Regiospecific Synthesis of Pyrido[3,4-b]- and Pyrido[4,3-b]carbazole-5,11-dione Derivatives. Evaluation of Their In Vitro Antifungal or Antiprotozoological Activities

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概要

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• Hetero Diels-Alder reactions between 2- or 3-bromocarbazolequinones 1a or 1b and azadiene 5 afford regiospecifically pylrido[3,4-b]- and pyrido[4,3-b]carbazole-3,5,11-triones 6a and 6b. The regiochemistry of the cycloadditions is controlled by the position of the bromine atom at C-2 or C-3 of the bromoquinone. The corresponding N- and O-methyl derivatives 7 and 8 are prepared. Structural assignment of the regioisomers is made by ^1H-NMR unclear Overhauser effect difference experiments performed on a diacetoxy derivative of pyrido[4,3-b]carbazole 9b. The in vitro antifungal and antiprotozoological activities of some prepared derivatives have been evaluated against Candida albicans, Candida krusei, Cryptococcus neoformans and Trichomonas vaginalis. None of the tested compounds have shown significant activity towards the yeasts or protozoa.

• 公益社団法人日本薬学会の論文
• 1999-05-15

著者

• Giraud Josette

  Department De Parasitologie Mycologie Medicale Et Organisation Animale

• Fillion Houda

  Laboratoire De Chimie Organique Faculte De Pharmacie Universite Claude Bernard Lyon

• Fillion Houda

  Laboratoire De Chimie Organique

• POUMAROUX Ambroise

  Laboratoire de Chimie Organique

• BOUAZIZ Zouhair

  Laboratoire de Chimie Organique

• DOMARD Monique

  Laboratoire de Chimie Physique et Chimie Analytique II

• PETAVY Anne-Francoise

  Department de Parasitologie, Mycologie Medicale et Organisation Animale

• Domard M

  Univ. Claude Bernard Lyon 1 Lyon Fra

• Domard Monique

  Laboratoire De Chimie Physique Et Analytique Ii Institut Des Sciences Pharmaceutiques Et Biologiques

• Poumaroux A

  Univ. Claude Bernard Lyon

• Petavy Anne-francoise

  Department De Parasitologie Mycologie Medicale Et Organisation Animale

関連論文

• Regiospecific Synthesis of Pyrido[3,4-b]- and Pyrido[4,3-b]carbazole-5,11-dione Derivatives. Evaluation of Their In Vitro Antifungal or Antiprotozoological Activities
• Total Synthesis of Maturinone through a Regioselective Diels-Alder Reaction of 5-Brominated Benzofurandione
• Generation of a Thiazole o-Quinodimethane from an Imino Derivative and Its Intermolecular Diels-Alder Trapping with Alkynes or Quinones
• Studies on the Oxidative Addition of N, N-Dimethylamine to Bromojuglones and Bromomethyljuglones
• Synthesis of Furnaphth[1,3]oxazine and Furo[1,3]oxazinoquinoline Derivatives as Precursors for an o-Quinonemethide Structure and Potential Antitumor Agents
• Synthesis of Mannich Bases of 5-Hydroxynaphthalene-1,8-carbolactone as Potential Antifungal or Antitumor Agents
• Synthesis and Diels-Alder Reactivity of ortho-Carbazolequinones
• Reactivity of an o-Indoloquinone to 1-and 2-Azadienes

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