DNA-cleavage and antitumor activity of designed molecules with conjugated phosphine oxide-allene-ene-yne functionalities

Chemistry and biology of natural and designed enediynes.

“…A selection of these model compounds covering the rather wide spectrum of structural types synthesized in this field is shown in Fig. 9 [63 (55), 64 (56), 65 (57), 66 (58), 67 (59), and 68 (60)]. …”

Carbon‐rich Compounds: Computational Considerations

“…All of these are present in the structures of enediynes, enyne-allenes and related systems; these are, per definition, carbon-rich as the parent reactions involve highly unsaturated moieties. The ring closure reactions of these and related polyunsaturated systems (Scheme 8.6), which are known as Bergman (cycloaromatization) [70], Myers-Saito [71], and Schmittel-cyclizations [72], are of particular significance both for medicinal and organic materials chemistry [73]. Such, or structurally related moieties, lead to DNA-cleaving biradicals, i.e., they are potent anti-tumor drugs [74].…”

The Substituent Effect on the Energy Profiles of Inter and Intramolecular Proton Transfers between Phosphine Oxide‐Phosphinous Acid Tautomers

“…These compounds could be presented by two tautomeric forms, phosphine oxide and Phosphinous acid [6]. Despite the many tautomeric processes that are impossible in the real world, this type of tautomerism has been observed in many chemical and biological systems [7]. The importance of this tautomerism can be better understood when we know that these tautomers have different chemical and biological behaviors.…”