2-[4-[Bis(2-chloroethyl)amino]benzyl]-5,5-dimethyl-2,5-dihydro-4H-benzo[e]isoindol-4-one (Cytotoxic Oxonaphthalene-Pyrroles, Part I)

Abstract

A bis(chloroethyl)amine containing side chain is attached to an oxonaphthaleneannelated pyrrol in expectation of DNA alkylating properties. The cytotoxicity is evaluated against two cell lines, KB-31 and KB-8511, respectively.

2-[3-(Aziridin-1-yl)-2-hydroxypropyl]-5,5-dimethyl-2,5-dihydro-4H-benzo[e]isoindol-4-one (Cytotoxic Oxonaphthalene-Pyrroles, Part III)

“…Besides that there are anticancer agents with the aziridine moiety, such as TEPA, thio-TEPA and triethylenemelamine with a 1,3,5-triazine nucleus. In continuation of our department's previous studies in the field of antitumor agents [2][3][4][5][6][7][8][9][10], we are reporting in this paper the synthesis of the oxonaphthalene-annelated pyrrole 2 with an attached side chain containing an aziridine group. The rationale is that the three-membered aziridine ring is struturally analogous to the immoniumintermediate formed from the nitrogen mustards.…”

2-[2-(Aziridin-1-yl)ethyl]-5,5-dimethyl-2,5-dihydro-4H-benzo [e]isoindol-4-one (Cytotoxic Oxonaphthalene-Pyrroles, Part IV)

“…Both compounds are believed to exert their antitumor effects by cross-linking DNA via aziridinium cation intermediates arising from the bis(2-chloroethyl)amine moiety [1]. In continuation of our department's previous studies in the field of antitumor agents [2][3][4][5][6][7][8][9][10], we are reporting in this paper the synthesis of the oxonaphthalene-annelated pyrrole 2 with an attached side chain containing an aziridine group. The rationale is that the three-membered aziridine ring is structurally analogous to the ammonium-intermediate formed from the nitrogen mustards.…”