WO2003089576A2 - Anthraquinones anticancereux et leur methode d'utilisation - Google Patents

Anthraquinones anticancereux et leur methode d'utilisation Download PDF

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Publication number
WO2003089576A2
WO2003089576A2 PCT/US2003/011302 US0311302W WO03089576A2 WO 2003089576 A2 WO2003089576 A2 WO 2003089576A2 US 0311302 W US0311302 W US 0311302W WO 03089576 A2 WO03089576 A2 WO 03089576A2
Authority
WO
WIPO (PCT)
Prior art keywords
anthraquinone
group
methyl
hydroxy
cancer
Prior art date
Application number
PCT/US2003/011302
Other languages
English (en)
Other versions
WO2003089576A3 (fr
Inventor
Muraleedharan G. Nair Nair
Robert H. Cichewicz
Navindra P. Seeram
Yanjun Zhang
Original Assignee
Michigan State University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US10/317,906 external-priority patent/US6800615B2/en
Application filed by Michigan State University filed Critical Michigan State University
Priority to AU2003230891A priority Critical patent/AU2003230891A1/en
Publication of WO2003089576A2 publication Critical patent/WO2003089576A2/fr
Publication of WO2003089576A3 publication Critical patent/WO2003089576A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/14—Acetic acid esters of monohydroxylic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/38—Quinones containing —CHO or non—quinoid keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des anthraquinones, qui présentent une activité anticancéreuse et antitumorale et sont utiles pour inhiber des cellules cancéreuses et des cellules tumorales in vitro ou in vivo. De préférence, les anthraquinones de l'invention sont représentés par la formule (I), dans laquelle R1 est sélectionné dans le groupe constitué par hydrogène, alkyle et alkyle substitué; R2 est un groupe contenant 1 à 12 carbones sélectionnés dans le groupe constitué par alkyle, alkyle substitué, aldéhyde, hydroxy, hydroxyméthyle, groupe acide, hydrates de carbone ou leurs combinaisons; et R3 est est un groupe contenant 1 à 12 carbones sélectionnés dans le groupe constitué par méthyle, alkyle, alkyle substitué, aldéhyde, hydroxy, hydroxyméthyle, groupe acide, hydrates de carbone ou leurs combinaisons. Les anthraquinones préférés sont 1-hydroxy-2-acétyl-3,6-méthyl anthraquinone; monoacétate de 2-acétyl-3,6-méthyl anthraquinone; 1-hydroxy-2-acétyl-3,7-méthyl anthraquinone; monoacétate de 2-acétyl-3,7-méthyl anthraquinone; 1,2,8-trihydroxy-3-méthyl anthraquinone; 1,8-dihydroxy-2-0-β-D-glucopyranoside anthraquinone; 1,2,8-trihydroxy-3-hydroxyméthyl anthraquinone; et 1,8-dihydroxy-3-carboxy anthraquinone.
PCT/US2003/011302 2002-04-15 2003-04-11 Anthraquinones anticancereux et leur methode d'utilisation WO2003089576A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003230891A AU2003230891A1 (en) 2002-04-15 2003-04-11 Anticancer anthraquinones and method of use thereof

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US37257602P 2002-04-15 2002-04-15
US60/372,576 2002-04-15
US38936802P 2002-06-17 2002-06-17
US60/389,368 2002-06-17
US10/317,906 US6800615B2 (en) 2002-04-15 2002-12-12 Antihelminthic anthraquinones and method of use thereof
US10/317,906 2002-12-12
US10/355,483 2003-01-31
US10/355,483 US6875746B1 (en) 2002-04-15 2003-01-31 Anticancer anthraquinones and method of use thereof

Publications (2)

Publication Number Publication Date
WO2003089576A2 true WO2003089576A2 (fr) 2003-10-30
WO2003089576A3 WO2003089576A3 (fr) 2003-12-31

Family

ID=29255565

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/011302 WO2003089576A2 (fr) 2002-04-15 2003-04-11 Anthraquinones anticancereux et leur methode d'utilisation

Country Status (2)

Country Link
AU (1) AU2003230891A1 (fr)
WO (1) WO2003089576A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7767719B2 (en) 2006-04-07 2010-08-03 Sunten Phytotech Co., Ltd. Anthracenedione compounds
CN112441925A (zh) * 2020-11-13 2021-03-05 宁波大学 一种蒽醌类化合物及其从刺果毛茛中的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5480873A (en) * 1992-02-28 1996-01-02 Lilly Industries Limited Pharmaceutical compounds
US5652265A (en) * 1995-03-29 1997-07-29 Wisconsin Alumni Research Foundation Production of rhein and rhein derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5480873A (en) * 1992-02-28 1996-01-02 Lilly Industries Limited Pharmaceutical compounds
US5652265A (en) * 1995-03-29 1997-07-29 Wisconsin Alumni Research Foundation Production of rhein and rhein derivatives

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CAMERON ET AL.: 'Synthesis of specifically O-alkylated anthraquinones by cycloaddition' TETRAHEDRON LETTERS vol. 27, no. 41, 1986, pages 4999 - 5002, XP002953283 *
LI ET AL.: 'Bioactive compounds from the root of myrsine Africana' JOURNAL OF NATURAL PRODUCTS vol. 52, no. 3, May 1989 - June 1989, pages 660 - 662, XP002953282 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7767719B2 (en) 2006-04-07 2010-08-03 Sunten Phytotech Co., Ltd. Anthracenedione compounds
US8466202B2 (en) 2006-04-07 2013-06-18 Sunten Phytotech Co., Ltd. Anthracenedione compounds
CN112441925A (zh) * 2020-11-13 2021-03-05 宁波大学 一种蒽醌类化合物及其从刺果毛茛中的制备方法
CN112441925B (zh) * 2020-11-13 2022-04-01 宁波大学 一种蒽醌类化合物及其从刺果毛茛中的制备方法

Also Published As

Publication number Publication date
WO2003089576A3 (fr) 2003-12-31
AU2003230891A8 (en) 2003-11-03
AU2003230891A1 (en) 2003-11-03

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