Synthesis of Carbazolequinone Derivatives as Inhibitors ofToxoplasma gondii Purine Nucleoside Phosphorylase

Abstract

Keywords: Alkaloids / Natural products / Cycloadditions / Nitrogen heterocycles / PNP inhibitors 9-Ethyl-6-hydroxycarbazolequinone (9) was synthesized and submitted to a hetero Diels−Alder reaction towards azadienes 10a or 10b to afford the hydroxypyridocarbazole-5,11-diones 11 or 12a,b. A Bracher cyclization applied to compound 12b led to the 9-hydroxyquinoneimine 15 admixed with its 9-methyl ether 16. These compounds as well as other carbazolequinone derivatives were evaluated towards a purine nucleoside phosphorylase isolated from two strains of

Diels–Alder reactions between cyclopentadiene analogs and benzoquinone in water and their application in the synthesis of polycyclic cage compounds

“…To expand the scope of this method in water, we found that the structure of 2,2′-bi( p -benzoquinone) was similar to that of p -benzoquinone and can be synthesized by oxidation of 2,2′-biphenol. 64 According to the structure of 2,2′-bi( p -benzoquinone) and the high reactivity of p -benzoquinone with cyclopentadiene, inspiration was drawn and a convenient synthetic strategy to construct two cages simultaneously in the synthesis of bi-cage hydrocarbon compounds was designed ( Scheme 4 ). In this scheme, the Diels–Alder reaction in water was applied and bi-cage hydrocarbon compounds HV-1 and HV-2 were synthesized.…”

“…2,2′-bi( p -benzoquinone) was prepared by the procedure described by Bouaziz. 64 1 H NMR (400 MHz, CDCl 3 ) δ 6.85 (d, J = 15.8 Hz, 6H).…”

Diels–Alder reactions between cyclopentadiene analogs and benzoquinone in water and their application in the synthesis of polycyclic cage compounds

“…To expand the scope of this method in water, we found that the structure of 2,2′-bi( p -benzoquinone) was similar to that of p -benzoquinone and can be synthesized by oxidation of 2,2′-biphenol. 64 According to the structure of 2,2′-bi( p -benzoquinone) and the high reactivity of p -benzoquinone with cyclopentadiene, inspiration was drawn and a convenient synthetic strategy to construct two cages simultaneously in the synthesis of bi-cage hydrocarbon compounds was designed ( Scheme 4 ). In this scheme, the Diels–Alder reaction in water was applied and bi-cage hydrocarbon compounds HV-1 and HV-2 were synthesized.…”

“…2,2′-bi( p -benzoquinone) was prepared by the procedure described by Bouaziz. 64 1 H NMR (400 MHz, CDCl 3 ) δ 6.85 (d, J = 15.8 Hz, 6H).…”

Synthesis and Diels-Alder Reactivity of ortho-Carbazolequinones

“…6) In a previous work we reported the synthesis, 7,8) the induction of caspase-dependent cell death 9) and the Toxoplasma gondii purine nucleoside phosphorylase inhibitory activity 10) of some carbazole-1,4-quinones. The purpose of this work is to obtain carbazole-1,2 and -3,4-dione derivatives and to report their behaviour as dienophiles in [4ϩ2] cycloaddition reactions.…”

A Diels–Alder Strategy for the Building of Imidazo[4,5‐g]quinoline‐4,9‐dione Derivatives

“…However, quinoline derivatives can be obtained by a Diels-Alder reaction of 1-azadienes [4] with a dienophile. [5][6][7][8][9] We wish to report here our results concerning this alternative strategy based on hetero Diels-Alder reactions between benzimidazole-4,7-diones I as dienophiles and α,β-unsaturated N,N-dimethylhydrazones.…”

Diels–Alder reactions between cyclopentadiene analogs and benzoquinone in water and their application in the synthesis of polycyclic cage compounds

“…To expand the scope of this method in water, we found that the structure of 2,2′-bi( p -benzoquinone) was similar to that of p -benzoquinone and can be synthesized by oxidation of 2,2′-biphenol. 64 According to the structure of 2,2′-bi( p -benzoquinone) and the high reactivity of p -benzoquinone with cyclopentadiene, inspiration was drawn and a convenient synthetic strategy to construct two cages simultaneously in the synthesis of bi-cage hydrocarbon compounds was designed ( Scheme 4 ). In this scheme, the Diels–Alder reaction in water was applied and bi-cage hydrocarbon compounds HV-1 and HV-2 were synthesized.…”

“…2,2′-bi( p -benzoquinone) was prepared by the procedure described by Bouaziz. 64 1 H NMR (400 MHz, CDCl 3 ) δ 6.85 (d, J = 15.8 Hz, 6H).…”

Synthesis and Diels-Alder Reactivity of ortho-Carbazolequinones

“…6) In a previous work we reported the synthesis, 7,8) the induction of caspase-dependent cell death 9) and the Toxoplasma gondii purine nucleoside phosphorylase inhibitory activity 10) of some carbazole-1,4-quinones. The purpose of this work is to obtain carbazole-1,2 and -3,4-dione derivatives and to report their behaviour as dienophiles in [4ϩ2] cycloaddition reactions.…”

A Diels–Alder Strategy for the Building of Imidazo[4,5‐g]quinoline‐4,9‐dione Derivatives

“…However, quinoline derivatives can be obtained by a Diels-Alder reaction of 1-azadienes [4] with a dienophile. [5][6][7][8][9] We wish to report here our results concerning this alternative strategy based on hetero Diels-Alder reactions between benzimidazole-4,7-diones I as dienophiles and α,β-unsaturated N,N-dimethylhydrazones.…”

Diels–Alder reactions between cyclopentadiene analogs and benzoquinone in water and their application in the synthesis of polycyclic cage compounds

“…To expand the scope of this method in water, we found that the structure of 2,2′-bi( p -benzoquinone) was similar to that of p -benzoquinone and can be synthesized by oxidation of 2,2′-biphenol. 64 According to the structure of 2,2′-bi( p -benzoquinone) and the high reactivity of p -benzoquinone with cyclopentadiene, inspiration was drawn and a convenient synthetic strategy to construct two cages simultaneously in the synthesis of bi-cage hydrocarbon compounds was designed ( Scheme 4 ). In this scheme, the Diels–Alder reaction in water was applied and bi-cage hydrocarbon compounds HV-1 and HV-2 were synthesized.…”

“…2,2′-bi( p -benzoquinone) was prepared by the procedure described by Bouaziz. 64 1 H NMR (400 MHz, CDCl 3 ) δ 6.85 (d, J = 15.8 Hz, 6H).…”

Synthesis and Diels-Alder Reactivity of ortho-Carbazolequinones

“…6) In a previous work we reported the synthesis, 7,8) the induction of caspase-dependent cell death 9) and the Toxoplasma gondii purine nucleoside phosphorylase inhibitory activity 10) of some carbazole-1,4-quinones. The purpose of this work is to obtain carbazole-1,2 and -3,4-dione derivatives and to report their behaviour as dienophiles in [4ϩ2] cycloaddition reactions.…”

A Diels–Alder Strategy for the Building of Imidazo[4,5‐g]quinoline‐4,9‐dione Derivatives

“…However, quinoline derivatives can be obtained by a Diels-Alder reaction of 1-azadienes [4] with a dienophile. [5][6][7][8][9] We wish to report here our results concerning this alternative strategy based on hetero Diels-Alder reactions between benzimidazole-4,7-diones I as dienophiles and α,β-unsaturated N,N-dimethylhydrazones.…”