Title:
NOVEL QUINONE DERIVATIVE AND ANTI-TRYPANOSOME AGENT CONTAINING THE SAME AS ACTIVE INGREDIENT
Document Type and Number:
Japanese Patent JP2016006043
Kind Code:
A
Abstract:
PROBLEM TO BE SOLVED: To provide a novel compound that has an anti-trypanosome activity.SOLUTION: Provided is a compound represented by the formula (1) or a pharmaceutically acceptable salt thereof. (Ris C1 to 10 alkoxy group or the like; Ris alkyl group, alkoxy group, aryl group, heteroaryl group, alkenyl group, amino group or the like; Ris H, alkyl group, cycloalkyl group, cycloalkyl oxy group, aryl group, aryloxy group, heteroaryl group, heteroaryl oxy group, alkoxy group, cyclic amino group, cyclic amido group, alkenyl group, alkenyl oxy group, alkynyl group, alkynyl oxy group or the like; and Ris H.).
Inventors:
SHIMADA JUNKO
IWASAKI GENJI
SUDO YUTAKA
IWASAKI GENJI
SUDO YUTAKA
Application Number:
JP2015108983A
Publication Date:
January 14, 2016
Filing Date:
May 28, 2015
Export Citation:
Assignee:
UNIV GUNMA
TAKASAKI UNIV OF HEALTH & WELFARE
TAKASAKI UNIV OF HEALTH & WELFARE
International Classes:
C07C50/28; A61K31/122; A61K31/16; A61K31/166; A61K31/4015; A61K31/4164; A61K31/4172; A61K31/4196; A61K31/4406; A61K31/4704; A61P33/02; A61P43/00; C07C50/30; C07C233/61; C07C233/76; C07D207/27; C07D213/65; C07D215/227; C07D233/94; C07D249/08
Domestic Patent References:
| JPH03109388A | 1991-05-09 |
Foreign References:
| WO2009068322A1 | 2009-06-04 |
Other References:
TASDEMIR, DENIZ; BRUN, RETO; YARDLEY, VANESSA; FRANZBLAU, SCOTT G.; RUEDI, PETER: "Antituberculotic and antiprotozoal activities of primin, a natural benzoquinone: in vitro and in viv", CHEMISTRY & BIODIVERSITY, vol. Vol.3, JPN6019000984, 2006, pages 1230-1237
VOAK, ANDREW A.; GOBALAKRISHNAPILLAI, VITHURSHAA; SEIFERT, KARIN; BALCZO, EDINA; HU, LONGQIN; HALL,: "An Essential Type I Nitroreductase from Leishmania major Can Be Used to Activate Leishmanicidal Prod", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. VOLUME 288 NUMBER 40, JPN6019000985, 2013, pages 28466-28476
FANG, JING; BEATTIE, DIANA S.: "Rotenone-insensitive NADH dehydrogenase is a potential source of superoxide in procyclic Trypanosoma", MOLECULAR AND BIOCHEMICAL PARASITOLOGY, vol. 123, JPN6019000986, 2002, pages 135-142
GU, LIAN QUAN; YU, LINDA; YU, CHANG AN: "Effect of substituents of the benzoquinone ring on electron-transfer activities of ubiquinone deriva", BIOCHIMICA ET BIOPHYSICA ACTA, BIOENERGETICS, vol. 1015, JPN6019000987, 1990, pages 482-492
PERRI, STEVEN T.; MOORE, HAROLD W.: "Rearrangements of cyclobutenones. Synthesis of benzoquinones from 4-alkenyl-4-hydroxycyclobutenones", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 112, JPN6019000988, 1990, pages 1897-1905
ENHSEN, ALFONS; KARABELAS, KOSTAS; HEERDING, JULIA M.; MOORE, HAROLD W.: "Synthesis of hydroxyquinones and related compounds: semisquaric acids, (±)-terreic acid, (±)-pere", JOURNAL OF ORGANIC CHEMISTRY, vol. 55, JPN6019000990, 1990, pages 1177-1185
