Gold complexes
AssigneeUniversity Court of the University of St Andrews
InventorSteven P. Nolan
Life of this patent
Estimating the term…
Abstract
Gold (I) hydroxide complexes of the form Z—Au—OH and digold complexes of the form Z—Au-(μOH)—Au—Z where groups Z are two electron donors are provided. The groups Z may be carbenes, for example nitrogen containing heterocyclic carbenes (NHCs), phosphines or phosphites. The complexes can be used as catalysts, for example in reactions such as hydration of nitriles, skeletal arrangement of enynes, alkoxycyclization of enynes, alkyne hydration, the Meyer-Shuster reaction, 3,3′ rearrangement of allylic acetates, cyclization of propargylic acetates, Beckman rearrangements and hydroamination. The complexes can be used in medicine, for example in the treatment of cancer.
Claims13
A method of catalyzing a chemical transformation, the method comprising:
- contacting a gold (I) hydroxide complex of the form Z—Au—OH;
- or
- a digold (I) hydroxide complex according to general formula V:
- wherein the groups Z are the same for each occurrence or that are different for each occurrence and are nitrogen containing heterocyclic carbene ligands of the form:
- wherein the groups R, R1 R2, R3 and R4 are the same or different and the dashed line in the ring represents optional unsaturation, wherein W and R2 are absent;
- and
- wherein each R and R1, R2, R3 and R4 are, independently for each occurrence, selected from:
- H;
- substituted or unsubstituted primary or secondary alkyl group;
- substituted or unsubstituted phenyl;
- substituted or unsubstituted naphthyl;
- substituted or unsubstituted anthracenyl;
- or
- a functional group selected from the group consisting of:
- halo, hydroxyl, sulfhydryl, cyano, cyanato, thiocyanato, amino, nitro, nitroso, sulfo, sulfonato, boryl, borono, phosphono, phosphonato, phosphinato, phospho, phosphino, and silyloxy;
- and
- A− is an anion, with a substrate;
- and
- chemically transforming the substrate;
- wherein the complex is used as a catalyst, or for the in situ production of a catalyst, for catalyzing a chemical transformation of the substrate, the chemical transformation selected from the group consisting of:
- hydration of nitriles, skeletal arrangement of enynes, alkoxycyclisation of enynes, alkyne hydration, the Meyer-Shuster reaction, 3,3′ rearrangement of allylic acetates, cyclisation of propargylic acetates, Beckman rearrangements and hydroamination.
A gold (I) hydroxide complex of the form Z—Au—OH;
- or a digold (I) hydroxide complex according to general formula V:
- wherein the groups Z are the same or different for each occurrence and are nitrogen containing heterocyclic carbene ligands of the form:
- wherein the groups R, R1 R2, R3 and R4 are the same or different and the dashed line in the ring represents optional unsaturation, wherein R1 and R2 are absent;
- and
- wherein each R and R1, R2, R3 and R4 are, independently for each occurrence, selected from:
- H;
- substituted or unsubstituted primary or secondary alkyl group;
- substituted or unsubstituted phenyl;
- substituted or unsubstituted naphthyl;
- substituted or unsubstituted anthracenyl, with the proviso that for the Z—Au—OH complex both R3 and R4 are not methyl or ethyl when R1 and R2 are absent and R is H;
- or
- a functional group selected from the group consisting of:
- halo, hydroxyl, sulfhydryl, cyano, cyanato, thiocyanato, amino, nitro, nitroso, sulfo, sulfonato, boryl, borono, phosphono, phosphonato, phosphinato, phospho, phosphino, and silyloxy;
- and
- A− is an anion.
A pharmaceutical formulation comprising a gold (I) hydroxide complex of the form Z—Au—OH or a digold (I) hydroxide complex according to general formula V:
- wherein the groups Z are the same or different for each occurrence and are nitrogen containing heterocyclic carbene ligands of the form:
- wherein the groups R, R1 R2, R3 and R4 are the same or different and the dashed line in the ring represents optional unsaturation, wherein R1 and R2 are absent;
- and
- wherein each R and R1, R2, R3 and R4 are, independently for each occurrence, selected from:
- H;
- substituted or unsubstituted primary or secondary alkyl group;
- substituted or unsubstituted phenyl;
- substituted or unsubstituted naphthyl;
- substituted or unsubstituted anthracenyl;
- with the proviso that for the Z—Au—OH complex both R3 and R4 are not methyl or ethyl when R1 and R2 are absent and R is H;
- or
- a functional group selected from the group consisting of:
- halo, hydroxyl, sulfhydryl, cyano, cyanato, thiocyanato, amino, nitro, nitroso, sulfo, sulfonato, boryl, borono, phosphono, phosphonato, phosphinato, phospho, phosphino, and silyloxy;
- and
- A− is an anion;
- or
- a physiologically acceptable salt, ester or other physiologically functional derivative of the complex of the form Z—Au—OH or of the complex according to formula V together with one or more pharmaceutically acceptable carriers.
Dependencies are inferred from the claim text.