WO2012021409A3 - Anthraquinone Analogs - Google Patents

Anthraquinone Analogs Download PDF

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Publication number
WO2012021409A3
WO2012021409A3 PCT/US2011/046794 US2011046794W WO2012021409A3 WO 2012021409 A3 WO2012021409 A3 WO 2012021409A3 US 2011046794 W US2011046794 W US 2011046794W WO 2012021409 A3 WO2012021409 A3 WO 2012021409A3
Authority
WO
WIPO (PCT)
Prior art keywords
anthraquinone analogs
anthraquinone
analogs
methods
diones
Prior art date
Application number
PCT/US2011/046794
Other languages
French (fr)
Other versions
WO2012021409A2 (en
Inventor
Cheng Wei Tom Chang
Original Assignee
Utah 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
Application filed by Utah State University filed Critical Utah State University
Publication of WO2012021409A2 publication Critical patent/WO2012021409A2/en
Publication of WO2012021409A3 publication Critical patent/WO2012021409A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/22—Naphthotriazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Anthraquinone analogs, methods for synthesizing anthraquinone analogs, and methods for inhibiting growth of one or more types of cells using anthraquinone analogs. Anthraquinone analogs can be synsthesized according to methods described herein. Optionally, the synthesis methods described herein include choosing an appropriate leaving group for selectively producing 1-alkyl-1H-naphtho[2,3-d]triazole-4,9-diones or 2-alkyl-2H-naphtho[2,3-d]triazole-4,9-diones. Anthraquinone analogs can include various functional groups that affect their ability to inhibit the growth of various cell types. For example, some anthraquinone analogs disclosed herein have antimicrobial activity while seemingly similar compounds demonstrate anticancer activity but lesser antimicrobial activity.
PCT/US2011/046794 2010-08-11 2011-08-05 Anthraquinone Analogs WO2012021409A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US37253010P 2010-08-11 2010-08-11
US61/372,530 2010-08-11

Publications (2)

Publication Number Publication Date
WO2012021409A2 WO2012021409A2 (en) 2012-02-16
WO2012021409A3 true WO2012021409A3 (en) 2012-05-24

Family

ID=45568143

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2011/046794 WO2012021409A2 (en) 2010-08-11 2011-08-05 Anthraquinone Analogs

Country Status (1)

Country Link
WO (1) WO2012021409A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103880715B (en) * 2012-12-19 2016-04-06 张家港市国泰华荣化工新材料有限公司 A kind of method of continuous production trifluoromethanesulfonic acid ethyl ester
CN108467370B (en) * 2017-11-29 2021-11-23 四川大学 Triazole naphthoquinone bi-aromatic ring derivative or triazole naphthoquinone bi-aromatic heterocyclic derivative, and preparation method and application thereof
CN109293588B (en) * 2018-11-14 2022-02-01 四川大学 Small molecular compound with IDO1/TDO dual-target, and preparation method and application thereof
CN110218198B (en) * 2019-05-22 2022-06-28 广州中医药大学(广州中医药研究院) Naphthoquinone triazole core skeleton derivative compound and preparation method and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0033215A2 (en) * 1980-01-23 1981-08-05 Beecham Group Plc Process for preparing anti-allergy naphthotriazoles
EP0033214A2 (en) * 1980-01-23 1981-08-05 Beecham Group Plc Process for preparing therapeutically active triazoles

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0033215A2 (en) * 1980-01-23 1981-08-05 Beecham Group Plc Process for preparing anti-allergy naphthotriazoles
EP0033214A2 (en) * 1980-01-23 1981-08-05 Beecham Group Plc Process for preparing therapeutically active triazoles

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
JIANJUN ZHANG ET AL.: "Divergent Synthesis of Three Classes of Aryl N-Glucosides by Solvent Controle", JOURNAL OF ORGANIC CHEMISTRY, vol. 74, no. 2, 2009, pages 685 - 695 *
JIANJUN ZHANG ET AL.: "Synthesis and antibaceterial activity study of a novel class of cationinc anthraquinone analogs", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 19, no. 11, 2011, pages 498 - 503 *
SATISH G. BODIGE ET AL.: "2-Amino-1,2,3-triazole derivatives", JOURNAL OF CHEMICAL CRYSTALLOGRAPH, vol. 29, no. 12, 1999, pages 1225 - 1234 *

Also Published As

Publication number Publication date
WO2012021409A2 (en) 2012-02-16

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