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2 Ullmann and Buchwald-Hartwig Diaryl Ether Coupling Reactions

T1 - Synthesis of 2,6-diaryl-3-(trifluoromethyl)pyridines by regioselective Suzuki-Miyaura reactions of 2,6-dichloro-3-(trifluoromethyl)pyridine

The first total synthesis of a natural ellagitanninbearing a diaryl ethers is performed to demonstrate that the strategyincreases the number of synthetically available ellagitannins.

T1 - Design and synthesis of diarylamines and diarylethers as cytotoxic antitumor agents

2.1 Intermolecular Ullmann Diaryl Ether Coupling Reactions

The synthesis of the diaryl ether subunits of the marine natural products chrysophaentin A, E, and F is described. These natural products feature tetrasubstituted benzene rings with complex substitution patterns. The central strategy involves an SAr reaction between a complex phenol and a polysubstituted fluoronitrobenzene. Subsequent attempts to construct the unusual E-chloroalkene linkage through several different approaches are also disclosed.

N2 - The synthesis of the diaryl ether subunits of the marine natural products chrysophaentin A, E, and F is described. These natural products feature tetrasubstituted benzene rings with complex substitution patterns. The central strategy involves an SNAr reaction between a complex phenol and a polysubstituted fluoronitrobenzene. Subsequent attempts to construct the unusual E-chloroalkene linkage through several different approaches are also disclosed.

3 Synthesis of Diaryl Ethers via Nucleophilic Aromatic Substitution

AB - The synthesis of the diaryl ether subunits of the marine natural products chrysophaentin A, E, and F is described. These natural products feature tetrasubstituted benzene rings with complex substitution patterns. The central strategy involves an SNAr reaction between a complex phenol and a polysubstituted fluoronitrobenzene. Subsequent attempts to construct the unusual E-chloroalkene linkage through several different approaches are also disclosed.

N2 - Based on a shared structural core of diarylamine in several known anticancer drugs as well as a new cytotoxic hit 6-chloro-2-(4-cyanophenyl)amino- 3-nitropyridine (7), 30 diarylamines and diarylethers were designed, synthesized, and evaluated for cytotoxic activity against A549, KB, KB-vin, and DU145 human tumor cell lines (HTCL). Four new leads 11e, 12, 13a, and 13b were discovered with GI50 values ranging from 0.33 to 3.45 μM. Preliminary SAR results revealed that a diarylamine or diarylether could serve as an active structural core, meta-chloro and ortho-nitro groups on the A-ring (either pyridine or phenyl ring) were necessary and crucial for cytotoxic activity, and the para-substituents on the other phenyl ring (B-ring) were related to inhibitory selectivity for different tumor cells. In an investigation of potential biological targets of the new leads, high thoughput kinase screening discovered that new leads 11e, 12 and 13b especially inhibit Mer tyrosine kinase, a proto-oncogene associated with munerous tumor types, with IC50 values of 2.2-3.0 μM. Therefore, these findings provide a good starting point to optimize a new class of compounds as potential anticancer agents, particularly targeting Mer tyrosine kinase.

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5 Diaryl Ether Synthesis via Benzyne Mechanism


7 Diaryl Ether Synthesis via Oxidative Coupling

Based on a shared structural core of diarylamine in several known anticancer drugs as well as a new cytotoxic hit 6-chloro-2-(4-cyanophenyl)amino- 3-nitropyridine (7), 30 diarylamines and diarylethers were designed, synthesized, and evaluated for cytotoxic activity against A549, KB, KB-vin, and DU145 human tumor cell lines (HTCL). Four new leads 11e, 12, 13a, and 13b were discovered with GI50 values ranging from 0.33 to 3.45 μM. Preliminary SAR results revealed that a diarylamine or diarylether could serve as an active structural core, meta-chloro and ortho-nitro groups on the A-ring (either pyridine or phenyl ring) were necessary and crucial for cytotoxic activity, and the para-substituents on the other phenyl ring (B-ring) were related to inhibitory selectivity for different tumor cells. In an investigation of potential biological targets of the new leads, high thoughput kinase screening discovered that new leads 11e, 12 and 13b especially inhibit Mer tyrosine kinase, a proto-oncogene associated with munerous tumor types, with IC50 values of 2.2-3.0 μM. Therefore, these findings provide a good starting point to optimize a new class of compounds as potential anticancer agents, particularly targeting Mer tyrosine kinase.

Diaryl ether synthesis by etherification (arylation)

AB - Based on a shared structural core of diarylamine in several known anticancer drugs as well as a new cytotoxic hit 6-chloro-2-(4-cyanophenyl)amino- 3-nitropyridine (7), 30 diarylamines and diarylethers were designed, synthesized, and evaluated for cytotoxic activity against A549, KB, KB-vin, and DU145 human tumor cell lines (HTCL). Four new leads 11e, 12, 13a, and 13b were discovered with GI50 values ranging from 0.33 to 3.45 μM. Preliminary SAR results revealed that a diarylamine or diarylether could serve as an active structural core, meta-chloro and ortho-nitro groups on the A-ring (either pyridine or phenyl ring) were necessary and crucial for cytotoxic activity, and the para-substituents on the other phenyl ring (B-ring) were related to inhibitory selectivity for different tumor cells. In an investigation of potential biological targets of the new leads, high thoughput kinase screening discovered that new leads 11e, 12 and 13b especially inhibit Mer tyrosine kinase, a proto-oncogene associated with munerous tumor types, with IC50 values of 2.2-3.0 μM. Therefore, these findings provide a good starting point to optimize a new class of compounds as potential anticancer agents, particularly targeting Mer tyrosine kinase.

Synthesis of 1-[4-(1,3-diaryl-4,5-dihydro ..

Diaryl ethers form an important class of organic compounds, both in life sciences and in the polymer industry. In general, diaryl ethers can be synthesized by means of copper-catalyzed Ullmann diaryl ether coupling, palladium-catalysed Buchwald-Hartwig reaction, nucleophilic aromatic substitution, arylboronic acid diaryl ether coupling, oxidative coupling, and nucleophilic aromatic addition to metal-arene complexes. This review covers the progress in diaryl ether synthesis since 1999, with literature coverage through September 2005.

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