, as it affects the affinity of the pyrrolobenzodiazepines toward DNA and thus their cytotoxicity. This synthetic methodology represents a significant improvement with respect to those described in the literature so far, as it uses inexpensive and commercially available starting materials without needing derivatization or the use of protecting groups.
PB American Chemical Society
SN 0022-3263
YR 2020
FD 2020-01
LK http://hdl.handle.net/10259/5241
UL http://hdl.handle.net/10259/5241
LA eng
NO Consejería de Educación de la Junta de Castilla y León (project BU075G19)
DS Repositorio Institucional de la Universidad de Burgos
RD 24-nov-2024