Regioselective N-9 arylation of purines employing arylboronic acids in the presence of Cu(II)

Bakkestuen, Anne Kristin; Gundersen, Lise‐Lotte

doi:10.1016/s0040-4039(03)00576-8

Cited by 80 publications

(45 citation statements)

References 39 publications

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“…The following compounds were prepared as previously described: 6-chloro-9-(phenylmethyl)-9H-purine 3a, 17 17 2,6-dichloro-9-(phenylmethyl)-9H-purine 5a, 18 2,6-dichloro-7-(phenylmethyl)-7H-purine 6a, 18 6-(2-furyl)-9-(phenylmethyl)-9H-purine 7a, 3 2-chloro-6-(2-furyl)-9-(phenylmethyl)-9H-purine 8a, 18 and 9-arylpurines 14 and 15. 11 All other reagents were commercially available and used as received.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines

2005

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9-Aryl-, 9-arylsulfonyl- and 9-benzyl-6-(2-furyl)purines were synthesized by N-alkylation or N-arylation of the purine followed by Stille coupling to introduce the furyl substituent in the 6-position and the compounds screened for activity against Mycobacterium tuberculosis. The 9-aryl- and 9-sulfonylarylpurines exhibited weak activity toward the bacteria, but 9-benzylpurines were good inhibitors especially those carrying electron-donating substituents on the phenyl ring. A chlorine atom in the purine 2-position further enhanced activity. The high antimycobacterial activity (MIC 0.39 microg/mL against M. tuberculosis), low toxicity against mammalian cells and activity inside macrophages found for 2-chloro-6-(2-furyl)-9-(4-methoxyphenylmethyl)-9H-purine makes this compound a highly interesting potential antituberculosis drug.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines

2005

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“…[7] Recently, the direct N-arylation of purine derivatives with arylboronic acids in the presence of cupric acetate and a base under anhydrous conditions was reported. Thus, the successful N 9 -arylation of purine, [8] 6-chloropurine, [9] methylthiopurine, [9] 6-mercaptopurine [9] (with partial Sarylation), 6-(2-thienyl)purine, [9] 2-amino-6-chloropurine [9] and 2,6-dichloropurine [9,10] has been published. Also, the microwave-assisted N 9 -arylation of 2-substituted amino-6-chloropurines has been recently reported.…”

Section: Introductionmentioning

confidence: 99%

New Approach to the Synthesis of N⁷‐Arylguanines and N⁷‐Aryladenines

2009

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The copper‐mediated arylation of 7‐methylpyrimido[1,2‐a]purin‐10(3H)‐one (1) in dichloromethane or of N2‐(dimethylamino)methyleneguanine (2) in methanol in the presence of TMEDA as a base/ligand led to the preferential formation of 1‐aryl‐7‐methylpyrimido[1,2‐a]purin‐10(3H)‐ones (4) and 7‐aryl‐N2‐(dimethylamino)methyleneguanines (7), respectively. These compounds can be easily hydrolysed to the corresponding 7‐arylguanines. Similar arylation of N6‐(dimethylamino)methyleneadenine (15) in the presence of o‐phenanthroline instead of TMEDA afforded mainly 7‐aryladenines after hydrolysis.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…The compound was prepared by Stille coupling on 6-chloro-9-phenyl-9H-purine [26] (101 mg, 0.44 mmol), as described for the synthesis of compound 7d above. The crude product was purified by flash chromatography on silica gel eluting with EtOAc-hexane (1:3) followed by (1:1); yield 116 mg, (89 %) colorless crystalline solid, mp.…”

Section: -Phenyl-6-[(e)-2-phenylethen-1-yl]-9h-purine 7gmentioning

confidence: 99%

6‐Substituted Purines as Inhibitors of 15‐Lipoxygenase; a Structure‐Activity Study

Bråthe

Gundersen

Malterud

et al. 2005

Archiv der Pharmazie

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15-lipoxygenase (15-LO) has been implicated in oxidation of low-density lipoproteins (LDL), a process believed to be important for the development of atherosclerosis, as well as other pathogenic conditions. Potent and selective inhibitors of 15-LO may have a drug potential. In this study, purines with a variety of substituents have been examined as inhibitors of 15-lipoxygenase (15-LO) from soybeans. Several 6-substitued purines where the purine ring and a phenyl ring in the substituent were separated by a "spacer" were synthesized and their ability to inhibit the enzyme was explored. Sepa ration of the purine and the phenyl rings with none, one or two sp3-carbons resulted in essentially inactive compounds, trans-styrylpurines and phenylethynylpurines, on the other hand, they exhibited activity close to the well-known 15-LO inhibitor quercetin. High activity was also found when the "spacer" was a trans-cyclopropyl ring. The shape of the spacer was important; a corresponding cis-cyclopropylpurine exhibited much less affinity for the enzyme. Only minor differences in inhibitory activity against 15-LO were found regardless of whether an N-substituent was situated on N-9 or N-7, even when the N-substituent was relatively large. Also, a variety of substituents in the purine 2- and 8-position were well tolerated.

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Regioselective N-9 arylation of purines employing arylboronic acids in the presence of Cu(II)

Cited by 80 publications

References 39 publications

Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines

Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines

New Approach to the Synthesis of N⁷‐Arylguanines and N⁷‐Aryladenines

6‐Substituted Purines as Inhibitors of 15‐Lipoxygenase; a Structure‐Activity Study

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Regioselective N-9 arylation of purines employing arylboronic acids in the presence of Cu(II)

Cited by 80 publications

References 39 publications

Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines

Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines

New Approach to the Synthesis of N7‐Arylguanines and N7‐Aryladenines

6‐Substituted Purines as Inhibitors of 15‐Lipoxygenase; a Structure‐Activity Study

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New Approach to the Synthesis of N⁷‐Arylguanines and N⁷‐Aryladenines