2026-06-21T21:52:33Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/52412021-11-02T12:01:33Zcom_10259_3924com_10259_5086com_10259_2604col_10259_3925
Pertejo Fernández, Pablo
Carreira Barral, Israel
Peña Calleja, Pablo
Quesada Pato, Roberto
García Valverde, María
2020-03-11T11:23:12Z
2020-03-11T11:23:12Z
2020-01
0022-3263
http://hdl.handle.net/10259/5241
10.1021/acs.joc.9b02995
1520-6904
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.
Consejería de Educación de la Junta de Castilla y León (project BU075G19)
application/pdf
eng
American Chemical Society
The Journal of Organic. 2020, V. 85, n. 4, p. 2291-2302
https://doi.org/10.1021/acs.joc.9b02995
info:eu-repo/grantAgreement/JCyL/BU075G19
Mixtures
Inorganic carbon compounds
Adducts
Cyclization
Chemical synthesis
Química orgánica
Chemistry, Organic
Post-Ugi transformations for the access to pyrrolobenzodiazepine scaffolds with different degrees of unsaturation
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
info:eu-repo/semantics/openAccess
The Journal of Organic Chemistry
85
4
2291
2302