JACOBSEN, N.; TORSSELL, K.: "Synthesis of naturally occurring quinones. Alkylation with the silver ion-peroxydisulfate-carboxyli", ACTA CHEMICA SCANDINAVICA, vol. 27 No.9, JPN7019000102, 1973, pages 3211-3216
LULY, JAY R.; RAPOPORT, HENRY: "Routes to mitomycins. Application of iminium salts to the synthesis of 7-methoxymitosene", JOURNAL OF ORGANIC CHEMISTRY, vol. 47, JPN6019000992, 1982, pages 2404-2413
HIBI, SHIGEKI; ET AL.: "Novel Dual Inhibitors of 5-Lipoxygenase and Thromboxane A2 Synthetase: Synthesis and Structure-Activ", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, JPN6019000994, 1994, pages 3062-3070
KARABELAS, KOSTAS; MOORE, HAROLD W.: "Trimethylsilylmethyl-1,4-benzoquinones. Generation and trapping of o-quinone methides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 112, JPN6019000995, 1990, pages 5372-5373
VOAK, ANDREW A.; GOBALAKRISHNAPILLAI, VITHURSHAA; SEIFERT, KARIN; BALCZO, EDINA; HU, LONGQIN; HALL,: "An Essential Type I Nitroreductase from Leishmania major Can Be Used to Activate Leishmanicidal Prod", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. VOLUME 288 NUMBER 40, JPN6019000985, 2013, pages 28466-28476
FANG, JING; BEATTIE, DIANA S.: "Rotenone-insensitive NADH dehydrogenase is a potential source of superoxide in procyclic Trypanosoma", MOLECULAR AND BIOCHEMICAL PARASITOLOGY, vol. 123, JPN6019000986, 2002, pages 135-142
GU, LIAN QUAN; YU, LINDA; YU, CHANG AN: "Effect of substituents of the benzoquinone ring on electron-transfer activities of ubiquinone deriva", BIOCHIMICA ET BIOPHYSICA ACTA, BIOENERGETICS, vol. 1015, JPN6019000987, 1990, pages 482-492
PERRI, STEVEN T.; MOORE, HAROLD W.: "Rearrangements of cyclobutenones. Synthesis of benzoquinones from 4-alkenyl-4-hydroxycyclobutenones", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 112, JPN6019000988, 1990, pages 1897-1905
ENHSEN, ALFONS; KARABELAS, KOSTAS; HEERDING, JULIA M.; MOORE, HAROLD W.: "Synthesis of hydroxyquinones and related compounds: semisquaric acids, (±)-terreic acid, (±)-pere", JOURNAL OF ORGANIC CHEMISTRY, vol. 55, JPN6019000990, 1990, pages 1177-1185
JACOBSEN, N.; TORSSELL, K.: "Synthesis of naturally occurring quinones. Alkylation with the silver ion-peroxydisulfate-carboxyli", ACTA CHEMICA SCANDINAVICA, vol. 27 No.9, JPN7019000102, 1973, pages 3211-3216
LULY, JAY R.; RAPOPORT, HENRY: "Routes to mitomycins. Application of iminium salts to the synthesis of 7-methoxymitosene", JOURNAL OF ORGANIC CHEMISTRY, vol. 47, JPN6019000992, 1982, pages 2404-2413
HIBI, SHIGEKI; ET AL.: "Novel Dual Inhibitors of 5-Lipoxygenase and Thromboxane A2 Synthetase: Synthesis and Structure-Activ", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, JPN6019000994, 1994, pages 3062-3070
KARABELAS, KOSTAS; MOORE, HAROLD W.: "Trimethylsilylmethyl-1,4-benzoquinones. Generation and trapping of o-quinone methides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 112, JPN6019000995, 1990, pages 5372-5373
Attorney, Agent or Firm:
Yoshiyuki Kawaguchi
Shinichi Sanuki
Shinichi Sanuki