PMID: 2500528Jul 1, 1989Paper

Synthesis, mechanism of action, and biological evaluation of mitosenes

Journal of Medicinal Chemistry
E O OrlemansM C Bibby

Abstract

Mitosenes of both the pyrrolo- and pyrido[1,2-a]indole type have been prepared via modification of these heterotricyclic compounds. Several mitosenes have been studied for their reactions with nucleophiles under reductive conditions. The results of these experiments show that the biological activity of mitosenes is based on the mechanism of bioreductive activation. When both leaving groups at C-1 and C-10 in the mitosene are the same, the nucleophile preferably adds to C-10 under reductive conditions. All mitosenes were studied for their biological activities in vitro against L1210, WiDr, and A204. On the basis of these results a selection of three mitosenes was made for a more detailed biological evaluation. Several tumor model systems were used, viz. P388, human tumor xenografts, MAC 13, and MAC 16. The results of these studies show that mitosenes have a more limited range of activities than mitomycin C. Surprisingly, the in vivo activities of mitosene diol 8b and mitosene diacetate 10b against the gastric human tumor xenograft GXF 97 were very high and comparable with that of mitomycin C.

Citations

Jun 1, 1993·Cancer Metastasis Reviews·P Workman, I J Stratford
Mar 20, 2002·European Journal of Medicinal Chemistry·Seref DemirayakAhmet Cağri Karaburun
Feb 17, 1999·Bioorganic & Medicinal Chemistry Letters·M JaffarI J Stratford
Feb 24, 2012·The Journal of Organic Chemistry·Donald C RognessRichard C Larock
Apr 23, 2011·Organic Letters·Huajian ZhuHongbin Zou
Aug 29, 2019·Organic & Biomolecular Chemistry·Jitendra GourSrinivas Nanduri
Aug 29, 2014·Chemical Communications : Chem Comm·Xiaowei DouYixin Lu
Apr 29, 2021·Chemical Communications : Chem Comm·Thomas Varlet, Géraldine Masson
Jun 2, 2021·Organic & Biomolecular Chemistry·Guang-Xin RuGuang-Qin Gao
Feb 19, 2002·Chemical Reviews·Scott R. Rajski, Robert M. Williams
Jan 26, 1996·The Journal of Organic Chemistry·Zheng Wang, Leslie S. Jimenez
Nov 9, 2021·Organic & Biomolecular Chemistry·Tirtha Mandal, Jyotirmayee Dash

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