Abstract Title

Synthesis of Aziridinomitosenes for Exploration as Potential Chemotherapeutics

Disciplines

Chemicals and Drugs | Medicine and Health Sciences | Organic Chemicals

Abstract

Aziridinomitosenes (AZMs) are a group of potential chemotherapy compounds that are structurally and functionally similar to the anti-tumor agent Mitomycin C (MC). Both act by forming cross-links with the DNA of cancerous cells, thereby inhibiting cell replication and resulting in cell death. However, it is likely that AZMs do not require a reductive activation mechanism, which presumably contributes to some of MC’s adverse side effects. Additionally, past AZM investigations have shown that substituting a methyl group at the C7 electrophilic center creates the most potent analog. In order to enable further testing, C6-methyl and unsubstituted AZM analogs are being prepared using a 20 step sequence. Key structural features being incorporated into the compound include a quinone group, a carbamate at C10, and an aziridine ring at C1. Progress accomplished thus far includes the formation of the tetracyclic core that includes the aziridine ring, as well as installation of the C10 hydroxy group. These and other related results will be presented.

Comments

Poster #Th50

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Synthesis of Aziridinomitosenes for Exploration as Potential Chemotherapeutics

Aziridinomitosenes (AZMs) are a group of potential chemotherapy compounds that are structurally and functionally similar to the anti-tumor agent Mitomycin C (MC). Both act by forming cross-links with the DNA of cancerous cells, thereby inhibiting cell replication and resulting in cell death. However, it is likely that AZMs do not require a reductive activation mechanism, which presumably contributes to some of MC’s adverse side effects. Additionally, past AZM investigations have shown that substituting a methyl group at the C7 electrophilic center creates the most potent analog. In order to enable further testing, C6-methyl and unsubstituted AZM analogs are being prepared using a 20 step sequence. Key structural features being incorporated into the compound include a quinone group, a carbamate at C10, and an aziridine ring at C1. Progress accomplished thus far includes the formation of the tetracyclic core that includes the aziridine ring, as well as installation of the C10 hydroxy group. These and other related results will be presented.