Studies on Chemotherapeutic Agents. V. A Synthesis of Benzimidazole Nucleosides of D-Glucopyranuronamide

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概要

• 論文の詳細を見る

• Direct condensation of D-glucuronolactone with o-nitroaniline (Ia) or 5-nitro-o-4-xylidine (Ib) afforded o-nitroanilino-or 5-nitro-o-4-xylidino-D-glucuronolactone, IIa or IIb in an excellent yield. On treatment with ammoniacal MeOH, IIa and IIb were amidated to give VIIa and VIIb, respectively. It was found that they held a furanose structure. VIIa and VIIb underwent conversion of the lactol ring from furanoside to pyranoside form by the presence of AcOH, affording o-nitroanilino-and 5-nitro-o-4-xylidino-D-glucopyranuronamide, XIa and XIb. Hydrogenation of the nitro group in the acetylated derivative XIIa or XIIb was effectively made over a palladium or platinum catalyst. Ring closure of the phenylenediamine derivative XIIIa or XIIIb with ethyl orthoformate or ethyl formimidate hydrochloride followed by acid or alkali hydrolysis gave 1-deoxy-1-(1-benzimidazolyl)-or 1-deoxy-1-(5,6-dimethyl-1-benzimidazolyl)-β-D-glucopyranuronamide, XVa or XVb. The corresponding benzimidazole nucleosides of D-glucuronolactone and D-glucofuranuronamide could not be obtained by the same ring closure procedure. XVa, XVb and 1-deoxy-1-(5,6-dichloro-1-benzimidazolyl)-β-D-glucopyranuronamide (XVc) were also formed by the chloromercury method of Davoll and Brown.

• 公益社団法人日本薬学会の論文
• 1969-12-25

著者

• 岸川 虎比古

  Research Laboratories, Morishita Pharmaceutical Co., Ltd.

• 岸川 虎比古

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• 岸川 虎比古

  Research Laboratories Morishita Pharmaceutical Co. Ltd.

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