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Design and synthesis of two cytotoxic analogs of the novel pyrrolo[1 ',2 ': 1,2][1,4]diazepin [7,6-b]indol-5(6H)-one nucleus

Tsotinis, A; Vlachou, M; Kiakos, K; Hartley, JA; Thurston, DE; (2003) Design and synthesis of two cytotoxic analogs of the novel pyrrolo[1 ',2 ': 1,2][1,4]diazepin [7,6-b]indol-5(6H)-one nucleus. CHEM LETT , 32 (6) 512 - 513. 10.1246/cl.2003.512.

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Abstract

The design and synthesis of the two cytotoxic derivatives 15 and 16 of the novel pyrrolo[1',2':1,2][1,4]diazepin[7,6-b]in-dol-5(6H)-one nucleus is described. Readily available methyl 2-indolecarboxylates 5 and 6 are nitrosated with NaNO2 in AcOH to give the analogs 7 and 8, which are then oxidized with KMnO4 in aq. NaOH to provide the 3-NO2 acids 9 and 10. These, in turn, are subjected to amidation with (2S)-pyrrolidine-2-carboxaldehyde diethyl thioacetal in the presence of EDCI and HOBt and then to a 7-exo-trig cyclization reaction to give the target molecules 15 and 16. The new analogs were evaluated in the human leukemic K-562 cell line and were shown to have micromolar potency.

Type: Article
Title: Design and synthesis of two cytotoxic analogs of the novel pyrrolo[1 ',2 ': 1,2][1,4]diazepin [7,6-b]indol-5(6H)-one nucleus
DOI: 10.1246/cl.2003.512
Keywords: DNA, AGENT
UCL classification: UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Medical Sciences > Cancer Institute
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Medical Sciences > Cancer Institute > Research Department of Oncology
URI: http://discovery.ucl.ac.uk/id/eprint/109013
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