Synthesis, structure, and antitumor activity of 2,9-disubstituted perhydro 2,3a,7b,9,10a,14b-hexaazadibenzotetracenes

Abstract

Catalytic methods for the synthesis of previously unknown 2,9-disubstituted 3bR*,7aR*,10bR*,14aR*-cis-14c,14d-perhydro-2,3a,7b,9,10a,14b-hexaazadibenzotetracenes with pronounced antitumor activity have been developed.

A New Synthesis of Polyheterocyclic Compounds Containing Nitrogen and Boron Atoms

“…Thus, in the present study we have demonstrated that the intermolecular heterocyclization of polyamines with tetrakis(dimethylamino)diborane provides for the synthesis of novel diboron-containing tetraazatricyclanes. The obtained compounds may be of interest as precursors in the further synthesis of functionally-substituted tetracyclanes, which have potential cytotoxic and antitumor activity [11][12][13].…”

Recent Advances in the Chemistry of Saturated Annulated Nitrogen-Containing Polycyclic Compounds

“…An efficient one-pot method for the synthesis of previously undescribed 2,9-disubstituted hexaazaperhydrodibenzotetracenes 128 has been developed [ 73 ]. The synthesis was based on tetraazaperhydrotetracene 124 b derived from (±)- trans -1,2-diaminocyclohexane ( Scheme 35 ).…”

“…The broad spectrum of biological activity of the heterosystems with an adamantane moiety [ 78 ] attracts the attention of researchers and stimulates the development of efficient methods for the synthesis of new cage molecules. In this regard, the same authors [ 73 ] performed the one-pot cyclocondensation of adamantylamines with formaldehyde and tetraazaperhydrotetracene 124 b in the presence of granulated H-Ymmm zeolite to give previously undescribed diadamantyl-substituted hexaazaperhydrodibenzotetracenes 129 ( Scheme 36 ). The hydroxyadamantane-substituted hexaazaperhydrodibenzotetracenew is shown to possess a cytostatic activity (a proliferation-restrictive activity) against six tumor cell cultures (Jurkat, K562, U937, A549, A2780, and T74D).…”